can I teach a very disorganized employee to be more independent?

A reader writes:

I have a question about helping my employee get organized. She has two pivotal job duties which are closely tied but not directly linked — I could technically have two people doing each piece separately, but the volume as a small business doesn’t warrant that number of employees. Think the relationship between taking orders and billing/collecting for orders, but not producing the product.

Lenore is great at taking the orders — we almost never have an issue with making sure we got the order and it’s complete. There’s still some handholding she needs after three years, but overall, like I said, no issues here. The billing and collecting for the orders, however, is a bit of a problem. Continuing this overly simplified example, if a person pays their bill on time without question, then Lenore has no issues. She can take the payment, enter it into the system properly, done. But there are three problems:
• keeping track of the orders that have not yet been paid and chasing them down;
• remembering what she has previously done regarding trying to get paid on that account; and
• remembering how to do the stuff that is more complicated — I often have to sit with her and guide her step-by-step, mouse-click-by-mouse-click repeatedly.

I love her, and as far as work ethic and loyalty to the company goes, I wouldn’t fire her for the world. But this is DRAINING me. I am picking up the slack AND losing the time to do my own job. I think it’s important to note that I was promoted from the role that she is doing and while there were times where it was a lot of work, I usually found that with good organization and task management, I didn’t have any major issues.

I see two major problems that no matter how I try to deal with them, I can’t find the right solution. First, time management. I have worked with Lenore to come up with a monthly schedule to work around (since tasks tend to have a monthly routine), then working on other things at down times, but she can’t stick to it — she can’t even remember it. We’ve put it on a literal calendar, but she misplaces it. We hung it on her wall and she just forgets it’s there.

Secondly, organization as a whole. Lenore’s desk is littered with papers. She just puts things in piles. When I ask for something, she has no idea where it is. She’s digging through piles opening drawers, going through folders, flipping through several notebooks. She has no idea where anything is and no memory of what she has done with the tasks. I have sat with her and asked her what would be helpful, and she always says, “I have no idea.” I helped her organize into neatly labeled folders; she has a file drawer and a file tower sorter. I have tried using the task management system that is built in our software, and I have tried Asana. I have tried an online Kanban board (my personal favorite). I have tried a tabbed notebook. She doesn’t use ANY of the tools. She likes the idea of using them but then just … doesn’t. It’s like she puts it down after using it once and forgets it exists. When I ask her about using them, she just says something like, “Oh, I forgot about that. Where did I put it?”

I know she has a lot going on in her personal life and I want to be sympathetic, but that can only go so far.

What are other organizational tools I can give her so that she can be more independent? Especially those that are not electronic/computer based. Can you teach organizational skills and time management skills, and if so, how?

Sometimes you can teach organizational skills and time management. Other times you can’t — at least not in the amount of time that’s reasonably available to a manager.

You’ve tried all the things you should try with Lenore, but you can’t be more invested in getting her organized than she is … and right now, she doesn’t sound that invested in it.

Is there any chance that’s because she doesn’t realize that the level of support you’ve been providing — all the coaching and training and suggestions — isn’t something you want to be providing? Is it possible she doesn’t realize she’s performing way below the job’s requirements? I’m curious how clear you’ve been with her about that, because there’s a lot in your letter about all the coaching you’ve tried but nothing about any serious conversations where you’ve told her that she’s not meeting your expectations in key areas … and that the amount of support you’ve been providing is an effort to help her keep her job, not something that you can sustain long-term.

At this point, you’ve got to be very clear with her about those things. Rather than investing more and more time in trying to figure out the magical system that will finally work for her, focus less on the “how” and more on the “what” — the outcomes you need — and let her know that she needs to figure out how to get there. You’ve made lots of suggestions, and she can try those or she can develop her own systems. But the message needs to be: “Right now you’re not meeting the basic requirements of the job, and I can’t keep you in the job if we can’t solve this.”

Then, be specific: “I need you to come up with systems to follow up on orders that haven’t been paid yet, to track what’s previously been done on each account, and to remember what needs to be done throughout the month — as well as systems for knowing where papers are, so that when I ask for something, you’re able to quickly find it. I’ve suggested a lot of methods and you could try any of those, or you could find your own — it doesn’t matter what system you use, but I do need you to be on top of all of this. I also need you to figure out how you’ll remember the steps for doing things like X and Y since I can’t sit with you each time and walk you through it.. I can walk you through it one more time while you take notes, but after that you will need to manage it on your own.”

I do think you need to be prepared for the (strong?) possibility that Lenore simply isn’t a good fit for this job. Work ethic and loyalty are great, but they aren’t enough on their own. If she doesn’t have the skills to do the job, even after the extensive coaching you’ve provided, you’re better off figuring that out and bringing things to a relatively swift conclusion than continuing to invest more and more time, while you get more and more drained and don’t have enough time for your own work. At a minimum right now, you should be looking into what your company’s processes are for handling it when someone isn’t able to perform at the level needed, and start laying some of that groundwork. (For example, if you’re required to do a written performance improvement plan, start working on that now so that you’re not starting from scratch in two months.)

{ 386 comments… read them below }

  1. Ask a Manager* Post author

    A reminder that armchair diagnosing is against the commenting rules. It’s fine to say “this reminds me of my own ADHD and here’s how that possibility would change the advice I’d offer.” But simply diagnosing an internet stranger isn’t permitted here (nor is it generally useful rather than offering practical advice for dealing with the person in question).

  2. Ashley*

    Is it possible to created an automated follow-up system in your software for unpaid bills? If a report auto generated into her email (or you or someone made it) that might help with one step.
    Also is there a way to reduce physical paper so it is harder to lose what needs saved? Having a set scanning /shred system will help with the piles. And has she ever used the simple handwritten to do list or post it? I love the online post-its on my screen so I can remember longer term things but I suspect she is a person with a few dozen icons on her screen so she may not see it every morning.

    1. Snow Globe*

      Digital documents may make her desk look neater, but probably won’t make it any easier to find things. She sounds like the type to just save all her documents to her desktop, with no organization and file names that don’t make sense.

        1. Old and Don't Care*

          Or my dad. Why, exactly, does a Christmas card list from 2016 need to be on the desktop? Why?

          1. MigraineMonth*

            Every single Christmas my mom asks for help organizing her digital life, and I never know what to do. She knows how to make folders for her files, photos and mail, she just… doesn’t put things into them. Which is not a technical problem, and therefore beyond my ability to solve.

            My organizational style is “search” (thank you, Gmail archives!), but she doesn’t seem like a fan of that either, possibly because you have to remember what you’re looking for.

      1. AnonInCanada*

        You meant my two office colleagues, I gather. I don’t know what their desktop wallpaper looks like with all those icons on it :-P.

        1. JustaTech*

          I had a boss once who was a very senior, very important scientist (and a straight-up nasty human being) who’s *only* document filing system was the desktop on his Mac. And when he couldn’t make the icons any smaller he would tell his assistant to order him a new, bigger screen. (This was back when all Macs were the screen and computer in one, with no external monitor.) So because this grown doctor couldn’t figure out how to use file folders, he would spend like $2K of grant money.

            1. Get To Yes*

              Right? This is why we need good research administrators. Signed, a research administrator who would not have allowed this (despite the user name). :D

              1. JustaTech*

                Yeah, this guy was a Big Deal and a real terror. I don’t know how he treated his administrators, and he was fine to me the like 3 times I interacted with him directly, but his operational style was confrontational to the max – he loved to get into pissing matches with other Big Deal researchers in meetings and lived to make post-docs cry.
                I think he brought in enough grant money that both of his institutions let a lot of stuff slide.

      2. Katara's side braids*

        I wouldn’t write this off completely! I see a LOT of myself in Lenore – in my case it’s ADHD, but I obviously won’t diagnose a stranger based on an advice column letter. But I have very similar struggles dealing with paper, follow-up, systems that stop working after a short time, etc.

        My efficiency has improved SO MUCH since I started switching to doing things digitally. I created a digital filing system that works for my brain and minimizes clicks/tedium – anyone who only saw my computer desktop would think I was extremely organized. A HUGE part of it is that things are searchable – I have a very precise document naming system so know exactly what to type to find things in seconds.

        Filing paper, by comparison, feels like walking over hot coals. I know that when I need that paper again, I have to physically go to my cabinet, open it, find the file, and physically page through the documents until I have what I need. Even with my medication, it takes a herculean effort to force myself to even begin that process.

        It’s not perfect; I still have piles of paper on my desk from higher-ranking colleagues who I don’t feel comfortable asking to email me things. The process of taking the papers to the scanner, removing any staples, scanning the documents, going to my email, saving the documents, etc causes a similar immune response to the paper filing process. But the volume is WAY down and it’s made a huge difference in my work output.

        1. mango chiffon*

          I have a suspicion I am undiagnosed (and unmedicated) ADHD and I’m probably the complete opposite! I MUST write down my tasks physically or it doesn’t register to me at all. So for me, I need a physical notebook to add my daily tasks and check off what I complete. I put things off a lot, but I think a lot of my motivation ends up coming from anxiety/fear of messing up. I have no motivation to clean my house 90% of the time but if my parents are stopping by, I suddenly have the motivation to do that.

          1. milkdudsnotdrugs*

            The anxiety procrastination you’re describing is called “Analysis Paralysis”, “ADHD Paralysis” and “Executive Dysfunction”.
            For my ADHD, it’s often a form of task anxiety that’s part fear of failure and part perfectionism.
            These combined make simple things feel overwhelmingly complicated.
            Other times, I just can’t engage the “go” part of my brain unless there’s an emergency (like unexpected guests). It’s beyond frustrating.

            1. Katara's side braids*

              The task paralysis is definitely the biggest struggle for me! I’m in a “meaningful” job, which unfortunately means that everything I do is important. If I don’t get something done, I’m not just losing money for a company – I’m letting down a person in need.

              I thought these kinds of stakes would help motivate me, but all it means is that it’s physically painful to prioritize. It would be impossible to get to everything, which means that choosing what to work on is *also* choosing who to let down. Prioritizing just feels like an elaborate game of “who will I disappoint today?”. Eventually my brain just shuts down and refuses to do anything at all. I now dream of working somewhere “meaningless” or even evil, because at least then my executive dysfunction would be preventing bad things from happening.

              1. But what to call me?*

                The evil workplace thing sounds like such an interesting (if impractical and unethical) experiment: How does executive function respond when the most ethical thing to do is to accomplish as little as possible?

        2. Sorrischian*

          I’m very much the same – My Outlook inbox is immaculately sorted, I can find any file on my computer in 30 seconds or less, but it’s a constant struggle for me to keep track of the few things I still have to manage in paper copy.

          It’s not going to work for everyone, but that doesn’t mean it’s not worth trying.

        3. kicking-k*

          Yep. This is me too – and I’m an archivist. One of the best things my work has done for me is digitising some of the large documents I use the most. They didn’t do it just for me! but it has been so helpful.

          I come up with great systems which I then struggle to use because I get much more dopamine from the creative process of devising them than actually filling them in. I try to put information in as few places as possible so I don’t end up with “Where was that again? What was that, because I only dimly remember it?” It’s the formal tracking system (just a spreadsheet) plus OneNote for everything that won’t go into that. And a folder labelled For Filing that gets cleaned out on Fridays.

          I also copied someone on here and have a password-protected “everything I ought to know” file which contains not-a-task things like the copier code, rules for taking leave in the winter holidays, how to access the payroll system and basic instructions for software I rarely use.

      3. Saturday*

        But at least her computer can search for her – digital documents might be an advantage for that reason.

        1. Worldwalker*

          I (PC, but I think there’s wMac flavor) use a program called Agent Ransack. It’s like Google for your hard drive. You can search by all kinds of criteria. And there is, or was at least, a free version. It’s a sanitary saver for digital hoarders.

          1. perstreperous*

            Everything (by voidtools) is a faster and lighter version of Agent Ransack. As you say, this sort of tool is invaluable – it automatically and continuously indexes your C drive in the background, then you can search as required.

            (Unfortunately it is Windows-only)

            1. mgguy*

              OS X/macOS has had a pretty deeply imbedded tool called Spotlight since about 2005(OS X 10.4 “Tiger”). It builds an index when you first set up your computer(or reinstall the OS, or back when you could actually do this replace the drive) then continuously updates it.

              It’s only gotten better in close to 20 years, and it searches everything. In fact it’s what powers the search in mail, messages, etc, but the global Spotlight search looks in all of these as well as your files. It parses documents enough that if you can just remember some key phrase it will generally find them, and it’s basically instantaneous(it will update results live as you type) and has functions to “quick look” at a document or whatever so you can see if it’s what you’re looking for. It even searches the internet too. Much to my delight, and I didn’t know this until maybe 2 or 3 years ago, it’s a fairly powerful scientific calculator too.

              I absolutely love Spotlight, and it’s so integrated into my workflow for pretty much everything work and personal that it’s one reason why I personally am such a stubborn Mac user. When I’m on Windows I get frustrated by it not being there, especially as the keyboard shortcut for it is command+space(same key locations as alt+space on Windows) and I’m just so use to pressing it to do so many things, including launching programs.

      4. Miss Chanandler Bong*

        Not necessarily. I’m terrible with paper and I will lose it. My filing system on my computer is about the neatest you’ll ever find, though. When I worked in person in an office, I explicitly told people to send me things via email rather than give me paper, or if it was absolutely an inconvenience, I scanned it into the computer and either shredded the original or gave it back to the original owner. In my personal life, I have everything sent electronically because I will lose paper. I even take pictures of receipts I need and discard the paper copies. Don’t know what in my brain is broken, but thank goodness computers are part of our everyday lives because I could not stay organized with paper everything.

        1. Oh my gosh*

          Okay, I just needed to comment to thank you for changing my life by mentioning that you take photos of receipts. It never occured to me to do that! I’ll screen grab digital receipts from webpages all the time, but…. genuinenly, after years resenting it when a store doesn’t offer an email receipt option, I NEVER thought of that. Thank you!

          (And yes, I’m also someone who’s better with digital organization rather than physical methods)

          1. MigraineMonth*

            I used to love it when my photos of receipts or parking garage level numbers used to be included in those auto-generated “X years ago today” slideshows. “Ah yes, I fondly remember that time 3 years ago I bought a burrito with guacamole and submitted the receipt for reimbursement. What a treasured memory.”

            1. Eff Walsingham*

              Same! “Ah, yes, what a day that was, when the Fire Chief made me responsible for instituting and maintaining a fire watch over the winter holiday season.”

              Actually, those occasionally serve as useful reminders to make sure I Did the Thing with the original document so I can delete the image. Maybe more useful than the endless slideshows of my cats from software that can’t distinguish between a black cat and a dilute torbie? Ha.

      5. Hosta*

        If the software they’re using has good search capabilities and Lenore can identify unique keywords to look for a giant pile of digital documents all on the desktop can work. I used to be someone who neatly filed every document and every email.

        Then some life stuff happened and I realized I was actually faster just using search every time I needed to find something. I still use folders to organize things that needed to be shared with other people since folders make it easy give access to a few related documents.

        It looks like chaos and the visual clutter bugs me sometimes, but it saves me the mental energy of deciding where to save something and that’s been a win.

      6. rebelwithmouseyhair*

        Digital documents are searchable. She could put everything in one document then at least she knows where it is and simply search for a name or term that she would necessarily have had to write when making a note.

        … But I don’t actually think she is a good enough fit for this job. I mean, I can be pretty disorganised and forgetful, but I’ve devised systems that help me. I put things in the calendar with about ten different reminders, in my to-do list on the laptop, in a to-do list in my paper notebook, in a list on my phone. And I mostly manage to keep on top of stuff like that, with just an occasional mishap. It doesn’t sound like this is the case for the employee.

    2. Nesprin*

      +1 this sounds like a job for quickbooks + a routine time block for “check all open invoices and send late notices”.

      1. Hannah Lee*

        Yeah it feels like although Lenore should in theory be manually scheduling time to, say, review unpaid invoices, the *business* should have some mechanism in Quickbooks or other software tool where OP or Lenore could see and print a report of all unpaid receivables quickly, repeatedly and reliably.

        Even in a small business, knowing what people owe you, how aged it is …that’s stuff that should be kind of at your fingertips in a repeatable way. Both for a sense of overall status of the business and also for whether to do another job for a customer who hasn’t paid for the last one. It shouldn’t usually depend on someone going through pieces of paper each time.

        It feels like there are some business systems and processes missing or only vaguely defined and Lenore’s performance issues are just bringing them to the surface.

          1. Banana Pyjamas*

            I have a strong preference for the full-back sticky notes with lines. They don’t detach and get lost.

      2. Adds*

        I agree. +1 for accounting software.

        Any decent software with a reporting function for AR will help solve a part of this issue. But if we’re talking about specific software … Intuit is pushing everyone to their Online software all you have to do there is check a box to have open invoices automatically emailed to the customer with a reminder to pay at set intervals if they are still open.

        1. KatieP*

          Came here to say this.

          It’s been a while since I worked with Quickbooks, but any decent accounting package should have some kind of automatically scheduled AR aging process that at least generates – and emails – customer statements. That doesn’t solve the entire problem, but it should be able to take care of some of it.

      3. Bruce*

        My employer has an automated system for tracking invoices and payments, and it sounds like there are commercial solutions available. If OP’s company is doing it manually then no wonder there are issues.

        1. allathian*

          I work for a governmental agency that requires e-invoicing by all suppliers, even if they’re individual freelance contractors. It’s made the life of our purchasing and payroll departments *much* easier. Nearly 95 percent of our supplier invoices are processed automatically, all that’s needed is for the person/department who authorized the purchase to approve the payment. Most of the manual processing has to do with incomplete references.

          We also strongly favor e-invoicing our customers but because we mainly deal with the general public and provide a number of public services that we have a monopoly on, we still send out some invoices on paper to ensure an equitable treatment of all customers, including those who don’t use any online services. It’s only a matter of time before we’re allowed to charge a processing fee for paper invoices because our government is currently pushing e-services as the primary channel for the general public, and I don’t see that changing any time soon.

          1. KatieP*

            Speaking as someone who works both sides of the AR/AP aisle, at a really big public university, the supplier portal-style e-invoicing is a double-edged sword. My university uses it, and it’s great for AP – reduces errors, fewer invoices get lost, etc.

            On the AR side, 75% of the portals I’ve had to work with are a pain in the rear if you work in a large entity that has multiple independent departments that generate invoices. When you all have the same FEIN, and you’re billing different parts of a huge multinational organization with hundreds of subsidiary companies, it’s a mess. Took six months to untangle the last one so that we could submit our invoice to the portal, and have it go to the correct subsidiary, and show the correct payee.

    3. Bee*

      Yeah, I was going to say, it should not be up to any one employee to remember that you haven’t yet been paid for something. Maybe it’ll still be her responsibility to run the report once a month, but that’s SO much easier to keep on top of than checking a list of invoices to see what’s missing. Quickbooks can do an outstanding payments report, and so can a lot of databases. (My company has a good system for this regarding one-time payments but is currently reliant on the “someone realizes it hasn’t come in” system for recurring payments, so it’s very top-of-mind for me as we try to fix that!)

      1. Banana Pyjamas*

        Thirding reports. There should be a report for each level from first missed payment to final notice, then collections. Lenore’s responsibility shouldn’t be keep track of which accounts are paid; it should be run reports for unpaid accounts. Then she either makes the calls or does the mailers. If the company is using mailers, the report should have the information she needs to do a mail merge. If she’s supposed to make calls the report should include phone numbers. Obviously she still needs to log each action and the date, but that should be in your system not on paper. If your payment system doesn’t support that then you have an issue because key software doesn’t support your business needs.

    4. Whyamihere*

      My thought when reading this is what software are they using for billing what resources are the company providing to do the tasks. I am shocked in 2024 this is not more automated.

  3. ThursdaysGeek*

    Or, could you have two part-time employees, and let her just do the part she’s good at? At least, if Alison’s advice still doesn’t work, you could give her the option of working part-time.

    1. Sloanicota*

      I agree. I realize I’m probably going to be in the minority here, but as someone who used to oversee an Army of Temps, I’d be pretty happy to find someone to do their core duties well and responsibly, even if I had to make their role part-time and take other things off their plate. Obviously I’m aware there are plenty of circumstances where this doesn’t work. The question is, how confident are you that you can find someone at basically the same price who can do *all* these tasks well? If you’re very confident, then yep, this employee’s days are numbered. But I found that good help really *is* hard to find, at the level I was working in.

      1. FricketyFrack*

        I mean, even if they have to pay someone more, it’s not likely to add up to what it’s costing in the LW’s time. They’re essentially paying two staff members to do a lot of the work with all the coaching she needs. And honestly, those duties don’t sound *that* high level/difficult. Following up on unpaid invoices is pretty entry-level stuff.

    2. Keeley Jones, The Independent Wonan*

      Organization issues aside, I’m wondering if she is really uncomfortable asking people to pay the invoices. She seems to manage taking orders and there’s no issues when the bill is simply paid.

      As someone who very early in my career worked in accounts payable, it’s not for everyone. Some vendors are rude, and you have to be firm when they come up with all kinds of excuses not to pay. It can be quite adversarial feeling. One of the many reasons I got out, I am a “conflict” avoider and I hated it. I was great at a lot of things but that was not one of them. Someone else just for billing/collections might be the solution.

      1. BlueWolf*

        Yes, I could see this. I previously worked for a small office doing both billing and collections. I hated having to ask people for money. Now my job is only billing and collections is a whole other department and I am much happier!

      2. Freya*

        I had great success when I was doing the same thing early on with cheerfully ringing up when the invoices were only just overdue and asking if they’d got the invoice, because of course they’d have paid it if they had! And did they want me to re-send it? And while I’m on the phone, could I check that we had the right contact details so that we could get things to the right people the first time? I had mental scripts for the whole thing, all being very obviously assuming the best, and the majority of the time, people responded very favourably and paid.

        Some people that that workplace dealt with only paid invoices when the reminder came in, and I HATED it – they literally had a stack of invoices and when you rang up, your invoice would be moved to the top for payment.

        People who didn’t pay after a couple of reminders and people who were insulting or outright rude got passed on to the 60yo male boss who had a lot less tact and a lot more forcefulness than anyone else in the business, including the female boss who was the one I actually worked under, and who normally dealt with things requiring diplomacy. Knowing that I could pass people who were a pain to deal with to someone who could do it made the whole thing easier.

        1. Frances*

          I had the opposite issue at another organization. I often received accounts payable bills to be processed and paid. But this organization had many outside people working who would wait until the last minute to mail the accounts payable stuff to the main office and then they would get upset when we didn’t promptly pay bills on time except they would wait till the last minute to send the invoices and blame the accounts payable person that is me. Eventually a new boss figured it out and eventually started sending things on time so I didn’t have to deal with these phone calls.

      3. New Jack Karyn*

        I think that ‘billing’ isn’t really billing; it’s just a shorthand the LW used to categorize her sets of tasks.

      1. ThursdaysGeek*

        Losing your job altogether also means losing benefits, and a bigger income cut. If nothing else, it would give her something while she found a job that should could do all the way.

      2. Mad mad me*

        It sounds as though this person is just not a fit for the job in any format, part- or full-time. I can’t help but question the LW’s commitment to keep this employee on at any cost and wonder what kind of manager she will be going forward if she thinks likability is the most important criterion for a detail-
        oriented position like this. If any situation calls for a PIP, this is it.

        1. MigraineMonth*

          It sounds like the employee does half of her job well (taking orders) and half very poorly (billing), so the suggestion is to move her to part-time and take the latter responsibility away from her.

    3. LCH*

      yeah.. i feel like, at this point, you just have to find someone who can actually do the second part of the job. however you want to work that out.

      1. ArtsNerd*

        Agreed. Lenore is just not suited to the role and LW has been spending far too long trying to make it fit.

    4. Lomus*

      OP noted that after three years Lenore still needs some handholding with taking orders. In the context of all the other issues described it makes me wonder if Lenore is really doing as well with that portion of the job as OP thinks.

      1. SarahKay*

        Yes, that was the bit that leapt out at me too. I actually said out loud “After three years?!? Goodness, get rid of her.” And that was before I got to the bit where she utterly fails at the other half of her job.

        Admittedly, the ‘get rid of her’ is not necessarily actually reasonable; easy to say from this side of the computer screen but I know that in real life I’d be far more reluctant to take that step.

        All the same, OP, you’re burning yourself out trying to train someone who just isn’t retaining the information, and organise someone who doesn’t seem to be coming up with any of her own solutions to be more organised. If you’re being honest with yourself, how much time (and mental effort) would you save if you were just doing the billing and collecting yourself?

      2. Kstruggles (Canada)*

        It really depends on what the help she needs is. I worked at a place for two years, where I couldn’t remember the word they used for the “metal box full of wires” can’t quickly recall it for my current employer either. Same objects, different words used. (also my spelling sucks and I couldn’t spell the first word)

      3. MigraineMonth*

        If I had a nickel for every letter Alison has published about a wonderful employee who the manger definitely doesn’t want to fire, but who also isn’t performing the basic requirements of the job, I could buy an ice cream bar.

        We shouldn’t be cavalier about people’s livelihoods, but letting someone go should always be an option for an employer, just as leaving for a better job should always be an option for an employee.

    5. rebelwithmouseyhair*

      and there may be other tasks she is suited to, that some other employee is struggling to keep on top of? If she’s good at dealing with orders coming in, maybe she could also help out with preparing the workshop for the orders, ordering the supplies needed to be able to fill the orders?

  4. kjf*

    A lot of companies keep stuff like this in a CRM system or billing software system. Is that an option with this? Something that can be updated on each customer record that can be seen across the companies. These systems often have reminders and tasks that can be set on each record for follow up. If you are doing things like this manually, it could be good to invest in that. Of course if your real life example doesn’t apply to this – ignore me.

    1. Rocket Raccoon*

      Is that a kind of software that can be purchased? I’d love it if I could just buy something like that (other than Quickbooks)

      1. kjf*

        yes! look at ERP (all in on financials/billing/CRM) or just the CRM side.

        NetSuite is one for ERP, CRM there’s Hubspot and Salesforce. There’s lower cost ones too. All of these are going to be 10k and up annually.

      2. AnonInCanada*

        “Quick”Books? Updating a paper ledger manually with an abacus is faster :-P. Can we sue Intuit for false advertising?

        1. Reluctant Mezzo*

          You can actually do a lot of this with plain old Excel (yes, yes, burn me for an aging heretic).

    2. Feral Humanist*

      A lot of this does sound like things a CRM would help with, but she’d still have to commit to using the tool. Getting away from paper as much as possible might help, though. You can’t have piles if you don’t have paper.

      1. Brain the Brian*

        You can have a totally disorganized email inbox, though — or its equivalent in unread reminders in another software package.

        1. Pottery Yarn*

          BUT, those typically have a search feature, which can make it 1,000 times easier to locate lost files.

            1. Banana Pyjamas*

              It very much leapt out at me that the company is not using any sort of reporting system to keep track of this.

        2. Dust Bunny*

          I create email folders for specific researchers and projects, too, both so I see that I have a folder and to help keep me from deleting them by accident. I can delete them once the project is complete, but it’s helpful to have them in once place until then.

          But at this point it’s on Lenore to put some work into figuring out what will work for her, since everything her boss has suggested hasn’t stuck.

      2. Seeking Second Childhood*

        Not dusty piles no–but electronic ones yes.

        Disorganized computer files are just harder for a manager to see.

        1. Lenora Rose*

          You’d be surprised. I have no idea where to put a variety of papers currently on my desk (“I don’t want to make a new file for one paper but I don’t have one for this project unless the person who transferred it to me does somewhere…”) and a lot of old physical files never got moved around so who knows whose desk they’re at if I want to track down something from the past — but my *electronic* files are in an order that makes sense to me, and I can use search functions to track down my predecessors’ legacy electronic files most of the time, even when their filing system doesn’t work for me at all.

      3. LCH*

        right? when this letter mentioned piles of paper i was expected it to be a much older letter. then they mentioned Asana and Kaban and i was like, oh, nope.

      4. Hannah Lee*

        I want to speak up in defense of piles –

        For some people, piles and stacks are a perfectly wonderful organization system. Lenore does not seem to be one of them, but they ARE a preferred and effective system for some people.

        For whatever brain reasons, I have found over the years if I put something in a drawer, or otherwise away someplace enclosed I might as well have Yeeted it out of the solar system for all the good it does me. I am very much a visual/horizontal surface/stacks of stuff organizer, particularly for anything that is in process. I’ve organized the majority of my job to be done electronically using spreadsheets, databases, pdfs, ERP and other systems. But if there is something that involves pouring over reports, or something I’ll be working on intensely for a few days, or a complex, multi-components-from various sources thing that requires attention over a period of time I’m going, it is going to live in a stack somewhere in my workspace until it is fully dispositioned.

        There may also be other stuff, paper with usefulness of limited duration, that someone else generated, where it’s just not worth me taking the time to scan it (including figuring out a filing/naming structure) , it’s less time/effort just to stack it in a pile on the back of a file cabinet and periodically dump the bottom of the stack as time goes on.

        I can retrieve information and documents very quickly, because stuff is stored in a way that’s easy for my brain to work with and there IS absolutely a system, even if it’s not one that people who prefer visually clear desks and work surfaces recognize or understand.

        Lenore’s issue is not simply that she has piles of stuff.

    3. Fluffy Fish*

      This. I know they said no technology but I think there is the opportunity for the RIGHT technology that can automate the billing processes.

      Outside my wheelhouse but software definitely exists as most businesses don’t manually have someone doing those tasks. And there’s always companies who specialise in solutions for small businesses. It’s worth looking into.

    4. Sloanicota*

      I agree it sounds like there are some tools that might help make it *really easy* to see what accounts are outstanding, and perhaps some automation would make a big difference here (eg, “regardless of what last communication you had with them, all outstanding accounts get an auto-reminder every week, and accounts a month out of date get a daily ping”). You may be able to lift some of the mental load and standardize tasks so they’re almost *all* pretty basic, or at least make it easier for you to know when to jump in.

    5. higheredadmin*

      I also immediately thought CRM or billing software. Although with all software packages, if the person isn’t putting the correct information in then it’s garbage coming out on the back end.

      1. Worldwalker*

        From what I can see, the problem isn’t with the tools; it’s with the willingness or ability to use them. That won’t be changed by adding more tools. The issue to be addressed is doing the work at all.

    6. another fed*

      I would need some kind of CRM to track all of this simply because I would want a place my notes were stored and so I could run reports about what is outstanding and how far outstanding. Technically, I could figure out a more manual system, but an all in one system that allows orders to be placed, all communications stored, and likely automates initial and follow up billing notices would also allow the next person to see the whole picture. That would also allow me to see if certain vendors seem to pay at certain intervals, are habitually late, etc.

    7. J!*

      Yeah, all of this billing stuff and tracking payments/relationships is exactly what a CRM was designed for. Beyond the reminders and easy-to-pull reports, you can also track conversations with customers to build up the knowledge base of what you know about them. So if you chat about something with a customer, the next person calling them doesn’t have to rehash the entire conversation and can build on the last thing.

      Popular ones are things like SalesForce or Pipedrive. You can often automate processes and customize fields that you need. Definitely think about it! You deserve to take a vacation sometimes, staff turns over – it’s 2024, you shouldn’t have to run your business on paper or just in people’s heads.

      1. nnn*

        Those are expensive and this is a small business. I doubt it makes sense to invest in that for an employee who also can’t remember basic simple steps to complete tasks.

        1. Allonge*

          Totally depends on the needs of the business but what OP describes could well be managed with a semi-sophisticated spreadsheet. As long as it’s filled in!

        2. Jellyfish64*

          There are free/cheaper options we use as a small business without the bells and whistles.

          Most important is to make it something you as the manager would use to track this stuff, not as a system for Lenore. Don’t ask her to make a system, you’ll need to make it and hold her accountable to following it in the shared system.

        3. Nesprin*

          Quickbooks gets a lot of grief, but honestly it’s cheap (<20$/mo) and fine for a small <10ppl company.

        4. MsM*

          Even the tiniest, most technology-phobic nonprofits I’ve worked for were willing to invest in CRMs. If you’re not small enough to know all your customers on sight, or if you have any ambitions to grow, I feel like they’re kind of a necessity.

        5. Banana Pyjamas*

          Okay well Access is included with Microsoft for Business, and it’s incredibly easy to set up anything you need including forms.

    8. Rachel*

      I think giving advice about specific billing programs isn’t super helpful because the LW was using billing as an example, not the literal problem.

      1. OnyxChimney*

        While that’s true I think it’s fair to suggest looking ino a technology example. The OP makes no mention of looking into any technology solutions and then used billing as an example which has a lot of moving parts to remember. If this is the “oversimplified” version all the more reason to invest in a technology solution.

        It’s also a great example of how over “anonymizing” the actual function can hamper advice. If the employee is struggling to say, keep track of donor promises and follow up on payments there is software for that.

        1. Rachel*

          I think the LW needs to compare which option is better: replacing the software/technology or replacing Lenore.

          One thing I’ve noticed in this comments section is that people seem to think organizations have unlimited resources. It’s possible there is a technology they can afford to solve this problem for Lenore. That’s great!

          For one tiny second can we discuss what the LW can do with the resources they currently have? Just once.

          1. Bee*

            Ok, but what if they replace Lenore with someone who’s SO good at this and SO on top of things and can keep it all in their head and then they get hit by a bus? There are reasons to suggest technological solutions here that aren’t just so the OP can keep Lenore. And for what it’s worth: my 11-person company has this capability. It’s perfectly possible for small businesses to automate some of this stuff, but among all the technological solutions the OP has suggested for Lenore, this one doesn’t even seem to have come up. That’s why everyone is suggesting it.

            1. Rachel*

              They already have software that at least the LW can access and use if Lenore gets hit by a bus.

              This comment thread is suggesting a Lenore-specific software program that is specifically for her organizational needs.

              I don’t think it’s a good idea for only one employee to have institutional memory. I do think it’s worthwhile to think about what is better for the company: replacing Lenore or replacing the systems.

              People here jump immediately to replacing the systems and I think that’s a mistake.

          2. Feral Humanist*

            It actually costs LESS MONEY to have good systems in place, though. It frees up time for your employees to do things that generate revenue, and in this case, could make it easier to actually get paid for the work they’ve already done. It’s not about unlimited resources but about being thoughtful about where those resources are invested, and knowing where it is worth paying for good software that will improve overall systems.

            I say this as someone who moved from an organization that refused to invest in systems because it didn’t value employee time to working for myself, as a small business owner. Systems are worth investment.

        2. Also-ADHD*

          The LW mentions some tech examples (online Kanban etc). But I’m unclear if the files can be digitized?

      2. another fed*

        While I appreciate that billing isn’t the literal problem, this discussion does help OP consider tech solutions that might be possible. Small businesses may not invest in Salesforce, but law firms, dental offices, and other small businesses use tech solutions that meet their business needs all the time. While billing as a standalone may work with a spreadsheet, the conversation pieces from the other side of her job would not work as well.

    9. Venus*

      It may not be billing:
      “Think the relationship between taking orders and billing/collecting for orders, but not producing the product.”
      “Continuing this overly simplified example”

      1. Hannah Lee*

        But whatever the actual *thing* is, the LW should have some fixed process for it, step by step. And as part of that process there should be some way to get a snapshot of status, which is then used to decide what next steps are needed to move the process along.

        In the example, the ‘status’ is Bills that have been Issued and are Currently Unpaid. 3 pieces of data: 1) basic information about each bill (Billed to who, for what, how much) 2) Status = Issued (and when, to whom and when due) 3) Payment Status = Unpaid
        And yes, there is are computer based tools ($$> $$$$: scanned SW packages, add ons to other SW packages, but also $: spreadsheet or database SW that OP might already have that can be easily used to do a basic version of this if someone has the info in 1 and updates it as events occur ie invoices get sent 2 , payments come in 3.)

        But just about every business process has similar elements of: A thing happened, the details of the thing, when it happened, when something else needs to happen, whether or not those things have happened yet. If those things aren’t defined, documented in such a way that Lenore or anyone doing that job can look to a diagram/document/workflow/whatever to know the process, the inputs, the expected progressions, status changes, the outputs, there is an issue with how that business is being run. In small businesses, the repository for that stuff may for a while be “owner’s head” + “moleskin notebook with scribbles”, but as soon as you’re bringing in employees and giving them responsibilities, there should be another repository that can be viewed, agreed on, referenced repeatedly.

        And for many many business processes, there is either canned SW for managing, viewing all that or something can be set up using spreadsheets or simple database files or some physical set up (as a teen, part of my job was opening mail containing insurance premium payments, going to a card file, finding the card for the policy being paid, and stamping the current date in a box on a grid where Row “2024” + Column “Feb Premium Paid” met. The manager would, after the end of every month, flip through all the policy cards and pull any where there was no stamp in that month’s box, and call those customers. My task was very easy and her task more complex as far as the calling, escalation where needed, but both were very doable by someone showing up and paying attention, and referring back to written instructions where needed.)

        The particular SW suggestions are just people illustrating that there ARE tools available, some can be used for a variety of business processes or others could allow OP to search online for IDK “Quickbooks but for llama groomers” to find something for their needs, or realize that SW they already have could be applied to focus Lenore and create a task list she can be managed to.

    10. Freya*

      I was doing this 20 years ago with MYOB. Make a note on the client card saying “called about invoice xxxx, talked to yyyy, got promised payment on date zz/zz” and tag it for follow up in a week.

      When I logged in a week later, the to-do list would pop up with the things I’d tagged to follow up in a week, as well as the recurring tasks I’d set up. Once I’d reconciled the bank account (checked whether they’d paid the invoices) I’d follow up on the things I’d tagged for follow up.

    11. Olive*

      I read the part about needing to instruct her mouse-click by mouse-click as them having software that she isn’t capable (for whatever reason) of using.

  5. Yup*

    Removed — please do not armchair diagnose here, per the commenting rules. It’s fine to say “this reminds me of my own ADHD and here’s how that would change the advice I’d offer.” But “this is ADHD” is against the site rules. – Alison

    1. Ellis Bell*

      Very peculiar and specific opinion coming up: I did kind of snort laugh whenever OP seems to expect her to just remember. Like, I know that’s the default of the world, but I have ADHD and so do my students and expecting our memories to do the work, or help us out in any way has been filed under rank folly now. I mean, we always get the stuff done and have ways and means that appear to be “remembering” but really we didn’t.

      1. Sloanicota*

        Well, OP did say they tried calendaring systems and apps and lists. They don’t just expect her to keep it in her head.

        1. ADH...Squirrel!*

          ADHD is about not remembering the calendar exists, that you bought it, you opened it, you marked it up, that you hit your thumb with a hammer when you nailed it up.
          The calendar event is gone.
          A big deskblotter calendar that you see when you sit down, you will remember that.
          If it is hung behind you, it might as well be in another room. My brother pointed out the one I have hanging in my house is still on October.

            1. ADH...Squirrel!*

              I was replying to your comment about trying calendars. If it is ADHD, that won’t do much. Ultimately, this just seems like the wrong job for this person.
              OP’s job is to tell her employee as much.
              I’m floored that OP has spent this much time, energy and resources on this employee. It’s one of those situations where Alison says it’s not fair to tell someone the truth. This is not the job for employee.

          1. JustaTech*

            Re: desk blotter.
            My FIL, who does not have ADHD, was once found to have a desk blotter calendar that was 3 years out of date on his work desk. (It was found when my MIL cleaned his desk for him – something she did *once*.)

            1. SarahKay*

              Eh, sometimes you just want something under they keyboard.
              I still have the desk blotter calendar pad from when I started with my current company – in 2005.
              Every so often it gets too filled up with jotted down phone numbers or reminders and I tear off the top sheet and start again on the next one down. At current rate of use I reckon it’ll be good for another ten years. Although I don’t use the calendar much….

              1. amoeba*

                Yeah, I absolutely also still have a wall calendar from 2022 in my office. That’s just because… I don’t really use it much at all and would never bother getting my own, but our former assistant put that one up for me in 2022 and I just… can’t be bothered to do anything about it.
                Doesn’t necessarily mean that I wouldn’t notice if the calendar I used daily was out of date!

                (On the other hand, paper calendars really just don’t work for me… but I’m fully capable of using Outlook/Google calendar, I promise! Same with papers/files – I’m fine with file management, but physical papers are a mess. Luckily, our office is paperless…
                So I know the LW asked specifically for paper-based systems, but depending on what the reason for that is, maybe trying partly electronic solutions instead could be something to try before you give up?)

          2. Katara's side braids*

            The “create task from message” and “create appointment from message” buttons in Outlook are GAME CHANGERS for this. It takes minimal clicks, and you’ll get a pop-up once it’s time to follow up.

            1. Brrr*

              Thank you so much for this! “Create appointment from message” can replace the “focus” new appointment button that disappeared from my Outlook last week ( I swear it was right beside the New Appointment button, I had been using it quite successfully for 3 months, then it was just… gone!). This new way will be better because I can set it to automatically attach the email to the calendar appointment, instead of dragging it in there like I did previously. You’ve made my day, week, and month!

              1. Katara's side braids*

                In my Outlook it’s in the “Quick Steps” section of the Home menu (or the Message menu if you’ve opened a message in a new window)! If you’re not seeing it, you may need to right-click the menu and select “customize the ribbon.” You should have the option to add Quick Steps to the “Home (Mail)” menu.

              2. General von Klinkerhoffen*

                I think Tasks have been removed for the newest version (I revertedb in horror) but in the last twenty years’ versions you simply drag the email on to the Tasks icon and it would create a Task with the subject line and text body of the email, which you can then edit and also add deadlines, comments, attachments, etc. It is so much more useful than just flagging an item.

                I have “tasks from email” with due dates in 2028 and beyond. No way I could keep track if they were pinned/flagged emails in my inbox!

      2. Dust Bunny*

        Yeah, but that’s why you develop other coping mechanisms and systems, and Lenore is putting zero into developing those right now.

        1. NobodyHasTimeForThis*

          THIS. I have ADHD and most of the time my coworkers would never know. I have mechanisms, I have systems. I have reports I run just to check to see that I did my job that I thought I did yesterday but cant remember.

          In the long run Lenore needs to be put on a PIP. Nobody else should be putting in that kind of effort to give you the tools, you need to find the tools that you need for yourself and right now Lenore doesn’t recognize it as a priority.

          1. Helewise*

            Same here, except that I’m not diagnosed – I just see myself in every description I’ve ever read. I have very very detailed checklists, and a paper calendar on my desk with non-negotiable dates for recurring tasks, and the same in my Outlook calendar with multiple reminders set, and written task lists for “today” tasks and “don’t forget this exists because you need to do it soon” tasks, etc. People think I’m really organized, but I actually have no natural detail orientation and my brain doesn’t hold ANY of this – but my job has a lot of important details to keep track of.

            The bottom line is that *Lenore* needs to be doing the work here, not the OP.

          2. NotJane*

            Same! My job consists of keeping track of a lot of things and I have SO MANY systems and tricks in place to make sure nothing falls through the cracks. I know I can’t count on my memory so I’m super organized and if I don’t know specifically where something is, I know how to locate it.

        2. Slow Gin Lizz*

          Yes, and it actually is somewhat counterproductive for OP to be developing these systems and mechanisms. From what I’ve read, it’s actually a lot more effective for the person who needs the systems to develop their own systems. What works for one person will not necessarily work for someone else. OP, what you can do as a manager is explain to Lenore that it’s on her to figure out how to keep track of these things and give her a little time to think of some ideas that she can implement. Like AAM said, she can try some of your ideas or come up with some of her own, but bottom line is the system needs to be something she will use every time, not something that’s there if she wants to use it.

          And you’ll have to make it clear to her that it is also her responsibility now to keep track, not your responsibility to make sure she’s keeping track. It sounds hard, yes, but it’s entirely possible that she’s gotten used to relying on you to track everything so she figures it’s probably fine that she’s not tracking it. Be clear that you need her to do it herself and she might be more likely to step up and do it.

          1. Boof*

            Yup; a diagnosis of ADHD doesn’t mean someone is incapable of doing the things someone without ADHD does (probably, I’m sure there are very servere cases or combos of neurologic stuff that renders one effectively disabled rather than I guess differently-abled); it DOES mean they may have to work harder/develop their own strategies for doing things than someone without ADHD.
            … I learned this eventually in medical school when the smarts finally couldn’t compensate for the ADHD and the meeting where those who did well on a high-stakes test (And who coincidentally clearly had great attention spans) shared how they studied (sat down and studied a book for a month straight!) failed miserably for me. Vs going back to old study techniques + just accepting I’d do better shelling out for a prep class that does things more interactively if I really need the high score* with lectures etc, was better for me. I’m pretty sure my IQ is on par with those who scored high but I burned myself out hard trying to force myself to study a book for a month straight and then couldn’t even focus on the test when it was time. My follow up test scores improved just by taking a total study break a few days before any big test.
            … which for the LW just means IDK, you can’t force your employee to get a dx or find coping strategies, but you can tell them their attention to detail/follow up is a critical problem and maybe if your company has some other resources your employee can go to if they choose let them know about it. (I can’t remember how other AAM letters have suggested managers can let employees know about company resources for getting check for mental health support if that’s thought to be a possible issue but not actually a diagnosed/declared issue without overstepping)

        1. Worldwalker*


          It doesn’t matter if she has to make Clippy pop up every 10 minutes to remind her what to do, she needs to get it done in whatever way works for her. But get it done. This is basic work performance: “do the job you’re getting paid for.” And there is a limit on how much the OP should be expected to help with that. Unless the OP is a job coach in a sheltered workplace, that limit was passed two and a half years ago.

    2. JustaTech*

      Yes! The whole “I’ve offered all of these organizational tools and she doesn’t use them” really resonates with my experience.
      It doesn’t matter how awesome a tool is for someone else, if it doesn’t jibe with *my* brain and the way *I* think, it’s completely useless to me. It’s like trying to wear someone else’s shoes. Backwards.

      Since there’s no diplomatic way to say “Hey, Lenore, have you considered that you might have ADHD?”, then the OP needs to jump straight to the next step, which is to say:

      “The organizational tools I have offered you clearly aren’t working for you, but for this position you must be organized to follow up on tasks X, Y, and Z. I need you to do some serious research and find an organizational tool or tools that will work for you. I would suggest starting with [resource for people with ADHD, resource for people who are visual processors, resource for people who are auditory processors] and see what resonates. By the end of the week [or whatever is reasonable] please bring me a list of at least three systems you are going to try and why you think that they will work.”

      Because on some level it doesn’t matter to the OP why the organizational tools aren’t working, what matters is that Lenore finds some that *do* work for her (and that OP lets her use them, even if they seem weird to the OP, as long as they work).

      1. Sloanicota*

        Nice, I like this framing. To be completely honest, picturing my boss in this role, I don’t know that she would want to push Lenore towards getting a diagnosis that would then protect her job when it might be necessary to fire her in short order for disorganization … but as a fellow human, at least flagging it, and pointing out that the tools can benefit *all* types of brain, is great. I don’t have ADHD but some of the tricks still make a lot more sense to me than other advice.

        1. amoeba*

          Yeah, I feel like saying “Oh, actually, the ADHD online community has tons of useful tips for being more organised, maybe you could steal some of those?” would be a way without implying a diagnosis…

          (And yeah, I apparently have something like Schrödinger’s ADHD – showed symptoms in the diagnostics I did, but not enough to qualify) and I still go to those sources without a second though – even for somebody without any symptoms I’m sure a lot of them are super useful!)

      2. Lana Kane*

        Completely agree with this. I have tried so many “systems” and “ADHD hacks” and ultimately they didn’t work for me because ADHD comes in a variety of flavors depending on the person. I’ve had to learn to find what does work for -me-, which wasn’t easy and honestly isn’t foolproof either. But I have learned that day planners are useless to me, no matter how cute, because I have to have the executive function to use them and apparently I do not. I’ve tried going higher tech, but things have to be In My Face (so phone lists for my household To Dos, for example, don’t work for me). She may also find that In Her Face is good up to a point, and then it’s just too many sticky notes and her brain just cancels them out.

        This may take Lenore some time, especially if she hasn’t come to the realization that this isn’t a matter of willpower or whatever, which is what I thought almost my entire life, and that she will need to invest time and effort into trial and error-ing her way into being able to be just organized enough to do the job.

        1. Sloanicota*

          Eep, okay, so I realize I sound kind of brutal right now, but *OP wrote in* not Lenore – and at this point, Lenore has not requested any kind of accommodation for any kind of disability. OP can decide that she doesn’t have the patience to wait for the long process of Lenore figuring out what she needs to do to meet the bar necessary for the job. OP can legally fire Lenore tomorrow, free and clear – or say, “one last chance, if you miss one more follow up or lose one more paper, I will be forced to fire you,” and then do it – and maybe she will find an employee who can handle both sides of the tasks at the same price with less drama. (Ducks incoming barrage).

          1. Dust Bunny*

            It’s been three years. The OP has tried everything and has asked Lenore what would help. Lenore has said, “I don’t know,” and apparently not pursued it beyond that. I don’t know how much more babysitting the OP can be expected to do for an employee who isn’t doing for herself.

            I do think the OP needs to make very, very, clear to Lenore just how much help Lenore has been getting, how inappropriate that is given how long she’s had the job, and how necessary it is that this change, because I can’t tell from the letter that that has actually been done, but after that, the ball is in Lenore’s court and the OP shouldn’t have to keep her on out of sympathy.

          2. JustaTech*

            You’re very right about the OP needing to decide how much more patience she has for this. That’s why I suggested that the OP set a specific (and soon!) deadline for Lenore to come back with specific tools that Lenore was going to try using (and why she thought they would be effective).
            If Lenore doesn’t come back with anything in that week, or just picked the first three things with no reason why she thinks they’d work, or otherwise shows that she *does not understand that this is a problem* then yes, the OP needs to fire her.
            What I was trying to suggest is a way to help the OP see if Lenore really is trying (because trying often isn’t visible) or if Lenore doesn’t get it or doesn’t care.
            And if Lenore still doesn’t get it or doesn’t care, you’re right, she needs to go.

            1. Worldwalker*

              Honestly, it doesn’t matter at this point if Lenore is trying as hard as possible or couldn’t care less. She isn’t doing the job she was hired to do, and she hasn’t been for years. And all generosity aside, that work needs to be done.

          3. Lana Kane*

            Oh yeah ultimately it’s on Lenore, no question. I agree with JustaTech that it’s time for OP to name the issue and that it’s on Lenore to find her own solutions. I just dont think Lenore is getting that right now and it needs to be spelled out.

          4. Ellis Bell*

            Oh, though I think OP really does want to understand Lenore, I completely agree and I don’t think OP can do this for her. Theres an outside chance that there’s a solution that doesn’t rely on Lenore’s memory, like automative payment systems, but if OP needs Lenore to just find the right aids and routines, that’s Lenore’s job to do. If Lenore has to be fired, well I found being fired helpful as a way of understanding how far off route I was, and “have you ever been fired for x” is something that gets used for diagnosis purposes. That’s how unavoidable it can be.

        2. ADHD brain*

          The “too much in her face” is me to a tee! I decided to use the reminders function on my phone for daily/weekly/monthly tasks I needed to take care of. And then got to the point where the notifications got annoying so I just silenced them without actually completing the tasks. (These were not work tasks, so I’m not dropping the ball or anything.)

          1. Ellis Bell*

            I will turn it off, think “okay I’ve been reminded”, and go right back to forgetting about it. I don’t do this at work either but home stuff is still a mountain.

      3. Oh yeah, me again*

        Not *3* systems to try, PLEASE! I think OP may be partially to blame for offering too many alternatives, overwhelming the poor employee. If she offers a different solution every week, it’s less surprising that none of them stick. Employee has to be told: “This has got to change for us to keep you in this job” (having let it go on for 3 years is way too long; at this point she may think it’s a minor deficiency) “I’ve made suggestions, but you are the one who has to put something in place to get us the results we need. Now, of all the things we have talked about, which one sounds best to you? Good! Do that. Come to me if you have any questions about specifics.”

        1. amoeba*

          I’d frame it more as “have a look and see which one of those you’d like to try”, not as “try all three”, that would certainly be bad!

      4. EchoGirl*

        I agree with this. I have ADHD as well and I actually find it actively frustrating when people try to push specific programs/systems at me* as not only are they often completely ineffective, but trying to use said system can actually add more steps and thereby increase the mental burden of trying to finish the underlying task. I much prefer that someone explain the end goal and allow me to figure out what steps I need to take to get there.

        * To be clear, when I say “pushing”, I’m not talking about suggesting something once; I mean someone repeatedly raising the subject or even trying to force me to use it. (That being said, if the thing you’re thinking of suggesting seems incredibly obvious, consider that the other person has probably already considered it as well; it comes across as pretty condescending when someone seemingly assumes I’ve never heard of (for example) calendars.)

    3. DramaQ*

      But after three years she hasn’t figured out her own coping mechanism and ways of remembering? How long is an employer supposed to hold your hand and walk you through tasks step by step?

      I’m ADHD myself and I am the same way about planners and wall calendars and all the things suggested to keep track of stuff. I set it down and promptly forget it or it trails off a few days/weeks/months from now.

      Instead I have an army of sticky notes all over my monitor. I plug things into Outlook so it yells at me 20 times a day. I use my phone and put a really annoying ring tone so I have to get up to make it stop.

      I take a stupidly high level of detailed notes if I need to. I have a whole diagram on how to retrieve my sample information from a certain software. I wrote this down as I was trained on it. I am horrible at just remembering what to do on software so I set up a system where I don’t have to rely solely on memory. I joke that these are my “crazy lady” notebooks.

      I have learned what learning methods work for me. Sometimes I am highly visual/hands on and sometimes I need to read/write. I express my preferences to whoever is training me so we can work together easier and I actually retain what they are teaching me.

      I am not perfect by a long shot and I’m still considered disorganized by people who the former systems work for but I get my job done and I don’t have to have someone looking over my shoulder every day or walking me through basic tasks.

      If after 3 years my supervisor was still having to tell me how to do basic functions then I would not be shocked if I was let go. After a certain point I have to be able to perform without hindering other people’s work. Occassional questions are totally fine I don’t do 100% of my job 100% of the time so yeah I forget some things or have a brain fart but to not be able to do 1/2 of my day to day job after three years? That is unreasonable to expect an employer to accomodate.

  6. ArtsNerd*

    Getting ahead of this: the struggles with the tasks and forgetting the systems and solutions LW has proposed could be a neurodivergence or medical thing, yes.

    But the employee doesn’t seem to be doing any problem-solving at all, or seem to realize it’s her responsibility to. If all the employee needed was a quick check-in or a nudge from her boss, that’s a very different response. But I’m with Alison — I can’t see how LW can keep her in this role without major changes.

    1. Brain the Brian*

      I have a job that requires a similar level of tracking outstanding payments. I had to sit down with different product teams at one point and figure out what they were okay with me tracking — some wanted me to track it all, some wanted to use their own tracker and just give me access, etc. — so that I wasn’t stepping on any toes. Lenore could be similar: you need to spell out for her exactly *what* she should and should not be tracking, LW, not just *how* you think she should be tracking it. I wonder if there’s also an element of being afraid to call customers with outstanding balances — a part of my job that I absolutely *loathe* — and whether some phone scripts and practice might help ease anxieties that Lenore may be having on those fronts.

      1. Endorable*

        That was one of my first thoughts too.. she doesn’t want to be a bill collector, so she’s just avoiding the whole thing! She doesn’t want to follow up on overdue accounts so all the systems in the world won’t help her. If for some strange reason they won’t fire this woman, splitting the job into two part time positions seems to be the way to go.

        1. Brain the Brian*

          Yep. Bill collection is a horrid, horrid job, and I wouldn’t wish it on anyone. Thankfully, most people pay us on time… but not everyone. I’m currently chasing a payment from 2017. Yes, that 2017. Sigh.

        2. Bast*

          I’ve never done bill collection, but I have had “swallow the pill” clients who are just miserable, awful people, screamers, etc where I needed to just shut off my brain and call before I could think about it. My method was to do it first thing in the morning, usually earlier in the week before burnout set it, so that I could get it off my plate, not worry about it the rest of the week, and I’d feel 10x better for getting it done. Sometimes I needed to give myself a little pep talk before calling and get some extra coffee, but the more I put it off, the more onerous a task it became, and I hated the feeling of it being Friday afternoon and thinking, “Damn, I still need to call Mr. X before I leave today.” Mr. X would be a wound that would fester all week if I let it.

          1. General von Klinkerhoffen*

            I know this tactic as “first, eat the frog”.

            If you know you have to eat a frog today, the best thing to do is get on and eat the damn frog so you don’t also spend the entire day dreading the frog-eating.

            This can be helpful when neurodivergence activates “waiting mode”, where we become fixated on a future event and can’t do anything else in the meantime.

        3. Llama Llama*

          I used to deal with intercompany billing. Ie our company was billing each other. It was pulling teeth to get some people to remit. And that was company to company!

          1. Brain the Brian*

            The payment from 2017 I referenced above is, in fact, from a company that has paid us many times since then for other things. They need One Specific Email from back then before they’ll send us this one. Sigh.

    2. Ellis Bell*

      What problem is the employee definitely aware of though? When you’re doing a certain amount of struggling, and always have done, it seems totally unremarkable to have some things drop through the cracks, or for people to discuss tools that might make life easier. It really doesn’t seem like a weird topic, or like you are really discussing an unreasonable number of mistakes. When it’s brought fully to their attention they may solve it, or they may be unable to solve it quickly, or without accessing the right kind of help. For years, I tried hard to be punctual, but the only strategies I would ever hear about were “leave early”, “set your watch five minutes fast” and “care about being on time”. These never worked at all for me, because they are ‘strategies’ designed by people who find time easy to manage. All they had to do was care about leaving at a particular time, and they just could! Or they’d only be five minutes off track at the most. The strategies that work for me took months and years to perfect and I have to work on them every single day. TLDR: You have to know you’re failing before you look for solutions, but sometimes we are not talking about quick, easy or obvious solutions.

        1. Jackalope*

          I’m in a similar position and I honestly just,,, got used to being late. I have a job that’s flexible in the time we can come in, a church that doesn’t care if we start 5 min late, a group of friends that’s willing to be flexible on time, etc. So that means a lot less pressure on the regular to be perfectly punctual and makes it easier to focus when being right on time is needed.

          My biggest thing is not starting a new thing before leaving. I always underestimate the time it will take and then get stuck. Alarms on my phone can help too.

        2. NobodyHasTimeForThis*

          For me it is being annoyingly early. Which works most of the time except when I have to go someplace with my husband who is a “get to the theatre at 7:59:59 for an 8pm show” person.

          I got enough anxiety about being late eventually that now I am ridiculously early. To avoid being late I will drive to where I need to be and then just sit in my car until the alarm that I have set already goes off if I can’t go in yet.

          I have all my meeting reminders with multiple alarms, one to go to the bathroom and get water, one to just sit there waiting for the meeting to start.

          Otherwise I will start working on something that just takes a minute and 45 minutes later I am still working and late.

        3. Nesprin*

          Technology helps. As an outlook user
          -set all my appointments to 50min by default (outlook lets you do this) so i have transit time
          -when I accept an invite, it has to go on the calendar. If it’s not on the calendar, it doesn’t exist.
          – I immediately block off travel time (of never less than 30min, or 30min+ travel time if it’ll be far) on my calendar for offsite meetings (30min gives me time to pack up, drive somewhere, park, find the room and of course find my lost keys or decide how I’d want to repaint my dining room etc.
          -outlook is setup to ping both my computer and my phone when i have a meeting coming up (never hit dismiss all!)

        4. Katara's side braids*

          For me it’s setting my clocks 17 minutes fast. Nice, round numbers don’t work because I can do the math too quickly and end up right back where I started. But my brain is more willing to just assume I’m running late and activate Damage Control Mode (which makes me very efficient) than it is to subtract 17 from most numbers.

        5. Oh yeah, me again*

          Phone alarms have helped greatly. It’s easy to think: “Oh, it’s a ten minute drive” or “only a 4-block walk” when it’s much more than that! Allow time to get to the car, not just the travel time. At my Mother’s place, we have to allow and additional 10 to 15 minutes for the long corridor, the elevator, the massive lobby, the enormous parking lot. . . . And no, don’t decide to use the toilet etc, at the time you need to be walking out of the apartment. Allow ANOTHER 10 to 15 minute AFTER you are dressed to use the bathroom, wash hands, check the mirror, retrieve and put on coat, retrieve purse/keys.

          1. Is it Friday yet?*

            I map out my day in advance, leading up to when I need to be somewhere. to the minute. and then add a buffer on top of that. similar to what others mentioned, I never start anything right before heading out. after a lifetime of chronic lateness and stress, I have to be extremely rigid now to be on time places.

            1. Azure Jane Lunatic*

              And I never collapse the buffer times. Each buffer time is for the unforeseen delay like a cat disaster, not being able to find the pillbox, a car problem, someone else’s car problem in the middle of the freeway… and if you decide “oh, these 5 steps all have a 5 minute buffer, that’s 25 whole minutes, surely I can do it with only 5 minutes!” … that’s where things can get exciting the first time something goes extremely wrong.

        6. coffee*

          Always add a “buffer time” when planning the journey (usually I plan to arrive five-ten minutes before the event), always get ready to go earlier than you think you need to so you’re not on the clock while getting ready, and then always take something with you to do if you wind up arriving early.

          Phone alarms are sometimes useful.

        7. Ellis Bell*

          Routines. You have to move through your day like it’s a dance routine. Get stuff ready the night before, go to bed early. I have playlists to get me through my evening prep for the following day, and playlists to get me through the morning routine. Forming the routines takes a lot of tweaking and working methodically in order. Giving yourself more time than necessary is a double edge sword. I do need down time in the morning but not enough time for me to go off track.

          1. Ellis Bell*

            Oh, and my strategy for not forgetting things is to use rhymes. I use a rhyme before I leave the house, a rhyme at the start of my workday to set up, and one at the end of my workday to leave nothing unfinished. I also write any pending task that’s unexpected and off-rhyme on post it’s on my screen, or in my planner where I will see them, (a planner that I have to use because I’ve made sure there’s routine info in there I have to view). No one but me would ever have been able to come up with that stuff. No one but me should try. What I need from other people is a really clear, serious, and early warning if I’m fucking up and not realising it. The other thing I need is for people to not assume I can ‘just remember’, to not make me pretend that I will remember things, or for them to ask me to start using a tool which honestly will take me on a horrible detour away from my own solution.

      1. ArtsNerd*

        Yeah I have both ADHD and medical issues that cause these kind of problems and don’t have permanent solutions to them in my own life. (In fact I am currently having a bit of an existential meltdown about my ability to succeed in ANY job once the newness/novelty wears off.) My current team lead is a gem, and works with me as I cycle through problem-solving strategies, including check-ins every few days to get my priorities straight. I can relate HARD to the employee side of this.

        I did assume that Lenore realizes there’s a problem and is just relying on LW to fix it for her. This could be off base. In any case, in LW’s shoes, I would not (necessarily) be looking for Lenore to have everything figured out so much as being in the process of figuring *something* out that can mitigate the impacts. Like the punctuality strategies you’ve cultivated over time. (And I relate to that again. I have an ADA accommodation for a later start time and still can’t nail it.)

        1. Ellis Bell*

          I mean, I think the OP sounds like a wonderful boss, but her actions do kind of suggest to Lenore that OP sees herself as a coach and is responsible for helping her fix it. I think that’s probably because OP went into this thinking everyone is the same and it’s an easy fix; “I’ll just show her what I do; calendars!” If OP backs away it will relieve the pressure on OP to develop magic teaching skills, and will give Lenore space to experiment.

    3. bamcheeks*

      Yes, I was thinking exactly this reading the comments above. LW is curiously quiet on whether Lenore thinks there’s a problem and is trying but unsuccessful, or thinks everything fine and each individual failure is just a “whoops! never mind!” moment. All the internet-diagnoses and software recommendations in the world won’t help if Lenore isn’t motivated to figure this out herself! Or maybe she is super-motivated but just Can’t, but LW should definitely make sure she knows which it is.

      1. Dust Bunny*

        Yeah, I’m not sure from this that the OP has made it clear to Lenore that this is a big problem and not just something that the OP helps her with because it’s a small business and all hands on deck.

    4. juliebulie*

      She doesn’t seem to care. I think that’s it. She might remember the things OP has been walking her through for three years if she cared. Sounds like Lenore won’t lift a finger without the boss’s guidance.

      I have ADHD and it’s part of my work ethic to devise ways of staying on top of what I need to. And that was the case even before I was diagnosed. I knew I was “disorganized” and would have to take special measures.

      1. ArtsNerd*

        I don’t even think remembering itself is correlated with caring, but she should at least be noticing that she can’t remember and trying to reduce the impact on LW. (Note-taking, screen recordings, practicing with dummy accounts, whatever!)

    5. allathian*

      Yes, that’s what I thought as well. She simply seems to expect detailed instructions on every task, every time, regardless of how many times she’s done the task before. Some people are like that, and they’re the ones who thrive under micromanagers.

    6. TopBanana*

      I think this is a great point. And because LW has been engaged in so much hand-holding through the process, it hasn’t empowered (or incentivized) Lenore to stand on her own two feet, so to speak. If LW has provided this amount of support for three full years, Lenore likely has no reason to think something is “wrong” and is more likely to think this is just how her job works.

    1. pop tart*

      Came here to say the exact same thing. It’s me. It’s the doom piles that really nailed it for me

      1. canary*

        For me it was all the great new systems that just die on the vine. “She likes the idea of using them but then just … doesn’t. It’s like she puts it down after using it once and forgets it exists.” I identify so hard with this it hurts!

        1. Long time listener*

          This is my ADHD kiddo too. I can see my kid in Lenore, just like 10 years in the future, and it makes me worry (even more) for them.

          1. Minimal Pear*

            If it helps, my ADHD ass is working in admin keeping everyone else organized despite my strong Lenore tendencies.

            1. New Mom (of 1 6/9)*

              Yeah, some of us end up overcompensating. Or if the task is interesting enough to you, you can hyperfocus on it.

        2. Oh yeah, me again*

          Probably because using it doesn’t get reinforced. OP ignores situation till next failure; is non-plused at failure to use system; decides system doesn’t work for this employee; and suggests a DIFFERENT system. Instead try: select system (allow employee to help choose) follow up 1 to 2 days later (“How’s is going? Show me what you have done so far”) continue loosely following ( 1 to 2 days) up till month’s end, when hopefully, she understands it. Do not keep changing systems.

        3. Jaydee who bought a new planner yesterday…*

          The whole time I was reading this I felt like LW was earnestly and seriously describing all the things that ADHDers use memes to commiserate about.

          LW: “She likes the idea of using them but then just … doesn’t. It’s like she puts it down after using it once and forgets it exists.”

          ADHD meme: “Me every January: THIS is the planner! THIS is the year I finally get organized!”

    2. Seeking Second Childhood*

      Me too. But if that’s Lenore’s issue, she may need to learn to bow out of some roles. Accounting and purchase orders are not for me, for example, so I’ve avoided a management track that requires all that.

    3. Ellis Bell*

      Same. Trying so hard not to project my own “I don’t know what’s wrong with me” days of piles of paper and forgetting about the calendar on the wall! Buying a cool planner or notebook and just not using it! Arggggh. I am so glad I have strategies that work for me now, but it’s only due to knowing myself intimately; what I can and can’t do, and making my own strategies into reflexive habits was what got me there. I’m sure this holds true for non ADHD disorganisation as well.

    4. canary*

      As someone with ADHD this sounds EXACTLY like me. Ironically, I have a high-level program management role but I have a lot of systems in place (and am medicated). It’s so tricky because as a manager you can’t really say “Hey have you considered you might be neurodivergent??” but if she does have ADHD and ends up getting treated, it could be a game-changer for her.

    5. Anonynon*

      Oh yes, exactly what I was thinking! The just not remembering things are there, especially, is familiar to me!

    6. Ruby Soho*

      I was thinking “Oh, so Lenore is me, pre-Adderall” lol
      The thing is, if she is still so unwilling and/or unable to get it together at this point, it’s not going to change, unfortunately. Most managers wouldn’t put anywhere this amount of energy into helping her. So if it’s still hasn’t sunken in…well, this isn’t the right place for her.

    7. WantonSeedStitch*

      Whether she is or not, I wonder if some of the tools that some ADHD’ers use would be helpful to her. I hear lots of raves about Goblin Tools.

      1. Virtual Light*

        Thanks for the Goblin Tools mention! I just had a look. The tools to help make lists from braindumps and to break tasks into parts look like they could be soooooo useful. AI for good, not evil!

        I have been using WaterDo (from the same people as the Forest pomodoro app). While it’s not perfect, it’s been helpful to have a digital checklist with cute in-app rewards (building islands) that I can think of as “today” or just “not yet.” Cuts down on the cognitive load and gives me a place to put my tasks that I can’t lose.

    8. fidget spinner*

      Yep this sounds so much like my ill-fated attempts to be a secretary/receptionist.

      I have a lot of skills… but those skills aren’t my skills….

    9. FionasHuman*

      Yes, absolutely. I was finally diagnosed last summer and it explained So Much! Large part of Lenore’s job as described sound like my idea of one of the inner circles of hell.

      1. Katara's side braids*

        SAME. I know no one likes tasks that involve delivering bad news/the general possibility of someone being upset with them, but ADHD rejection sensitivity turns that up X10000. I really struggle with the parts of my job that require me to be the “bad guy,” and chasing people down for late payments sounds like exactly that.

        In my case, I’ve realized that I’m not really a good fit for this job and have started looking for alternatives. I think Lenore could really benefit from doing the same.

    10. I feel your pain, sorta*

      Diagnosed with ADHD in middle age. It’s why I am am avoiding office jobs as of late. I have been mostly unmedicated due to no insurance. This letter kinda triggered me. lol I was great at the immediate/unavoidable stuff, but just-okay to terrible on the planned follow up stuff with quote/job tracking & payment follow up.

      Digital productivity systems are a best intentions fantasy plan for me. So are flat file folder racks.

      Going more analog/visual and out in the open improved things somewhat in the end. Printing out hardcopies of the super important stuff. Immediately DIY tabbing those with the company/client name in block Sharpie (so that it sticks out on the top and can be seen in the accordion file folder(s) or on my desk so others more than myself can see it). Kept my open file system on a desk, not a drawer. Structuring accounts receivable email subject lines to find things in search more easily helps. Working with her on straightfoward systems/timelines for calling/contact in if not this then that ‘flow chart’ situations.

      Mostly though, more accountability. Say, having her report back to you on a (monthly?) basis as an absolute requirement on accounts over X # of days payment. Assuming you guys can run reports and pre-ID customers as longterm or short term payers to structure follow up accordingly (corporate ones 90+ days net per purchase agreements or smaller bizzes according the payment contracts they sign off for your job/product).

      In the end, after about a decade, I ‘fired myself’ from this office job because being handled with kid gloves when it came to my executive function deficits (and some other non-helpful to me things) kept me there. You already sound invested, so figuring out some last tries and, yes, consequences to facilitate a hyper focus on meeting an important / uncomfortable deadline vs. succumbing to ADHD paralysis.

      For me, my higher up(s) were not as collaborative as you in the help me help you sense, so maybe there is still hope for your staff member.

    11. Specks*

      Yes, it all sounds familiar as hell.

      If I were Lenore, I would intensively keep trying organizational systems until I find one that just works for my brain. For me, that’s Trello with reminders set and a particular organizational structure I finally nailed + Google calendar. Anything that doesn’t go on those doesn’t happen. For my husband, who generally had a much worse handle on his adhd for a long time but is now honestly more on top of things than me, that’s shooting himself e-mails and then organizing the inbox. He’s also medicated, though. But OP, other than recommending a bunch of different software or strategies you find by googling things helpful for women with adhd, I don’t see what you can do – this is very much something she has to figure out on her own.

  7. Sloanicota*

    Okay this is a bit of a shot in the dark, so OP please forgive me if I’m off base, but: is this job basically entry level / not well paid? If so, I’m sorry to say that “able to handle basic tasks well but unable to step outside that box” is pretty par for the course, in my experience. I realize it’s tough when you yourself started that way, excelled, and went beyond it but … Lenore may not be seeing that path forward (and it sounds like it’s not in the cards for her, so she’s correct about that). Sorry if my personal biases are showing up here.

    1. ThisIsNotADuplicateComment*

      There’s a difference between “unable to step outside the box to take on more advanced work” and “unable to step outside the box to correctly process a standard but less basic use case.” And it sounds like Lenore is struggling with the latter, not the former. Keeping track of unpaid orders is not above entry level work.

      1. LingNerd*

        Absolutely! I’m great at the former – taking on more advanced/complex stuff – and okay but not great at the latter – doing a routine task that requires an extra step or followup.

        It isn’t super intuitive if your brain doesn’t work like that, but some people are very poorly suited to entry level work but would thrive with things that are supposedly harder. The “proove yourself with easy work in order to advance” model can be a nightmare to get trapped in

    2. Dust Bunny*

      The OP says it’s a small business, for one, so there may not be a step forward without leaving for a different or bigger company, but that’s not an excuse to just blow off the job, if that’s sort of what you’re implying (why should Lenore bother if she can’t move forward?). Also, if you can’t demonstrate that you can do the basics, it’s not reasonable to expect to move forward, anyway, or to get the kind of recommendation that would help you get a job elsewhere. So . . . that’s still on Lenore.

      But if Lenore is dissatisfied and feels stuck, she’s free to job hunt.

      1. Sloanicota*

        I think this relates to the discussion below that there’s some ambiguity if Lenore does a solid enough job on the basics, or if even there she’s not really performing up to par after three (!) years. On my first read, I felt that she was doing a solid job on, say, 60% of her tasks, but upon re-reading, I see there’s room for a different interpretation.

        1. bamcheeks*

          I thought that explanation about “small company, limited business for two different roles” was that it’s not really that either part is “basic” and the other part is “higher level”, but that they’re different functions requiring different skill sets and in a larger company you’d hire different people. LW could just as easily ended up with someone who is good at the financial tracking but can’t cope with the type of attention to detail that means the orders are always correct and out on time.

  8. Susan*

    It sounds like the LW doesn’t want to replace Lenore. If there are reasons to keep her that are greater than this problem, is it a possibility to swap this task for another that some other employee is doing? So let this task go to whoever does accounts payable, and let them also do accounts receivable, and then have Lenore also do …I don’t know…inventory? …ordering materials?… instead?

  9. Llama Lover*

    OP, do you have SOPs at all? Maybe you do a screen recording the next time you walk her through it step by step and tell her she needs to refer to those when she’s working instead of expecting/getting support from you. I have a small business, and SOPs are a life saver!

    1. Sloanicota*

      This is a good point. What would happen if OP refused to walk her through it next time and instead asked her to use documentation first (or asked her to create documentation next time she explained it) or said “show me what you’ve tried” with her own arms crossed, as we sometimes advise people here. Would the employee just melt down into a puddle? If so, I agree, there’s probably no hope. But sometimes it takes a strong nudge and then positive change.

    2. Anne Shirley Blythe*

      This not snark for snark’s sake, I assure you. But from what we see in the letter, Lenore will probably forget how to access the SOP, misplace the hard copy, forget the hard copy is pinned to the bulletin board, etc.

      1. ArtsNerd*

        Yes but LW saying “check the SOP on the bulletin board” is still less labor than covering it click-by-click again.

      2. Also-ADHD*

        I think whatever the solution is needs to be tied to ensuring Lenore realizes it’s a big problem—it sounds like LW hasn’t had that discussion. Why would Lenore be trying very hard if she doesn’t see an issue? So I think that part of Alison’s advice is dead on, but I think the notions she’s problematic may be premature. People just don’t try to fix stuff if they don’t think it’s a big deal, especially if this is a more entry role.

    3. Panicked*

      This is what I was going to suggest. I have video walkthroughs, a written training manual, and a checklist with screenshots for a majority of my processes. If anyone comes to me and asks for help with something we’ve already gone over a few times, I always ask “What did you try before coming to me?” It’s been a very helpful method in my experience.

    4. TPS Reporter*

      I agree, I know I have trouble remembering if I’m only shown a task in process. I need to actually have a checklist or SOP then do it myself. a video could definitely help too but could be tedious to get through.

      like a Heimlich poster, you could post the very important high level steps in a visual way right in front of her.

  10. Language Lover*

    I supervise someone like this. I gave them recommendations on tools to use to track weekly and monthly duties.

    They seemed to hear me and kind of not care because I’d eventually remind them.

    When things slipped again, I finally made sure I didn’t hide my displeasure (not mean but also not ready to pretend it didn’t bother me as much as it did.) I told them that I didn’t care what they used but they had to come up with some way of staying on top of routine but not daily tasks. It was their job.

    They did a spreadsheet. They’re still not great at organization but they’re much much better and the routine things get covered.

    1. JustaTech*

      When one of my coworkers was laid off I was told to take over her stocking and ordering duties. Which was, frankly, terrifying. I am completely terrible at regular duties that are not on a specific schedule but are merely “regularly” where that could be once a week, once a month, or once a quarter. Like, that is just not information my brain is going to store.

      But I had to do it.

      So I warned my boss that this might not go well, asked a remaining coworker to help me keep an eye on stock levels, and then put “check the stocks of dyes” in my calendar for every week (even though we absolutely did not need to check every week). And then I wrote a detailed list of everything I had to check on. And a detailed SOP on how to order stuff (and where to record the orders). And another detailed SOP for how to follow up on when stuff was delivered, and if we had paid. And then all those things had to go into my calendar too.

      All of that for something my coworker was able to manage with one list. I was so glad to hand it off to a new coworker!

  11. Smithy*

    Assuming the OP’s assessment of the job is accurate – that these are two jobs that it makes sense for only one person to do, then all of the advice above makes sense.

    However, based on the nature of this job and if Lenore is truly a solid performer at what she does well – the other approach would be to consider what things could look like if the part of her job she’s bad at could be assigned to someone else? I say this reflecting entirely on a student job I had where I was initially hired to support two parts of an agency. For one supervisor I’d do data entry, and then the second supervisor I’d provide general administrative support. For data entry, I felt like I was doing a good job and could work fairly independently. For the admin support, I likely needed to be able to operate more independently and be able to see what needed to be done, and do it. For a part time student job, I never reached that level and therefore really disliked that half of the job and I’m sure was not amazing.

    At the midway point, I was able to ask if it was possible to do the data entry only – and after deciding there was enough there to do, I was happily reassigned. I bring all this up to say that where I was doing well, was where I wanted to spend all my time. And where I was struggling, I didn’t want to be there which likely made how I was doing that job worse.

    Now this may not be possible, there may not be budget or cause to bring on anyone else – and no one else already there wants to do this task either. But I do want to put this out there as another way to think of solving this issue. Instead of trying to make her better at what she’s not, just let her focus on what she is good at and think about the size of this role being better suited managed by multiple people.

    1. Dust Bunny*

      The OP specifically said there wasn’t enough work to justify splitting the job. It may be that they need Lenore to do both of these things if they’re going to keep her at her current hours.

      1. Smithy*

        While there may not be enough work to justify splitting the jobs – it doesn’t mean that the tasks can’t be split. Yes, it’s a small business and that might not even work – but maybe there’s another junior performer doing well and looking for a stretch task? Maybe there’s a vendor who can take on some of the billing?

        The OP has presented this problem as wanting to not let Lenore go, and Lenore being poor at one half of her job duties. While focusing on fixing the weakness is one way to solve this, another way would be to no longer have Lerone do the work they’re weakest at. May not be possible, but if the OP has put themselves in that corner – this might provide another way out.

      2. Cmdrshprd*

        The way I read it is each job/task does not have enough work to merit hiring an extra person so each that one person does task A and another does Task B.

        But what I think @smithy I suggesting is reassigning the tasks so that the total head count says they same and they don’t hire. new employee.

        let’s say lana does task A and B right, and lana is bad at A but good at B. another current employee Sam does tasks C and D and is good at both. it could be possible to give task A to Sam, and task C to Lana.

        this is all contingent on Sam being okay with the new task and being able to do it, and lana being able to do the new task.

        1. bamcheeks*

          Yes, and it could well be that the main reasons these two bits are stuck together is because back in the day, there was Someone (possibly LW themselves) who was hired to do X, and picked up Y because it made sense at the time and they were good at it, and it got fossilised as “this role has to do X and Y” regardless of whether that’s actually the most practical or optimal arrangement of tasks for the people you’ve got now. It’s definitely worth looking at whether there’s more flexibility across the whole workforce. There might not be! But it might just be a question everyone’s forgotten it’s possible to ask.

          1. bamcheeks*

            (Oh I saw I’d messed up that close tag right after clicking Submit before it loaded. So annoying!)

          2. Garblesnark*

            Big, big agree.

            Even in a small business, the people who are great at taking orders and figuring out what will make the customer happiest and set the ball rolling are vanishingly unlikely to also be the people who are great at calling and insisting that, no, the customer needs to take out their credit card NOW and read the numbers so the bill can be paid. They are dramatically different skill sets!

          3. Katie Impact*

            Yep. It does sound like there’s some degree of logical connection between the two tasks, but small businesses don’t always run on abstract logic. It’s worth considering whether work could be shuffled around in a way that everyone’s schedule is full of stuff they’re able and willing to do. Just make sure any attempt to do this doesn’t come at the expense of any other staff who are currently thriving.

        2. Smithy*

          Absolutely this!

          Fair enough, in my example there ended up being enough of “Task A” to do – so I could keep my same hours and just drop the half of work I didn’t care for/wasn’t great at. But I think whenever you hire someone to cover two areas of work, there’s always a risk that they might end up being a good hire for one task – and then not at the other.

          And big picture, I think for supervisors and employers more broadly – do you start the road to ultimately letting someone go because they can’t do half the job? Or are they a solid enough hire in the other area where it’s worth finding another solution where you keep them and reassign tasks. The answer for the OP’s workplace might still be no, but the bigger reality might be that they’ll only know what they gave up with Lenore until she’s gone, they hire for her replacement, onboard, and see the reality of who’s there next.

          When someone is doing poorly at most of their job, no matter how well they’re liked – letting them go is one thing. But if it’s truly a job that is essentially two part-time jobs made into one full-time job, the likelihood of struggling to get someone who thrives at both will always exist. So it can always be a value add to ask if those specific two part-time roles have to be combined that way, or if there is any other option.

      3. Mzteryutr*

        I’m still a little confused about the OP saying that after three years, she still isn’t excellent at the basic part of the job. But she needs occasional handholding. This sounds to me for whatever reason like a problem employee — if she’s having a hard time after three years recording the payments that came in and still needs handholding. I don’t think this is a good fit

        1. Smithy*

          I think the OP is in a better place to determine if that “some hand holding” is inevitable based on how the junior the role is overall – or something more extreme.

          My first role in front facing fundraising was in a smaller nonprofit where I was the only person in the Development team. Based on the size of the organization, there was no need for more than one fundraiser and given the overall budget the often were recruiting candidates early in their career with limited fundraising experience. The way this organization managed that experience deficit was that while I was technically directly supervised by the Executive Director, our Finance Director had previously been a fundraiser and I essentially had a dotted line into him. I needed longer hand holding/management to meet the needs of a smaller employer who didn’t need or want to invest in a larger fundraising team or a more expensive fundraising professional.

          Now – at that organization, the job being done by the Finance Director (leading all finance duties and mentoring the fundraising team member for years) was likely not a job all nonprofit Finance professionals could do. Had he been replaced by someone unable to do that, the realities of who they could hire for fundraising and still be successful would have changed. For smaller employers where staff do have cross functions, it’s a different balancing act. Especially when you’re hiring a more junior person for a role that at other employers would be done by someone more senior or a hierarchical team.

    2. BethRA*

      Honestly, I don’t know that Lenore really IS a solid performer at one half of her job, because OP follows up praising Lenore for her ability to handle the ordering side with “There’s still some handholding she needs after three years, but overall, like I said, no issues here…”

      So that bit feels like sugar-coating to me.

      1. Bunny Lake Is Found*

        Yeah, but “a bit of handholding” can also mean “on the trickier parts, she asks me to check her work or weigh in” or even “She needs me to show her click-by-click how to do this one task, no matter how many times I have shown her, but the task only comes up once a quarter. Everything else she’s got down.” Or it could mean “I handhold a lot, but the handholding for that half of the job doesn’t get in the way.” It is really hard to tell.

  12. ThisIsNotADuplicateComment*

    There’s a difference between “unable to step outside the box to take on more advanced work” and “unable to step outside the box to correctly process a standard but less basic use case.” And it sounds like Lenore is struggling with the latter, not the former. Keeping track of unpaid orders is not above entry level work.

  13. Midwest Manager*

    “ There’s still some handholding she needs after three years…”.
    THREE YEARS??? She still needs “some” handholding for the straightforward half of her job after 3 years? And she is completely failing at 75% of the more complex half of her job? I’m stunned that your business is such that this has been at all sustainable for this long. 100% agree with Alison that you need one very clear, direct conversation, but then I suspect you’ll need to move to whatever your process is to terminate. I had one direct report who I worked with for 6-8 months and I was still having to do the sort of things you describe (“click here, now open this menu, do you have your notes from the last time we went over this?”) and when I said she wasn’t making sufficient progress, she was *shocked* and finally confessed that she thought I would just be able to sit at her elbow and show her how to do her job…forever. If Lenore doesn’t realize after 3 yrs that she’s not actually _doing_ her own job, I don’t have a lot of confidence that she’s capable of it. Good luck!

    1. Sloanicota*

      I agree, I wondered what that looked like. I think we’re all reading into it with our own past experiences. I will just say, there’s *no* worse supervisor than someone who was promoted from your exact job, in my experience. So is this, “she occasionally still asks me a question I would have figured out for myself when I had that role” (good for you! That’s why you got promoted!) or is it, as you said, the basic part is still barely getting done after three years.

      1. Mariko*

        ??? I have to say I disagree. If your boss has done the job before, they can give very concrete advice. I’d say there’s nothing worse than a boss who has NOT done your job but is a micromanager. Obviously anybody can be a good or bad manager, but all things being equal, having experience with the job you supervise is a very good thing.

        I think OP is doing everything they can do, and I would have thrown in the towel 2 years ago. The biggest concern for me is that the employee just doesn’t seem motivated to improve. Unless they really do a 180, I can’t see how the situation can change.

    2. Snow Globe*

      Yes, I also noticed the part about still needing some hand-holding on the part of the job she is supposedly good at. Maybe she is only good at that part of the job in comparison to the other part that she can’t seem to handle at all.

    3. mango chiffon*

      My manager recently had to let someone on our team go after 6 months on the job because of this very basic “not able to do the job without hand holding” and I would spend hours the last few weeks before she was let go on calls with her walking through a spreadsheet and it was clear she didn’t understand the reasoning behind the things I was explaining. It’s not worth the time spent on this and three years is FAR too long. I understand feeling bad about letting someone go (I felt bad about my former coworker), but the work has to happen.

    4. Bunny Lake Is Found*

      Unfortunately, I think it is REALLY hard to tell because the OP is telling us that Lenore’s job is LIKE billing etc. The issue might be that Lenore’s job is the kind of one where the substance of what the job is matters a lot. I have talked about this before on these comment threads, but if the job is closer to high function work (like drafting documents based on knowledge and expertise) then it is easy to see how someone can be struggling at a lot of admin aspects of the job while STILL maintaining a high enough level of work to justify keeping them on.

      It’s like, if you hire a lawyer to draft contracts and those contracts need to be entered into a database, you would always rather have an attorney who was good at the contract drafting and only 50% on the database entry than an attorney who was great at the admin and only hitting the 50% mark at the actual drafting. And if the one who is only hitting the 50% mark on admin is also good for morale etc., it makes sense to keep them on and keep working with them rather than go looking for a new person. Because you need well drafted contracts. Full stop. Well organized shitty contracts do you no good.

  14. mad marketer*

    Saying that “she doesn’t sound that invested” in trying to stay organized feels icky to me. This is absolutely how my ADHD presents and it’s not that I’m not invested in trying to stay organized and remember things, it’s that my brain physically does not function that way- especially the whole “if I can’t see it then it doesn’t exist” problem. I don’t have any suggestion for solving the problem because I’ve ultimately been fired before for poor organization and I know it was warranted, but it sucked and really hurt my confidence because I *was* trying. I feel for Lenore.

    1. Sloanicota*

      That said, I anticipate a lot of comments saying that Lenore may have ADHD and – that’s not really actionable advice for OP. If Lenore doesn’t raise a disability need and start suggesting what would work for her, OP can’t do that for her, that’s not how the ADA works.

    2. alto*

      Right? I have definitely been in Lenore’s shoes before but the person upset with me and my forgetfulness was a lot less afraid of shaming me for it…

    3. JustaTech*

      Oh man, the whole “try harder” thing! Like, no one can *see* how hard I am trying, so if I’m not able to get the output they want (a clean floor, a clean desk, that report sent in on time, the quarterly supplies ordered) then the assumption is that I’m not trying and I don’t care, not that I am trying twice as hard as someone without ADHD but still not getting the results I want.
      (I just read the “How to ADHD” book from the library and I ordered a hard copy for myself so I can underline parts of it and give it to my husband to read in the hopes that he will understand my experience and why some things really upset me.)

    4. Carp is a fish I think*

      Is the no-diagnosing still a rule? I’ve seen dozens of comments talking about ADHD but there was nothing like that in the letter.

      1. Lana Kane*

        Indeed, I am trying to word my comments around this being “ADHD-like”. May or may not be it, but it sounds like maybe understanding ADHD could be a starting point, given the similarities.

      2. LingNerd*

        It’s because for the folks here with ADHD, the letter sounds like it could be describing them exactly.

        Diagnosing isn’t helpful, but I think looking at it through the lense of ADHD might be. Because even if that’s not what’s going on, the employee is struggling with things that people with ADHD often struggle with, and traditional strategies and tools obviously aren’t helping. So maybe tools and strategies geared toward ADHD will help. Stuff like accountability, clear deadlines, visual reminders, and flexible organizational tools.

        1. Carp is a fish I think*

          Agree with that, I just wouldn’t want the OP to go back to the employee mentioning anything about ADHD or any kind of medical condition since that would be inappropriate

    5. Lana Kane*

      It took me decades of my life to come to the conclusion that I wasn’t just lazy. So many of these ADHD-style issues are seen by society as being lazy, or not trying hard enough, or not caring. Really it’s that you don’t even realize that you may have an actual issue that you need to work with. I tried “will-powering” myself for so long to get results the way everyone expects you to – by remembering things, or using a planner, etc, and those things are just nonstarters.
      Once I realized it’s not a moral failing on my ,part I really started to look at things differently and came up with my own tools. A lot of them may seem like overkill to a lot of people (and that’s part of the problem, someone will see what you’re doing, remark on how over the top it is, and then you feel like you’re “doing it wrong” and why can’t you be normal?) But I’ve learned to internalize that there’s no reason to do things the way others expect you to. It’s been kinda freeing, honestly. Getting there is hard though.

      1. I went to school with only 1 Jennifer*

        This. “Why can’t I be normal?” I figured out at about age 20 that for some reason, I didn’t remember things and I HAD TO put them on a calendar. And after a couple of social disasters, I learned to never commit to anything until I had checked my calendar. (This was well before smart phones, and also before I learned to carry a small calendar with me.)

        I never understood why this was different for me but I am glad that I just accepted it as my quirk. Decades later – no exaggeration – I learned about ADHD and remembered that early accommodation I had created for myself and had a big ol’ ah-hah moment. (And then I took myself off to get diagnosed. Medication plus self-awareness have made a huge difference in my life.)

      2. JustaTech*

        I had an interesting realization recently about the whole “lazy” thing when it comes to invisible disabilities. I was watching a car program where they were following an Iraq war vet who had lost three limbs and was doing a very intense form of car racing, and the presenter mentioned that this driver was burning three times as many calories as the able-bodied drivers *because* he was having to compensate for his missing limbs.

        It had never occurred to me that I was actually expending *more* energy than an NT person might to accomplish the same thing, and that this might impact my energy levels.

    6. Banana Pyjamas*

      A whiteboard was life changing for me. It worked so well at work I instituted it at home. Planners go somewhere to languish, and my phone is too distracting.

      1. EJane*

        Yes!! Also the sensory input with whiteboards is very satisfying. I use that, and I set time aside to clean up my stacks of papers at least twice a month, usually more, and I swear by my whiteboard and an absolute metric fkton of post-it notes. So many post-it notes. stacks and stacks of post-it notes.

    7. Kella*

      I know that “You’re just not trying hard enough” is something that ADHD and other neurodivergent folks hear all the time and it’s really painful because it’s usually in the face *of* trying extremely hard and repeatedly failing. So I understand where you’re coming from.

      In this case, “she doesn’t sound that invested” seems to stem from the fact that we haven’t heard any examples of Lenore attempting to implement her own systems, offering her own solutions, or even an acknowledgment that her current way of operating is causing problems and needs to be fixed. The problem isn’t lack of effort but it vary well may be that she’s putting effort in the wrong places, and currently, OP isn’t seeing evidence that that effort is being put toward developing the necessary systems to do Lenore’s job.

  15. HonorBox*

    I think a very direct conversation is in order. Agreeing that the “what” is more important than the “how.” You need to outline very specifically what the expectations are, and they do sound reasonable. What isn’t reasonable is the amount of time you’ve had to invest in continual training and suggesting the how. Give her a bit of time to figure it out, of course. It can’t be that she is expected to have a solution tomorrow. But not too much time. You could tell her that you’re willing to sit with her once more, answer questions once more, and she has two weeks to come up with a system that will work. She may not be able to do that, and you need to be OK in saying that while she is a good person (loyal, etc.) she isn’t a good fit for the role. She and you need a reasonable deadline, either for her to figure it out or you need to find someone who can do the job without the oversight you’ve had to provide her.

    1. L'étrangère*

      Frankly I think OP might have been muddying the waters a bit by introducing too many possibilities. Which could well have added to the general impression of disorganization in Lenore’s head. Why bother to learn this system when you know there will be another next week/month? My suggestion would be to pick one, and insist that Lenore use it properly. She’s passed up repeatedly the opportunity to pick one that might work for her, so pick one that works for you. A system that makes it easy for you to check whether the work is being done, to detangle what she’ll inevitably mess up at some point. And stop presenting a stream of alternatives – in order to do this job you need to do this, the only thing on your desk should be this documentation. Focus, both of you!

      1. Martin Blackwood*

        Eh, Lenore has been in the job for three years. Round the five examples give. up to six, that’s two a year. Even if it was four in a single year….that’s months plural between tasks for Lenore to “try” them out, and OP getting frustrated from things falling through the cracks.

  16. sagc*

    For all the people recommending CRMs/specific software tools:
    a) The taking orders/following up on payments is an *example* that’s extremely simplified
    b) Lenore isn’t using the existing task management tools built into “their software”, so adding a different piece of software probably won’t help a lot anyway.

    1. OnyxChimney*

      Asana and Kaban aren’t built into “their software”. That’s like saying your office offers OneNote but someone is struggling to manually track all the late bills and their conversations with their customers(using the example the OP gave) and it’s their fault for not using a system that would just be another manual step for them to track.

      Asana IME is very high level and usually a top down software. Meaning management pushes tasks on it to the end users. It makes no sense to use it to manage the task the OP gave as an example.

      Kaban is for projects and specifically for agile projects, so again it makes no sense that it’s a tool Lenore should be using in the context of the example OP gave.

      Everyone is suggesting a software solution specific to the task at hand because it’s really the best practice and expected operations for that type of work in small and large businesses alike.

      Of the ops example is so different from what they are actually doing that the advice isn’t relevant then that’s kind of on them.

      1. Martin Blackwood*

        Sentence before the Kanban one explicitly says the software for this task has tracking capabilities and Lenore tried and didn’t use them.

  17. higheredadmin*

    LW, you sound like a newer manager. You need to separate Lenore’s performance from yourself and your professional success. Your job is to create a framework in which Lenore can be successful, and there are some great ideas on that in here so far. But what Alison is saying is that you also need to make Lenore’s responsibilities clear to her as an employee, and realize that if she fails at her job after you have done so it does not mean that you are a failure as a manager – she could be a bad fit, she doesn’t really have the work ethic you think she does etc. The “she’s going through a lot of personal things” is a teensy flag for me, because as kind people we can let unsatisfactory performance drag on because we think we are giving someone a break, while the employee starts to think that their subpar level of work is acceptable. (There are also some people whose lives just seem to be constantly chaotic.) We cannot successfully “coach” everyone to be able to do every job perfectly. We coach, we put in accommodations, we make sure the employee is clear on expectations, we treat everyone fairly and with respect – and if they can’t cut it, then you need to step away with a clear mind.

    1. Devo Forevo*

      Seconding this. I had to let someone go who had many of the problems OP describes. Loyalty and dedication to the job don’t translate to good work all the time, and it was hard to balance empathy with fairness to everyone else who was picking up the slack, especially as a new manager. Be fair to yourself and to your employee by being clear about what level you need her to be working independently at and when you expect that. Otherwise, you’re both ultimately stuck in an unhappy situation and wasting time.

    2. see you anon*

      The “going through a lot of personal things” comment caught my attention too (as well as the handholding after 3 years, which has been acknowledged in other comments). I find that personal and professional relationship dynamics can get muddied, especially in small workplaces like the one OP talks about. This can cause how you feel about a person, or know about their personal life, to inform your assessment of their work.
      OP, I think you need to separate personal from professional, and have the direct conversation Alison advised. Hopefully Lenore will get the message, and find a system that works for her. Best of luck!

    3. Sara without an H*

      This. LW, you may be contributing to the problem by stepping in to “support” Lenore and never making her responsible for actually doing her very own job. Have a very clear conversation with her about what needs to happen in her job for her to be successful. (And put it in writing.) Then step back and focus on her results, but do NOT step in and try to find an organizational system that works for her. She needs to find this for herself.

      This doesn’t make you a bad person or a bad manager. But if you keep carrying Lenore, the problem will only get worse.

  18. JSPA*

    If there are really only a few variants, and you emphatically want to keep her, record a video for each–with her input–or make a visual flow chart with check boxes (again, with her input).

    Make sure there are numbered steps, and if it’s a video, include pause points.

    For video, you can make dummy account examples, or use real ones and put a piece of tape on the screen to hide names and account numbers. If it’s a flow chart with pictures of the screen, that’s easy to hide identifying details.

    Yes, it’s a minor waste of paper. But if she can go through a paper flow chart with a pencil–trace the route–and check off steps as she takes them, then you’ve taken yourself out of the process.

    But there can also be an emotional component.

    I can’t know if this really is about billing (or reposession or foreclosure or hikes in interest rates anything else that can be similarly fraught) or if that’s purely an example. So some of this may not apply. Discard where not applicable.

    Maybe she feels some level of pain or distress at dealing with people who don’t follow the rules. Or she is distressed by adding stress when people might be short on cash. Or the whole process just feels too authoritarian. Or there’s some other emotional thing that’s blocking her ability to function.

    While you absolutely can’t ask about the roots of possible distress (!) I think you could ask if she feels that reminding people about [past-due payments or whatever it actually is] is more stressful for her than it is for most people.

    If she says yes, and if you have any sort of EAP or other employee support program, I think you could then mention that the EAP might be able to talk her through coming up with strategies that she can use, to mitigate that distress.

    Or at minimum, point out that you know her reactions are coming from a good place, but that it’s actually helpful for the company and for the clients to keep their billing on track.

    Similarly, if she’s worried that the elapsed time makes any mistake more high-stakes, it might be worth talking her through the implications of an actual mistake. (What happens if she hits the decision point, do A or B, should do A, and does B?)

    For some people, once there are (say) four rather than three possible wrong choices, the perceived risk of “doing something wrong” skyrockets, because each one feels like an independent risk. If you’re open to an occasional mistake, and willing to repair that, it might free her from the tyrrany of perfection.

  19. The Wizard Rincewind*

    As a disorganized person, I’ve been so ashamed of the times I’ve had to tell my boss that something didn’t get done on time. Lenore’s under reaction (as told by LW) is weird to me and seems to indicate that she really doesn’t understand how her work is impacting others. I think Allison’s advice to spell it out more explicitly is extremely warranted here.

    1. Dust Bunny*

      Denial? I was a horrendously disorganized kid and spent most of my school years in utter and complete denial about how much trouble I was in.

    2. A Manager for Now*

      I 100% underreact to (even just perceived) criticisms. The shame is absolutely still there, but I learned in my family that showing that hurt/shame/fear/emotion was even more unsafe than the mistake or failure in the first place. So I will nod, agree, and generally keep my face pleasantly neutral. Inside, I will absolutely be berating myself and ashamed and afraid that I’ll be losing my job/the relationship/whatever and coming up with strategies to either rectify the situation or prevent it from happening in the future.

      Not saying that’s what’s happening with Lenore, but wanted to offer an example of someone not outwardly reacting and why that may be happening.

  20. Bast*

    I’m really concerned that this is the level that she is at after three years. If the letter said three MONTHS, I’d think there is time to improve… but not three years. You should have a good grasp on your position by then. To me, this letter screamed that part of this job is just not a good fit for Lenore, no matter how great her personality is, or how loyal to the company. She can either do the job needed, or she cannot, and it doesn’t look very promising if three years in she needs that level of handholding. The only solutions I see:

    –The role is split in 2, with each position working part-time. You might still lose Lenore, if she cannot afford to be only working part time.

    –You make each position its own full time role (which you had already stated is not feasible).

    — Lenore exchanges certain other job duties with someone else, as is mentioned, perhaps something else that plays to her strengths (which seem to be in the moment tasks, and not things that need to be planned or diaried out).

    — LW keeps handholding until either burn out, or Lenore quits/gets fired. (not a sustainable solution)

    –Lenore is let go.

    I know the last one is not what LW wanted, but the first and last seem the most likely to be met with success, given the details presented in the letter.

    1. Avi!*

      Frankly, it sounds like the op is letting the fact that they like Lenore as a person blind them to the fact that she is 100% unsuited for the position that she’s in. If they still have to be shown step-by-step how to do their job *three years* in, it’s quite simply a job that they’re not capable of doing.

      1. Bast*

        I agree, however, there is something to be said for having an employee who is easy to get along with, appears loyal enough to the company to stay 3 years, and doesn’t stir the pot. It can remarkably hard to find people like that, and depending on the field and/or turnover already in the company, I can understand why it may be hard to let go of a “personality match.” I’m not saying keeping her is the best decision from a business standpoint but I’ve met and managed “Lenore” before, and upper management has nearly always dragged their feet about firing them.

        1. Bunny Lake Is Found*

          Word. I think this comment section really underplays the dynamic in the workplace sometimes (as evidence by the near universal hatred for any kind of out of work socializing or team building). Like, I cannot imagine determining what level of improvement in a new employee’s ability in that other half of the job would entice me to risk getting someone who didn’t gel with the office.

  21. In The Same Boat*

    I manage an employee like this (I could have written this letter), and after almost three years of trying everything under the sun to help her/get her organized, as well as numerous serious discussions regarding her performance needing to improve, I was just told by my boss that it is time to let her go. I really like her, she is a wonderful person, but her continued lack of attention to detail and disorganization is now costing us clients/income. Sometimes the job just isn’t the right fit for someone, as Alison said.

  22. JSPA*

    Adding, sometimes people get into a very different headspace when they’re asked to teach, rather than take in information. Next time, “ok, Lenore, pretend I’m a temp, and teach me how we proceed here, step-by-step.” A couple of those (for different cases) and she may have finally gotten over the hump of teaching herself.

  23. Critical Rolls*

    There’s a saying, “don’t set yourself on fire to keep someone else warm.” You are doing your own job, plus a .5 FTE coaching and covering for Lenore. If you were managing someone doing what you’re doing, would you consider it reasonable after THREE YEARS? (I’m frankly a bit gobsmacked that you think any amount of hand-holding is part of a decent performance of any segment of her job after that much time.) It can be true that Lenore is pleasant and well-intentioned and even has a good work ethic, and still be true that she can’t do this job. So if you feel like she has not been made to understand the seriousness of the situation, sure, have a sit-down and give her a 427th chance. But ultimately you need someone in the role who can perform its functions with a reasonable degree of independence, and Lenore sure doesn’t seem like she can.

  24. Ganymede*

    Does she have slightly dainty ideas about money? Maybe she hates the idea of nudging people to pay what they owe. People can be brought up to feel very squeamish about asking for money and it might mean that she’s pushing the unpleasantness of the follow-up tasks away in her mind.

    I write as an adhd person and agree with lots of people upthread, but perhaps she likes to think her work is done when she asks for money the first time and hates the chasing and risk of offence in either direction (ooh, RSD, come to think of it). So many people haaate talking about money.

    1. Rachel*

      First of all, the LW was giving examples, not Lenore’s literal tasks.

      Second, if Lenore is “dainty” about money and took this job anyway and dodges that part of the job well….that’s on Lenore.

      1. Ganymede*

        Or, its a learning opportunity. I used to be squeamish about money for all sorts of reasons, not least being English lower-middle-class, and a colleague talked me out of it in a really kind and forthright manner. It has helped me enormously and made me much more effective. It really is something you can snap out of with a little help.

    2. ADHDadult*

      As an ADHD person who is an extroverted introvert, I struggle with phone calls — especially cold calls or something like that. And collections type calls make it even worse.

  25. Anne Shirley Blythe*

    I suspect this can only end in a layoff, and this is difficult when the person is truly likable and well-intentioned. Offer a generous severance and offer yourself as a reference, focusing on her positive qualities.

    1. Sloanicota*

      Right! There’s probably a job for Lenore where she will be great. This may not be it, and it’s possible it can’t exist here (despite what I said in other comments above haha). I know how hard it is in a small company, but it’s totally possible you can give someone else, who is amazing, a great opportunity in this role, and you might be astonished by how much smoother everything runs, particularly your own life, once you have someone great in this spot.

  26. Coverage Associate*

    Just echoing that it is weird to me that only physical calendars have been tried. I know they work for some people, but digital calendars where you can automate recurrence and reminders sound much better for this situation.

    As for digital documents, all the scanners I have used default to a document name with the date, so even if the employee forgets to use meaningful document names, some information is automated. Also, assuming the documents are searchable as soon as scanned, echoing everyone else that this is better than physical documents that can only be searched by hand.

    I am surprised that any bookkeeping software this business is using can’t at least sort accounts by date outstanding, etc. Even Excel can do that.

  27. Doc McCracken*

    As someone who is not naturally organized, you trying to teach Lenore multiple ways to organize that don’t stick for her means those meetings just don’t match her brain. They make sense to your brain, not hers. A few practical steps. 1. Identify Lenore’s organization style. Class from Clutterbug on youtube has 4 categories based on if the person is a visual organizer or not and if they are a micro or macro category organizer. There’s a free quiz and everything and lots of videos on how to organize for each type. Step 2. Ruthlessly cut the amount of paper in your office. If you can’t access it when you need it, it’s not helping anyways.

    1. Rachel*

      Maybe Lenore should watch the video and figure out what her organizational type is.

      It seems suspect for the LW to judge that.

      1. el l*

        Exactly the problem with the entire ADHD discussion we’ve seen here.

        If Lenore can’t get motivated to (a) Figure out why she can’t do her job properly, and (b) Figure out remediation strategies that work for her…

        …Then what chance does OP have with either of those questions? No wonder nothing’s worked.

        Hard enough for OP to manage their own headspace. Trying to guess Lenore’s and come up with usable responses is just not their job.

        1. Doc McCracken*

          I’m going to accept responsibility that I wasn’t clear enough in my advice. Yes, Lenore should be the one taking the gosh darn quiz. As a woman who has adhd and wasn’t diagnosed age 41, if Lenore has adhd, she is likely hyper aware of her failings. It’s just where do you go when all the conventional wisdom just doesn’t work for you? With very few exceptions, organization books are written by organized people…who organize for fun, not the rest of us.

    2. AndersonDarling*

      I was a bit shocked that an organization still had enough paper to stack up into piles on a desk. If the entire organization is running on paper, I’m wondering if the whole organization is a bit chaotic and it’s bottlenecking on Lenore’s desk not because of Lenore, but because everything everywhere else is disorganized.

  28. Hamster on a Wheel*

    I’m on the neurospicy spectrum and I have trouble remembering rules and processes that don’t make sense to me. It’s kept me from a certification because I can’t internalize the study questions, so I’m not able to pass.

    Even if that applies to Lenore, she’s still responsible for following the procedures. A manager once came to me, not sure how to get one of her reports to be more productive. I suggested structuring her time. “From 9:00 to 11:00, process incoming orders. From 11:00 to 1:00 follow up on the orders that haven’t been paid.” It worked for that person.

    It may be that Lenore was never taught, and has never figured out, time management and organization on a life-skills level. She needs to take responsibility for that and not drain the LW’s time and mental resources. LW needs to draw some boundaries of what is required.

  29. In My Underdark Era*

    one thing I notice is that all the organizational tools described are about putting things *away* and for some people (ahem, see the armchair diagnoses in the other comments, ahem) things that go *away* simply don’t return. she may have piles and a desk littered with papers because she needs to see something in order to remember it exists. for this reason techy or traditional organization tactics may not work for her.

    if you’re still interested in passing along different tactics for organizing whatever she’s forgetting: corkboard + push pins, whiteboard/chalkboard, daily alarms for forgettable tasks (on phone, email, an alarm clock on her desk, whatever), things that allow her to have *more* stuff in view rather than less. if she has a problem with not seeing calendar events and stuff, an extra monitor that exists solely for outlook helps me a lot. and just keep in mind that “organized” for her may look “messy” to you.

    not to throw a bunch more organization tactics to try on the pile when you’re burnt out on offering them! it needs to be her responsibility, not yours. I just don’t have much else to offer!

      1. In My Underdark Era*

        ah, didn’t mean to imply that the piles were helping her, just that they might be a product of that mindset, in which case they’d be doomed to fail because yeah, things end up out of sight and get lost. piles do work for some, but clearly not Lenore.

      2. linger*

        One starting point would be to work with the existing piles.
        Insist Lenore organise and label the piles, and then stick to that classification system when adding new documents. Then she only has to search through one, not multiple locations, for a missing document.
        As a later refinement, the piles could then be split into labelled folders or boxes, again reducing the search space and thus wasted time.
        But if Lenore can’t even do that initial step, there is no hope for any long-term improvement.

    1. Indolent Libertine*

      It isn’t “organized” for her, though, because she can never find anything when asked for it.

  30. OnyxChimney*

    Why on earth does Lenore need to manually track who is late and what she has said to them!??? Do you not have a collection system or billing and invoice system that automatically tracks due dates?

    Lenore should just be able to pull up a list each day of what is still late and review the call notes from past discussions. It’s bonkers OP expects anyone to have all of that memorized.

    The technology for this isn’t new or expensive either. I was using systems like this 14 years ago in 2010!

    1. Deo*

      I’ve worked in nonprofits for most of my career. The “shoulds” are never helpful advice. Assume the OP has a system that is reasonable and appropriate to their budget.

    2. Dawn*

      The point isn’t that this system isn’t available, the point is that Lenore isn’t using any of the tools available to her.

      At my workplace we track things we need to follow up on through Outlook, which has any number of tools for that, and which Lenore is almost certainly using; the problem does not exist with the tools. As the OP themselves has indicated, Lenore’s desk is quite literally littered with failed attempts at providing organizational systems.

      1. Two Fish*

        That’s true, but in most cases any version of “what did I last say to [entity outside my company]” should be solved by looking at one’s email.

    3. ArtsNerd*

      Haha I was once handed a program that included accounts receivables but with very little direction or policies to follow. I called my counterpart in another location to ask how she tracked hers, and she started telling me about how there was one spiral notebook for the order details and another for the billing…. and I taught myself how to customize a microsoft access database to generate the bare minimum of what I needed because NO.

  31. BellyButton*

    We recently let an employee go for this sort of executive disfunction. I gave her every single tool possible to be successful with her organization and time management, but she wouldn’t or couldn’t use them. After 9 mo her manager was overwhelmed and frustrated, as the development person I was frustrated because I was meeting with a low level employee weekly to hold her hand to do the basics. She either wasn’t capable or wouldn’t implement any of the tools/suggestions I gave her. Unless someone was holding her hand through basic things she wouldn’t get them done. I would ask her the following week- did you use X method/tool? And when she said no, and I asked why she never had a decent answer. I did all I could to give her the tools that would help with this kind of thing. It wasn’t sustainable for her manager, for me, or for the employee’s success.

    At some point you have to decide is this best for everyone.

    1. Sloanicota*

      In the linked post, the lead quote is “You can’t be more invested in saving his job than he is.” This is the corollary of something I say all the time about my own job, which is, “I can’t care about the organization more than the people in charge do.” This OP sounds more invested in keeping the employee than they do.

      1. Grumpy Elder Millennial*

        I’m curious whether Lenore knows that she has to do anything to save her job. It sounds like the manager hasn’t even considered managing her out, so I’m assuming there have been no serious conversations. Yes, ideally someone would put 2 and 2 together and be aware that if they’re struggling with key parts of their jobs, they are at risk of not having the job anymore. The challenge is that the skill to assess your success at a task is the same as the skill to be good at the task. People who are bad at something often don’t realize how bad they are at it. And since the LW has been letting this go on for 3 years, Lenore may figure that everything is OK.

  32. Dawn*

    For what it’s worth, I am strongly ADHD, and Dave Crenshaw’s time management system really worked well for me. He’s ADHD as well and his methods instantly clicked with me.

  33. el l*

    This is a classic “What’s their deal?” issue with an employee. Yes, it’d be great to figure out why Lenore is still not capable of doing more complex tasks. Yes, it’d be huge too for Lenore to develop habits to reach the job’s requirements about being organized.

    But it is not OP’s job to figure out Lenore’s deal. That’s the boundary where this has to end.

    Because sometimes there isn’t enough time and energy to figure it out, nag, enforce habits, etc. And sometimes even if the time and energy is spent, which it certainly was on organization, you just won’t end up with a useful answer or the right habits that will lead to a competent independent individual.

    So – that’s exactly right. Define a standard, and state “what” is needed. Leave the “how” to them. Then enforce that, and be willing to have tough talks and fire if they’re not meeting it.

    1. Avi!*

      Yeah, I’m not impressed with the idea of trying to figure out what her ‘deal’ is, because it’s well past the point where that could help. This is a job that requires a certain degree of organization, and for whatever reason Lenore is incapable of meeting that standard or acknowledging that it’s a problem. At this point it feels akin to having hired someone who failed all their math classes to be your accountant.

  34. LingNerd*

    This absolutely sounds like me and the way my ADHD presents. I really, really struggle to follow up with people because I’m barely managing my own time and tasks and don’t have the energy/organization to track down other people’s pending tasks. But responding to something that pops up is fine because there’s a sense of urgency with it. I try out systems and if they work at all, they usually work for a week at best. If I have to use an entirely new program for that organizational tool, I’m flat out not going to remember to use it. The only thing that works for me is a blank notebook that has not been pre-filled with suggested ways to lay things out or organize them. For home that means a lined notebook – but even that can be challenging because I feel like I need to get the system I set up “right” the first time, so I actually need a refillable planner, which I have. For work that means onenote, since everything I’m doing is on the computer and I can have it open in the background.

    Obviously we can’t diagnose. But that doesn’t mean ADHD strategies can’t help, because she obviously has challenges similar to those with ADHD even if that isn’t the cause. It sounds like none of the suggested tools or traditional organizational methods are working. So, she needs to come up with an organizational system on her own. She may need to be explicitly told to not make it perfect too – some people need a reminder that 80% is better than 0% and it’s worth doing something even if you can’t get to 100%. Just because she hasn’t had ideas before when asked directly doesn’t mean she won’t, it may just mean that her mind goes blank in the moment. And also, accountability and firm deadlines might be very helpful, perhaps more helpful than you trying to directly solve the problem for her – e.g. “By noon on Monday every week, I want you to start sending me a list or spreadsheet of all the currently overdue invoices and how many days overdue they are.”

  35. Hashtag Destigmatize Therapy*

    Alison’s advice is spot on: to be really explicit about Lenore’s responsibility and put the ball in her court to find an organizational method that works. I suspect that up to this point, she’s thought her current work is acceptable, and the organizational tools LW has recommended were optional suggestions to help her out.

    She might get pretty upset when she finds out that her work *hasn’t* been acceptable, but it’s better for her to find that out now than when she’s getting fired. She may not be able to turn this around before LW has to let her go, but even in that case, she might be closer to where she needs to be to succeed at her next job if she knows she needs to be improve.

    1. Grumpy Elder Millennial*

      And I don’t think it would be wrong for the LW to apologize to Lenore for letting things go on this long, if it makes sense in the context of the conversation.

  36. J!*

    I strongly recommend a tool like Tango that lets you walk through a task and uses AI to capture and save a step-by-step instructions with screenshots and directions. They even have a guide mode that shows you what to do on the screen.

    That way your staffer can refer to those directions instead of having to remember it (which doesn’t seem to be working) or relying on notes (which are sometimes vague or incomplete). And if she can’t use those resources to refresh her memory after being trained, you might want to think about whether she’s right for the role. People learn in different ways – it’s one thing to not get it or need reminders, but it’s another to just not retain or know how to find help that’s not another person for something that’s job critical.

  37. Anon attorney*

    I think LW is trying to find a way to avoid firing Lenore.

    while losing your job is a massive deal and I’m not trying to suggest that it’s not – struggling on in a role you can’t do (and I think Lenore knows that) is also very stressful. For as long as she stays in this job she’s not getting any closer to finding a job that’s a better fit.

    Maybe it’s actually not a kindness to keep shielding Lenore from consequences. LW could provide severance and help with finding another job so she has some kind of cushion on the off ramp – wouldn’t that be kinder for everyone? including LW who is allowed to be kind to themselves too.

    1. Grumpy Elder Millennial*

      The only upside here is that there are a few possible outcomes and the LW can have a conversation with Lenore about what makes sense, given that a few things are non-negotiable (e.g., the LW can’t be helping as much, unpaid orders need to get prompt follow-up). Is she willing to commit to finding and implementing a plan that will let her be successful in the parts of her job that are currently a struggle? How would it work for everyone if Lenore shifted to a part-time position doing only the parts of her job she’s good at? Does it make sense to give her an extended off-ramp?

  38. work our way back*

    How fill-able is this job? Can you replace her? Because if you cannot replace her, split the job, make it part-time if you absolutely must. But she is either unwilling or unable to do part of her job and it’s been three years. Accept that she isn’t going to be able to that part of the job. Either that’s okay (because it’s been okay so far) or it’s not okay, but it’s not going to change. Either replace that part of her job, or replace her.

    1. Bast*

      LW still might lost Lenore if they make it part time. Many people need the full time hours, and would quit if their position’s hours/pay were cut. I do agree that Lenore is not successful as is and either way cannot remain doing (not doing) the same tasks as she is now. Nothing will change unless LW makes it happen.

    2. Bunny Lake Is Found*

      Also, is it fillable at the price point you are paying? Everyone is really focused on the fact Lenore will “need to be fired” at some point without considering any factors like “If I fire Lenore, I will need to hire someone at $25K more a year because of what these roles are now paying.”

      I have to assume Lenore isn’t entry level or she would have been fired by now–I am assuming Lenore has enough of a skill set to make what she has been contributing for the last 3 years of a sufficient enough quality the OP has been trying to improve these organizational systems to try and bring Lenore’s weak spots up. So unless we assume the OP is just so besotted by Lenore’s dedication and work ethic she does not see that Lenore should be fired if she can’t handle basic entry level work, it makes more sense to assume Lenore is high enough level that she brings actual skills to the table the OP wants/needs for her business–there are just other skills Lenore hasn’t been able to demonstrate that OP is realizing are just not improving over the years.

  39. ijustworkhere*

    Sounds like Leonore can only keep up with a very few things at a time. She needs a job where she has fewer balls to keep track of.

    I’m convinced that learning how to organize things is a skill (like learning a language) that has an optimal developmental window, and if you miss that window it’s really difficult to learn later. Not impossible, but difficult.

    And you have to be very motivated to do so. It also sounds like it isn’t clear to her just how much is riding on this.

  40. NobodyHasTimeForThis*

    I think the problem with suggesting more techniques to try, is that Lenore hasn’t shown that she will use a technique. Throwing more and more techniques might be making things worse. Focus exclusively on what you need the outcome to be with deadlines and offer to support her if she feels there is a tool that would help her.

  41. Garblesnark*

    Taking orders and collections are dramatically different jobs, and disorganization aside, I don’t think it’s that wild that Lenore is only great at one of them. I mean, at the very barest level, one is about making the customer happy with you, and the other feels like asking the customer to yell at you (to me, someone who has done both).

    Is there truly no reshuffle of responsibilities that could put Lenore more on her strengths? It sounds like Lenore might be good at reception or general CS escalations, because she’s getting enough people to order that there’s plenty of payments to collect. Then maybe someone else – someone who delights a bit more in telling people “no, this is your responsibility” – can collect the payments.

    1. Grumpy Elder Millennial*

      I’m imagining that part of the problem is that the sales part is more of a one-and-done thing, or is customer-led. Whereas the other part needs ongoing follow-up and attention. Though, admittedly, this is based off the hypothetical scenario, not Lenore’s actual job, so who knows. But I agree with you that when tasks are thematically related, but very different in execution, it makes sense that people wouldn’t be great at both.

  42. Advocate of automating drudge work*

    My take is that the billing process should be automated, so unpaid bills can pop up in a report, and overdue bills can be sent out via email, with links for online payment. There are many good billing systems out there.
    There are also good document management systems that can organize documents by categories that you can define. Some people can’t handle physical systems and will do better with automated systems.

  43. Engineer*

    Some sort of digital ticketing system that tracks orders and has a notes area. You can probably even set it up so the system automatically reports every two weeks on overdue statuses. Thinking on the lines of Jira.

    However, the employee MUST start using the system to its full potential.

    1. Hastily Blessed Fritos*

      There’s got to be something between a spreadsheet and Jira they can use. There’s no way Lenore will remember to keep Jira up to date even if she can figure out how to use it. (I’ve been using it for years and STILL keep forgetting to populate one field or another).

    1. Grumpy Elder Millennial*

      This jumped out at me, too. The best case scenarios involve Lenore being in a job where she can succeed and the LW being able to focus on her own work. Maybe there is a way to figure out how to support Lenore in managing that half of her job well. The only way to have a chance at getting there is to start having honest conversations with Lenore about what needs to change in terms of outcomes. There’s flexibility in what processes she uses to accomplish those outcomes, so she can take the lead in figuring out a system, but that there needs to be a workable system. Or, as at least one commenter has pointed out, turning it into a part-time job that only involves the tasks Lenore succeeds at could be an option worth discussing.

      My suspicion is that the appreciation the LW has for Lenore in terms of the half of the job that’s going well and the loyalty, and what seems to be a refusal to consider firing, may have led her to not have the serious conversation with Lenore. But that’s part of management. You need to give Lenore the information she needs to make good choices about her own life and employment.

  44. ADHDadult*

    This is how my ADHD manifests too – I have tons of piles of things, and need a system to keep track of different tasks. Lists are my friend, as is a checklist or outline of specific tasks that need to be done (eg task, with a breakdown of what tasks are involved), and a calendar or two (one on my fridge, one on my phone) and a bullet journal.

    My husband can attest to how frustrating it can be for a neurotypical to deal with a neurodivergent person. I hope you and Lenore can figure out some systems to work together better. Just keep it straight forward.

    Good luck!

  45. Grumpy Elder Millennial*

    The only thing I have to suggest would be to have a short meeting once or twice a week with Lenore where she updates you. Each time, she has to bring a list of the current unpaid orders and talk you through what’s up. Set these meetings for either later in the morning or later in the afternoon (i.e., not right at the start of the day and not right after lunch), so that she has time to prep for the meeting. As someone who has some tendency to procrastinate, having regular points where I have to report on what I’ve accomplished is helpful.

  46. Volunteer Enforcer*

    I believe in if your system works then it’s your business. It is very much OP’s business to either get her employee up to snuff or gone.

  47. The Gollux, Not a Mere Device*

    If she has had a lot going on in her personal life for the past three years, that fact is unlikely to change soon. Cutting someone slack for a while can be both kind and a reasonable choice, but it sounds like those things have been going on for as long as Lenore has had this job, if not longer.

    Based on that, I think you should disregard whatever is going on in Lenore’s personal life, because knowing about it isn’t helping you solve the problem.

  48. Quill*

    So I used to track documents with relatively long turnaround times, and part of the problem for me was – if you do not hear about something for more than a week, other priorities will replace it in your memory no matter how organized you are. It sounds to me like OP has two different problems: it takes longer than OP would like for Lenore to find evidence of what was last done with item A, account B, or how to do monthly task C, and also Lenore isn’t chasing down unpaid bills.

    For the finding evidence thing – many people have suggested a lot of different software for organizational purposes, *but* if Lenore does not perform tasks in existing software often enough / in enough volume to retain how to do it, that’s unlikely to help on its own. If some of these are standard tasks (input the invoice number of every single account, mark if it was paid…) then Lenore needs instructions to reference so that OP does not have to explain anymore.

    Frankly, even if you have to replace Lenore, having the instructions written down is only going to help. Even if it goes into such detail as “at the top LEFT of the screen, left click file, scroll DOWN to Save, click Save As, and then input a file name consisting of the account name and the date (i.e. Warbleworth 02.28.2024)”

  49. I went to school with only 1 Jennifer*

    This. “Why can’t I be normal?” The shame….

    I figured out at about age 20 that for some reason, I didn’t remember things and I HAD TO put them on a calendar. And after a couple of social disasters, I learned to never commit to anything until I had checked my calendar. (This was well before smart phones, and also before I learned to carry a small calendar with me.)

    I never understood why this was different for me but I am glad that I just accepted it as my quirk. Decades later – no exaggeration – I learned about ADHD and remembered that early accommodation I had created for myself and had a big ol’ ah-hah moment. (And then I took myself off to get diagnosed. Medication plus self-awareness have made a huge difference in my life.)

    1. Grumpy Elder Millennial*

      Same – if it’s not on my calendar, I’m not going to remember. I have a recurring weekly alarm to remind me to deal with my food box order. Otherwise, I forget and end up with whatever the default meal kits are and they often include at least one ingredient I hate. This happened more than once before I set the weekly alarm.

      1. Hastily Blessed Fritos*

        Whether or not Lenore has ADHD, her issues at work are very similar to those someone with ADHD would experience, and the same approaches may be successful. LW, you’ve tried a lot of things that haven’t worked so I think, if you want to give Lenore a chance to stay in the job, you say something like “You need to be able to do A, B, and C independently. I’ve tried the techniques I know and none of them have worked, so you need to figure something out – you’ll need to research organization tactics and executive function help (even just mentioning the phrase “executive function” may be helpful since it gives her something to google) on your own to figure out what works for you.”

  50. CommanderBanana*

    Also, work ethic doesn’t help in a situation like this, because Lenore can be working hard and still be really bad at the job. Some of my worst coworkers were always busybusybusy but couldn’t actually produce what their job required them to produce.

    This is actually a great opportunity to come up with a really solid job description, task list, and description of what qualities and skills you absolutely know you need from whoever is in this position. It just doesn’t sound like it can be her.

  51. Apricot*

    I use a physical daily planner that’s set up this way: a space at the top for something I’m grateful for, a To Do list section, a space to write what movement I did that day, a space to write something I learned, and a blank bit for notes or a bit of journaling at start or close of day. I’m wondering if something like that combined with actual audio alarms on Lenore’s phone might help her stick to a schedule, if out-of-sight-out-of-mind is a problem for her. I understand a recurring sound in a shared workspace might be disruptive to others, but it sounds like we’re in last resort territory anyway.

    For example, first alarm goes off, write down all the items to do for the day. Second alarm goes off, write what you’re grateful for – and oh look, now you’re looking at those to-do items, better do one. Third alarm goes off, time for a quick movement like stretching or walking to the break room to fill up your water bottle, write down what you did – and oh look there are those to-do items again!

    LW, from all of us who try hard but struggle with things, thank you for having the patience and understanding to continually seek out solutions and do everything you can to help Lenore! Like others have said it might not work out, but I appreciate that you’re putting in effort to make it work instead of jumping to giving up on her.

  52. Annie B*

    The only thing that has ever worked for me, a super unorganized person, is a very basic spreadsheet system. Either Excel or Google sheets. The items I need to do are all in it. I have a column for the deadline, for the date of my last contact with the person or project, for notes, and for overall status (Complete/In Progress/Waiting for Information). I highlight items when I add them to the spreadsheet. I highlight items in a different color when they’re newly complete. Every day or every week, depending on what’s agreed on, I send the spreadsheet to my boss.

    It’s extremely simple to use, it keeps me accountable, and it keeps me from spiraling because I know I can only hide issues or procrastination for so long. I’d recommend trying something like this!

  53. Pilot On*

    I totally resemble this. The tools I try to implement I lose (like every task list I make will be lost within one or two tasks if I carry it with me; if I post it, it becomes wallpaper that I don’t see; digital requires a learning curve that becomes a new item on the list, etc.)
    But sometimes the right new thing will help at least temporarily, so I’m eager to make a note of some of the suggestions here. I’m not a candidate for medication, but some alternative supplements help me focus a bit better (like matcha powder, gingko tincture and chestnut bud Bach flower essence– don’t come for me! I use what I can and derive some benefit from them.) I just have to remember to use them!

  54. Regina*

    I had a lot of the same issues, for what I think are probably different reasons, and went through absolute piles of Kanban boards and project management software and various organizational tools to help me deal with a lot of structured-but-irregular tasks (like, “I have to do a thing today that I do not have to do most days, because today is the due date for all the invoices this month,” for example) and eventually, it turned out that I just needed a very particular kind of basic to-do list app. Specifically, it needs to send me push notifications on my phone, and then those notifications need to stay on my phone until I actually physically go in and interact with it to mark it complete or push back the deadline or whatever.

    I use TickTick for this, but I’m pretty sure there are plenty that will do it. I had tried a few to-do apps before among the rest of everything, but it was too easy to accidentally or thoughtlessly swipe away the notification and then become distracted by some fresh new chaos, and boom: forgot again. Now it stays there and glares accusingly at me from the top of my screen until I unfold the little widget and do something with it.

    It’s a very simple solution, and my phone is something I can’t / won’t lose or forget to look at, and that’s the exact reason it works. (I literally have to be reminded by my phone to take my lunch break and like, clock out for the day. I seriously cannot be trusted without my phone reminders.)

  55. Hastily Blessed Fritos*

    Whether or not Lenore has ADHD, her issues at work are very similar to those someone with ADHD would experience, and the same approaches may be successful. LW, you’ve tried a lot of things that haven’t worked so I think, if you want to give Lenore a chance to stay in the job, you say something like “You need to be able to do A, B, and C independently. I’ve tried the techniques I know and none of them have worked, so you need to figure something out – you’ll need to research organization tactics and executive function help (even just mentioning the phrase “executive function” may be helpful since it gives her something to google) on your own to figure out what works for you.”

  56. theletter*

    so it sounds to me like the two tasks, though they are linked, have different mindsets – taking orders is reactive. Lenore waits for the phone call or email, handles it, then waits for the next task.

    The handling of follow-ups from unpaid orders is proactive. She has to remember to follow a set of tasks without any prompting.

    Option one would be to turn the proactive tasks into reactive tasks – So when there are no orders, she has software that has ‘ringing alarms’ that will walk her through things that are important but not urgent – sometimes the best way to get that quadrant of work done is to just pick a due date and tell yourself it’ll be urgent on that day, even if it’s really not.

    Another option is to strictly divide the time – let’s say there’s 4 hour blocks where all she does is react, and 2 hour blocks where she’s proactive. Sometimes it’s easier to start the day with the proactive -> log in, set the project management system to your home page, so when you open a browser, the first and only thing you see is the list of things that need action.

    But you might find that the best thing to do is the simply say that the task will be taken away from her and there’s consequences if she doesn’t figure out how to do this. There’s always a small chance that something buried in her mind is convinced that all this coaching you offer isn’t actually coaching, you just keep changing your mind as to how you want it done. If you make it clear that you’re going to stop trying to help her and she has to figure it out or she’ll be fired, the ‘engineer’ part of her mind might take over. Sometimes you just have to send the panic monkey in there to force the brain to disregard all other concerns and figure it out.

  57. Serious Silly Putty*

    Here are my struggles and what helps:
    1. I don’t know where to put things that don’t have a home, and I struggle to create new systems/homes. I know OP has already recommended systems, but by presenting it as “I NEED you to file things in X way so that I can access them too”, that could provide both the support and motivation to deal with The Piles.

    2. I get zero “dopamine hit” from organizing, and I don’t get stressed by visual clutter… I only get stress once it’s to the point of creating distinction, and by then it’s overwhelming. That’s hard to overcome/support someone through, but see #3

    3. There is always something more urgent than tidying. I feel guilty tidying when there are more urgent things. But a directive from my boss: “I want you to spend the next two days reorganizing; let’s plan a 10 minute checkin each morning and after. Feel free to bring music/audiobook/podcast to make it more enjoyable “ — that could actually be freeing.

    4. I am not Type A, but I fantasize about being as organized as my Type A peers, so I used to take their advice. It never worked. I got the best advice online from a professional group where I flat out asked “looking for time management strategies for non-type-A people” and another group focused on neurodivergent life skills (I don’t have a particular diagnosis, but several tips for ADHD people have helped me as well). So they may have something even better than the system I just suggested to OP insist on… but for important things I wouldn’t wait on that to appear.

    5. I have no streaming video memory. It drives me bonkers when my boss’s way of teaching a new skill — complete with specific numeral settings— is to show it to me once.(Apparently that’s enough for him? Maybe?) We have good enough rapport — and I feel an obligation to MY underlings — that I will deliberately slow things down enough to take notes, ask clarifying questions, and create documentation myself. TBH I think part of training should BE documentation, but since OP likes this person, perhaps a novel task would be: “I want step by step documentation on X task. Can I show you how to do it, and then you make a file with screen shots that you or anyone could reference in the future?”

  58. I'm just here for the cats!*

    I feel for both OP and Lenore in this situation. I have some thoughts. First not everyone can follow the same organization system. The OP sounds like with physical materials the OP is organized very detailed. Such as using clearly labeled file folders and a file system. That doesn’t work for a lot of people because they get overwhelmed (Does this invoice go to the Johnson folder or in orders, or billing?) so they just don’t do it. She may be a Macro organizer where OP is micro.

    Also, for some a physical calendar is great but for others can be forgotten about. The OP mentions Asana but maybe Lenora needs something that will physically alert her, and maybe several reminders. I like Microsoft Todo because it pings on my computer and on my calendar, both visually and with sound. I would recommend both the OP and lenora check out clutterbug. Cass has a quizz that defines your organization style. Great thing is she has ADHD and has been in Lenora’s shoes. (not diagnosing but there are similarities)

    For the difficult tasks and retraining, I think it would be a good idea for both OP and Lenora to create a Standard Operating Procedure manual that gives very specific details on what needs to be done and how to do it.

    What type of software do you use to track these orders and such? Do you use something like zendesk? Is there any way that when Lenora opens up the information for that client there can be a note section that states specifically what she has done in the past. This way she can easily go back to the notes and see that she spoke with X person at Y time about the june billing statement.

    And finally like a lot of people have said, I think OP needs to look at this from a larger point of view. If Lenora is great with everything else but this one orders area, is there someone else who could do it or help her? Another thing that I noticed is that the OP had this role and was promoted. From personal experience I wonder if OP has been a little too involved and has not allowed Lenora to do the work on her own, so now she has given up because it’s either not done correctly (meaning the way OP wants it done) or she feels overwhelmed. I think OP needs to let her fail.

  59. Former Gremlin Herder*

    Oh goodness, I could have written this letter about one of my team members with very minor tweaks. The biggest difference is I’m in a weird middle manager role and don’t have the authority to make moves towards termination, but it’s a weird place to be.

  60. Michelle Smith*

    I am not going to impugn anyone’s character here but…is there a possibility that she is intentionally failing at this task in the hopes that it gets reassigned? One of the punishments I’ve found for doing good work on a boring, tedious, undesirable project is more of that kind of project. Is it possible that Lenore just really, really, REALLY hates doing some aspect of the collections process? Does she really feel uncomfortable confronting people about unpaid bills or just hate some other aspect of it or feel like she has too much to manage and so she’s just going to stick to the stuff that feels easier until someone recognizes the problem and takes the task off her plate?

    Again, not accusing her of anything nefarious. But I do wonder if there is an element of that anywhere, either consciously or unconsciously.

    1. Why am I always tired????*

      I really hated calling overdue bills – it was the same people, over and over, and the same excuses over and over, and I had no capacity to sack them as clients. Then I moved to a medical practice and learned to hate it all over again – for different reasons – calling someone about an overdue account only to discover they had passed away and I’d have a sobbing, grieving partner on the phone (I had it down to a fine art – I’d flick my office door that was usually always open, shut with my foot, then spend 30 mins (minimum) on the phone with the usually elderly person talking them through how to claim via insurance – not USA, so I would know that insurance would pay without querying it. Loved that job, hated that part of it!

  61. Audrey*

    I work for a small business, and collections is my LEAST favorite thing. It blows my mind how many people avoid paying for a service they requested. Learning how to follow up on payments and ask for the business I work for to be paid was a skillset on it’s own I had to learn. I think Alison’s advice is spot on, AND for that piece of it this might be helpful to keep in mind.

  62. Oh yeah, me again*

    I stated this above in response to a comment, but on reflection, I think this is the biggest reason why Lenore is unsuccessful is because of the amount of choice the OP has offered (allowing the problem to go on for three years hasn’t helped.) Op keeps throwing out – and demonstrating solutions but it doesn’t seem any of the learning has been reinforced. OP ignores situation till next failure; is non-plused at failure to use system; decides system doesn’t work for this employee; and suggests a DIFFERENT system. Instead try: select system (allow employee to help choose) follow up 1 to 2 days later (“How’s is going? Show me what you have done so far”) continue loosely following ( 1 to 2 days) up till month’s end, when hopefully, she understands it. Do not keep changing systems. I know from experience that a company that offering lots of
    different “help” and “resources” available on lots of different “hubs” and “portals” and “systems” and then tosses them out and/or renames them every year or 18 months won’t get the results that one good, clear, set of directions repeated once, twice, possibly even three times – but with no other confusing information thrown in – will get.

  63. Caramellow*

    M fear is that LW is looking for something….anything….to avoid firing this employee. But ugly as it is, sometimes they have to go.

    1. Danie*

      It’s certainly preferable to the alternative approach: looking for any excuse whatsoever to fire someone, no matter how small, exaggerated, or completely untrue it may be.

  64. TrixieD*

    I have Asperger’s and reading this post about Lenore is really hitting home. I have *so* much trouble remembering things, even if they’re written down, because I literally forget that I have written them down. It makes my boss a little nuts, but she also sees that it’s not an intentional oversight–I just can’t remember a damned thing.
    NOTE: I was so concerned about my memory that I saw a neuropsychologist to see if there was anything really wrong with my head. A CT scan and memory test ruled out anything like early-onset Alzheimer’s, but it’s still an ongoing issue. Sometimes, people’s brains are just built differently, and try as one might, things can’t be fixed with traditional methods or tools. It sucks, but that’s just reality for some of us.

  65. Dina*

    I think the OP is focusing on the wrong thing here. What you really want is the work to get done! So make that clear to them. No amount of notebooks or online task management programs you hand them is going to fix that.

    (And fwiw, I am saying this as a person with ADHD myself. I know I’ve been this person for previous managers. This is what worked for me.)

  66. Nat20*

    To add on to Alison’s suggestions for having that conversation with her: it might also help to tell her to think of this as a task you are assigning her. As in, this isn’t just a general, amorphous “thing to get better at”. Instead, she needs to consider implementing a clear system of organization and sticking to it to be a distinct part of her job description, one of her specific job duties that she needs to prioritize right alongside the billing. That mindset may help make this more concrete for her, and more of a clear priority.

  67. Student*

    You said that your employee is detail-oriented and well-organized when it comes to taking work orders, but can’t follow up on billing to save her life. I don’t buy it.

    I would step back at this point to carefully evaluate whether this is weaponized incompetence or not around billing. Is she only forgetful for billing tasks, but has a normal memory for other, similar things?

    I would also find a way to independently assess whether she is actually handling work orders as well as you think she is. Maybe go up and down the process chain to try to figure out if she’s just ignoring a bunch of work orders. Double check to make sure the details that seem right when you initially review them actually are accurate and fulfill the customer needs and the info needs for people down-stream of your employee.

    1. Raida*

      Mmmm I know what OP means but – Having a conversation, planning, nailing down details is focussed, and very well done.
      Later on it’s not fun/interesting/immediate and just…. drops away because there’s no driving dopamine or pressure to keep it powered.

      It’s common in women with ADHD.

      It’s why I’m great at helping out other people – I LOVE PLANNING but SUCK at executing because it slows down. I only need to help with researching and options and so forth when it’s not for me, and all the execution is done by the other person.

      1. Student*

        That doesn’t really help, though. I can understand that neurodivergent people need different coping mechanisms to get through parts of their job that are “not fun/interesting/immediate”. But, we all hate those parts of a job. It’s not realistic or a reasonable disability accommodation to just take away any boring or unpleasant responsibility from a job. It’s very, very unlikely that any individual (with or without ADHD) is going to land in a job that is fun all the time, or even most of the time.

        It’s reasonable to work with any employee to figure out a good coping strategy that fits their circumstances – but the OP is well past that point.

        Plus, this is employee is an adult who has been working at this specific business for three years. She knows she fails at certain employment tasks on a regular basis, because she is getting her boss to do them for her repeatedly. If she’s in the US, it is profoundly unlikely she’s never heard of ADHD. At some point, it is on her to figure out whether she has a disability, what accommodations might be reasonable and effective, etc. She’s not some helpless waif. OP is neither her doctor nor her family, and so is not generally in a good position to do anything but say, “I’ve tried to help you informally and it has failed. This is the outstanding problem. Here’s your PIP. You need to find the fix within the PIP deadline”.

        I’m hard of hearing. It was on me to figure that out from context clues at work and at home. It was on me to get my butt to a doctor for a diagnosis. It was on me to identify the solutions and accommodations I needed. It’s on me to explain those needs to my co-workers when it arises.

  68. Raida*

    God this sounds like my ADHD, only more so.

    Overall what worked for me: Five minute (max) meeting in the morning outlining tasks for the day, keeping a clear desk with just ONE notebook, end of day 15 minutes (max) dedicated to ensuring comments and notes are in the computer appropriately.

    Just having someone else giving a little time to keep me nailing the start and end of day helped massively – and it focussed questions into those times, it allowed a chance to set up meeting times if needed, it was good for feedback, it meant my manager knew the status of everything at a glance.

    For processes that aren’t done regularly – document them. With video and/or screenshots. If you had to train a new person tomorrow, how would they do a once-every-two-months task you showed them quickly on day 2? She can’t follow along with something that doesn’t exist.
    For processes that are done regularly – document them too.

    Possibly these more involved parts of the job just aren’t for her – maybe you drop her hours to 2/3 days a week and the other days you have someone else doing the work? That person could probably be virtual as well

  69. WestsideStory*

    Can I just be real simple here? Is it possible you can offload billing to an outsourced provider? Getting the invoices paid is critical to a small business. I would urge you to look into your options if you don’t have the time to do it yourself or constantly follow up on her efforts.
    Your employee would do better I’m sure if you take this task away, and then see where she might be able to add value elsewhere in your company.

    1. WestsideStory*

      Also I know the billing issue is an “example” but whatever the second task is can most likely be outsourced.

    2. Rachel*

      It is entirely possible it is less expensive to pay for 1 full time position than a part time position and the outsourcing company.

  70. Wha……?*

    This reminds me of my own ADHD. Despite this, as a manager, I make it my business to stay up to date with training and guidance from neurodivergent (ND) experts who are ND themselves as to the best ways to support my ND team members and colleagues, as well as any ideas I can implement for myself

    Basic things that I find really helpful include: clearly written SOPs (no missing steps or assumed knowledge); written deadlines and written notification of any changes to deadlines; as part of training and professional development, providing written examples of a completed task/project that are excellent, good, bad, and adequate, with notations as to what’s excellent, good, bad, adequate, etc about each example, why they have that rating, and what could be improved or avoided; and really clearly written job descriptions and to do lists.

    Clear expectations and goal posts that do not move are essential. Flexible schedules, adjusted start and finish times, and WFH/hybrid work are also absolutely essential for many ND workers. Ask them what you can do to support them and set them up for success.

    I could write an essay on this, to be honest. But whether your employee is ND or neurotypical, don’t even consider thinking about a PIP, formal or informal, until you have put accommodations in place and given the employee at least 3 months to adjust to them. It’s an absolute waste of everyone’s time and effort otherwise.

  71. Hosta*

    I see a lot of people in the comments suggesting even more tools and potential accommodations, including ones I suspect you’ve tried. At the end of the day Lenore is an adult and whatever the root cause of her problems is, she needs to own them and either ask for the accommodations she needs to find the systems that work for her.

    One of my direct report manages his daily task list in email, including emailing himself tasks. Another person uses Asana. Someone else uses a spreadsheet. I use a combo of a bullet journal and my calendar (literally scheduling time for things like followup). At my insistence we use a common tool for tracking collaborative work, but for independent work I focus on the outcomes “You need to meet your deadlines”, “You need to be able to give me an accurate status report within 5 minutes on any of your ongoing projects”, “You need to be able to independently do core job skills after a tutorial or two.” And then I let them figure out what works for them. I show them my methods, point them at other resources we have, but mostly I let them be responsible for themselves. I will offer coaching on organizational skills as part of an improvement plan, but it always has an end date, usually 3 months, and we discuss from the beginning that I’m going to help them for 6 weeks and then spend 6 weeks removing myself so they can do it on their own.

    And one potentially unhelpful solution. If she’s struggling to remember which buttons to push for specific tasks has she tried looking on youtube or just on Google for video tutorials for those tasks? Personally I don’t learn well from video, but a lot of folks really like it. That said, it sounds like she’s the kind of person who would forget that she could look up a tutorial online.

  72. Lizzie (with the deaf cat)*

    What kind of work did Lenore do before she started this job? That might give you an idea of her capabilities in general.
    I think the OP is getting a bit trapped by having done Lenore’s role herself, in the past – so she knows how to do it, what is involved, what strategies to use etc – and is assuming that IF ONLY the right strategies can be found for Lenore, then she too will be able to do the job. Whereas Lenore has been showing that she actually cannot do the job as required, for three years. She can apparently do the simple part of the job, with some oversight from OP, but cannot do any of the more complex and necessary parts of the role. And has not shown herself able to do them over a three year timespan with a lot of assistance.
    OP, this looks like an “if I can do it, anyone can do it” type of thinking trap. But Lenore is not able to do the job. There is no indication at all that this will change (or that this distresses her).
    Help her to find a job elsewhere which only requires she use the ability she has, and hire someone who can do the job as you require it done.
    People can be loveable, and loyal, and you can be very attached to them, but that does not guarantee they have the ability to do a particular job, no matter how much help to provide.

  73. Cacofonix*

    Sorry to say, the problem isn’t Lenore. After 3 years she’s not the right fit. The problem is the LW placing more value on the person rather than what she needs from a person in this role. And that’s okay, as long as you’re willing to do what Lenore can’t or won’t. Sorry, LW. You’ve bent yourself into a pretzel to serve Lenore’s needs. Not your own and definitely not for your organization. 3 options: Change the role, change the employee, or accept that your role is to hand hold for as long as you work there or until you decide that “I will never fire her” doesn’t work for you anymore.

  74. Chocoglow*

    Honestly, Lenore needs to be fired. It sounds harsh, but this is nearly identical to a former friend of mine in terms of inability to handle the job. That friend had to be written up three times, PIP-ed, and finally fired because she would act as clueless as this and let others handhold her when I refused. (I had no say in her hiring, it was Arby’s and my manager thought I was being mean when I warned her.) Do I think Lenore is doing it maliciously? No. Do I think she’s gotten used to LW’s covering her? Yes.

    LW, please, please take Alison’s advice and sit her down with clear expectations, and frankly, make it clear that her job is 100% dependent on HER doing it. There’s no magical organizational fairy to help Lenore be better, only dropping the coddling will.

  75. StarTrek Nutcase*

    I think LW’s intentions are admirable and she has already suggested more than enough options & help. I had a coworker who also had no organizational skills, and I tried numerous ways to train/teach her very basic ones for her one task (processing invoices). For whatever reason (and ultimately it doesn’t matter), she simply couldn’t do so. Ultimately, I gave up and discussed with our supervisor my unwillingness to devote more time to a hopeless cause. Because no one wanted to be “mean” & fire her (I would have), at least 4 times that year we had critical vendors cut us off (think oxygen for patients) and I would be forced to straighten out her clusterf*ck. I retired 2 years later, with her still unable to do her basic job.

  76. DefinitiveAnn*

    Years ago I was talking with a client about one of their subordinates that I often worked with. I mentioned “They work really hard and are great to work with.” The response was, “Yeah, they work hard, but they aren’t at all effective at their work.” It was an interesting perspective.

  77. ADHDinPNW*

    Oh, Lenore…
    I remember being in the exact same situation with a very similar job. I realized it wasn’t going to work out and quit pretty early in though. Now I work somewhere much more suited to my skills.

    It sounds like Lenore is not a good fit. I hope she can find something else to do. Giving her a PIP that gives her enough time to find another job is probably the kindest thing at this point.

  78. Yap, yap, yap*

    It’s time to both find a simple automated system AND let this employee go. As a.former small business owner there are literally dozens of inexpensive ways to accomplish tasks but it requires an employee willing to do the work which this one is unwilling to do. Doesn’t matter why, just needs to happen. A topic for another letter, but why on earth does any employer tolerate this?? Seen it dozens of times, but don’t understand at all.

    1. Drowning in Spreadsheets*

      …which this one is unwilling to do.

      I did wonder if there was some Bartleby, “I would prefer not to,” going on.

  79. Danie*

    OP, have you asked Lenore what systems and tools work best for her? And are there systems in place to help her track the orders she’s meant to be tracking, or is she expected to create it herself?

    Is it a case of her doing a job that is technically a full time job for one person, but that the job is badly designed? Or is it a case of her doing the work of 2 or more people? Can you maybe split the job so she can focus on the duties she’s great at, or can you split the days/week so that she’s focused on Job A 50% of the time, and Job B the other 50% – whether it’s 2.5 days a week each, or a fortnightly cycle where Week 1 is Job A, and Week 2 is Job B?

    I’ve got ADHD, but wasn’t diagnosed or treated until I was in my mid 30s, and it did create issues for me in some earlier jobs. Flexible and adjusted work hours and remote work have both been extremely beneficial for me as it allows me to work in my own space, with my own systems, and at the time of day that I am most productive. I’d ask Lenore – or get someone in HR with DEI experience to ask Lenore – what would help her be her best and most productive self at work.

  80. homewort*

    I have to agree with Alison here; it comes across as you trying to fix this for L, but she needs to be equally invested in gaining these skills and developing her own strategies. Continually suggesting different fixes might actually be contributing to her struggling to find and stick with a system, which can take practice. I think having a conversation with L where you get on the same page that this is an important part of her job and explain that what you need her to do, is a really good idea. And if L does have these issues across her life, it might prompt her to review that and as other commenters have discussed, figure out what might be going on for her; but as her employer, that’s not on you to do, nor is appropriate.

  81. Pink Candyfloss*

    LW, when you walk her through one of the complicated tasks, can you screen record the steps as you do them and then leave her the video file to watch next time? That at least keeps you from having to sit there and do it again and again.

    Agree with AAM that Lenore may not be the right fit for this role. It sounds like she is failing some key skills necessary to perform well at this job.

  82. Alexander Graham Yell*

    This reminds me of the job I had before I got my ADHD diagnosis – and unfortunately this letter could have been written by my old boss. We all liked each other a lot, but the things I was good at were not the key requirements for the role, and it was impacting the business.

    Things my boss did that I appreciated: Set clear expectations with deadlines. Trusted me to do my job. Let me find solutions to the problems he raised. Making it clear that just because I could find something didn’t mean my organization was up to par – it had to be clear and easy for anybody walking into the file room looking for something.

    Things I was incapable of doing: Staying organized. Staying on top of things. Maintaining a filing system. Keeping track of key dates.

    Things I tried: Calendar reminders. Colour coding. Email reminders. Signs on my door. An hour-by-hour system that I designed. Focus mode on all devices.

    Ultimately, no matter how much we liked each other, I was not a good fit for the role. It sounds like it’s the case for you and Lenore, as well. When my boss let me go, he was really clear about what parts of the job I was good at, what kinds of roles would be a good fit for me based on that, and what he could give an enthusiastic reference for. (I’m not in any of the roles he suggested, but looking back he was absolutely right about what my strengths were and I put them to use in my current role.) It may be that the best thing you can do for Lenore is help her figure out what her next step is, and help her get set up for it as best you can (without compromising your ability to do your job).

  83. kiki*

    It sounds to me like Lenore isn’t trying with the new systems and failing, but that she’s really not using them at all. I’m wondering if LW has been really clear that the expectation is that Lenore will use a tracking system of some sort and that updating it and keeping it going is actually a core responsibility of her job?

    Something I’ve seen folks have trouble with is realizing that taking time to organize and use organization tools (Asana, a ledger, whatever) is actually time well-spent and part of what they’re being paid for. I’ve seen a lot of people who are really harried at their jobs say, “Oh, I don’t have time for that tracking tool! I’ll just remember– I’m being paid for outcomes not fiddling with Asana” but they’re not connecting that creating maintainable processes for remembering and getting things done well is part of what they’re paid for. I’m wondering if it might help Lenore to say, “hey, you have to use Asana. I expect this to be updated every day. Updating Asana daily is a core task of your job now.” Don’t give her a bunch of tool options, don’t give her the option of just not using one. Tell her that there is a system and she has to use it going forward. If in a few months she suggests another system she prefers, let her have at it, but for now, Asana is the system for her.

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