how to tell an assistant “don’t tell me the process — just fix it!”

A reader writes:

I got a new job about a year ago as a deputy director. This is my first time managing anyone, and it has been quite the learning experience. I’ve been here a year, and my boss has been in this role for 18 months. I really like my job and the people I work with. It is very busy, so I’m working on time management.

The director and I share an executive assistant. When I started, the exec assistant had held this role for over 10 years for multiple directors. The office was a well oiled machine, and she was fantastic — saw ways to make our lives easier and just did it. She got a promotion and we hired someone new, who I’ll call Amy.

Amy had been the exec assistant for a director at our sister company before, so we expected a smooth transition. She’s been here a few months. It’s going okay (B-, I’d say), but I’m trying to figure out which of the following things are worth trying to fix with her, and which are just personal quirks and to let it go. She excels in other areas of the job.

1) Amy constantly tells you the process she is taking to fix a problem, instead of just fixing it. Example: The director asks Amy to find out the status of X document. Amy calls Bob, who isn’t there. Amy tells the director that Bob isn’t there and asks if she should keep calling around (yes). Amy calls Sue, who isn’t there, and again asks the director if she should keep calling around (yes). This happened yesterday literally five times while Amy called various people until she got someone. This is a daily issue. How do we address that, or do we give it time since she is new and maybe unsure of the process? (My dad’s line is “Don’t tell me how to build the clock when I just asked for the time.” It’s that issue constantly.)

2) She is loud. Very loud. She is just outside my office (less than five feet from me). It may be a hearing issue, so I’m tempted to let this go and close my door for all phone calls and meetings instead.

3) She schedules a lot of meetings for us, and this was brought up in the interview and she said she had experience with that. Well, she seems to get constantly stressed about it. I’d like to decrease her stress about this, but it is also a primary function of the job. She also does the process thing with us about this too, which is unnecessary.

4) Frequently she has questions about the job or a policy that neither the director nor I know (and honestly don’t need to know — for example, I don’t know how we order toner). She knows who to ask of the other exec assistants. When these things come up, I will say “I don’t know, ask Dave or Sue.” But she will continue to discuss what the problem is, even after I say this. I’ve started reiterating, “Again, I don’t know, ask Dave or Sue” and then walking into my office to keep working. When she does find out, she will then update us on whatever it is — which we really don’t need to know.

Lately I’m working on prioritizing my time better at work, and a big time suck are all of the conversations surrounding 1, 3, and 4. Since Amy started, I’m spending probably 45-60 minutes a day on these items. Suggestions? Since she is new, I’d like to start off on the right foot and she is going great in most areas. I do want her to enjoy her job and feel like she can talk to us and communicate with us, so I’m worried about shutting down all of it.

Be straightforward with her!

If she were doing a technical part of her job wrong — for example, printing something upside down or saving files in the wrong place — you probably wouldn’t think twice about explaining what she needed to do differently, right? You just need to do the same thing here, but I suspect you’re feeling less confident about it because these feel like personality issues, and those feel more awkward to address.

But if you reframe them in your mind as work issues that are no different from printing something incorrectly, you’ll probably find it easier to address … and as a bonus, you’re more likely to use a tone and approach that won’t make Amy feel weird about it either.

Do you have regular check-in meetings with her where you talk about her work? If so, that will make it easier because you already have an existing place where it’s normal to give feedback. But if you don’t, ask to sit down with her to check in on how things are going since it’s been a few months since she started. Tell her about the things that are going well, and then address the stuff you’re hoping she’ll tweak.

I think you can combine #1 and #4 since they’re similar. You could say something like this: “I’ve noticed that you’ll often give Jane and me a lot of information about the process you’re taking to fix a problem, like with X earlier this week or Y today. I appreciate that you want to keep us in the loop, but I’d actually rather you not keep us posted to that extent, because we have other work we’ve got to stay focused on. Instead, I’d rather you just fix the problem and only loop us back in if something happens where we need to be involved. It can be pretty distracting to get updates along the way, and we trust you to handle it.”

Then if she keeps doing it, then in the moment you can say, “Actually this is the sort of thing we were talking about that I’d rather you not bring us updates on. Go ahead and do whatever you need to do to handle this, and just let me know if you run into a problem you can’t solve on your own.”

You may need to repeat that a few times before it fully sinks in. If you don’t see any change after a few times of this, then you’ve got to have a more serious conversation about it (“Hey, we talked about this but it’s still happening; tell me what’s going on that’s causing our disconnect on this”) and start to consider whether she’s the right fit for the job. But for now, start with just telling her directly what you want her to do differently, and that may solve it.

About her stress in scheduling meetings: As part of the conversation above, you could also say, “I could be off-base about this, but my sense is that you’re finding the process of scheduling meetings to be pretty stressful. It’s a core part of the job so I want to make sure that you get to a place where you’re comfortable with it, and don’t need to pull us into the process. Is there a particular part that you’re having trouble with, or anything that would help?”

With the loudness, you’re better off addressing that in the moment rather than in a meeting about her performance generally. Again, being really matter-of-fact about it will keep it less weird: When she’s being too loud, stick your head out your door and say, “Hey, could you keep it down out here? I’m having trouble hearing my phone call.”

If you do that a few times and the problem continues, at that point you’ll need to say something like, “You’ve probably noticed I’ve asked you to keep it down a few times. Your voice carries into my office and sometimes makes it hard to hear when I’m meeting with someone or on the phone, so can you keep it down generally?” After that, if it proves hard for her to control, then yeah, you may need to just start closing your door for meetings and calls, but I’d at least try to address it first.

With all of this, though, the idea is to be matter-of-fact and direct. The basic format is “here’s what I’m seeing, and here’s what I’d like you to do differently” — since if you don’t tell her, then she won’t know. It doesn’t have to be a huge deal, just a simple correction the same way you’d correct anything else work-related that felt less personal.

Read an update to this letter here.

{ 248 comments… read them below }

  1. Snark*

    I hate to jump right to the airlock lever, but….does this person actually sound like a particularly good fit for an executive assistant role? She’s not coming off like a good fit, and instead of being an assistant, she’s being distracting, loud, and demanding of a very high level of input and labor in the course of “assisting.”

    1. hayling*

      Airlock lever, that’s a great metaphor. (And yeah, I am tempted to agree with you.)

      1. Letter writer*

        OP here –
        I work for the government and letting someone go is next to impossible (ex: employee wasn’t working her required hours, arriving 2+hours late daily for a job where customer service role where the desk must be covered. Did a performance improvement plan, coaching, etc. Her behavior didn’t improve, but she’s still here. HR /legal wouldn’t let us fire her). Her 6 month probationary mark was last week. Also, I do think this could be manageable, especially using Alison’s script.

        1. LBG*

          If she is still in her probationary period, can’t you remove her without cause? I work for the Gov’t and we have a 1-3 year (depending on which office you are in) probationary period. Can be fired for any/no reason. Although it sounds like you want to work through this with her. I’d just keep an eye on that final probationary end date. Our HR used to email us when an employee was getting close to the end.

          1. Middle School Teacher*

            Sorry, if I read the letter writer correctly, her probationary end date was last week, so it’s gone. They missed their chance to just fire her.

            1. Middle School Teacher*

              To add: assuming her probationary period is six months? If it’s longer, then LBG is correct.

          2. Safetykats*

            You can also absolutely dismiss her for cause if she misrepresented her experience in her application – which, if you posted for someone who had experience as an executive assistant, it sounds like she did.

            I would definitively be talking to HR to see how you wound up with somebody so clearly unqualified. Honestly, you need to do that anyway or you’re not likely to do better the next time around.

            1. Confused*

              Oh come on. This isn’t misrepresenting! Execs have different styles and believe it or not, some will harp on every employee, including assistants, for every detail of their day. OP says this woman is good at other parts of her job and not only that, she hasn’t even talked to the woman about this problem! She can’t adjust her style if she doesn’t know!

              1. Focus People*

                Thank you! She might have worked for a micromanager before. They exist in all organizations and at all levels.

                1. Mytwocents*

                  I was just coming here to say this. I know that I have a habit of too much updating due to a previously micromanaging boss (stuff like this can really get ingrained), but would be happy to hear someone tell me they trust me and don’t need so much info!

        2. Bea*

          This is why she’s still there…I knew there had to be a catch. None of my bosses would deal with this BS.

        3. MakesThings*

          When you say HR/legal wouldn’t let you fire the person who came in late every day… I know it’s true because you say so, but I’m super curious, how does that actually work? Like, there must be a termination process with clear steps somewhere on the books. How is it not possible to just… use it?
          I get that it’s challenging, but surely it has to be possible?
          I’m just curious. If you want to blow off steam by describing this particular dysfunction, I’m happy to read about it.

          1. Cacwgrl*

            I work HR for the gov’t, but no idea if it’s the same as OP… but, terminating someone in the pro period can be easy, if the management chain agrees. A supervisor can document everything, counsel the employee, consult HR and labor relations and get buy in to terminate, but if the deciding official doesn’t agree, we can’t make them terminate. The general mood depends on support in the highest levels of the organization. Right now, senior leaders support removing those people so terminating is easier, but again, HR can only recommend and not force a term. I have at least one issue where we all supported it but at the last minute, the deciding official “felt bad” and stopped it, then left the org. We’re now stuck with the not great performer and we’re outside the pro period. Ugh.

            1. MakesThings*

              And if an employee decides to start sucking after the pro period ends? What’s your recourse? I always assumed that in government jobs, there must be a series of steps, outlined in an official document somewhere, of what has to happen to initiate, process, and complete, a termination. Is that not a thing?

              1. Letter writer*

                OP here.
                Government jobs – we are constantly in fear of being sued. And we are sued a lot.
                During the probationary period it is easy. Afterwards it is hard.
                I’ve only been here for 18 months. There was a big change in leadership (for the better) but we are working through it.
                That particular employee hadn’t had an annual review in years. I wasn’t her direct supervisor, but her managers boss. The manager left in a blaze of glory (1st management lesson here – she had been a problem employee for years and my predecessors never addressed it. I did, and she left. She was key to the roll out of a massive multimillion dollar IT system on 9/1… and she 15 days before with no notice. Then all of this other stuff came to light.
                Her entire team teleworked poorly. Always unavailable, never met deliverables. When I became their direct supervisor I also found out that at least half of their jobs had been made obsolete, so I have NO IDEA what they were doing at home, but clearly not working. We pulled the entire team back to the office, knowing morale would be hit but that this was a toxic team and situation. That’s when the employee (who I’ll call Barb) routinely arrived late every single day by at least 2 hours. I coached her, we did a performance improvement plan, etc. In the end legal wouldn’t even consider firing her because – I’m a 36 yr old white female and she’s an over 40 black female. She’s a protected class and could sue the pants off us. Plus, from the outside it looks like her old boss (who left) didn’t have issue and now she reports to this young white lady who has problems with her. Note – that’s what our legal department said to me.
                Instead we split that team up, none of them report to me directly, and we were strategic about where we place Barb. We’re documenting everything and will try again. Good news – the rest of the team have done a complete 180 and are thriving in their jobs. They seem happy, engaged, and most got salary increases this year too (which is rare – gov’t).

                We do have a series of steps we have to do. It is just incredibly time consuming and legal rarely goes for it.
                Agree with the general comment about needing exec leadership buy in. We have 4,000 employees and every single firing has to run through the head guy. Some days he agrees, some days he doesn’t. We have cleaned house on some other situations, it just usually takes at least 6-9 months of tons of documentation and coaching, many meetings with legal, and then we go for it.

                1. MakesThings*

                  Thanks for the background- interesting perspective from the inside!
                  I feel like I don’t know enough about legal issues to weigh in on the lawsuit likelihood, but I completely get how the fact that everything needs to pass through the head honcho can slow down your process.

        1. No Green No Haze*

          (Just finished Persepolis Rising. Holy cow. There is no such thing as “too much.” Need more.)

          1. Jules the 3rd*

            Need more.

            So, we can *totally* start using Expanse characters here, right?
            – Jules Pierre, Strickland and Errinwright for bad bosses;
            – Julie Mao, Diogo and Prax for inexperienced interns;
            – Holden, Bobby, Naomi, and Drummer for various manager varieties;
            – Miller and Clarissa (and Amos?) for troubled co-workers;
            – Alex and Cotyar for sane co-workers
            – Chrisjen for Owners / CEOs / Board Chairs / Preferred Deity.

            I love Chrisjen Avasarala with a fiery passion. But Bobby would be a better boss.

          1. Snark*

            “It can be pretty distracting to get updates along the way, and we trust you to handle it, sasa ke?”

    2. beanie beans*

      To me it doesn’t sound like she is a terrible employee, just needs some guidance, especially if she is new. She may just be unsure of herself in a new position and wanting to make sure she’s going through the right process (and continuing to for longer than most might…).

      I’m glad Letter Writer says the situation could be manageable – I think if she’s told directly how to approach these issues in the future, it will be a big help for everyone!

    3. Wintermute*

      I think she’s a potential great fit who is carrying some battle scars from working with a micromanager, myself. Everything she’s doing sounds like she worked for someone who expected her to be a mindreader and magically know where the line between “calling enough people to get something done” and an expletive-laden “why are you wasting half your afternoon [it’s actually been half an hour] on this?!? What am I paying you for anyway?!?!?!?” was a moving and impossible-to-hit target.

      It sounds like she came from an environment where she was expected to have the minutae gone over and to explain exhaustively, and to not take much initiative. This also explains stress around meetings because they can be particularly fraught because your boss is worried about them and projecting that anxiety all over you, or has unrealistic expectations of your ability to manage their image in front of clients (internal or external)

      1. Confused*

        Exactly! Some of these comments are so mean! Some execs are micromanagers and want an assistant like the one described in the letter. OP hasn’t brought this up yet and the woman is not a mind reader!

        1. someone*

          Letter writer has brought the issue up: “But she will continue to discuss what the problem is, even after I say this. I’ve started reiterating“

          1. Clare*

            I think this is a classic problem of a manager not being as direct & clear as she thinks she is.

          2. Elsajeni*

            But it sounds like that’s been in response to saying “I don’t know, ask Dave or Sue” each individual time she asks a question, not in response to telling her something like “You keep asking me questions about XYZ procedures — please just go straight to asking Dave or Sue, who are the experts on XYZ, and only let me know if they aren’t able to help you.” That’s what I’d call bringing the issue up; saying “I don’t know, ask Dave or Sue” is just answering her question (and maybe reinforcing that you’re the right person to ask and will direct her to the right resources).

      2. Girl Who Likes the Trolley Song*

        Thank you. This is exactly what I was thinking.

        I’ve dealt with many years of “that’s not the way I would have done it” that I’m occasionally hesitant to make a move without getting “permission” first. Of course, I rarely do this with something so simple as ordering toner, except on days when I can tell the irritation level is already high.

        If she’s doing the job well otherwise, let her know, but don’t be patronizing about it. Eventually her self-confidence will build and she won’t feel the need to run to you for every little detail.

        1. TardyTardis*

          And loudness can be cured. I was kind of loud myself when I first started at the library, but developed an Indoor Voice which I can switch to at need (husband is slightly deaf, so I talk louder at home).

      3. TerDickison*

        I definitely agree with you that it sounds like she worked for a micro-manager before. These are the classic symptoms of someone who had to deal with that. I’m an executive assistant for the CEO and COO of a company and much of my job comes down to adjusting my “assistant style” to fit each of them individually. One is a very particular type who can veer into micromanagement while the other is the very traditional “make magical things happen for me and don’t tell me how you did it.” I end up being two different assistants on a daily basis.

        I was the assistant to the CEO only for 15 years. Two years ago, the COO was added to my responsibilities and I can tell you that even for someone with many years of experience, that adjustment period was stressful. It took a good 6 months to a year before my previous comfort level returned. It’s difficult to figure out the psychology of all the people you’re supporting, but eventually you do and I think this assistant will as well.

      4. Kelly O*

        I was about to say something very similar.

        Sometimes what you think you’re saying and what you’re actually saying is not the same thing. Amy may be trying to clarify in a tactful and polite way rather than just pointing out that what you’ve said and what you seem to expect may not be the same thing.

        I’ve been an AA/EA/some sort of administrative support role for 20 years now. In my experience, it is more often true that the instructions will change than remain the same. EA/AAs are supposed to be “mind readers” – we try to figure out what it is you need before you need it, or figure out what changed in the interim.

        Amy may have had a horrible boss before and is mimicking behavior because that’s what she knows. I’m not saying everything is excusable, and yes you need to get over past experiences and move the heck on, but before you pitch her out of the boat, stop and think about how you’re presenting information, and how you can coach her.

        Support staff need coaching too. We’re often stuck as “overhead” – everyone wants to mentor the flavor of the month sales guy or the person who is making big waves, but a great support person can save you in more ways than you realize.

        Talk to her. Just sit down and talk about how she’s doing, what you expect, and see if you can get to know her. There is so much trust required to be truly successful, and she may need a little encouragement, while you might want to be as objective as possible about yourself.

  2. Detective Amy Santiago*

    #1 makes me feel like she may have worked for a micromanager in the past. Someone who forced her to justify every single decision she made. I’ve been there and that is a difficult habit to break. Alison’s script is a good place to start and just keep reiterating that you trust her to make those decisions without your input.

    1. Hills to Die on*

      Yes, there are so many people (my current boss included) who love the nit details of every little thing. It’s terribly inefficient but some people really like running their professioanl lives that way. I’d bet anything that’s the case here.

      1. Oxford Comma*

        A friend of mine worked for a boss who wanted her to email her for everything–even questions or instances where a simple verbal communication would have served just as well. It sounded insane. The boss moved onto another position and now the new boss could not understand why my friend was constantly emailing him. They worked it out, but it’s something my friend still struggles with because the old boss had drilled it into her that This Is How You Will Do It.

        1. Bigglesworth*

          I’m currently dealing with this to some extent. My previous position required me to know my time down to the minute (ex. clock-in, clock-out, lunch, etc.). My current role is very lax about such things. Get your work done and don’t eat lunch at your desk and you’re fine. 2 months in and I’m still struggling.

          1. Kyrielle*

            My previous job needed me to track my time pretty tightly (down to 1/10 of an hour), because it was used in part of the revenue realization formula (well, some of it was) and in other metrics.

            My current place doesn’t want me to tell them anything about my time unless it has to do with time off. They don’t care. I found it really hard to adapt to and notice when I was under or over – so I actually installed a free-lancer’s time-tracking app on my phone and keep rough track of my hours (but not what they’re on, so much easier than my last job) just so I have a feel for where I am.

            It’s pretty silly and maybe someday I’ll give it up – but it solved the problem of my being uneasy with a “short” day for one day and a “long” on the next and whether I actually was there a reasonable amount of time.

        2. Adlib*

          Yep, it can be very hard to un-train. Some people continue to do things even if they don’t make sense and are actually inefficient.

        3. I like rusty spoons*

          I had a boss who wanted to review every single e-mail to clients or suppliers before I sent it. One time a client replied to an email with a question. “Did you take {xyz} into account?” Something like that. I replied that yes, we did indeed think about that and we determined that it won’t be a problem. Boss had a “talk” with me about it. Told me I should have discussed it with him first. Even though we already discussed it the day before, and detimined that it won’t be a problem. Which is what I told the client when he asked.

          This boss eventually resigned because the stress was killing him. His own damn fault.

          I hate micro-managers.

        4. TardyTardis*

          I wanted one boss to email *me* on everything because she’d forget she told me to do stuff and then got on me for doing the stuff.

      2. AliceBG*

        Same — in my case, it was my own manager who did this to me. Some people just love to regale you with every last detail of every little thing they do!

    2. MuseumChick*

      This was my first thought. It can take awhile to break the habit of clearing everything when you go from a micro-manager to a non-micro-manager.

    3. Serin*

      Yep, I was just about to say that. Learned helplessness is one of the traits people develop in response to micromanagement — when every decision you make, no matter how small, will be the wrong one, you just stop making any decisions at all.

        1. AnnaBananna*

          I know, right? It perfectly encapsulates this poor assistant.

          LW, you’re going to need some patience with her. Just reminding her that you hired her for her judgement, not for her ability to follow instructions should be a good thing for her confidence. She was likely stripped of it at her last role. Just keep reminding her that you totally trust that she can get things done without hand holding. You may have to remind her quite a bit for the next while but she’ll slowly get it.

          As for scheduling, she’s probably dealing with other schedulers who have their own processes that don’t jive with her own. It can be an adjustment. Is there anybody else in the office who has dealt with the scheduling/schedulers that could maybe be her point person for a while? That way she can go to them for questions and be less verbally stressed right outside of your office.

      1. No Green No Haze*

        This is a much better way to phrase what I was trying to get at in discussing the post about the employees who wouldn’t complain about the water being off or the internet being functional. You keep getting your head chopped off, you stop sticking it out of the hole for any reason, no matter how petty.

      2. I like rusty spoons*

        I have been damaged by my micro-manager.
        I do something, it’s wrong. I have to do it HIS way. So I say OK, and I do exactly what he told me. Nope. Still wrong. Now it’s too long, now it’s too short. Too long again. Eventually he gets fed-up and does it himself, and make a mess of it. I ignore it, because seriously, it’s his own damn fault. But when he eventually discovers the mess, it’s somehow still my fault.
        Now I just don’t care anymore.

    4. Turquoisecow*

      I wonder if it’s also a new person thing. It sounds like she hasn’t worked with OP long, so maybe she’s not sure of the process and thinks OP wants to be more involved. I know that there have been times in which I’ve wanted to go about fixing a problem a certain way and then after I’d fixed it was told that wasn’t proper procedure.

      OP, are these constant check-ins on things she’s never done before (like fixing a printer jam) or are they things she’s done multiple times. If she’s still asking how to fix the printer and checking in to update you after the eighteenth time, that’s a problem, but if it’s the first time then I can understand why she’d think you want to be kept in the loop.

      Also, as a new person, I’m generally very hesitant to go to people or ask questions of them for fear of appearing stupid. Maybe this is what’s happening.

      1. Letter writer*

        OP Here. I wrote in a few months ago. It has gotten better, since many of the issues were things she hadn’t done before, and were more about policy questions (how do you get a bill paid, etc). After she has figured out how to do it, she doesn’t constantly check back in. Then she just fixes it.
        That’s gotten better, but I do like these scripts. I’ll have to see how it plays out the next time it happens and address it.

    5. Princess Consuela Banana Hammock*

      I agree. We had an admin who did this, and it turned out the previous Director was extremely abusive and belittling, and that Director would blow up at the admin for doing very basic (and reasonable) things like contacting the appropriate people to fix a problem. It took us 2 years to get her to feel ok with taking initiative on her own.

    6. LilySparrow*

      This is the very first thing that jumped to mind. I have had bosses who would spend significant amounts of time every day badgering me about every detail of my work process, and took some kind of twisted pleasure in questioning the most minor errors or deviations from their instructions.

      Sometimes to an insane degree. I once transposed two digits in a phone number on a routine, non-urgent, non-client related call. Wrong number, “sorry,” dial again, right?

      My boss spent at least 20 minutes questioning me repeatedly about “why” I transposed the digits. “Why?” Because it was a mistake. No, there had to be a reason it happened, and my boss was determined to find it and wanted me to develop and present a strategy to prevent it ever happening again.

      For a freaking wrong number.

      When I finally had results-oriented managers who trusted my skills and common sense, it was a revelation!

      1. Be the Change*

        Ooof, your boss sounds like my, um, I won’t say which relation. In his life, there was no such thing as a “mistake,” only egregious carelessness, apathy, and f*ckwittery…. Unless he was the person who screwed up, in which case it was the result of the tremendous pressure he was under from dealing with all the eejits in his life while being responsible for hundreds of people and making Very Consequential Decisions.

        1. Violet Honey*

          I have a relative like that, too. Every mistake you made is either an overt slight against him or an uncovering of the unconscious antipathy you must actually hold against him. It is soooooo exhausting.

      2. Corky's Wife Bonnie*

        Ugh, I once dropped a stapler (it didn’t break, it was perfectly fine) and my boss kept saying, “Why did you drop that??? What did you do wrong that you dropped that?? How do you hold things in your hand?? You should carry things differently.” You would have thought it was a priceless Faberge Egg the way he was going on.

      3. Tax Nerd*

        Oh dear. I have had bosses like this, and currently have a dotted line boss who does this. It’s not just time-sucking, it’s soul-sucking to deal with. It’s like a toddler with the “Why? Why? Why”, but you can’t just say “Because that’s the way it is.”

        As for OP’s #3 – does your assistant have rights to actually see what’s on your calendar? I’ve had a boss who tried to get me to schedule client meetings for her. However, her schedule showed as constantly busy in Outlook. I knew she’s put in commuting time, email-checking time, etc., and mark it to show as busy, but I’d always have to check whether she was really too busy, or actually available for a client then. If she just needed to listen in on a call, she could do it during her long commute, but if she actually had another client call, she of course couldn’t attend. If it was an important client meeting, it could pre-empt email checking time.

        I had to constantly check with her about whether it was okay to schedule a meeting or not. If she’d given me rights to see her actual meetings, or even just marked things as “tentative” or “working elsewhere”, it would have saved me a lot of grief.

      4. Jessica*

        Ugh, I related to both this wrong number and Bonnie’s stapler SO MUCH. Except add a twist—it’s also awful being the manager of the person who is not trusted. On one hand, I’m pressured that I should be delegating more to Employee. On the other hand, if I let him make a phone call and he transposes the digits, I hear about it for a year. And have to examine his process for dialing, and send him to keypad training, and develop strategies for distinguishing one number from another, and report back about it all, and have endless meetings with both him and my boss about it. So maybe next time I just make the damn phone call myself. Then I get told how overworked I am and how I need to make Employee responsible for some phone calls.

    7. Let's Talk About Splett*

      This is exactly I thought of. This happens a lot as an admin, actually. I will attempt steps A, B, C, D, E, F & G to deliver something, and when I go to my boss and tell him I can’t, he will 9 times out of 10 respond, “Just do B”. It’s just easier to explain what I have already attempted before I update him.

      1. Anononon*

        But here, it sounds like the admin is going back to the OP after each step and requesting more help.

        1. Detective Amy Santiago*

          I got the impression that it was more like:

          Amy: Okay, Thing is not working, I tried A to fix it and it didn’t help so now I’m going to try B.
          LW: Okay
          Amy: Well, B didn’t work either so now I’m going to try C, okay?
          LW: Yes, fine
          Amy: Ugh, C also didn’t work so now I guess I’ll do D.

          And so on and so on. That’s how I was reading it and that’s why my suggestion was for LW to clarify in no uncertain terms that Amy has the agency to take those steps without checking in.

          1. momofpeanutLiz*

            I read t the same way. The other thought I had was time. Bob isn’t in so should I wait for Bob to respond or move on to Sue? Making sure Amy understands which tasks can wait and which require immediate follow up might help.
            LW – please find out where X document is. I need to know by 2 pm
            LW – please find out where X document is. I have to have it back by next Thursday

            These scenarios require different action. Many bosses treat everything like A and admins burn good will getting everyone hyped up over something that could wait until Bob came back on Monday.

    8. hayling*

      I also had a passiveaggressive, micromanaging boss, who on top of that was hot and cold about how much she micromanaged. It drove me insane trying to predict how much she wanted to be looped in on. It took me a couple months in my new job (and my boss saying “really, I trust you”) to break the habit. And if I’m honest, I probably haven’t completely.

    9. Snack Management*

      I was thinking the same thing. When I’ve managed staff who came from micro-managed environments, I often used phrases like “I trust your judgement on this” to reinforce my trust in them doing their jobs on their own.

      1. SansaStark*

        I feel like this is the crucial second part to this issue. If you really don’t need the details AND you trust her to make a good decision, let her know that you have her back on any decisions/course of action she takes, even if it’s not the one that you’d take.

    10. Letter writer*

      OP here –
      An odd part of this – I/my director both know her old boss. My director worked for old boss awhile ago and he was very hands off. We assumed (wrongly I’m betting) that he was with his admin as well. I bet y’all are right and he used to micromanage Amy. I can proceed assuming that, and it is likely to help my mindset in coaching her.

      1. Observer*

        It’s highly likely that OldBoss treated you and your director VERY differently than the “girl who does stuff”. Please don’t kill me for the disrespect in that phrase – that’s not how *I* see it, but it’s quite possibly how Previous Boss saw it, and that would be reflected in how he managed her.

        1. Specialk9*

          Exactly. And, having worked in a lot of depts of the govt, it seemed like people of color were almost exclusively admins (women) or bosses (mostly men). I’m wondering if there might have been an intersection of color/gender that was at play too.

          1. Letter writer*

            OP here. Good points, but everyone in this situation is white (which is a whole other can of worms when it comes to diversity)
            Amy is mid 50s, white female. Her previous boss is mid 50s white male.
            Current director here is 50 white female. I’m mid 30s white female.

            1. Detective Amy Santiago*

              It could be more of a power differential than a diversity issue. Like, previous boss could think that since Amy is “just” an admin, she needs more hand holding than someone at a director level.

            2. Observer*

              These demographic details totally support this idea. Statistically speaking a middle aged white male is probably the most likely person to think this way about a woman of any age and color.

              Of course, that’s statistics, so it doesn’t prove anything. But the fact that Amy is white would not be likely to make much of a difference.

    11. That Would Be a Good Band Name*

      Like so many others, this was also my thought. It’s such a hard habit to break. I had toxicboss for 3 years and then awesomeboss for 6 years. I thought I had dropped many of my habits from toxicboss after working for awesomeboss for so long. However, when I got a new job I found myself slipping back into some of the habits from toxicboss because I just didn’t know how newboss was going to be and it was safer to assume the worst of newboss. (Safer in that I hate to be reprimanded at work, not safer in that I actually feared danger)

      1. Annoyed*

        It’s really like having PTSD from being abused, just abused at work instead of domestic abuse.

    12. green*

      I came here to say this. I worked for someone who was a MASSIVE micromanager, and if I didn’t check in at every step, it would come back and bite me in the butt. I think letting her know that you trust her judgment by telling her directly, and then by not criticizing her process after the fact will help break her of the habit.

      It could also be that the person she supported in her last position liked this kind of checking in constantly. I currently work in a similar sole, supporting a director who is also relatively new, and she likes to be in the loop on everything. But we also communicate openly and regularly about everything, which would include her telling me if I was checking in too much.

    13. CoveredInBees*

      Yup. This! I have worked for both a micromanager or someone who is totally uninvolved unless she felt like it, at which point she wanted a run down of everything going on. The OP’s assistant sounds like she worked for one of these.

    14. LSP*

      This used to be me, after working for someone who would fluctuate daily between “I feel out of the loop and need you to communicate with me more” and “I’m busy with other things right now. STOP EMAILING ME!” She was incredibly hard to read and impossible to anticipate, although she expected her staff to read her mind.

      When I started my first job directly after that, I had a habit of telling my new boss everything that I was doing. He never came right out and told me to stop, but I realized after a while that no one else in the office was doing that, so I began to only bring him in on things he needed to know. We ended up having a fantastic working relationship once I started trusting myself to do my job (and once I realized that no, he was not going to bite my head off).

    15. LizzE*

      One of my boss’ directors is a total micromanager. When she hired a temp assistant, everything this assistant did had to get this director’s sign off first – everything! The worst thing about it was the director didn’t even have the correct information, so I often found myself intervening to help this assistant. However, she was always reluctant to listen to me at first because “the director told her to do it this way.”

      There was definitely a lot of balls dropped initially until my boss intervened and told this director that once she delegates the task off to her assistant, she shouldn’t worry how it gets done. If assistant has questions or needs to understand the process better, she can talk to me. Worked out great – assistant not only had the correct information, but under my guidance she became more autonomous with her day-to-day work.

    16. aebhel*

      MTE. It could be a personal quirk, but I’ve seen this a lot with people who’ve had to get in the habit of justifying EVERY second of how they spend their work-days to their bosses, and don’t realize that good bosses don’t expect or want this.

    17. MissDisplaced*

      This was my immediate thought! Amy may have been “trained” by a former manager to be like this (except for the loud talking, which is probably just how she is). It will be hard to break and may take some time for here to feel she won’t “get in trouble” for not reporting every step.

    18. Laurelma__01!*

      I was wondering the same thing. She might have been in the habit of justifying everything she did. OR had a manager that questioned everything she did. There could be a lack of self confidence. Tell her about the loudness, etc. She’s new to the position, and she may be getting some pushback from others when it comes to the scheduling that you’re unaware of. The prior ex assistant might have been used to some of the personality quirks of other management members, known what worked and didn’t work to get cooperation. She might be dealing with someone that is just a pain in the rump. She would have also worked with an information hoarder, which might explain why she’s not aware of how things were done, some of the instructional knowledge that you expect her to have, might be if she worked with people like that.

  3. Hills to Die on*

    “Don’t give me the labor pains, just give me the baby” is a popular saying for a reason. When I am long-winded about telling my husband something, he will occasional say ‘just give me the baby’ or ‘can we skip the labor pain on this one?’. It may help as a quick reminder after you’ve had the larger discussion with her.

    1. Patches023*

      But what if she wants credit for the “labor pain” as well as the baby? It is a lot of effort to do all this tracking down. Maybe in the one on one meetings give her a space to talk about a project she feels she really did a lot on?

      1. SheLooksFamiliar*

        Even in one-on-one meetings, I hope the assistant keeps the ‘labor pain’ to a minimum. What’s being described here sounds like regular work – challenging for a new hire to get used to, but well within her ability. If the assistant knocks it out of the park for a special project or truly goes above and beyond, she absolutely should get some recognition from her boss. But everyday stuff? I hope she can take it in stride more.

        I also agree with other posters who wonder if the assistant had a micromanaging boss in her past.

      1. Letter writer*

        OP here –
        agreed, love the labor pains statement. Also, since reading this website, I’ve used “is this a hill we want to die on” so often.

  4. Oxford Comma*

    You mention that she had experience in this role before. I do wonder if she was expected to loop in her supervisor about process before. If that’s the case, Amy probably needs (and might even welcome) direction about how you want her to communicate.

  5. MuseumChick*

    The explain the whole processing thing could be something that has been expected of her at her previous position. I’ve had bosses like that where they either outright or subtly expect that I explain every step I am going to take/have taken/clear everything with them first.

  6. Victoria Nonprofit (USA)*

    One quick note: it doesn’t sound like the issue about giving too many updates is actually about updates, but more about ownership.

    I describe it as the difference between “wiping the counters” and “making sure the counters are clean.”

    You need an assistant who can be given a goal (“make sure the counters are clean”) and who has the ability (and authority) to do whatever she needs to do to accomplish that goal. When she hears her assignment, she should identify the best way to achieve it, try it, and if it doesn’t work then problem-solve until she gets it done. She’s coming back to you as soon as she’s finished wiping the counters, even if that didn’t get them clean.

    It actually goes a step beyond the counter metaphor. What you really need to be able to say is something like “Your job is to make sure that the kitchen is in good condition, so everyone can use it,” and she needs to be able to assess what that means and what she’ll need to do to accomplish it.

    1. Snark*

      This is really well put, and it’s so central to the role of an exec assistant that I wonder how much coaching she’s going to need before she’s effective at it.

    2. Princess Consuela Banana Hammock*

      This is a great analogy, and very apt. Hopefully it will help OP reframe their feedback so that Amy can understand what’s missing.

    3. Detective Amy Santiago*

      The key component here being that she has the ability and authority to do what she needs to do. And that she *knows* she has that ability and authority.

      1. Luna*

        Exactly, and those things don’t just happen overnight. She’s new, and it sounds like no one has yet had a conversation with her about these things, so she doesn’t realize what she’s doing wrong.

    4. AnotherAlison*

      I like this, too. The OP says that Amy is giving her the play-by-play of how she is fixing the problem, but the rest of the description seemed like Amy was actually asking for permission/direction at each step.

      I’m the type of person who will naturally give you the who story of the five people I had to call and the hoops I had to jump through to get your problem resolved, but I’m not going to ask your permission to call each of those people. I can also NOT give you that detail, but it helps if you have directly told me that you only want the end result. In engineering (my field), some people want to hear the process so they can pick apart what you did and tell you how they would have done it better, ha.

      1. RandomusernamebecauseIwasboredwiththelastone*

        I was just about to say NOOOO to this part “I’m the type of person who will naturally give you the who story of the five people I had to call and the hoops I had to jump through to get your problem resolved”

        right up until I read

        “I can also NOT give you that detail, but it helps if you have directly told me that you only want the end result. In engineering (my field), some people want to hear the process”

        and thought, oh carry on that’s normal and expected :)

      2. Nesprin*

        I’d flip it around-instead of asking her not to update you, give her an outlet for these instincts. Ask her to keep a log of the things she’s done for performance review time, or a Gantt chart of project stuff, so that you can keep up on her progress, then let her know that you only want to be notified verbally/email-ly if something is going wrong. If she brings something up uncessarily, point her back to the log.

        1. Babs*

          Please don’t ask her to do pointless, meaningless log work. It’s demeaning and sends mixed messages. I’ve been asked to create “tracking” mechanisms for sooo many things and when it isn’t used or dropped after a short period it feels crappy. I could only imagine how an asking to track all of her work and log how she’s completed something would come across. (It also is very micromanager-ly, in my opinion.)

    5. LQ*

      I love this metaphor and am going to go use it now with someone to explain why “I need you to make me a checklist of every single item in the kitchen that needs to get cleaned” isn’t appropriate for that role.

    6. Letter writer*

      OP here. Agreed – this is a central issue.
      Since I’ve written in, it has gotten somewhat better. But that is the central issue – for her to have ownership of these areas.

      1. LarsTheRealGirl*

        So it’s really important that you make sure that expectation is clear to her, and that you make it clear that she has the authority to make decisions.

        It really does sound like previous micromanagement PTSD, and you may need to overly communicate (for a short period of time) that you trust her to accomplish these tasks independently.

      2. designbot*

        I think that’s worth a higher level conversation, explaining the ownership issue to her. I’d also add that, as an executive assistant, it’s her job to make your jobs easier, which includes being really mindful of where your time is best spent. It’s not best spent instructing an assistant how to make phone calls, unless you need to provide the contact information for those calls.

    7. Blue Anne*

      This is a fantastic description, thank you. I’m actually having similar issues with my PA and I think I’m going to explain it to her this way, because just saying “unless it’s going to have a big impact on me, just do it and tell me what you did, don’t wait for approval” hasn’t worked.

      I don’t need to approve her using paper towels instead of a sponge, I just need to be able to trust that the counters are clean and only have to think about it if the counters are literally on fire now.

    8. JeanB in NC*

      I really want to steal part of your answer to include on my cover letter! I love that last paragraph.

    9. SusanIvanova*

      The story I got from my grandfather (career master sergeant from before WWII until he retired in the 70s):

      You are a new first lieutenant. You have a flagpole of height X, a rope of length Y, a hole, a sergeant, and 5 privates. How do you raise the flagpole?
      Correct answer: you say “Sergeant, raise that flagpole!”

    10. Courageous cat*

      This is good, and I will add to this that she might benefit from being given examples as to how to clean the kitchen. She may be coming back to OP over and over again because she doesn’t know if she’s allowed to/supposed to ask other people, or do X to make the counter clean, or try Y.

      If that’s a conversation that hasn’t been had, it would be worth trying to make sure she feels empowered to use all the tools in her arsenal to get things done.

  7. Lora*

    Is it possible that in her previous job her bosses didn’t really trust her to handle things on her own? I’ve had to train this type of behavior out of a LOT of technicians and assistants and the thing usually turned out to be, “previous boss thought I was an idiot and didn’t trust me to do my job”.

    It usually popped up initially when they’d over-explain why their time sheet had 41.325 hours or some such on it, and I was like, “you have done the job of three people this week, it’s cool, don’t worry about it,” and the very next week they’d over-explain a time sheet with 40.764 hours on it or whatever. If they needed a day off or a sick day there would similarly be a long explanation of every detail even AFTER I said “it’s fine thanks for letting me know, hope you feel better soon”.

    Takes a while to train it out of them. I’d say six solid months of reassurances that it’s totally fine, they are doing a good job, I trust them to be adults.

    Very occasionally there were some who felt like I should know how to do the job of everyone who ever worked under me if I thought I was the manager, but that was fairly rare and in more old school type companies where people really did rise out of the mailroom to CEO, sort of thing.

    1. Libervermis*

      I get the explaining-to-death from my college students a lot, even though I begin the semester telling them (and remind them periodically) that all I need is “I’m ill, I’ve turned in the assignment and I’ll get the notes from Friend” or “work really caught up with me this week, could I turn in the assignment by midnight tomorrow?” They’ve been so trained into a system that assumes they are lying or lazy that the response is to over-justify and to get explicit instructions before doing anything at all. And the more conscientious the student, the more repetitions it takes before they believe me that they’re not going to get in trouble for sometimes being human.

      1. Not So NewReader*

        This! When I returned to school, I could not believe what I was seeing. People were reduced down to 4 year olds to appease SOME certain individuals. It felt like kindergarten.

    2. Ruth (UK)*

      Sigh… I realise this is/was me a bit. My previous boss was very micromanagey and I had to justify everything. He was the sort of guy who wanted to be sure you had a very good reason for needing to leave work 5 minutes early as a one off, or would want you to make up the time if you were 3 minutes late, or quiz people about symptoms of they were ill etc. We frequently had to justify what we’d spent our time on etc which meant he really did want a step by step walkthrough of the process of anything we’d done. Who we’d called or asked, etc. I worked there for 4 years and it was my first office job.

      I’ve been at my current job 7 months now. I’ve only recently got used to not having to rehearse an explanation and/or justification for everything in preparation for interactions with my boss.

      1. Thankful for AAM*

        Same for me, 6 months post the micromanager (who also “picked on me” as the rest of the staff called it) and the current supervisor has to say to me all the time, “I trust you to do your job.” It can be both embarrassing and sad bc you know it means you are still wrestling with old manager in your head.

        I see myself in Amy and it is a good reminder that I still have more to undo. I read in AAM all the time about the damage that a toxic workplace can do but even knowing what it is, it still gets you!

  8. stephistication1*

    The previous director may have requested to be in the loop on everything or made Amy feel less inpowered to work autonomously. Great opportunity to empower her both for this role and the future.

    1. Decima Dewey*

      Just because your last boss was a micromanager doesn’t mean your new boss will be. I’ve been in the system for over 25 years, and I’ve had a *lot* of bosses. So when I get a new boss I know to watch and see how they work. For example, I had yesterday off because I’m working at another location on Saturday. Mr. Lastname hadn’t done the monthly report before he got here. When I came in today, I checked and saw he hadn’t gotten the numbers for June’s turnstile count, so I did that (I had shown him in the beginning of the month, but it probably slipped his mind). I knew that he didn’t know how to get the number of computer users for June, so I did that too. I’ll show him both things again in August. Otherwise, I will let him do the monthly report, answering questions as needed.

      Work with the boss you have, not your last one.

      1. TardyTardis*

        True! But sometimes it would be nice to have a boss to tell you how they want things, instead of expecting you to read their minds about the One True Way, especially since every boss has a different One True Way.

  9. caryatis*

    I think you’re going to have to live with the loudness. Loud people are loud, quiet people are quiet, and although a person can turn the volume up/down occasionally when needed, they’re just going to go back to the volume level that feels natural to them most of the time.

    1. Snark*

      You’re not wrong, but ultimately this person is there to help OP and the director. If she can’t manage her volume, then there’s reason to wonder whether she’s a good fit for this position and this office.

    2. Antilles*

      Some people are naturally louder than others, but it’s perfectly reasonable to ask someone to quiet down a bit. Will you still have some occasional times when she makes way too much noise or gets excited/angry and too loud or whatever? Sure. But if you ask politely (and remind her as appropriate), you can at least get it in her head to try to stay quiet most of the time.
      Expecting a loud person to be quiet 100% of the time might not be likely, but you can at least get her to talk quietly 80-90% of the time, which is still a huge improvement.

    3. Detective Amy Santiago*

      As a naturally loud person, I’m going to disagree with you. It is definitely something that can be coached/worked on.

        1. Detective Amy Santiago*

          I’ve gotten a lot better, but when I get really excited or angry, I tend to get loud and need a reminder. I think I shared this story before, but the most recent example of this was when I was having lunch with my mom, brother, and his fiancee and was explaining a spreadsheet I made for them. I got super loud because I love spreadsheets.

          (Yes, I chose this username for a reason)

          1. I'll think of a clever name later...maybe.*

            I once was asked to leave a bar for being too loud and passionate about Harry Potter. I was stone cold sober but very, very excited about discussing the finer points of the books (I think there were only 5 books released at the time) with another fan. My point is – I can get loud about things that I am passionate about so I make a point of not bringing those subjects up at work.

      1. hayling*

        Agree too. I used to be super loud, to the point that my nickname in college was Loud Hayling to differentiate me from another Hayling on my floor. I have just learned to moderate it.

    4. Oxford Comma*

      Possibly. Possibly not. I think once you’re made aware it’s an issue, you can work on it. Amy might need reminders to keep working on it, but it’s not a trait that can never be fixed.

    5. Tea, please*

      As a person with a quieter voice, I have to be conscious of when I need to be louder and regulate my volume accordingly. Like anything it takes practice— it took a bit more brain power at first but now it’s easy
      She can learn to control it.

    6. LQ*

      I am a Loud person. I will go back to my natural volume. But I also know I need to mitigate that in some circumstances. Luckily I have a door I can close so right now most of that mitigation is just, close the door when someone needs to talk to me or I need to be on a phone call. But can I just be at about 30% at work? Yes. An occasional full volume thing will slip out when stress, joy, frustration happens. But I can do 30% for a long time.

    7. Alli525*

      Nope. I am naturally quite loud (although my extended family is apparently descended from a trumpet, given their proclivity for brass instruments and yelling as loud as possible at all times), and I have been asked at almost every job to recalibrate my volume, since every office has a different noise level. It’s not EASY, so I’m very grateful for my coworkers’ patience, but it’s a necessary part of having an office job.

    8. Middle School Teacher*

      Hard disagree. I am naturally loud (thank you 30 years of voice training teaching me how to project, and 14 years of teaching). I also have a slight hearing impairment. But I work hard to be quiet in specific settings.

    9. Cat Herder*

      Nah, I’m a naturally loud person but I can control it at work. I do have to be conscious about it, but that’s part of being a good colleague. Plus I have an office with a door and my colleagues are comfortable closing it when I slip up.

    10. Not So NewReader*

      My boss says I get a little loud sometimes. Well, I have to talk over the background noise. Part of her solution was to tell everyone to lower it a few decibels so we can hear the people next to us.
      OP, if she is loud on the phone it is might be because of a lousy connection. Just my opinion but most phone calls now are lousy connections. I have to ask the person to repeat themselves three times on an average call. If I try to use a conversational level tone, I have to repeat everything I say.

      1. Letter writer*

        OP here.
        No, sometimes she is talking to herself… loudly.
        Other people have made comments about it too.
        I’ll start calling her out on it in the minute and go from there. The previous admin was bizarrely quiet so it was a hard adjustment.
        I’m naturally loud and I watch it at work. So I get that it takes work and time to temper that habit.
        Honestly can’t believe I never thought of just calling her out on it in the moment. It is a great idea, simple and direct.

    11. Bea*

      I went from a quiet mutterer to loud and not garbled. It’s about being aware your volume is not at the right level and adjust appropriately.

      It’s not her voice that’s the issue, that can’t be fixed. Volume is absolutely adjustable. Unless you have a medical condition, I don’t know any that make you scream but some that make raising your voice difficult or painful.

      We’re taught inside vs outside voices in grade school…

    12. Hodie-Hi*

      When Loud Guy started, we called him Loud Guy to differentiate from Normal Guy, and we often asked him to use his inside voice. Eventually he was able to maintain low tones without reminders.

    13. Thankful for AAM*

      At old job I was constantly told I was not loud enough. At new job I am constantly told how loud I am.

  10. thingsworkout*

    Sometimes people who keep you “informed” about everything they are doing to assist you do for one or more of the following reasons: They
    1. have previously been micromanaged and made to pay if they didn’t check in every time they did anything.
    2. think you don’t appreciate the efforts they are making for you or understand how difficult your request has been,
    3. aren’t sure they have the authority or freedom to do the things they are doing to assist you–and may have even gotten into trouble for overstepping their bounds in a previous job.
    4. aren’t sure of what to do next.

    You can address the first three with the same conversation. Sit them down and explain your work style and the type of work relationship you expect to have with them. Let them know that you trust them to do their work. You do not need to know about or manage all the tasks they do to accomplish their work. You are interested in their results. You can help if they truly get stuck, but before they come to you, they should be out of ideas and able to explain everything they have already tried in an effort to get the job done.

    1. NicoleK*

      5. they need a lot of hand holding and need to be told what to do next
      6. they’re insecure about their skills, job, or just insecure in general

    2. MuseumChick*

      Yes so much to #1 and #3. Especially when you are new to an office and not sure how much authority you have.

      1. Alton*

        Or what the office politics are like, or exactly what the hierarchy is like. Maybe your boss doesn’t want you to escalate the question to Bob because Bob is a bigwig who expects those sorts of questions to go to the people under him, for example, so it’s better to keep trying the people you’ve already called.

    3. VioletDaffodil*

      I am probably an over-explainer to the people I support. I BCC or CC them on needed emails, or may forward them an FYI email here and again. I send out reports on bigger projects. I share the details of things, though I try to avoid being long winded.

      It is partially my own insecurity, but it was fed by having a supervisor who didn’t trust me, didn’t ever give me any feedback on that, and then blind-sided me in a review. I had been quietly completing my work for a year, only letting them know when real problems arose or when things were complete because they literally never asked the status of anything and were rarely present for day-to-date matters. As someone who takes pride in solving problems, this was devastating to me. I was eventually able to earn more of this person’s trust, but in some ways the bell can never be unrung. I will always want to be a person who documents my efforts and let’s people in on the process, because I never again want to be faced with a person who secretly wanted more information all along.

      For the OP, I would recommend trying to talk with your assistant about this, but also giving them some kind of regular space to discuss status updates or work processes. You may only care about the results right now, but if something goes wrong or isn’t the way you want it to be, the why may matter a lot one day. Having a space to outline, even if it just a weekly round up email from your assistant, can be a big help for you both.

      1. Letter writer*

        OP here.
        Good point, thank you! Especially since she is wanting more special projects, and we’re creating some. Having regular checkins should help with that too.

        1. Babs*

          Please don’t cancel your regular check-ins because “something more important came up.” There will always be something more important. I have had that happen and it makes you feel like a 3rd class citizen. And don’t let it devolve into a time that is just passing paperwork around and such for your signature.

  11. Future Homesteader*

    I used to be Amy (at least on 1 and 4). There were two reasons – one is that I’m long-winded in general, so I tend toward this kind of thing. In those cases, I’ve been working on policing myself, and it never hurts to get a gentle “get to the point, please” as a reminder from others (coworkers, bosses, friends) to stay on track.

    The other reason, though, was because I had a Mean Boss who didn’t trust me. Her trademark Side-Eye and Sigh when things didn’t go exactly her way exacerbated my tendency to be long-winded, because I was afraid she’d blame me if I didn’t tell her exactly what I’d tried. Then that spilled over into my next job, where I have a Very Good Boss who trusts me a lot. What helped me there was having a series of conversations over the first few months with VGB about how she wanted me to handle things in general, and what she trusted me to do on my own. It felt weird at first, but it’s become much more natural and I bother her a lot less about everything. Part of it was learning my role, and part of it was learning that my boss *did* in fact trust me, and that I had the authority to go ahead on things on her behalf.

    1. SoSo*

      Very valid points. I also want to point out that it can also stem from a lack of good training. I started my current position a few years ago and the person who’d previously held it was long gone. There was no formal training on any of my job duties, just a “figure it out on your own” mentality. And even though I’d been in a similar position before and was plenty qualified, I did a LOT of checking in with my manager because I didn’t want to do something wrong or screw up. Even if they didn’t have the answer, checking in with them was a bit of a safe guard against a huge mistake. And if I did muck it up, they at least knew that I was trying to keep them in the loop. It took a while to really get comfortable owning something because I had no clear direction on the systems in place.

      Now, it sounds like the amount that Amy is doing is pretty excessive, but it should lessen over time as she learns the processes in place AND the manager’s expectations of her.

    2. hayling*

      Are you me? Last boss was exactly the same, down to the side-eye and sighs. I didn’t realize until I left how traumatized I was.

      1. Future Homesteader*

        It’s amazing how quickly a bad boss can screw you up. I knew I was getting ground down, but it ended up taking months at this new job to readjust.

  12. Write Everything Down*

    Can you give Amy a list of who to contact for X issue, for Y issue, etc.? And the order people should be contacted in? “To check the status of a document, contact Bob at ext. 1 or If Bob isn’t available, then contact Sue at ext. 2 or, etc.” Or “For issues concerning the printer contact Dave at ext. 3 or (backup contact: Sue at ext. 4 or” Or you could ask her to put together a list of what she thinks the contact process is for the things you have already told her about (Document X, printer) and what processes she is unsure of, and then review it with her to verify.

    It might take a little bit of time to get such a list together, but then you could refer her to the list, and keep saying “Please check the list,” until she starts doing that naturally. If she’s unsure and doesn’t have any SOPs to fall back on, she might be constantly asking you the process because she’s afraid of screwing up (refer back to the comments on having a micromanaging manager), so having a document you both know is accurate should give her the confidence to “take charge” rather than checking to make sure what she’s planning on doing is ok.

    1. RandomusernamebecauseIwasboredwiththelastone*

      That sounds like what an assistant is supposed to do. I would expect an EA to be capable of putting this together or finding their own resources especially as it sounds like there are others in the same role who could help.

      1. LarsTheRealGirl*

        Agreed. It’s not a director’s job to even know these things (i.e. the toner), and it certainly shouldn’t be something they need to take time to find out and build.

        1. Not So NewReader*

          The one way out of that is to refuse to answer the question, even if OP knows the answer. “Oh, supply questions need to go to Sue, she will help you.” Here I have gone from the specific to the general and wiped out a whole series of questions in the future. Hopefully. If not, then I still have my go-to answer for any more supply questions. I’d keep repeating, “Supply questions are Sue’s.”

          1. Letter writer*

            OP here.
            I wrote this in March.
            Since then I have been more consciously always responding to those sorts of questions with “Ask Sue” as opposed to even guessing or answering if I knew. It took awhile, and I felt like I was being really unhelpful, but it is working out better. Especially for the routine stuff like ordering toner, IT issues, etc. Now the constant questions are more focused on brand new issues (we’re setting up our first staff off-site in years.) which is more understandable but still a bit extreme. It will be a good one for me to address with the scripts.

            1. Nellie*

              I will say for general onboarding purposes, the director may not be responsible for compiling this information, but the director is responsible for making sure it gets complied and is available, assuming the EA is reporting to the director. It’s not unreasonable for someone to expect their supervisor to at least answer initial questions. When I was early in my career I was unknowingly making mistakes and not checking with the appropriate people because my boss simply hadn’t told me I had to. I worked in a tiny off-site office of a larger organization and my boss was one of the only other people I interacted with, so it seemed fair and reasonable to expect my boss to make me aware of organizational policies/practices. (For example, I signed vendor contracts without running them by a finance person first. I was 22 in my first job and had no idea what our finance people did. Perhaps I should have known to ask to handle, but perhaps my manager should have realized I wouldn’t have known.)

              It doesn’t sound like this is the case here, but too often supervisors delegate out so much that an employee truly has no idea how to do things or find things, especially in big offices/agencies. Managers are paid to manage employees and part of that is ensuring they can field at least a first line of “who would I talk to about X” questions if the answer is not readily apparent. Ultimately a manager is responsible for making sure things get printed, so a manager should be able to at least tell an employee where to start ordering toner, or at least a general “talk to Sue about supplies” at the onset.

  13. MrsMurphy*

    Dito that previous micromanaging might be part of the issue, so I‘m not going to elaborate more on that. But I‘d like to add:

    As an exec assistant myself (of sorts – I‘m in a law firm) I absolutely appreciate open and honest feedback from my boss. The job description pretty much consists of making sure my boss can work effectively; it‘s be really annoying to find out he wanted me to act differently and never said so. In that light, OP, I absolutely encourage you to talk to her. If you see the potential for things to improve, then by all means, the sooner the better.

    1. Luna*

      Yeah, as a former assistant it was really frustrating to do something (the way I thought it was supposed to be done), have the other person say “okay great!”, and then find out later that they really preferred it be done differently but never told me because they were afraid to appear too critical/hurt my feelings. Like, I don’t actually care how it’s done, I just need to know! Your assistant can’t read your mind!

      1. Letter writer*

        OP here. Thank you. A lot of this is about feeling like I may hurt feelings, and some age issues (that are really all in my head – she’s 20 yrs older than me, but that’s pretty common, cause I’m young in my role). Allison’s right – I have no issue correcting on if she printed something wrong, etc. But the others feel like personality ones. I like the script to separate that. Also, good to hear that the feedback would usually be welcomed.

        1. Not So NewReader*

          I was in my 30s supervising people who were over 50. I used an explanatory tone and said, “here is when to ask and here is when to decide on your own.” Usually the shortest version was to list off when I wanted to be looped in. Most times I had a logical explanation why they should ask. This was to help remind them to ask and to lower any stress from uncertainty.
          Sometimes things were unusual and had special circumstances. In those cases, I would say, “When you are finished make sure that this has A, B and C done to it. We will only need five, so when you have the first check in with me. Then after that you will be able to finish the other four. This is the built-in stops as in stop and check with me. I was surprised at the feedback on this. “You don’t let me make a jerk of myself, you tell me how far to go so I don’t get off-course.” I also got feedback encouraging me to keep letting them know what where the critical points BEFORE they started the project.

          One exception I do have is when the boss just has way more experience in a particular area. Where I work now, my boss has a graduate level degree in her field. She told me to go ahead and decide on all Xs. This is a decision that I feel is loaded with too many angles I am not aware of. Since she is the one who would be held accountable, I explained, I would be turning to her when it’s time to decide about Xs. I said if I make the wrong decision this could blow up in a spectacular manner. She thought and realized, yeah, that is right.
          OP, if your employee does push back listen to the reason why. If the employee is not correct about her concern, explain why it is under her watch and/or not a big concern.

        2. Jean (just Jean)*

          Speaking as someone older than my supervisor and (over several jobs) many of my colleagues: Don’t worry about being the younger person in the work relationship. I figure that everyone has something to contribute, whether that be admin skills, life skills, general knowledge or specific expertise. I may not be the rising expert in XYZ, but I have a good head on my shoulders and I take full responsibility for choosing not to devote myself solely to professional advancement. (It helps that I have non-work outlets for some of my ambitions.) If my ego starts quivering, that’s my problem to solve on my own time. Usually the problem goes away when I proceed with confidence and cheerfulness.

          1. Letter writer*

            Thank you. At my old job this was never a concern. In this position is happens off and on. I also look much younger than I am, divorced, no kids, which sometimes makes me seem younger as well. Overall I’ve gotten better, but with this one it was an odd adjustment. I do admit it is in my own head, and I’ve mostly moved past it. All about reframing it – similar to Alison’s suggestion on how to reframe these conversations about work and stop thinking of it as personality issues.
            Great perspective for me. Thank you!

  14. Madame Secretary*

    I suspect Amy is very new to the assistant role just needs feedback and reassurance. Keep working with her and encourage her to find ways to figure out how to solve problems independently. When she comes to you with a problem, ask her what she steps she has taken on her own to resolve the matter. Give her a better idea of what sorts of matters you want to know about and which you don’t. It can take months to get good at anticipating what the bosses want. You have a great opportunity here to mold her into the type of assistant you want! Hang in there with her a bit longer. See if she blooms.

  15. NW Mossy*

    OP, regardless of what happens with Amy, I think she’s taught you something important about onboarding. You note that you were expecting a pretty seamless transition because she was an internal transfer, but it’s pretty darn rare for it to go that smoothly even in the best case scenario. Even if Amy knew the job up, down, and sideways, she’s still new to understanding you, and that relationship is even more significant here because she’s in an EA role. It just plain takes a while to learn the basic lay of the land, and it can be easy to underestimate how long that takes, especially when the new person is replacing a long-serving employee.

    That said, there’s stuff you can do to make the process go faster. For that new relationship to take a good shape, it helps tremendously to have a well-thought-out mold for it before the employee’s first day. Alison’s advice is good for how to refine the mold after the fact, but for future hires, take what you’ve learned from where Amy has struggled and aim to define that more clearly for new people. You can use this as your benchmark for hiring in the first place, and then explicitly state it in your initial meetings with the new employee so that they’re totally clear on what you expect before they wander too far down a wrong path.

    Sometimes what goes without saying needs to be said, and that’s never more true than when you’re working with a new employee. You won’t insult or patronize them by being upfront about what you expect – you’ll be giving them much-appreciated clarity at a time when they feel like they don’t know anything about anything. Tell them how you like to communicate. Tell them how you’d like them to behave in the office environment. Tell them how you want them to go about solving problems and escalating issues. Give them lots of opportunities to try to hit your mark, and tell them how they did (dead-on, off-center, or wildly off) so that they can calibrate their judgment. I know that’s a lot of work and time on your part, but the investment up front pays major dividends when you then have an employee you trust to handle stuff independently.

    1. Letter writer*

      OP here.
      YES. First time for the director or I to have an exec assistant, or to hire or train one. We had the previous one come and sit with her for a couple of days, and really naively assumed that would be it.
      I’ve learned a lot about what I look for in an exec assistant now, and what the job duties really are. Huge learning experience. Also, the director and I took it as a chance to think about how we want the office run, and we didn’t have a clear idea of what that would be. We definitely have a better idea of it now. the step by step in the last paragraph – yes exactly. I left a lot of the coaching to the director, and I shouldn’t have. The director is pretty hands off and was trying to be hands on, but it didn’t work well.

      1. Babs*

        ugh! I absolutely refuse to “go sit with” a new EA. I think it is the worst way to train someone for this job. It does a disservice to that person, simplifies a job, understates the importance of working with their director, in their style. This is a long living assumption that “one secretary” can teach another secretary because they are all the same and their jobs are just so simple….ugh. guess I’ve been on both ends of this too often to take it lightly. Now if that EA wants to come talk to me about things she struggles with and bounce ideas off me. Great! lets learn together.

        1. Letter writer*

          OP here –
          Oh that’s good perspective. In most jobs I’ve had (not as an EA), it has been pretty common for someone to sort of sit with me for a few days to get me up to speed. Didn’t occur to me that in this scenario that may be counterproductive.
          Also just reminded me of one job where my predecessor spent at least 30 minutes going over the different colors of font she uses in email for different topics. Meanwhile I was just thinking “nope, never doing that. unprofessional and hard to read.” Yeah, that type of training does backfire.

          Thank you and good points.

  16. RandomusernamebecauseIwasboredwiththelastone*

    I have a bit of a question at large (although related to this letter and from the previous one today about the team that won’t tell their manager anything)

    I understand bad work environments, bad bosses, bad coworkers, etc. I’ve managed teams directly after they had a bad boss. I’ve had all of them at different points in my career. At a certain point though it’s up to the individual to break that cycle.

    So in this case, even if this person worked for a micro-manager, they clearly know they are not working for this person now. At what point is it less about the previous bad experience and more about the current employee? Some of this could very well be learned behavior but does that previous learned behavior stop the employee from learning new behavior?

    1. Detective Amy Santiago*

      I think it’s on the new manager to name the issue and communicate how they want it handled.

      1. RandomusernamebecauseIwasboredwiththelastone*

        That seems a little backwards to me (but I’ve been known to be backwards). I’ve asked every new boss I’ve ever had as a professional. “What’s your comfort level for involvement?” “When do you want to be brought into the loop, I generally default to x” “Are there any exceptions to the previous answer” “Anything else I should know, any hot buttons I should be aware of right off the bat?”

        Now, even with those questions answered I’ve had a few instances where answers didn’t match reality, so based on observation I changed.

        1. AdminX2*

          That is the WORST. I had a boss swear up and down and sideways every time I asked him if he needed me to get him lunch or some personal thing that he would NEVER expect that.

          Yet somehow every week on my way out to grab something, he would pull me over and give me an overcomplicated sandwich order. So much more frustrating than just expecting and getting on with it.

        2. Thankful for AAM*

          I did that with old bad boss and got it hammered out of me. Asking for the level of involvement was bad (looking back, she did not know). And adjusting based on her behavior was bad bc it was always wrong or changing. One coworker even said to her, we are on your side, we want you to look good, succeed, etc. It made no difference.

          And now I am wondering if I should be over it by now. When does my clock run out on eradicating the learned helplessness? I am pretty sure that years from now I will do x and realize, oh, that is another holdover from bad boss that I did not realize I do.

      2. RandomusernamebecauseIwasboredwiththelastone*

        Also, I agree with you on specific issues, but my original question was more of a broader non-specific issue question (if that makes sense).

        Like we want to give an unlimited pass to people’s behavior because of a past experience.

        1. LarsTheRealGirl*

          I wouldn’t call it a pass on bad behavior, (not a permanent pass, anyways) but an understanding that they’re not doing “seemingly weird annoying inefficient thing” because they’re unqualified or incapable, but because that’s what the prior expectations of them were. And those things can usually be unlearned, when pointed out.

          I left a high level role under a terrible micromanager and it took my new boss telling me a month in “you really don’t have to check in with me for permission for this, you can just do it” before it clicked for me that what I was used to was Not Normal.

        2. Observer*

          No. We want good bosses to be aware of it, so they can change the dynamic. The employee doesn’t know what the new boss wants, so they keep doing what is “safe”. It’s generally not easy – and sometimes not even possible – for the employee to really know what the new boss REALLY wants, so laying it out and reminding the person changes the dynamic.

          Of course, if the employee can’t get over it even once it’s pointed out, etc. that’s a different discussion. But the first step is having those conversations and reinforcing the behavior you want.

    2. AdminX2*

      At least six months, with solid, consistent, clear, direct guidance. Fear responses aren’t ingrained in a week and they won’t be erased quickly either.
      We can “know” a lot of things, that doesn’t stop us from FEELING fear and reacting based on that fear out of a desire to protect our status.

      1. RandomusernamebecauseIwasboredwiththelastone*

        That’s an interesting thought. Again I can really only compare to my situations (which is why I’m asking), but I was always so happy to get out of those bad situations my first thought with a new boss/work situation was “Thank goodness I don’t have to do that (whatever ‘that’ was) anymore” and more or less left it behind me. I mean sure there were some things that invoke some of those past feelings, but mostly were non issues.

        1. AdminX2*

          That’s some excellent compartmentalization!

          And I say six months as in a real full turnaround, what you really want to see is positive progress, which can start in a few weeks.

          I had a toxic job once which included constant unreasonable requests at all hours of any day. The next job I got I realized halfway through the first Saturday I had been holding my breath waiting for the dreaded texts to start coming. It took a few weeks to really TRUST that this was the new norm.

          1. RandomusernamebecauseIwasboredwiththelastone*

            That’s a great observation. I’ve been told I exceed in the compartmentalization arena.

            Now you know why this phenomenon doesn’t exactly compute with me :)

      2. Not So NewReader*

        I’d agree with at least six months and maybe closer to a year depending on some variables. If the whole department had a toxic boss before you, then I’d say closer to a year. (They all share the distrust. To break it and built trust is a on-person-at-a-time project.) If it’s one new hire then closer to six months. (The one new hire has her cohorts to help with settling in and building trust.)

        I think a wise boss never looks for it to go away entirely. But if you have been consistent and fair right along then much of the worry/fear should be noticeably lower as you approach the one year mark.

    3. medium of ballpoint*

      I think this situation has some mitigating factors. For one, it’s a fair assumption that if Boss A is a micromanager, Boss B likely will be too if he works in the same department/for the same company. For two, people tend to have more empathy for an insecure employee than a brash employee, especially if that employee is a woman. Women can get punished more harshly than their male coworkers for taking too much initiative or being too independent.

      In answer to your larger question, I don’t think you can expect to see change until it’s crystal clear that circumstances are different. With Amy, I don’t think it was clear to her as it was to the LW that the vibe in her current office is different. Making that clear to her would likely be more expedient than waiting for her to pick up on it.

    4. Cedrus Libani*

      If someone’s used to working under questionable management, they may simply not realize there’s another way. All bosses want to be updated with every mundane detail, right?

      I didn’t make this specific mistake, but when I started my first professional job, there were definitely some cringe-worthy moments. I’d taken behaviors that turned out to be context-specific (from previous college jobs) and assumed that was how things worked everywhere. I wasn’t a bad employee, I just needed to be hit by a clue-by-four on at least a couple of occasions (and I was, and then I fixed it).

      In these cases, I think it’s worth breaking out the clue-by-four and being very, very specific about what you want. If the employee can’t do it after repeated coaching, that’s a bigger problem. But sometimes people just don’t realize they’ve been trained badly, and they can fix it quickly once they know this.

  17. Letter writer*

    OP here.
    First off , big thank you to Allison for the advice. I like the script and will try them out. Especially the being loud one – I’ll start implementing that right away.

    It is sort of odd – Amy reports directly to my boss (the director) but supports both of us. She has one on ones with the director, but not with me. I could institute them, or I could join theirs. The director has the same issues with Amy, and frequently punts it to me to deal with (as in – OP please set up this meeting cause I don’t want to deal with the million questions from Amy). Even if she is addressing them in her one on ones, it obviously isn’t effective. I’ll talk to the director with Allison’s advice/script and see about the separate 1-1s or joining theirs. Amy’s gone this week anyway, so a good chance to discuss.

    I’ve learned a few things:
    a) Amy has been asking for more work because apparently the director and I don’t require a lot of assistance than she is used to. Which was an eye opener. Points to maybe a micromanager, which would make sense. It also points out that the meeting scheduling isn’t a huge time-suck for her.
    b) She does so much better with direction in writing vs. verbal. Shocking so. Meeting scheduling – some of the stress was when I’d verbally ask her to schedule the meeting and rattle off the details. When possible, I’ve been putting those in writing and it makes a huge difference.
    c) Confidence booster. Recently we implementing a new travel reimbursement system identical to the one at her old job. She is the go-to person for the entire executive wing and doing a great job of it. Also, by doing that, she is building up rapport with the other admins which is going a long way. The level of questions about policy stuff (#4) has decreased drastically since then.

    1. RandomusernamebecauseIwasboredwiththelastone*

      Thanks for the update! Always good to hear how things are going.

    2. Fabulous*

      OMG about the in-writing thing. As a former admin assistant of a severe micro-manager, I always HATED it when my boss gave me instructions verbally. Not only is my short term memory is terrible (literally, if something isn’t in writing, it’s in one ear and out the other) but he was SO particular with details that if it wasn’t written down he would come back to have me fix each tiny thing – and separately at that. I would always redirect him to email me, or to email him a recap of what I think he told me so I could get any mis-remembering fixed right away so as to avoid the constant re-do’s. Having things in writing (via email) also helped with my task organization and prioritization as well! I am so meticulous about using my inbox as my To-Do list that if something isn’t in there, it might get overlooked.

    3. Close Bracket*

      I’m glad that you are the type of manager to figure out that you have learning curve and to work on how to work effectively with a particular person. I think this will make you a far more effective manager than the people who jump right to “she can’t do the job, can’t you fire her?” It does take several months, perhaps more than a year, for a new person with complex responsibilities to really integrate into a new corporate environment and work at peak productivity.

    4. MrsMurphy*

      Thanks for the update!

      Those sound like great developments. It really is a learning curve on both sides. I‘m now working for a manager whose last assistant was… well. Useless. In the first few months I was often shocked to see the sort of work he wouldn‘t delegate to me, and it took time to build trust. That‘s par for the course. But it‘s SO important to work on an honest relationship there – maybe that‘s my latent workaholic tendency speaking, but really: Your assistant is the one person in the company who must know your mind best, who knows the most about you and (ideally) who you can depend on completely. In my view, candid feedback may be uncomfortable, but it‘s necessary to get to that level.

      To me, the fact that she asked for more work speaks in her favor. And #4 sounds excellent to build up her confidence.

      1. Letter writer*

        OP again. It really does speak highly of her. The travel system is a bear too, and it has been awesome that she’s helped out so many of the EAs up here. We’ve gotten so many kudos about it, and have made sure to pass them on to her.

    5. Not So NewReader*

      I like instruction in writing, too. Because I handle Things A-Z by the time I get around to M that my boss told me about yesterday, I no longer remember what she specifically wanted. It’s not about doing the 17 steps the item required, it’s remembering what the 17 steps were.

    6. Detective Amy Santiago*

      This is a great update! It sounds like things have already improved. Hopefully Alison’s advice can get you the rest of the way there!

    7. Dr. Doll*

      Instructions in writing. By the time I write the instructions I could do the task myself! That’s definitely part of my delegating problem.

      I could not help but envy Miranda Priestly: Call so and so about the thing, the other so and so about the other thing, go here, go there, pick up this, pick up that, take care of this problem, that problem, the other problem, get an unpublished manuscript delivered in an hour, book me a flight in a hurricane, and stop falling off your Jimmy Choos….that’s all.

    8. Babs*

      True that in this neurodiverse world that some people take written instruction better than verbal instructions. However, it’s just not possible to always operate in written only and in Government, we try to avoid creating unnecessary public records, even if they are transitory.

      Verbal instructions take lots of practice and it can be nerve racking. I created a form that was a quarter of a sheet big with the details to fill in so that when my boss popped up, I could grab it and ask him/her all the pertinent questions right then and not pepper them later. What to name the meeting, who to attend, who is most important to attend (if not all can because of their schedules), by when do you need to hold that meeting, location preference (their place or ours?), any materials a head of time, do you need prep time before the meeting. That was years ago and now I do it out of habit and sometimes it forces my boss to rethink what he was going for because he realized he had a half baked idea.

      People always assume scheduling takes more time than it does, it’s a good percentage twisting arms and the other parts are up to good luck.

      And by the way, the other director avoiding her because she talks too much is a jerky thing to do and say. I’ve seen really good people sterotyped and dismissed because of some personality flaw that some talking head didn’t have enough human decency to look beyond to see their talents.

  18. AMT*

    I can see this problem being framed positively. The LW trusts her to use her professional judgement and make decisions without their input, which is a good thing! I’d make sure to throw in encouraging phrases like “I trust your ability to do X and Y without looping me in” or “I’m confident that you’ll be able to solve Z and A problems independently” during the initial conversation. In other words, the tone could be “You can do it!” rather than “Stop bugging me!” even if the underlying message is that the LW really, really doesn’t want to be bothered with minor stuff.

  19. nnn*

    Something I’ve found useful in general when dealing with different or unknown levels of supervision expectations is to explicitly state an “err on the side of” guideline. For example, at my job, we have “If you need overtime to meet a client deadline and can’t get a manager to approve overtime, err on the side of meeting the client’s deadline.”

    So in OP’s case, you could say “Err on the side of using your own best judgement, and ask the directors only if you’ve truly exhausted all options you can think of.”

    1. Not So NewReader*

      Rules of thumb are great.
      One place my boss wanted me to pick the answer that was the easiest to fix if it was wrong. For our setting that worked so very well.

  20. Miss V*

    LW said they share the assistant with their boss, ao are they sure the assistant isn’t behaving this way because boss told her to? If this behavior is all because the director asked for it (or at least approved of it now) then LW may just be stuck.

    The other thing I would note it, like a lot of people have suggested, this may be a holdover from the assistants previous boss. I keep thinking of the advice Dan Savage gives when someone asks him what to do because their partner is a terrible kisser (is it sacrilegious to mention other advice columnist?) He says instead of saying ‘your a terrible kisser’ you should say ‘this is how *I* like to be kissed.’

    I think LW could very easily apply the same advice. Not ‘you’re a bad assistant’ but ‘This is how i personally would like your role to support me’

    1. Letter writer*

      OP here. Thanks for the comment. The director has the same frustration that I have with the play by play. I get more of the process info because of where I sit (physically my office door is closer to the EA). So the good news is that the director and I are on the same page on this. So we can do a united front in next steps.

      1. Miss V*

        That’s good news! If your boss is on board then I hope you three can all find a resolution (although it looks like you’re well on your way already.)

  21. Ms MicroManaged*

    She may have worked for a micromanager before. I currently work for one (I’ve been here two years and have had glowing reviews) but she wants to know *every* detail. So frustrating! I know my manager has many other things she should be doing, and could be doing, but yet she follows up on my every move. I really am good at my job – but now I feel so scrutinized it’s awful. Please give Amy the authority and autonomy to be the best she can be, there’s a good chance she really flourished if she’s let off her (invisible) leash!

    1. Argh!*

      I currently have one of those supervisors. It’s frustrating and she can’t do the things that only she can do because she wastes her time telling us how to do things we already know how to do. I want to say, “Yes, fine. Now about that email I sent 2 weeks ago and reminded you about last Friday…?”

    2. RandomusernamebecauseIwasboredwiththelastone*

      I don’t think we’re reading the same letter and updates. The OP doesn’t want Amy to be coming to her for each individual thing,. She wants Amy to be independent and get things done and is asking for advice on how to do that,.

      1. Ms MicroManaged*

        If I were Amy right now, based on my current situation, it has been ingrained in me to run every detail past my Micromanaging boss. If/when (please God) I start in a new place, I’m going to have to do a lot of un-training and I only hope (pray really) that my new boss will say “make sure the kitchen’s clean” and not tell me how to do it. You’d be amazed at the things she tells me to do, when I really am a very competent and confident 50 year old single mom (with a kid in college on Deans’ list 6/6 semesters!). And it’s not a culture thing here, my grand boss says “I should have known you’d have it under control, you always do”.

    3. Bea*

      I wish I had this confidence in others. I learned the hard way that everyone I’ve tried to coax out into the world of leading themselves, confirming you don’t need my approval for XYZ and so on has melted down either further. It’s so depressing and stressful dreaming that everyone else can be self guided as well. Sigh.

  22. drpuma*

    Seconding Alison’s suggestion of regular check-ins – not only because that makes it easier to give feedback, but also because it gives you a destination to reroute some of her explanations, within reason: “Don’t forget we have our regular check in on Thursday morning. You can tell me all about it then. For now I need to get to my next meeting.”

  23. Argh!*

    In general, she sounds insecure and perhaps needs a mentor (not you) or coaching (also not you).

    1 & 4 especially – she wants to be micromanaged, and you want to delegate. She needs to know that you understand that one of the downsides of delegating is that she may get things wrong occasionally and it’s not the end of the world.

    There are some people who really need to “think out loud” and can’t go from A to Z without going through B and the rest. I have supervised this type of person and it can be very tiresome but they do get to the point…. eventually. I’m not sure they can really train themselves out of it, but if you ask for a written summary that does that they can probably write what they would say and then you can scroll down to the end.

    I have a coworker who can’t answer a question without telling me how it was done 20 years ago, like I would care. She finds it interesting, and in my opinion it’s very selfish of her to waste my time with all this storytelling. I moved all my “why” and “how” questions to email and that has saved me time. Her supervisor doesn’t seem to worry about how she spends her time, so as long as her time is the only time being wasted, I’m happy.

  24. mf*

    EA here. I have a couple of thoughts:

    Regarding the whole “don’t tell me the process–just fix it!” issue… It sounds like she has either worked for a micromanager and/or feels she needs to update you frequently so that you’ll know she’s working on the issue. Have you told her: “I trust to you take care of it. You don’t need to check in with me about these things unless I explicitly ask for an update”?

    In other words, try being explicit about the fact that you expect her to operate independently–hopefully this will make her feel empowered to make decisions and handle problems without your input.

    About the meeting scheduling… Have you asked her why she seems stressed about scheduling meetings? A lot of times my boss will ask me to schedule a meeting, thinking it’s a short/simple task, when actually it involves around other meetings and negotiating with other people to try to get them to adjust their schedule. It can be more of a headache than you might realize, especially if other people aren’t flexible with their own schedules.

    1. Letter writer*

      OP here.
      Thank you. I’ll be more explicit to help her feel empowered and independent in her tasks. Some of this has happened naturally over time (I wrote to Alison in March) but it is still an issue.

      Meeting Scheduling: I did some of it verbally when I was in passing in between meetings, and that definitely added to the stress. Now I do almost all of it in writing. For awhile, I had two big meetings (70+ people, lots on conf call, its a nightmare) that were monthly. All required conf call, IT setup, etc. Of the 70, only 10 had to be available, but still. It was supposed to be only for a few months, but everyone liked them (seriously…) so now they are continuing for at least a year. We sat down and worked on ways to streamline the whole monthly process – reminders about due dates for setting the agenda, training materials, pdf all of the handouts into 1 big handout w/ page numbers, always having the IT guys phone number in case things don’t work right, making copies, etc. Honestly stuff the previous EA would just do to make it run better, but I hadn’t slowed down enough to articulate why it wasn’t working well. Now we have a process in place and those meetings are going pretty well.
      Amy’s still stressed when it is a tight meeting (everyone is booked but we must meet today) but that is understandable. Also with time she’s gotten more comfortable with when she can pull rank for us and pull people out of other meetings and when she can’t. We did articulate that early and often, but I understand that takes time to get used to it.

      1. ENFP in Texas*

        Having been an admin for much of my career, I can empathize with Amy. It is never easy to walk into a role that had been held by someone who did it so long and so well that you sometomes feel like you’re a let-down to your new managers because “Susan just knew how to do these things.”

        I saw it when the EA I worked with had to retire due to a sudden illness. She had been there for over 15 years, and has supported the same boss for most of that time, to the point where she could practically read his mind and knew what he needed before she did. When our new EA came in, there was an adjustment period on both sides. Not only for the new EA to learn the people and the processes and who to go to with questions, but also for the new boss, who had to be better about articulating his needs simply because the new EA did not have Susan’s wealth of experience and knowledge with his department and his work preferences. I know for a fact that it took almost a year for our new EA to feel comfortable and confident in her role and feel like she was living up to the standards that (in her mind) Susan had set.

        1. Letter writer*

          OP here – thanks and good points. It is hard to set into a role when the predecessor was there for so long.
          I’ll also say, to Amy’s credit, there are things we didn’t like but never thought to voice to her predecessor. ex: previous EA loved ordering colorful office supplies and we had way too much of them. Both the director and I prefer plain standard stuff and thought the other one was asking for all colorful stuff and went along with it. Amy asked about it on day 2 and fixed it. Traded with people to get rid of the colorful stuff and replace with what we like. It was great. I’ve never been so happy to have regular yellow post-its in my life. It was a great example when she saw a problem and solved it for us.

  25. Bea*

    This letter gives me so much anxiety. I wouldn’t be able to stay civil for long.

    There is no way in hell I would have asked a boss even on day one where to buy toner. Don’t you have a recordkeeping system *mind blown*

    This reminds me of the dude who asked the owner how to fix the copier instead of trying to follow prompts or asking the other admin. No.

    1. Letter writer*

      OP here. She’s much better now. But oh, early on. Amy would pass on the cold callers to us, or give us their message and follow up to see if we had called them back. It was… not good. The weird transferred calls ended within the first month.
      She has gotten much better about the spam callers.
      We do have record keeping and policies and procedures, although I’ll admit I’ve never looked into them. Early on I don’t think she was using them, despite us directing her there, or to the other admins.

  26. SusanIvanova*

    “I don’t know how we order toner”

    Well, definitely not from the cold-caller who asks you for your printer number!

    (And seriously, I would make sure she knows that. Experienced admins have been caught by that scam.)

  27. Letter writer*

    OP here. She’s much better now. But oh, early on. Amy would pass on the cold callers to us, or give us their message and follow up to see if we had called them back. It was… not good. The weird transferred calls ended within the first month.
    She has gotten much better about the spam callers.
    We do have recordkeeping and policies and procedures, although I’ll admit I’ve never looked into them.

  28. LGC*

    Okay, so, as usual I’m reading way too far into this letter, and I agree that she’s probably been micromanaged in the past. But also…I get that her performance wasn’t great when she started out, but I really got the vibe that LW was comparing Amy to the previous assistant.

    And yeah, job standards and all that, but also…they’re two different people. And I’m sure that the old assistant probably needed time to get up to speed herself – LW was in her position for a year and a half at the time she wrote this letter, and her updates say that Amy’s already improved.

    All that said, there were some red flags in the comments. But…correct me if I’m wrong, but these have also improved right?

    Back to the micromanagement – that’s a HARD habit to break! And it might not even be an abusive boss – you can get that from a boss that’s responsive to every little thing as well, because the employee ends up being trained to expect that their boss will solve all their problems. I’m in the process of doing this with one of my employees (who…he does sound a LOT like Amy).

  29. Kimberly*

    Everything that was mentioned had nothing to do with the quality of her work. If she wasn’t meeting deadlines, messing up scheduling, not providing accurate work, etc., then I would say it was a problem. However, I feel th ku s is more of a personality issue. Perhaps take the time to understand why she feel the need t ok so certain things… Ask her how she feels about working independently? There may have been an incident or rumors about your behavior to employees that was said to her.

    1. Kimberly*

      Sorry for typo…
      Everything that was mentioned had nothing to do with the quality of her work. If she wasn’t meeting deadlines, messing up scheduling, not providing accurate work, etc., then I would say it was a problem. However, I feel this is more of a personality issue. Perhaps take the time to understand why she feel the need to do certain things to question and confirm what she does… Ask her how she feels about working independently? There may have been an incident or rumors about your behavior to employees that was said to her.

      1. Lyra (UK)*

        I think it actually does affect the quality of her work – an EA’s prime responsibility is to help the people she assists focus on their core tasks by taking care of the rest as independently as possible. If she’s using up 5hrs/week of the letter writer’s time, that takes the LW away from the tasks she should be working on, and affects the organisation’s overall output. This is further exacerbated by the LW being senior in the business – presumably any delays in her work cascade delays down the rest of the business.

  30. JagoMouse*

    Hi LW, I’m an EA at the C-suite level and have been for several years so I know of which I speak. A lot of people have mentioned about micro-managers, and the impact that has – if so, I can sympathise, but here’s the thing. As an EA your very role is to shift your own behaviour, your methods of doing things to fit your boss, to their way of doing things. The first thing upon starting a role with a new executive is to sit down and ask them how they like to do things, to figure out who in the office is your go-to person, and to learn everything. There are many, many resources for Assistants out there – networking groups, mentoring groups, blogs, you name it to draw upon. I saw one the other day with a list of questions to ask your new boss when you get a new role, for example. It sounds like there are other assistants in your department even – so I am baffled as to Amy’s approach to simply ask you for information. And I know a lot of EAs (in their 50s no less) who would never approach a new job like this, putting the burden on their new boss to teach them everything.
    You mentioned later in the comments about the larger, regular meetings and sitting down with her and talking about all the logistical details – some of which it is good to ascertain (preferences for PDFs and documents for example) but she should not have to be told to keep the number for IT handy. Those kinds of details, the back up plans, the contingencies, the logistics of deadlines etc, that is Amy’s job. If she can’t figure it out herself, then I wonder at her ability to keep up with what you need, long term.
    I know it’s not an easy process to fire someone in your department, and it also sounds like it’s gotten a little better, however I’d be keeping your eyes open for another opportunity for her to move into, as it sounds like this role is not suited to her. That’s OK – different people, different EAs, different skills. She may thrive in a different role, more suited to her skills. Assistants aren’t interchangeable, however much people want us to be.
    Kimberly up thread mentioned personality issues – here’s the thing with an executive/assistant relationship – it only works if the personalities fit. It is a very specific, niche role with a different relationship to the one you’ll have with almost anyone else, and it is vital to get it right. Amy’s happiness, your productivity are both affected by it.
    I hope things work out for you and for Amy. Good luck!

    1. Letter writer*

      OP here.
      Thank you. This is great information.
      I don’t think we did a great job of talking generally about how we want the office run. Empowering her to take on issues, etc. Instead we focused on some details (yes handle my calendar, have 100% access to my email, etc). Big learning experience for what to do better next time, and how to amend it now.

      Good to know more about what makes sense for her to need more guidance (document preferences) vs basic (IT info). Of note, when we had the first IT issue and she didn’t have the number, she did troubleshoot to get it all fixed, was pretty mortified she didn’t have the number to start with, and checked in with us later on. I do get the sense that while she was an EA before, the type of work is different (we have a more meetings, busier office, more phone calls, don’t require a lot of email support, we don’t travel and she’s an expert in that system, we are pretty on top of our deadlines and don’t need her to run herd over it much, rarely do memos and she’s great at those, we need more basic excel and ppt skills). She does have a skillset, but it turns out it wasn’t as well matched as we expected

      Amy’s on vacation this week. I’m meeting with the director on Thursday to talk about this, next steps, the one-on-ones, the scripts, etc. I want to first see how it goes with coaching for awhile, but long term moving her into a different role is more of a possibility than firing. That could be a workable solution.
      The personality comment. Completely agree, and I learned a lot here.
      Thank you for your perspective! I really appreciate it.

  31. Wintermute*

    This sounds like the scars of micromanagement and a boss that had a nebulous and shifting window of acceptability that you somehow never manage to hit.

    Checking after each step? That smacks of a boss that will magically go from “make it work!” to “why are you wasting so much of my money and your time on this?!” in a single step.

    Exhaustively discussing process? That speaks to me of a survival trait from an environment where you could be expected, after-the-fact, to retroactively prove you’ve done nothing wrong, which is at best a frustrating task and at worst impossible.

    Anxiety around high-visibility tasks (scheduling meetings)? Again that just tells me they came from a place where these were stressful events, deserving of that degree of anxiety.

    This will go away in time if you manage her properly, especially by giving clear and regular feedback, both negative and positive. Especially if you live up to what you say about trusting her to have some autonomy.

  32. Lauren*

    Give the girl a break! I’d love to hear what she has to say about her direct supports at the end of each day. Empathy folks!

    1. Lyra (UK)*

      I think the Letter Writer is very much giving her a break and trying to find ways to improve the quality of her work all the same. If she didn’t care, she’d hardly have written in to ask for a constructive way to request changes in the EA’s assistant.

    2. Observer*

      Girl? I don’t want to nit pick, but I think it’s worth noting that this kind of language can be a symptom of the kind of problematic management people have been talking about. Even before knowing that she’s n her 40s, it was clear that she’s a full fledged adult with some years in the workforce. She’s NOT a child and shouldn’t be referred to that way.

    3. Letter writer*

      OP here. I actually had expected a lot more of these sort of comments, and this is the only one which is sort of validating.
      She wants to do a good job, she is generally in a good mood, and lately she’s been asking for more work and responsibility – which is fantastic. I wanted to make sure that there was a way to coach her to lay off the process talk that would come across as constructive, as opposed to digs on her personality.
      Oddly, it never occurred to me that she may have worked for a micromanager and these are trained behaviors. That changes my whole perspective of this and how to handle it.
      Thank you for your perspective though. Always good to hear both sides.

  33. Another Amy (also an Admin)*

    I think the big thing here is to let Amy know she has authority to act on your behalf. I am also an admin assistant. Knowing you are EMPOWERED to act on behalf of your boss/who you support is huge! Being new, she doesn’t necessarily know she has your trust to do this yet. Communicate to Amy that you don’t necessarily need to know the details, but TRUST her to take the steps to make it happen. She sounds like a communicator, which is a great asset in an admin. She just needs to feel empowered to make decisions, which she will learn.

    1. Letter writer*

      OP here. Thank you! I really appreciate the perspective from other admins. She is a communicator, and that’s a good thing to point out. Also knowing that some of it does just take time.
      I wrote this in March, and it has gotten better since then. Not 100% and still worth the conversation, but many pieces of it have improved. She is and will be a good asset to our office.

  34. Janet Aldrich*

    I’ll bet anything she worked with a micromanager who demanded to know how things were going — someone who was constantly on her case and now she’s been conditioned to react with every detail of what she’s doing because that’s how it was done before.

    Or, alternatively, she worked for someone who jumped all over her for not doing something when she was doing what needed to be done — it just hadn’t provided a result yet.

    Either way, sitting her down and letting her know you aren’t going to be either of those people would no doubt be helpful for her.

  35. Nathan Maharaj*

    Regarding the loudness, there’s something called The Lombard Effect, where people speak louder when they perceive their environment to be noisy. Often this is experienced as a coworker shouting on a call because the volume is turned up too loud on their phone. This can be a result of the person mistaking their volume control for a “call quality” control when reception is spotty.

    Turn down the volume of the call to the comfortable minimum (regardless of quality–volume doesn’t solve drop-outs and static) and the problem is solved. “Hey, how’s the quality of the phone audio? Good? Can you do me a favour then–please turn it down to the comfortable minimum? You’re speaking pretty loudly and it might be because you’ve got the volume up too high.” This might not be the issue in this case, but it’s worth a shot!

  36. Diane B*

    Could be a previous boss micromanaged her into some of these dysfunctional behaviors. If so, letting her know you trust her to have it handled might be a relief.

  37. Kitty*

    My feeling is she may have come from a job or culture where she was micro managed and is so used to doing these million check ins that she doesn’t realise it’s not appropriate. Hopefully once you talk to her and reassure her that you trust her to do her job, it will subside.

  38. Nanani*

    I don’t know how practical this would be, but maybe you could ask her to put her explanations into a log or report to be periodically emailed?
    (you don’t necessarily have to read it unless an issue actually comes up)

    This could serve as an outlet for her need to explain and/or cover her ass, which as others have pointed out has likely been drilled into her by previous jobs.

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