how to tell an employee he needs to figure some things out himself

A reader writes:

I have a new colleague, “Carl,” who is also new to the industry (and to the working world in general). I have worked in this industry for years, and in this role for three years. Carl’s role is new to my organization and is framed as junior to my role in some respects. I supervise him day-to-day, but we share a line manager and we have the same job title.

Carl’s role includes some of my old responsibilities and some that are new for our organization. And he asks … so many questions. All the time. A lot of these not cut-and-dry answers that I can give him, but very context-dependent that I know through experience, contacts, and proximity to other organizations doing similar things. He likes clarity and often I can’t give him this, especially in the new tasks (e.g., sometimes my answer would be, “I would do it this way, because of this historical context and because we are working with these particular people, whom I know, but if you feel another way would be better, that could well be the case and feel free to try”). I can tell this frustrates him a fair bit. Often I REALLY want to say, “I am busy, I’ve never done this either, we have the same job title, YOU figure it out” — but that’s not very fair; he doesn’t have experience yet to do so. What could take him quite a lot of time and many questions to other people, would take me far less.

I am starting to feel resentful that he asks so many questions and expects so many easy answers (possibly because I had not much support in the extremely chaotic earlier days of my own career, and this is manifesting in a weird jealousy?) which is starting to alarm me. I am not usually a resentful person, and I like my colleague and want to help him. But I spend so much time figuring out the best way to do things for my own role (which has grown considerably in scope and responsibility since I started it), and now I spend so much time trying to figure this out on his behalf, too. So I suppose my question is: how do I stop myself feeling resentful for simple supervisory responsibilities?

The fact that it would take him longer than it would take you to figure out some of these answers isn’t necessarily a sign that you should be doing that work for him. It’s very normal for junior people to take longer than more senior people, and working through those projects is often how they get better at them and acquire the expertise that lets them move into more senior roles. (It sounds like that’s how you learned!) If something would take Carl two weeks and you 10 minutes, that’s obviously different, but there’s likely value — to Carl and to your organization — in him learning to work through some of this on his own.

So I think you need to get clarity on whether or not he really can be expected to figure some of this out on his own. The answer might be yes for some and no for other things, but you can’t sort through this until you’re really clear on whether and when it’s reasonable to expect him to solve things on his own.

If you determine that it’s really not reasonable to expect him to figure out any of this on his own, then you’ve got to talk with your own boss about it, framing it as a workload issue for you — that you don’t have enough room on your plate to do this part of both jobs and so something needs to move, whether it’s this aspect of your role or something else.

But if you realize that indeed there are pieces of Carl’s work that he should be figuring out on his own, talk to him! Explain that part of the job is figuring out things that won’t always have clear-cut answers, and he can do that by things like XYZ. Give him some concrete recent examples of things that, going forward, you’d want him to work through on his own, as well as some recent examples of things where it does make sense to loop you in (assuming both categories exist). It sounds like you’ll need to be explicit that there’s a lot of ambiguity and figure-it-out built into the role, and that the absence of cut-and-dry answers doesn’t mean he’s doing something wrong or needs you to step in; rather, it’s an inherent part of the job that everyone new to it has to learn and get comfortable with. Really spell this out, because it sounds like it hasn’t been clear to him so far.

And from there, when Carl comes to you to solve something you want him to learn to solve on his own, ask what he’s tried so far, make suggestions for things he can try if he seems stumped (but don’t do those things for him), and ask him to work on it and come back to you in a few days (or whatever timeframe makes sense) to talk through the progress he’s made. The more you can coach him through doing it on his own, the shorter-term this problem will be, the faster he’ll build his skills (or the faster it will become apparent if there’s a fundamental mismatch between him and the role), and the less resentful you’ll likely find yourself.

Read an update to this letter

{ 179 comments… read them below }

  1. Lacey*

    I was in a role that had grown a LOT while I was in it and I got my knowledge little bit, by little bit over the years while new people just had to jump into it all at once. It sounds like that’s part of what’s happening here.

    I’m not like the LW though, I was happy to tell people how I would do it, largely because it was easier for me if they did it my way.

    That said, I do think it’s probably better for learning if you give more general guidance that super specific stuff.

    Like, when I started with my current job my more experienced coworker warned me about some quirks of our project process that would be different from other similar jobs. It wasn’t official rules, it was just, “This will go smoother if you ask for X up front” or whatever. That saved me a TON of time and was better for the department.

    But it would be insane if she had to answer questions about each specific project. That wouldn’t be good for anyone.

    1. Reluctant Mezzo*

      Maybe this would be a good time to come up with documentation? I hope Carl isn’t asking questions that have already been answered. I know the OP doesn’t have time to come up with this documentation…but forcing Carl to make copious notes for him to reference might be a very good idea.

  2. Katie*

    So lots of my departments work has transitioned elsewhere but I am still there in a managerial capacity. I have always been bad about just giving people answers, however it is a time drainer
    My manager has made me make the teams do two things before coming to me. The first is checking their extensive jobs and their learning logs. I am supposed to always ask have they reviwed those before coming to me.
    It has not always been successful but it has cut down on a few questions.

    1. Artemesia*

      So critical. The key to a highly needy person like this is to NEVER do it for them — Make them show you what they have done and expect them to have done 2 or 3 things before coming to you AND if you help them make them do it while you coach them. Make it more work to come to you than to do it unless they really are clueless. It is easy to fall into the ‘I know that and can do it easily’ trap where you become their go to for everything. You don’t have to say ‘let me google that for you.’ with snark. But if the first step is to google it, then you direct them to do that while you watch — never be the one doing the thing.

      1. Hannah Lee*

        The one thing I’ll add to your good advice is that if Carl comes to you and you ask him what he’s done so far to approach it, figure it out and he says “A D & F … but I’m stuck on this part” don’t respond “No No No! … that’s not how you figure it out! Why didn’t you look at A M & S?!?!” in words or tone. You don’t want to snap at or undermining someone who is learning while they are showing their work progress, even if they were going the long way around or taking a different approach than you would have.

        You want Carl to develop a growth mindset, confidence that he’ll eventually figure things out himself and come to you with things that are way out of his knowledge base when he knows he’s spinning his wheels or heading off into the weeds.

    2. hamsterpants*

      One of the most useful ways a former mentor taught me independence, and that I now use on my mentees, is to answer all questions… tomorrow. This is great at inspiring independence and alternate methods of problem-solving beyond simply asking the mentor.

      There are obvious exceptions of course if it’s a safety issue or gating something time-critical.

    3. Lego Leia*

      I started asking similar co-workers to tell what they thought before I answered, and then walked them my steps if they went astray. Sort of teach them how to arrive at the right answer. It phases them out of coming to me for quick answers, and gets them used to thinking on their own.

  3. Rusty Shackelford*

    Often I REALLY want to say, “I am busy, I’ve never done this either, we have the same job title, YOU figure it out” — but that’s not very fair; he doesn’t have experience yet to do so.

    Maybe he needs the opportunity to *get* that experience. I think it’s perfectly fine to say “Carl, I’ve never done this before either, so this is a good opportunity for you to work your way through it.”

    1. Ally McBeal*

      Completely agreed. I know how it feels to not know the answers when I feel I should. Learning to take that first Indiana Jones-style step of faith is nerve-wracking, but we’ve all been there and it’s now Carl’s turn to confront his insecurities/discomfort and just do his best. OP could offer to review his work before he submits it to their manager, or nudge him in the right direction if he’s looking for an answer, but that’s it.

    2. Rainy*

      I was in a similar situation once, in that the person who was hired into my old role used to come and ask me about elements of it even a couple of years and promotions later. In the beginning, if I knew the answer I’d give it but also explain either where I would have looked first, or else referred him to the documentation I’d written, but as systems were updated or vendors changed, my knowledge slowly but surely became too stale to help anyone. Luckily by the time that started happening, I’d realized it, so when I got a question like that I’d started to say “when I was in your role, we used X to do that, is that still true?” before I gave an answer, and so we sort of both simultaneously reached a point where we realized that I just didn’t have anything helpful to say.

    3. Susie SW*

      One of my favorite supervisory questions I learned to ask is, “How have you considered approaching this?” Or, “What’s your gut impulse on this?” It empowers people to figure out their own way without leaving them floundering if they’re way off base. I realized quickly that people stopped asking so many basic questions when I stopped doing all of the thinking for them, and they became much more effective in working independently without resenting me for telling them to figure it out themselves.

      1. BugHuntress*

        These are amazing scripts, and I’m putting them in my back pocket in hopes that I can use them one day!

      2. UShoe*

        I came here to say this, the first question I always ask when someone bings a situation to me (not a simple question) is “What’s your first instinct?” and work it through from there. It gets them in the habit of working it through themselves without feeling like they’re being left out in the cold.

      3. Yorick*

        This is good. Let them tell you their idea. Then say, “Ok, if that doesn’t work, try X.”

        Also, if there isn’t a right answer that you know (especially when you’ve never done it before), tell them that. You can talk through their problem without giving them an answer.

      4. fifteen minutes of indiscriminate screeching*

        seconding this!! i’m in a carl-ish position in a role where we do lots of triage with a lot of situations and my manager uses this one a lot as i’ve been learning how to handle things. for example, a ticket will come up that i won’t know how to handle and he’ll ask me what my gut instinct is and then i can sort of reason things out like, “via our documentation this seems like a similar situation to A where i would do X, but i’m not sure because of B” and then he knows where i’m at knowledge wise and can correct me as needed.

    4. No Name Today*

      Agreed. OP should be honest about what she can and cannot help/guide with. It’s not unfair to tell Carl that the XYZ project is new, you’ve never done it and you don’t want to do it incorrectly. He will need guidance from manager on those.
      (I’m particularly leery about telling Carl that “XYZ sounds similar to the XXZ project we do, so start that way.” I don’t feel like Carl would take ownership, try it and see what happens. I feel he would try it and if it failed, come back with “it failed. What’s do I do now?” Or “I did it like XXZ so I’m done” (and not look for differences.)
      OP. Trust your instincts that his requests are above and beyond. Step back and let him drive his own bus.

    5. LittleMarshmallow*

      I had an instrumentation specialist do that to me when I was early in my career. We were expected to call them if we hadn’t been trained to do certain things so we don’t mess up expensive lab equipment but in this case he’d never even touched this machine so when I called him he said “well… i can come in if you really want me to, but I don’t know any more than you do about this so if you’re cool with it just I’d prefer if you just figure it out yourself. Honestly I preferred that approach. Sure if he knew how to do it then instructions would’ve been nice, but I was also fine with just feeling like I had permission to fix it myself. It can be weird early in your career to know what you are and aren’t “allowed” to try to figure out yourself. Oh… and I successfully fixed the instrument. I had to get a tall guy to help me hold something up while I tinkered with it but when I was done it worked again. Haha! I’ve fixed many instruments since and wrote a little procedure to describe how to fix this particular issue for posterity.

  4. Trout 'Waver*

    I kinda see this as a failure by OP’s manager. The manager should be setting clear expectations to both OP and Carl about how far OP should be going to train Carl.

    Given that OP learned by training themselves, I’m not optimistic that OP’s manager will step up and do their job.

    1. WantonSeedStitch*

      I’m glad I’m not the only person who was thinking this. If my employee is having a hard enough time doing his job that he’s being a burden on someone else, it’s my job to determine if 1) there’s a problem with his fit for the role, 2) he needs more training (and if it’s the same person who’d be providing that training, I need to make sure they have the time to do it), or 3) he needs to simply start being more of a self-starter. I would have a conversation with the boss about this. If I were the boss and I determined that Carl has sufficient training and is suited fine for the role but just needs to start pushing himself a bit more, I would probably use a line a manager once used with me: “instead of bringing me questions, I’d like to see you start to bring me potential solutions. We can discuss them and see if they work, but I want you to put some thought into how YOU would solve this problem rather than just ask me of the bat.” I found that really helped me grow in my job, and also helped me realize I knew more than I thought I did.

      1. Momma Bear*

        Agreed. Where is the manager in this?

        Also, maybe Carl just needs express permission to do it any way they see fit. Some people are very anxious about getting it right and need permission to fail, or ask someone else, or dig around in the network on their own. But again, that should be part of the boss’ job, not OP.

        1. Trout 'Waver*

          100% agree. If the manager has never said “Carl, use your judgment to solve these problems” and OP keeps stepping in to rescue Carl, Carl may think that things are the way they should be.

          Also Carl may be coming from a job where learning through failure is considered a negative which makes him way more timid about using his own judgment vs the OP who sounds very take charge and learns through doing.

          1. Le Sigh*

            Yeah I wondered if maybe he worked in a place where using your judgment was punished. I worked in a place where office culture was to check in on every little thing; it was a time suck and things got bottlenecked. Of course, our boss would get overwhelmed and tell you to just figure it out. And then when you did, it was “all wrong” and “not what they were looking for.” Rinse, repeat. It can take a minute to unlearn those things and gauge the new office culture.

        2. Rose*

          I think this is esp common in recent grads who often have the idea that questions have an absolute right and wrong answer.

          1. Tara*

            I actually think university tends to help eliminate this kind of absolute view. At least to a certain extent. I’m working with a guy at the minute who started working straight from school, and I think he’s somewhat trapped in that school mindset (even 3 years out) that he only needs to do exactly what he’s told. I feel like I’m programming a robot trying to get him to complete tasks. (Of course, not all grads and not all school leavers apply, but a good university education should be exactly teaching you that some things require more thought and there isn’t a right or wrong for most things).

        3. TechWorker*

          Yeah I am kinda surprised the answer didn’t include ‘talk to your manager about it’ because the manager needs to know how long the ramp up is taking and also may be able to distribute some of the training or give more context specific advice than you’ll get in an advice column.

        4. ForeignLawyer*

          It would really help if the manager would clarify which of Carl’s tasks (if any) really can be done any way he sees fit. He may have an (unconscious?) sense that some tasks need to be done a specific way and some don’t, but no way to articulate that, so it’s manifesting in lots of questions about every step of every task.

          I’m fairly senior and have no problem making up my own way of doing things, but if I joined a new org/role and nobody told me which tasks were up for freestyling and which needed to follow a specific process — eg. to avoid making more work for the next person in the process, to ensure the audit trail is complete, because six steps down the line it has to be read by X software, or whatever — I’d also be asking a lot of questions.

      2. Antilles*

        Are we sure Manager even knows this is happening?
        Given that OP seems to be a quasi-supervisor, I’d bet that Carl has been going straight to OP with questions. And there’s nothing in OP’s letter indicating that they’ve flagged this for the manager.
        So I think it’s entirely possible that the manager either doesn’t know this is happening at all and/or doesn’t recognize the full extent.

        1. Putting the Dys in Dysfunction*

          That quasi-supervisor thing can be the source of many problems, when you’re supposed to supervise someone but don’t have actual authority or don’t know what your authority is. OP may not know whether she’s empowered to let the new guy figure it out or whether she’s supposed to ensure that he gets up to speed forthwith.

          Hopefully a conversation with the real boss will sort this out.

          1. BugHuntress*

            Yes, agreed. If OP’s boss has unrealistically high expectations, they might expect OP to somehow just “make it work” while still keeping the new employee from making any big mistakes.

            (I was the new person in a situation like that. My coworker had no time to train me, we were very overworked, and constant perfection was expected. Not Much Fun.)

        2. No Name Today*

          I see this as well. But I’m going to comment as senior most member of my team. Training falls to me. New people are assigned work. I help them through it, answer questions, provide my institutional knowledge and best practices.
          My manager follows up with me for feedback. If there’s something I’m seeing, like this level of questions, my manager will step in and take over.

          1. Polopoly*

            LP says that Carl is now to the working world as well as to the industry. Makes it seem like he’s he’s fresh graduate. When in school, students so very often learn that there is an answer key for all assignments. Obviously working world that isn’t always (or ever) the case. It may be that Carl needs the confidence boost to make certain types of mistakes, or go down dead ends, etc. Are you sure that your tone when he does make a mistake or go around the long way is still patient, instead of jumping in and saying “you’re doing it wrong !!!”. Is your boss the type to berate mistakes or inefficiency ?

    2. Nikki*

      Yes, this stuck out to me too!

      It’s one thing to help out a colleague in a pinch, but it sounds like OP is having to take on a lot of work around supervising and training Carl without getting the authority or recognition that should go along with that work. That would annoy me, too.

    3. Dust Bunny*

      Yeah, isn’t there someone else who should be in on this? Has the OP told her manager that it’s getting to be a problem?

      OK, maybe the manager expects OP to help, but there’s probably a limit to *how much* and there should be an allowance in OP’s own work to let her do so.

    4. Rose*

      My first thought reading this letter was of course when you give someone with a very little experience the same title as an experienced person and then ask the latter to do management type duties (training, mentorship) without the benefits of management, you get an employee with a strong urge to say “we have the same title, figure it out yourself.” And I can’t say I blame OP.

    5. No Name Today*

      I 100% see this as a failure with the manager. If Carl (even for his own reasons, like he had a bad manager or he’s just that person who won’t talk to manager) doesn’t check in with manager and let her know that he’s not confident, the manager should be checking in with him. And with OP.
      He should be going to manager.
      And manager should be aware of how much he’s relying on op.

      1. BugHuntress*

        I feel like this works in some orgs and not others. Some organizations have a culture where, because of informality or churn, everyone is expected to have very strong boundaries. They are expected to speak up and be extremely honest and noisy if they cannot handle their workload. The logic goes, we cannot help what we do not know about. Of course, you might say that Carl should be in this boat. But if Carl thinks that everything is perfectly fine, because OP always has all the answers, Carl is not going to tell manager there is a problem. I’m not saying it’s the way things should be at an org, but I think it’s common, especially in a startup that is growing messily. People might be completely unaware of what is going on somewhere else in the organization.

        1. Trout 'Waver*

          The attitude of “People will speak up if they have problems” is really, really bad management. The overwhelming majority of people minimize their issues to people in positions of authority. A manager who takes this attitude is ignoring one of their fundamental responsibilities to their team.

    6. Where’s the Orchestra?*

      I’ve been where OP was thru no fault of the manager. My “you’re my portable brain” coworker was trying to hide just how bad he was at his job by only asking the manager every fifth question he had, and asking me as the most senior person not a manager the other four. After two weeks of that i mentioned it to my team lead – who was pissed off on my behalf and told me to send “mr portable brain” to them every time. They were let go (and this is a government job) two months later for failure to independently complete their workload*.

      * they were two months shy of being out of the probationary period, which helped with the firing, but they should have been far more independent at four months in. This position has a six month probation period.

    7. Leela*

      I find that this is often so poorly handled by companies. They tell person A to train person B on “some stuff”, thinking it will magically align with whatever person B needs to get up and running. It often isn’t, person A often doesn’t have what they need to make a good training session (and it is VERY frequent IME that person A isn’t even checked out to see if they’re actually good at training at all, or just someone who knows the job already. Not that I’m implying this about OP at all, just a pitfall I see at a lot of places) leaving person B stressed out and wanting specific, hands-on instruction because they have *no* context for the information they’re getting and it’s extremely stressful to be on the receiving end of! Especially if the company has person B just looking over person A’s computer while person A flies through everything on muscle/sight memory and gets agitated that person B is seeing the ENTIRE screen and all the options, not just the few things person A knows to click on for various tasks

  5. animaniactoo*

    Would it work to tell him you haven’t done that either, but if he works up a way to do it, you’ll let him know whether you think it will work or not?

    Among other things, that gets him to tap his own knowledge of what he has already, and puts you in a position to:

    1) Have the background research done by him as much as possible.
    2) Be able to update the pieces that he may not have seen/made the connection on.
    3) Be able to say “That sounds good, go ahead and do it that way” as much as possible – building his confidence that the number of times you go with his plan means that he is probably okay to go with it some of the time when he doesn’t check with you.

    1. Aerin*

      Yes to the updating your documentation! I work in a role where I’m specifically there to advise agents when they get stuck. And sometimes it’s a matter of the information being there and they clearly didn’t try to find it, but sometimes it’s a matter of the information being a bit ambiguous, or relying on other information that everyone else knows but that didn’t actually make it into writing. In those cases we always try to go back into the article and rework it to avoid future confusion.

      Also, if a lot of the judgments that Carl’s being expected to make are based on institutional knowledge, and the only place that exists is in your head, then it’s not that surprising that he’s asking you. So the solution might be to either get that stuff out of your head (by making that a specific project that you carve out time for) or to make it clear that he’s not actually responsible for having that extra context, and if he makes a reasonable decision based on just the information he has, that’s okay even if you would have done it differently. He may be feeling some pressure, spoken or otherwise, to handle things exactly the way you would do, and clearly that’s not working. Either he needs better info/tools or he needs to be specifically told what the actual expectations are.

    2. The Starsong Princess*

      I think OP should set aside an hour or two a week where they formally sit down with Carl and go through his list of questions. No more adhoc interruptions by Carl. That way, OP can go into it with the mindset that Carl gets their undivided attention and they are going to both answer his questions and coach him into being more independent. Since Carl has to wait until his next session except for dire emergencies, he will start figuring thinks out.

      1. Yorick*

        This could be a good idea. If it doesn’t make sense to set formal meetings like a boss would, frame it as a weekly coffee or something

  6. Just Your Everyday Crone*

    A person who likes a lot of clarity and cut and dried answers may not be a good fit for a job that does not have a lot of clarity and cut and dried answers.

    1. Former Retail Manager*

      OMG!!!!! YES!!!!!!!!!!!!

      I have been training new people for my current position for years at this point (average training cycle is a full two years from new hire to fully trained), and this position is similar to what OP describes….a lot of context and fact dependent situations and the ability to differentiate your actions / responses based on those facts. People that we have hired who see things in black and white or who want if this, then that responses just don’t do well long term (or short term really). They end up frustrated, confused, and spinning their wheels and they make everyone’s lives miserable in the process.

      1. Problem solved*

        I have been in the exact same situation and it is overwhelmingly frustrating and work slows to a trickle — both the new hire’s work and my own. The solution I found, which I know gets a lot of hate, is screening for people who are high “N” types on the Myers-Briggs Type Indicator. People who are high “S” types need the step-by-step instructions spelled out for them and are extremely frustrated with being told to run with something and figure it out. I can’t tell you how much easier my work life is since I started hiring for this.

    2. ThatGirl*

      Yes. I did a stint in customer service and during that time I ended up helping train a few newbies. There was one woman who really, really wanted everything to be scripted, and step-by-step. But it wasn’t a call center; we had some standard language to use and if it was a matter of looking some information up she could do that no problem, but there were a lot of people who really just wanted empathy and understanding along with some creative solutions (which we were allowed to give!) and she didn’t know how to adapt to that. Ultimately it was not the right fit for her.

    3. Rose*

      This was my first thought too. I do think a lot of people leave school, where every test has right and wrong answers, and expect the workplace to be the same way. I struggled professionally until my first manager explicitly told me a lot of these questions are not going to have a right or wrong answer, and using your own best judgment is enough for me. I had a bachelors in bio and my first jobs were in a lab and it was so hard to wrap my head around the fact that in an office you could move forward with imperfect data and you could speak confidently even if you didn’t have “I bet this would pass a peer review“ level confidence about what you were saying .

    4. Koalafied*

      Yep. I had a similar issue with the LW, except in my case the type of work that I was constantly getting pulled in to help someone with, is very technical work that for historical reasons had ended up falling to non-technical roles. Myself and former employees in the roles happened to have more technical aptitude than the roles otherwise required, so as we integrated technology into our program we picked up these technical tasks along the way. But there had been some turnover, and we’d hired people into the roles who were excellent at 95% non-technical part of their jobs but would be beating their head against the wall struggling through the 5% technical part.

      When I’d be swamped with my own work and they needed help with something, especially complicated stuff that I’d never done before either, but I had a pretty good idea of how I’d start tackling it, I definitely had the exact reaction the LW had: I taught myself how to do this with nothing but documentation, product support, and trial & error – why can’t they just do what I did?!

      But thanks in large part reading this site, I was able to step back enough to realize that I was less annoyed at having to provide this kind of help to my colleagues, and more annoyed that I was having to provide the help on often short notice and short turn-around time and when I was already struggling to keep up with the core job tasks my performance is actually assessed based on.

      In fact, I realized I actually enjoy designing solutions like that! I ended up talking to my boss and making it clear that this was a work capacity issue, and proposing to make those tasks formally part of my job description so that 1) I could just do it without having to teach it, 2) I would be involved in projects from Day 1 with full context and an appropriate timeline to turn around a finished product and 3) other responsibilities could be shifted off my plate in exchange for me taking on the new responsibility. The workflow is far more efficient for the team as a whole now, and my non-technical colleagues are thrilled to no longer have to even attempt the stuff they struggled so much with.

      1. BugHuntress*

        That’s awesome! It sounds like you were able to effect a strongly impactful systemic change! Your company should give you all of the money for coming up with that idea.

        (Have you ever read Donella Meadows’ book “Thinking In Systems”? It’s this kind of thing— I love that book.)

        1. New Jack Karyn*

          My eyes skimmed your comment, and I swear I read that author as ‘Donatella Moss’ and I about had a heart attack.

    5. Trawna*

      Thank you for this. I was hyperventilating reading that question. I’m good at mentoring interns and new and/or junior staff, but good hires need to learn FAST how to pivot on new information. It’s mostly a question of having the right kind of confidence, though, which is hard to teach.

    6. Kevin Sours*

      Yes and no. It’s not always clear starting out what authority you have to make decisions or the difference between open questions and questions you don’t know the answer two. A clear response of “dunno, you figure it out” can actually be quite liberating simply because it gives somebody like Carl *permission* to go spend time figuring it out and doing it their way.

      1. RebelwithMouseyHair*

        I remember the first time I wrote a letter to someone for the NGO I volunteer at. I submitted it to the person who’d asked me to do it. She said, no need for me to check it, you’re qualified so you’re competent. As I had a boss in my paid job who tried to dictate “please find enclosed” emails to me, this was immensely liberating.
        But this works for the kind of person who likes figuring stuff out by themselves, and it doesn’t sound like Carl is.

        1. Kevin Sours*

          Maybe Carl isn’t the kind of guy who likes figuring things out for himself. Or maybe he thinks he’s going to get yelled at for spending three days figuring it out when the answer is something everybody knows. Or is in some process manual people forgot to tell him about. I don’t think you can really know that until you give him clear expectations for how much latitude (and time) he’s allowed to exercise.

    7. X-Man*

      Agreed. I’m a person who likes the clarity and cut & dry procedures and while Carl and the OP’s role might sound mundane to most people to me it sounds like absolute hell.

  7. CarCarJabar*

    Also- have you trained him to consolidate his questions into a once daily (or, weekly) interruption? It’s so much easier to manage if you set aside the same 30 minute block to answer all of his questions, instead of fielding them multiple times throughout the day.

    1. cosmicgorilla*

      This. This is what I came here to say. Set up a standing weekly meeting and have him bring you questions then.
      Maybe you have it more frequently at first, then taper off as he gets his feet under him.

    2. Lizianna*

      This works so well. I’ve had team members whose first instinct was to come to my office to ask a question. It was hugely disruptive to my flow. Having them save them all up for a regular check in really made them stop and ask, is this really important enough to hold for our meeting, or is there something I can do in a meantime to figure it out?

      (Obviously, there are exceptions in the case of an emergency, and helping them figure out the difference took some coaching too. If they’d pop in, and it wasn’t an emergency, I had to train myself to say, that’s a good question, and I want to give it the attention it deserves. I’m in the middle of something right now, but make sure you bring it up when we meet tomorrow morning.)

    3. A Feast of Fools*

      At this job and my last one, I did this automatically as a newbie when I realized that most of my questions / my department’s work isn’t hyper time-sensitive. And, in saving up my questions for the end of the day or twice a week or whatever, I found out that I could answer a huge chunk of them myself, given time.

      Sometimes it was by finding out who else in the org could answer my question besides my manager. Which then helped me build relationships across the company so I could gain some of the broader institutional knowledge that my manager had.

      So, yeah, if Carl isn’t coming to this conclusion on his own (i.e., “I should batch my questions.”) then you should definitely ask him to, OP.

    4. Where’s the Orchestra?*

      This only works if the person with the questions has/will work on other things while waiting to ask the questions at the meeting. Or if he will pick at the edges of the question while waiting. If they are like my former coworker, “mr portable brain” and just sit and twiddle their thumbs while waiting……..

      This is still worth a try though. And loop in the manager while you are implementing this “questions meeting” to see if it’s something that manager as the supervisor is doing/should be doing for Carl.

      1. RebelwithMouseyHair*

        yes of course. And the thumb-twiddlers are clearly not suited for the role, so that makes everything that much easier for OP. Either Carl manages to get on with the work despite not having all the answers (and maybe stumbles across the answers, or possible answers, while soldiering on), or he twiddles his thumbs and his productivity will plummet and it’ll be obvious that he’s not the right person for the job.

  8. Cafe au Lait*

    A thought–Carl might be getting push back from your manager and/or higher ups when describing his work on projects. I can see “Well, why aren’t we doing it the old (i.e. your) way?” Helping Carl people-solve might go a long way in getting him to stop asking you questions.

  9. Anonymous Hippo*

    I don’t know if the OP is in charge of training Carl, but I personally use these kinds of things as a learning tool, as a manager, and earlier as a senior in a role. This accomplishes one of two things…either they get better at working through the process, or coming to you becomes more of a pain then figuring it out themselves lol. Basically I make them walk through the troubleshooting steps themselves, with me giving hints, or pointing out errors in their thinking or what have you. Unless it is a straight forward yes or no question, as in they’ve already done the work and they just need confirmation, but even then, if it isn’t something that they need confirmed as part of the process (ie just insecurity) I won’t give a simple answer but have them walk me through the steps anyway, and I can confirm the overall thinking.

  10. Emily*

    The question of what it’s appropriate for Carl to be figuring out vs. getting help on isn’t OP’s to answer, it’s their manager’s. That’s part of managing someone, and the answer isn’t based on whether you had to figure it out yourself, or whether it’s annoying to help, or even about whether it’s your perception as a co-worker that they should have been able to figure it out by now, it’s about what each role entails and what a good use of everyone’s time is. The manager may be shocked that Carl still needs so much help, or they may think it’s entirely appropriate, or anything in between.

    1. AD*

      This is absolutely right and will also help Carl figure out, I would think, how to proceed moving forward.

    2. RebelwithMouseyHair*

      The thing is, there was nobody to help OP so she muddled through and managed to do a good enough job. Now she’s probably on top of her game after three years of it. Even if Carl has some projects that OP has no idea about, she is familiar with the work, and she’s right there, so it must seem perfectly logical to ask her when he comes up against a tricky bit.
      I agree with others who’ve said Carl needs to list all his questions and ask at a meeting rather than just butt in any time.

  11. MicroManagered*

    I think sometimes people learn that asking you is the fastest way to get a task done, to the point that asking you becomes their first option, even before “think about what to do myself.” There have been times in my working life where I’ve made a conscious decision to re-train someone that asking me is NOT the fastest way to go about every little thing.

    Sometimes, with my boss’s knowledge & support or their boss’s knowledge & support, I’ve consciously done things like screening calls, letting an email “breathe” for a day or two before responding, or when the only way for me to “help” would be to learn the details and essentially do a task myself (as opposed to answering one question, one step of the way) I say I don’t have the answer or I don’t know.

    The idea is not to be deliberately difficult or unhelpful, but just not to jump in right away every time a question comes up. Sometimes that helps to guide them away from ME as their only resource and start to use other resources, including their own problem-solving skills!

  12. IfLucid*

    Something I’ve used a lot over the years in this situation is to them “Where have you looked? / What have you tried?” as my first response. I’ll frame it as not wanting to send you down a path you’ve already gone down, so tell me what steps you’ve already taken to try to get the answer.

    If they’ve tried nothing and came straight to me I point out, good naturedly, that they should check the resources given to them in training, or take the standard troubleshooting steps, and come back to me if they aren’t able to find the solution.

    And because I don’t want to create an environment where people don’t come to me if there’s an actual problem, or struggle with bad solutions or workarounds, I put a reminder on my calendar to follow up later that day or the next morning to check in with them.

    It usually only takes a few times before they start coming to me prepared, staying they’ve looked in X and Y and tried Z and are still stumped.

    1. Don't Send Your Kids to Hudson University*

      I like this approach. And it helps to reinforce that LW isn’t the first stop and provider of the answer, but someone who can help Carl think through his own process.

    2. Smithy*

      Depending on the kind of work, if someone hasn’t done anything yet – it may be helpful to follow with a question of what they think they might want to try first.

      In my line of work, someone might feel blocked in doing step 1 because that includes outreach to another team – and a newer person might be concerned about making that incorrect outreach given the nature of the first step. In that situation I’ve found the following helpful on both sides (being both questioner and mentor). First option to ask someone to walk you through their thinking process for initial steps and then provided that approach is overall sound – even if it’s not your preferred first approach – let them do that. If their first steps are missing a critical step or person, make sure that’s included – but otherwise let it go.

      Depending on the nature of their question and the guidance they want, it’s also reasonable to identify that they’re looking for a more in-depth brainstorm or meeting. Asking someone to schedule a meeting and think through how to discuss the topic in more depth can save your calendar and bandwidth for bigger picture questions that can’t be answered quickly. But also help identify the difference in the kinds of questions that can get quick feedback vs those that require more investment both from a more senior colleague as well as themselves.

    3. Aerin*

      My main approach is not to just say “This is the answer” but “This is how you find the answer.” So even if I’m just pointing them somewhere in the knowledge base, it’s not “It’s article number x” but “it’s the third search result if you search ‘phrase'” or “I went to this department page and then pulled up this tool here.” (And yes, that’s after the “what else have you tried,” “have you looked here,” “have you asked these basic diagnostic questions” stuff.)

      Where we figure out if it’s an issue or not is if they come back to me with the same question next time. Because now I know they definitely know how to figure this out for themselves, and they are either failing or not bothering to do so. Then it’s a matter of figuring out which of the two it is and addressing accordingly.

    4. Miss Muffet*

      My version of this was ‘three before me’ – check 3 reasonable sources (requirements, training documents, prior versions of a similar thing, etc) for an answer and THEN you can come to me. And I will want to know what you checked (or tried) so that I get your thought process, too. It might be that you’re looking in the wrong place and didn’t even know that the right one existed (which in that case, boo on me as a manager/coach for not having covered that). It’s easier to coach someone having that baseline of what they are thinking/how they are approaching it. Similarly, with a problem or an issue, I like when my employees come to me with a suggested solution in hand. “These teapots keep breaking in the kiln. I think we should consider adjusting the temparature in the kiln”. Then I can say, yes that’s a good idea, or maybe there’s another check we need to do. But it makes the new learner start to think down the road a bit and not just YIKES THERE’S A PROBLEM CALL THE MANAGER.

  13. Don't Send Your Kids to Hudson University*

    I think the Letter Writer can probably make some small adjustments after talking directly with Carl. Instead of saying, “this is what I would do, but it’s fine to go another way.” I think you can stop providing the “this is what I would do” part and really lean into helping Carl learn the thought process of figuring it out. Ask some questions (even leading questions), point out what he already knows or has done successfully: “I think this is like when you tackled problem X, so what do you think you can do similarly for problem Y?” I think if LW sees their role as being about coaching through the figuring it out process, rather than provider of the answer, they will both be better off in the long run.

        1. knitcrazybooknut*

          I love it that everyone has their own pronunciation, but it’s always immediately recognizable. Mine is, “JUNG JUNG!”

      1. Don't Send Your Kids to Hudson University*

        I work at a university in a role that has been totally demonized on SVU (think: complicit in covering up sexual assaults), so my old coworker and started asking ourselves what they would do at Hudson University, and then we’d do the opposite!

    1. Tali*

      I was looking for something like this. I think this is the best solution for Carl. Often the hardest part of being new to a job or role is not knowing what you don’t know and not knowing how to learn it. Carl might not see the similarities between an orange and a lemon, but you know from experience that clients who want a splash of citrus might be OK with either but clients who want orange juice will not be happy with lemons. So if he asks which to use, you could coach him through the connections you’ve learned to draw, sharing your experiences so that he can reach the judgment part himself.

      “It’s fine to go another way” assumes that Carl has reason or expertise to suggest a better solution, but if he doesn’t have expertise and you do, he has no reason to do differently than you say, and he doesn’t learn from that interaction why one would do differently. Teaching him to think will let him use your expertise to develop his own judgement, instead of using your expertise to feed him the answer as it is now.

    2. Not So NewReader*

      Thank you.
      I have trained a lot of people and the way OP illustrates how they are teaching the new hire, it does not surprise me that the new hire is not catching on.

      OP, what to do in this situation is to tell them to do it your way until they catch on, then they will realize where there is wiggle room and they can start to make their own adjustments. The reason I recommend this is because they have to start actually working. If they are asking you questions all day long then they are not actually working. Have them copy you so they can at least get launched.

      What I see here is that the new hire’s indecision only mirrors the indecision you are showing them. I would not be surprised if this person quits the job.

      OP, if you don’t want to train then please tell your boss and ask for someone else to be assigned to this person. It’s not fair to you, it’s not fair to the new hire and it’s not fair to the company.

      I am sorry, OP, based on what you have here I would not learn the job either. And I have had a variety of jobs over the decades, so I do catch on to things. If you chose to keep training this person, have them do things your way on a temporary basis until the newness wears off and they can make their own decisions. You’re the trainer- it’s up to you to make decisions until the trainee can take on more and more decisions on their own. No, the trainee is not going to learn if you keep telling them, that it’s fine to do something else. Every time you say that they walk away not knowing what to do at all. I think if you stop using that framing things will change in this story line.

      1. Where’s the Orchestra?*

        My only question is: “who is the formally designated trainer for Carl?”

        I don’t see a clear answer up above – and I think that may be adding to the problem. If manager is supposed to be training, but is never around thus leaving only OP, who was never told that they need to train Carl that would be really frustrating for both OP and Carl.

        1. Not So NewReader*

          I have seen a lot of this type of thing.

          Of course, OP, has options. OP can just decide not to train if OP has not been told to train and let the chips fall where they may. Typically this does not play out well and in the long run involves more effort than if OP had just trained the person. But it’s within OP’s right to say no.

          I have opted to train because Dang! I need help. If I train the person I can get some insight on how they work and visa versa. It’s an investment that gives many returns over the years.

          1. Where’s the Orchestra?*

            Oh agreed – so long as the time spent training doesn’t end up getting OP in trouble because of workload not getting completed because they ran out of time (because they were training Carl – also a completely reasonable use of time). I’ve unfortunately seen that happen – in again crappy management situations where it wasn’t clearly defined “who” was responsible for training new employees.

      2. Don't Send Your Kids to Hudson University*

        I actually think we might be suggesting opposite approaches. I really think an effective way to teach Carl how to think through solutions is to stop providing directions and answers about what to do. Instead I think the LW should ask him a lot of questions, and give guidance and help draw connections he isn’t seeing, but actively stop telling him what to do.

    3. Sleeve McQueen*

      I often deploy “so what would you do if I wasn’t here and you couldn’t ask anyone else?” and then when they answer my response is that “well it sounds like you know what you are doing?”

      PS Viva Lennie Briscoe

  14. John Smith*

    I had this kind of issue with a job a while ago (me being the “asker”). The problem for me was that the basics and principles of the job, systems etc weren’t really explained properly, so when something went “off script” I didn’t have a clue what to do. That and people’s learning styles as well as conditions such as autism will play a part as well. Take physics. In school I just didn’t understand the subject, but later in life I had to take a crash course in some fundamentals and, honest to god, if I had just been taught those fundamentals in the first place I might have had a totally different career (and no, it’s not because I’m older).

    It could just be that there’s no good fit between you / your organisation / colleague. Hope it works out.

    1. Lalala*

      This was my thought too. I wonder if Carl is trying to figure out the basics of how things work with unclear/nonexistent documentation — but every time he asks OP for help, OP replies with a solution for the particular situation. If you’re trying to learn the decisionmaking framework for your role but a lot of your examples are exceptions, it is so hard to gain enough confidence to manage issues on your own (and takes a lot longer to figure out). OP, does Carl have good basic training resources? (Maybe he does! In my company training is nonexistent in my department — I an sure I was a Carl in my first year on the job!)

      1. Genie*

        Agree with both of you entirely. I’ve been Carl before, and it’s always been due to inadequate or nonexistent:
        * training, and/or
        * documentation, and/or
        * management, and/or
        * direction.

        No one is going to be a “good fit” for a role where the basic fundamentals of that role are not explained to them. Companies that continuously blame the personnel for their inadequate, incompetent systems and processes always end up burning through people until they either pull their socks up, and/or they get lucky and someone internally who knows the critical parts of the job is willing to take on the job.

        1. RebelwithMouseyHair*

          TBF it sounds like OP managed three years ago, I doubt that the job has got that much more complex since then. Had she been in the role for ten years, I would imagine that extra duties and layers of complexity have been added over time, to the point that only OP would even know what needed doing.
          Since OP muddled through well enough, her manager probably has no idea that she’s incredibly resourceful and that your average Joe would be floundering.
          I would suggest to OP that she draws up SOPs: this could be added to with each of Carl’s questions. Just in case he’s also forgetful.

  15. B*

    I am curious how your interpersonal communication mechanism is affecting this. I could imagine a colleague who drops by your desk and immediately wants an answer, or sends an email for each new question that takes a lot time to thoughtfully respond if you’re deluged in email.

    If that resonates, what about a weekly 1 on 1? Even if you’re not a supervisor they can still be helpful. Then when these questions drop in, you can ask him to add to his agenda to discuss. It will put boundaries on the time you spend and give you a little background processing time. Over time, you could shift the meeting to bi-weekly or monthly, or as needed.

    1. Eether, Either*

      Yes, the 1 on 1 is what I was going to suggest. It gives Carl time to organize his questions knowing, barring any emergency, that is his timeslot. It has the added benefit that Carl might figure out how to solve the issue(s) by the time the meeting happens. I’ve been this person. It’s very difficult. I started an admin job 16 years ago in a VERY niche industry. My VP and I were both new. I learned a lot fast. And, I realized I could figure out how to do a lot of things on my own, when someone was not available for help.

  16. GreenDoor*

    I don’t know if this would work in the OP’s situation, but I’ve often told subordinates something like, “Use X template, make sure you check Y resource, and draft something for me to look at.” Then when they bring a draft, I can tell them A needs our standard language, B is missing a fiscal analysis, on C you need less editorializing and more factual evidence, and you completely forgot to include D.

    That is so much less tedious than dropping what I’m doing to walk them through every little step and it trains them on how we cover each aspect of our work. This coupled with the “what have you tried so far kind of questions” and referring them back to any guidebooks/videos/etc. can dramatically cut down on my hands-0n time.

    1. Lab Boss*

      Yes! Asking them to at least try, before asking for help! I put a lot of emphasis on asking them to have an idea of what they want to do and why, and then we can work through whether it will work or needs adjustments.

  17. AvonLady Barksdale*

    I recently had my one-year review. I have plenty of work experience, but I’m still new. My boss praised my willingness to ask questions, that I’m not trying to forge ahead and reinvent the wheel. Carl should be able to ask for help, and the LW should not be afraid to say, “I’m not really sure; you should talk to X,” or, “I’m not sure, but if you want to brainstorm, let’s set up a time later this week.” Saying, “I would do it this way, but if you think there’s a better way, go for it” is kind of… I don’t know. He doesn’t know the logistics, he doesn’t have a better way, and he won’t until he’s comfortable.

    1. Just Another Zebra*

      Exactly this. I understand the frustration of frequent questions, but how else is he going to learn?

    2. anonymous73*

      The way she’s worded it probably needs to change, but it’s not her job to hold his hand throughout the entire process. Yes he should be able to ask for help, but it sounds like he wants her to do the job for him while he watches. With job duties that aren’t so cut and dry, sometimes you need to figure stuff out on your own (with a little guidance). That’s how you learn.

  18. Lab Boss*

    I sympathize with Carl as someone who values clarity- but learning to make the decisions is part of learning the job. I struggled with both “is this too important for me to risk making a mistake” but also “I might be able to do this one task right, but am I missing something important that I need to learn long-term.” There are two things that helped me a lot and might help Carl (although I don’t know if OP has the authority to make either of them happen).

    The first is to try to give him guidelines on which sort of things need to be done a certain way (ask for help) and which are more flexible (figure it out on your own even if you don’t do it the “best” way). The second is to have periodic feedback opportunities where Carl can meet with a designated senior colleague or manager to review how he’s solved problems and made decisions, along with what worked and what he can improve in the future. By designating a time for this it can keep it from seeping out to eat up too much work time.

  19. Nick*

    I am a frontline manager to 22 people. I have gone back to college to help me be better at my job. One of the papers I wrote about managing employee of different generations. The letter writer’s example of the young employee wanting a step by step process for everything sounds like it came straight out of several of the studies I read and cited in my paper. It has a lot to do with the expectations of success placed on children and the methods used in education today, i.e. teaching how to perform well on a test vs. teaching how to think critically and truly understand subjects. Today the youth are taught and given step by step directions to figure something out and that becomes their definition of success. “See, I followed directions and everything worked!”.
    It was found that new people had to go through this kind of trial by fire and good managers should be on the lookout for young people struggling with this level of independence and accountability. They are literally scared of failure and feel like they are being setup to fail since they are not given the formula to success. They never did learn that sometimes there is no formula, that you have to take in and synthesize information, and then must make the best decision you can. I bet the kid is gonna do great. Eventually!

    1. I edit everything*

      This is really interesting. I’m going to ask my son about this when he gets home from school.

    2. Aerin*

      I’ve definitely noticed that the newbies who seem the most anxious about doing things exactly right and having to stray from the script are younger. Although I’m not sure that’s necessarily something specific to this generation as much as a function of age/experience in general: when you’ve actually experienced failure and seen how to come through the other side, you can be a little bolder and willing to risk it again.

      For timid folks, especially when they’ve reached the point where they mostly know what they’re doing but still want to be absolutely certain, I tend to ask them to get very specific about the worst-case scenario if they do it wrong. That takes it from a massive, nameless dread to “I have to do a new draft” or “I roll back the change” or even “something gets delayed and a few people get grumpy but the thing still gets done and we all move on.” They need that push to see that no, the stakes aren’t that high, you really can just pick a direction and see what happens. Helps quite a lot with getting them to develop (and trust!) their own judgment.

      1. Nick*

        You are right in that is isn’t exclusive to today, but it became much more predominant beginning with Millennials (I am one, an older one, heck I am probably the first Millennial born). The studies I referenced ran the gamut from Baby Boomer to Gen Z. This was the extremely abridged version of the paper, there were more behaviors and motivations attributed to each generation in general, along with best practices to help engage each type of employee. It was very eye-opening.

        1. README*

          Could you share the paper title/author? I’d love to try and read this.. my library has access to a lot of academic journals

    3. Gracely*

      I think at least some of that comes from teachers trying to CYA themselves, because parents loooove to complain that their kid wasn’t told how to do something. Or “s/he did what the directions said, why didn’t they get an A?” when the work is still subpar.

      Kids really need to be allowed to fail in school when the stakes are lower.

    4. lemon*

      This is a really good point. I’m in a master’s program but also work full time and have a decade of experience. Most of the students in my program are newer to the working world. And I can totally see how our program is setting them up for a harsh adjustment once they get their first industry jobs. Success in the program means following a rubric to the letter and getting dinged points if you fail to do x, y, and z specific items in your deliverable. But success on the job often means just figuring out something that works, often in the absence of any clear guidelines. It’s been hard for me to adjust in the opposite direction, where I’m used to being able to figure out my own way of doing things on the job, but when I do that for a class assignment, I get dinged points for not following a rubric.

    5. Dust Bunny*

      I distinctly remember getting in trouble in school for not doing things exactly the way I was told, even if my way worked, too.

      1. RebelwithMouseyHair*

        ah yes me too. I also got told off for teaching myself the subjunctive form in French too.

        I remember my Dad watching me struggle with maths, and he suddenly said, “but you need to use cross multiplication for that”. He showed me and it was much quicker than the teacher’s method. I romped through my homework and got everything right, then I got blasted with a zero for not using the method taught. Dad was furious and went to see the teacher. He actually got a paper and pencil and started showing the teacher, who apparently didn’t understand. (It didn’t matter because I was intending to drop maths asap)

        I think this kind of thing has got worse since I was at school. Taking initiative is frowned on, yet often initiative is what sets the excellent worker above the good worker

    6. Generic Name*

      Interesting point. My son is in high school, and his teachers straight up give the students the grading rubric for each assignment. As in it says what constitutes an A grade, what constitutes a B grade, etc. Work just doesn’t….work that way in that nobody has the answer sometimes.

    7. Esmeralda*

      Very perceptive! Yes, this is a problem many of my first year students have. “I did the homework, I did the practice tests, but the questions on the test were completely different”. (They’re actually not different — students are not recognizing patterns and types of questions) Or, “I took notes, I read and reread my textbook, but the test asked for stuff we didn’t study’ (students need to take the information and apply it or compare it or evaluate it)

      If you haven’t had to develop some critical thinking skills earlier (and not just in school), it’s harrrrrdddd to develop them later. Not impossible, just hard. And with the added pressure of “I’m going to get fired if I don’t figure this out”.

    8. Genie*

      One of my favourite types of bad managers are those that whine when someone doesn’t follow the procedure (which has usually been very poorly explained, if it’s been explained at all)…but then whine even more when the employee doesn’t have the mind-reading abilities to know exactly when they’re meant to follow procedure, and when they’re meant to know that the procedure doesn’t apply (eg: if ABC happens), or that the usually completely rigid procedure suddenly becomes flexible under certain circumstances (eg: if XYZ occurs).

      Bonus points if the terrible manager has the employee in question on a PIP or are otherwise threatening their job at the same time as this crap.

    9. just a random teacher*

      The most frustrating thing that I’ve been seeing show up as accommodations in more and more IEPs and 504s (documents that k-12 students have stating how you have to adjust your classes for them due to disability) is something like “step by step directions provided for all assignments with over 3 steps” or something similar. The ENTIRE POINT of most of my bigger assignments is that I don’t given step-by-step directions, but rather than you have to try different strategies to see what approaches end up working! The actual thing you need to do is usually pretty straightforward once you figure out what to do, it’s the going from a described problem with no process specified to identifying a process that will work part that’s the entire point of that kind of assignment. (I offer to meet with students one on one so they can go over their approaches and what they’ve tried so far if they’re feeling stuck – they’re not totally unsupported, but figuring out what to is a much more important skill than being able to follow directions. Computers are great at following directions, so the jobs that are nothing but following directions uncritically all day tend to be automated away.)

      1. RebelwithMouseyHair*

        …which would mean that people with the type of disability that means they need step-by-step directions, are probably not a good fit for your course. Or probably any course where initiative and critical thinking are needed… which is surely the vast majority?

    10. Toffifee*

      Yup this was me back at school.
      It was ingrained in me that there was only one way to do things the right way, and that you had to have the perfect answer to everything.
      This mentality also rolled into my college years where I majored in Science, where the correct formula and sequence was needed.
      Suffice to say train of thought hindered me in the ‘real world ‘ when I entered my first big girl job, cause I wasnt able to think outside the box and Id never been taught to think critically.

      I thought it was stupid for workplaces not to implement a ‘correct’ way of doing things, but I now realise my attitude was stopping me from considering different methods.

      Children need to be taught that there’s no correct or perfect way to do things.

      1. RebelwithMouseyHair*

        yeah, if you only have one way of doing things, you get rigidified workers who then can’t handle the change manager coming along and telling them they’re rolling out new technology to automate most of their job and they’ll have to adapt.

    11. Yorick*

      I have noticed this more and more from my college students. They don’t seem to even understand the concept of problem solving. I don’t know how much it’s really changing, but I do feel like it’s gotten a little more common now than when I started teaching 14 years ago.

  20. Just Another Zebra*

    For some perspective, OP, I was Carl at my current job. It was my first professional job (only retail previously), and in an industry so far from what I’d been doing that it all felt very foreign and alien. I felt SO LOST, because the person who was supposed to be training me was “busy” and “didn’t have the time”. This was probably true, but I was being told to speak to X about my job, and she kept blowing me off. I’m seeing a little bit of this in your letter.

    You seem to indicate that Carl is young, since he’s new to the industry and the working world. It’s very hard to figure things out for yourself without any context. All that knowledge and history you have stored in your brain isn’t something Carl will pick up immediately. What could help (and yes – it’s a bit of work on your part) is to make Carl a general “cheat-sheet”. Something like “for customer A we always do this, customer B will except this or that, and customer C prefers that”. Give him some tools to help himself, so that he can grow into a better coworker for you.

    1. I edit everything*

      Yeah, I was wondering if there’s any documentation for Carl, or if he’s expected to simply get all the institutional knowledge by osmosis.

      1. Genie*

        I was thinking exactly the same thing. And even if things are documented, does Carl know where they are? Can he access them? And do these documents make sense to a new starter, or doi they only really serve those people who already have the knowledge needed?

  21. Person*

    Sometimes when someone doesn’t seem to be getting the hint that they need to figure things out for themselves, it can help to start answering some of his questions with questions and pointing them to resources where he can find out more, which can be annoying in other circumstances, but in cases where people start to rely on you for answers they should be finding themselves is really useful.
    Coworker: How do you do x?
    OP: What have you tried so far?
    Coworker: I wasn’t sure where to start, so I thought I’d ask.
    OP: Well, given y and z, here are some places, I’d start looking to find out.
    Coworker: But how do I do [specific thing]
    OP: Well, what does [resource you pointed him to] say about that?

    … and so on. But the main thing here is to lead him towards finding the answers himself rather than answering outright, which will take longer but will lead him away from relying on you as much to just quickly give him answers.

  22. Filosofickle*

    If I were Carl, one thing I might be worried about is the extra time it takes me to figure things out. Does he know he has permission to be less productive because it will take him longer upfront to find the solution? That it’s okay to try something even if it doesn’t work perfectly? That an important part of his job is independently creating his own solutions and plans? Assuming, of course, that’s all actually true — which only the boss knows. You can and should teach him to fish, but I’d start with confirming that expectations are aligned and he does indeed have permission to be slower and be imperfect while he learns.

    1. Missy*

      Yes. Carl needs to know that it’s ok if it takes him longer AND if he makes a wrong decision, as long as the logic is sound. If your workplace is one with missing stairs or secret bees…well then he can’t really be blamed for being terrified of doing something wrong. I’m thinking about a place I worked at previously that invited clients to an open house and grouped them together by last name, not knowing there were a pair of angry exes who would be grouped together like that. Employee who arranged it had no way of knowing but still got yelled at because…IDK, the idea that they should have figured it out somehow. It was a place where everyone was afraid to be wrong because of that.

  23. phira*

    Okay, bear with me for this analogy:

    Before emergency babysitting for my son a few years ago, my sister had never in her life even changed a diaper. She was freaking out because she didn’t know how to do anything, and I wasn’t going to be there to walk her through it and teach her. And I remembered thinking, “Changing diapers isn’t hard, man. You just have to do it.”

    But a while later, I realized that even though changing diapers isn’t hard, I had developed a lot of little shortcuts and had my own little automatic habits. Making sure to put my kid on the changing pad lying in a particular direction, flicking the diaper pail open and closed with my wrist super quickly, having a new diaper ready to go under the old one and sliding the old one out without making a mess, etc. etc.

    Not a single thing I just listed is something that you would really teach anyone if you were teaching them to change a diaper. You teach them the basics (take off old diaper, wipe bum if poopy, put on new diaper and secure tabs), explain the equipment (here is how to open the diaper pail because it’s not self-explanatory), and make sure they are aware of health and safety protocols (always have one hand on the baby, here’s where the diaper cream is, wash hands afterwards).

    Right now it sounds like you need a reset with Carl, where you can let him know what kinds of questions still make sense for him to approach you with. But I think it needs to be clear to both of you that right now, you’re answering a lot of questions about how to best flick open the diaper pail.

    1. Squidhead*

      I like your analogy, especially since I work in a field (ICU RN) where 1) We have a lot of very-specific tasks and 2) Some of those tasks fall into the category of “done is good” but 3) some of those tasks have particular details that need to be right or you’ll be immediately sorry or 4) you’ll be eventually sorry. I find new people learning a task tend to be very literal so if I say “insert it like this” they are contorting their hand to make it exactly like mine and sometimes it really just is a case of “however you open the diaper pail that lets the diaper get in and keeps the cat out after is good!” But they haven’t learned to differentiate between a stylistic detail and an essential detail (“open the pail however it works for you, but point male anatomy downward in the diaper or you’ll have a soggy baby later!”)

      Teaching tasks is a combination of recognizing all those types of details and then hopefully calling out the ones that are important *and* the learner wouldn’t immediately be able to see the problem…so I might say “hold this however you want, but this end right here can’t touch anything.” The last part is the critical part…the learner needs to understand the goal and adjust the steps or methodology to meet the goal and their own physical ability/other constraints of the project/etc. (I’m not saying they don’t need to be shown the steps a couple of times, but the steps need to become their own process that meets the actual goal.)

  24. West Coast Reader*

    I can see myself being Carl in the sense it’s not that I don’t know what to do, it’s that I don’t know how you want it to be done at the company. You may have a preference or standard operating procedure. If I need to come up with it on my own, then I know not to bother you or propose my own solutions.

  25. Sparkles McFadden*

    The best part of the advice is “Ask what he’s tried so far…” This is a really great way to get new hires to think for themselves, take ownership of their work, and understand what level of problem-solving is expected. It also may highlight issues with training and/or documentation that you and your management may need to address.

    If Carl’s answer to that question is always “nothing yet” then that’s an issue for your manager.

    1. Yorick*

      If you start asking him, “what have you tried so far?” then he’s going to start trying something before asking you. Or at least think about what he could try. He might even start bringing that up as part of his question.

      My coworkers and I often talk through our work together. Sometimes I even get an idea for my own work based on the problem my coworker asked me to help brainstorm. OP, think about whether this might be what Carl is actually looking for, or whether you can get him to expect that kind of conversation instead of an answer. He will definitely benefit, and you could even benefit too.

  26. El l*

    Carl understandably doesn’t want to make avoidable mistakes. While it’s not clear from your letter, it sounds like you’re in an industry where you have latitude in how you solve problems and run through day-to-day issues (in contrast to plenty of work situations, like my wife’s medical lab, where the key is to know and follow the procedure).

    He may not be sure what the consequences will be if/when he makes a mistake. He also simply doesn’t know what’s an easy problem, what’s a hard problem, and also what’s a big versus small problem. These are all just knowledge/experience issues.

    So if this rendering of the situation is true, my advice to you is to do a couple things, all of which are ongoing:
    1. Have some chats every week or so where you talk shop. Tell him what your experience was solving a problem. Tell him stories of times where he had to tell people, “The thing you’re stressing about is not a big problem.” (Or vice versa) Tell him your own style of work, in contrast to others. This will hopefully plant some seeds to him about developing his voice and skills.
    2. As suggested elsewhere, a few things to tell him in short-term situations: “Have you tried x/y/z? If not, do them, and let’s discuss in the morning.” Or: “This is new, I haven’t solved this problem before. What do you think, and why? It’s just off the cuff, I promise not to hold your answer against you (etc).” Or, “Do some homework, we’ll meet on this next week and discuss.”
    3. Finally, try giving him a set time every day that he can ask questions and talk through things with you; e.g. “Let’s talk at 10 for 15 minutes.” The rest of the time, unless it’s high-stakes/emergency, you need to set and observe the boundary of, “You’re just going to have to wait until tomorrow.” Repeat this until he gets the idea.

  27. Cube Farmer*

    This was a very helpful letter. I am also in a role that’s grown markedly since I started in it, and much of this has required me to come up with my own procedures and learn things on the go. I often wonder how I would train someone new in my role.

    1. Red Reader the Adulting Fairy*

      As someone who specializes in picking up the “other duties as required” miscellany and is not by nature a great teacher: practice now, haha. I pretty regularly, as I work through one of my ODAR tasks, am mumbling under my breath, explaining to my dog or the (literal) teacup of ceramic mice on my desk how to review the (figurative) teapot report, what I’m doing with it and why, so that when I eventually have to teach someone else to do it, I’ve got some practice in explaining it. (I keep hoping Jaq and Gus-Gus will do it while I sleep one of these nights, but I don’t tell them my passwords, so no luck yet.)

    2. anonymous73*

      If you haven’t already done so, document everything! Even if it’s something you can do without thinking about how, document it. Documentation is the first step in any sort of training, and allows you to point to it when someone asks questions (“please refer to document ABC”). Every time I start a new job it amazes me how few things are written down and documented for others. Even if there aren’t “standard” procedures for tasks, it’s helpful for others when things are written down so you have some place to begin when you’re new.

  28. Spinning_Sandi*

    What I’ve done in some similar situations where I want them to start figuring some of this out on their own is instead of doing it for them or telling them straight up what to do, I’ll ask them questions to help guide them to the best answer. Now, this does take some time to do but I’ve found asking questions back to them helps them to engage their brain in the troubleshooting instead of relying on someone else to figure it out. It starts building up their experience on what questions they need to ask to resolve the issue themselves.

  29. Laura*

    I work in project with decades-deep context, best practises, technical debt, expert knowledge, and documentation that is beyond anyone to keep up-to-date, and I feel for Carl. A person who just won’t stop asking just might lacks the experience to ask the right questions.

    Sometimes it’s not so much that one wants *answers* as that one needs *guidance*:
    – limiting the space of possible answers (“we are not looking for a new tool environment”),
    – clarifying the limits of responsibility (“you have an idea how to do it better, condense the why, how, and what for into a short informal presentation and talk me through it, I’ll give an evaluation”)
    – banishing the dread of the misplaced semicolon “Carl, just *do* it and have Doris review it before it goes live”
    – defining outlines (“In the end, this is what it should do”.)

    Scheduling regular Carl-Q&As, which are limited in duration will hopefully get Carl to ask better questions, help you to evaluate his progress, and be a more efficient use of your time.

    “What do you want to achieve?”, “Where have you looked for context and answers?”, “How are you going to go about this?” are some questions that might help Carl look at the things he does not yet know in a more useful way.

  30. Kevin Sours*

    “how to tell an employee he needs to figure some things out himself”
    File this under “questions that answer themselves”. Say “you need to figure this out yourself”. One thing that’s not clear is to what extend OP is in an informal mentor/manager role where they are expect to assist direct the work of a junior employee without formally being a manager. If they don’t have standing to direct Carl’s work at all, then looping the manager in is really the only solution here. Either directly or “I’m sorry, I don’t have time for that, can you speak to Jane about it?”.

    But one thing I’ve had success with is: “I don’t know, come up with a proposal and let’s talk about it”. That can take the pressure off Carl to get it right the first time while avoiding walking him through every single step. It also allows you to course correct if he really does flail (which is part of the process of training a junior employee).

  31. Jennifer Strange*

    I easily could have been the OP a few years ago! I also had a co-worker who was new to our org and to the industry, while I had been in the industry about 4-5 years at the time. I was more than happy to help her out in the beginning, but after 6 months she was still coming to me asking how to do pieces of her job that she either should have known by then or that she could have figured out on her own if she took the time to try it first using the tools/instructions I had already given her. It didn’t help that our desks were directly next to each other, so I was the closest person in our department to her.

    In the end when she would ask for me to help her with something that she really needed to do on her own I would just say I wasn’t able to help due to my workload, but pointed her to a folder on our drive where she could either find instructions or see examples to help her. It didn’t really do much, but I kept pushing her in that direction.

  32. Sasha Blause*

    I’m not sure how much this applies outside of tech, but when I had interns I taught them to follow a formula when asking me for help:
    1. What are you trying to accomplish?
    2. What have you tried? [I combined this with, “click around and try things, that’s what I do; but make sure to take detailed notes as you try things just in case something goes awry”]
    3. What did you expect to happen?
    4. What actually happened?

    It worked really well. Given this framework, they were often able to find the answer themselves, or at least get closer to it. If their ideas were totally off the wall — which rarely happened when they used the formula — that’s another teachable moment in the form of, “interesting approach, but I’m not sure how you got there; can you tell me about the thought process?”

    Teaching that formula is one of the best things you can do, both for your sanity and their career. I use a variation myself whenever I’m wrestling with something new to me, or when my ADHD is extra-severe and I forget how to brain. It helps organize my thoughts and keeps me from going around in circles. It’s such a simple thing, but I honestly believe it’s the strongest tool in my career toolkit.

    1. El l*

      This is really excellent – I’m sure you found that when they practiced it a couple times, they began to run through it first without asking you! Great mnemonic. Especially great when they learn to state – in their own words – what the objective is.

  33. Big Sigh*

    I was this person once!!! I am so grateful for my patient colleague who helped sometimes, and many (many many many) other times would say, “Where have you looked so far” or “What have you tried or considered trying to far?” That redirected me to take figure things out myself, or at least try, first.

    1. Anon Supervisor*

      Word…I was brand new to my field and had very few written resources and asked so many questions. My patient supervisor would always start her answer with “Have you called…” to the point where I would just start with that step first and could get most of my questions answered that way.

  34. CatMom*

    I’m the most junior person in a new leadership position at a non-profit I volunteer at, and so I’m a bit sympathetic to Carl’s position here. I find myself asking a LOT of questions and waiting on confirmation for things that I too don’t really think I need to be waiting on, but I do so because I’ve been given very little clarity on what I have *the authority* to decide on my own. Might it be helpful to directly inform Carl that he’s allowed to make his own calls on some of these things? For example, if my supervisor told me that she would do something a particular way, but that I’m free to do it a different way if I want, I would not necessarily extrapolate that this is an area in which I have the authority to make my own calls, period. I would need to just be told that, and I think I would feel that way even more strongly if this were my paid, full-time job.

    1. Saraaaaah*

      Agreed! He may not feel empowered to ‘figure it out’ himself. Either because of a message that OP is sending or messages that folks further up the management chain are sending.

      I also will just say that it has been harder for me to figure out those contextual, political, subtle things when working a job I started remotely, if that’s relevant here. I go to my colleagues a lot more with questions because it has taken me a lot longer to get a handle on what is the “typical” way to do things.

  35. Keyboard Cowboy*

    I wonder if you can point Carl in the right direction, rather than solving his whole question? Sort of the “let me Google that for you” approach?

    Carl: “How should I get this teapot design approved?”
    You: “In your shoes, I would start by finding out who the possible approvers are, and then from that list, find out which of them has expertise in avant-garde teapot design based on their internal portfolio, because this is an avant-garde teapot. I hope that gives you enough of a head start!”
    As opposed to….
    You: “Because it’s an avant-garde teapot, and I know Esmerelda hates avant-garde teapots, I’d avoid her and ask Theobald, who told me in the breakroom last year that he thinks we should be selling more avant-garde teapots.”

    It takes a little longer, but the thing you really want to teach Carl is the thought process, so if you guide him towards that thought process that will ramp him up more quickly. As a bonus, you will get to find out exactly which parts of your own thought process aren’t documented or learnable (e.g. relying on breakroom gossip).

  36. ecnaseener*

    I think it might be especially helpful to ask him what he’s tried/considered so far, even explicitly tell him that you expect him to come to you only after thinking through the problem on his own.

    When I was new to the working world, I probably was a Carl, but luckily I figured out relatively quickly that I got better reactions when I explained that I’d looked at X guidance and saw the similarities with Y but wasn’t sure if Z made a difference. It’s not immediately obvious when you’re starting out!

  37. EK*

    This can also be a sign of weak processes. If the whole thing is dependent on somebody hustling to make up for bad communication and trying to guess so-and-so’s vague expectations based on previous experience with so-and-so, that tends to become apparent when that person leaves the role. Sometimes it takes somebody new to say, “This is chaos and I don’t understand it.”

  38. just a thought*

    I had a technical job where we were working with very specific equipment. Every time I asked how I should know who to send things to, what connector to use, etc, I would get the response “oh you just know from experience”. But I didn’t have experience…so unless something was exactly the same as a previous project, I had no way to figure it out.

    Anyway, you might want to help Carl with the processes for finding the information or logic to get there. Saying something like “because of this historical context” may not help him if he has no way to find out that context for himself. But showing him what specific documents to look at or how to find the context within the company information will help him get that now and in future work.

  39. Don*

    I was one of the senior-most developers on a project many years ago and became one of the go-to guys for answering questions based on that length of experience with the product. Which was mostly great! I liked accomplishing things and helping other people accomplish things. But I noticed after a while that there were a number of people who would come to me for answers before they had apparently invested any real time in figuring out the answer themselves, and it also manifested by some folks asking me the same questions multiple times. Presumably because they didn’t invest the effort into understanding so it didn’t stick for them.

    The solution I same up with was pretty simple and resolved more than half the interruptions: be less immediately available. When people came in with a question I’d tell them I was in the middle of an issue right then but should be at a good point to stop in about thirty minutes, could they come back then? I don’t want to lose my train of thought on this thing, you see. Or I have promised something to the boss in the next hour and need to finish it. Or whatever. The only real goal was to interrupt their ability to get immediate gratification.

    Most of the time that was enough to send folks off to make some effort puzzling it out themselves and a lot of those folks never came back. It’s not impossible some of them went and used up some other senior’s time but that was beyond my ability to fix. Folks who seemed to be deliberately avoiding doing the work themselves got a lot of “where did you start with this?” and “can you show me where you got stuck?” sort of clarifying questions. That both made this less of a quick way to avoid effort and was a bit of an attempt to help the answers stick by contextualizing stuff for them. And once in a while was just a place where I could give them a “so clearly you’ve done diddly squat about trying to find this out yourself, huh?” sort of look.

    A guy named Dan Meyer got famous for his TED Talk about teaching math many years ago and I kept following his blogging and other work afterwards. His website’s subhed was “Be Less Helpful” and I have come to really embrace it when it comes to helping other folks learn. Sometimes it’s necessary to let people fail a little or a lot along the way so they can really learn.

  40. LilyP*

    I would say that before you tell him to figure things out for himself, think a bit about whether there are boundaries you need to put around that or things that he really shouldn’t be jumping off and doing on his own — should he be coming up with one or two proposals but running them by you (or your boss) before moving forward? Are there things he might get in his head to try that would get him in trouble, like directly contacting clients or using tools that aren’t approved? It can be really frustrating for a junior person to hear “figure it out for yourself” “no not like that”

  41. Reverend Bayes*

    Where’s that guy who was winding up his employees with his use of the Socratic method when you need him?

  42. It's Me*

    It doesn’t sound like this is the case (though maybe it is?), but when I was new, a lot of my checking was less about “mama-bird regurgitate the steps straight into me” and more double checking the nebulous internal processes that every place has and no one ever tells you. Like maybe I know how to do Task X, but that doesn’t mean that’s how this new company wants it done. Even with something completely true, the same fear holds true. “I can google how to do X, but then after wasting my time, they’re going to turn around tell me I actually should have sent A email to person B with the phrase ‘I need a water buffalo’ instead of ‘May I have a water buffalo?'”

  43. Three Flowers*

    One thing I do with student workers (often talented by equally often uncertain) is to say, “that’s an interesting question/problem/task. I’m interested to know how you’d approach it. Take some time to think it over, write up some notes, and I’ll give you some feedback this afternoon/tomorrow/next week.”

    I have gotten some excellent work out of this approach.

  44. 15 Pieces of Flair*

    As a people manager, I noted an underlying situation in the letter that may lead to an opportunity. OP mentions that they have the same title as Carl, despite having a more senior role and more experience. The letter also indicates that OP is acting as a mentor to Carl. These facts, along with 3 years with the organization, suggest that OP may be in a good position to ask for a promotion. If their position is more senior, shouldn’t OP have that distinction? OP would probably be more inclined to continue supporting Carl if given some recognition for that work.

  45. coffee*

    Since Carl and OP share a manager, I would suggest a) getting the manager to do more managing of Carl, and b) noting down how much time Carl needs and discussing with the manager what takes priority – supervising or doing other work.

    Honestly this situation sounds like a nightmare – hiring an inexperienced junior to do the same work of an experienced worker?? Of course this is failing to go well.

  46. Been There*

    Sounds like a communication problem at the manager/supervisor level. The lack of clarity would probably frustrate anyone, not just junior people.

  47. Retired (but not really)*

    When what you’re dealing with is a role that doesn’t have a set structure of do A then B then C, but rather sometimes you do D first then B then E, but sometimes none of these steps apply, it can be very confusing to the new person.
    If you can create a chart of most likely scenarios, with some clues as to how to recognize which is which, you will save both of you a lot of time and resulting frustration.
    The hardest part for a new person is recognizing which steps to start with each time, even if they have a reasonable grasp on what to do once pointed in the right direction.

  48. Techwriter gal 9000*

    Is there a way you can think about it like this: when Carl asks you a question, ask yourself if he can Google the answers. It doesn’t sound like these answers are googlable, but maybe you ask him gently to Google any questions that are. Also, can you ask him to write the questions on a list and have him email them to you or discuss them in a weekly
    meeting? I think that’ll make it easier for both of you.

  49. Anony4839*

    Op, it sounds like you are at the point of your career where you are willing to help someone with one-off questions but don’t want to take the time to “mentor” someone, bc someone like Carl who is new to the working world is more used to being told what to do rather than a I’ll come up with a solution on my own approach. They will need much more guidance and handholding.

    Make sure it’s not a training issue. I was in Carl’s shoes before where my coworker wasn’t a good “trainer” and made my job harder to learn bc it was tasks that can do but it was organization policy specific and I had to know where the files were, program apps etc and would have been quicker for me to learn had coworker was a better trainer and explainer.

    1. Where’s the Orchestra?*

      I had that happen once. My requests for help involved me taking my training notes and the process directions with me to the lead (not the same person) and saying I’m trying to follow “Janie’s” training, but I’m lost here. Can you show me where I’m going wrong.
      Janie was a nice person, but she wasn’t a good trainer. She’s been moved back to an IC role, and Jess (her replacement) is a very good trainer.

  50. Genie*

    If there are procedural and policy documents that should theoretically answer at least some of Carl’s questions, sit down with him and make sure that he has been shown exactly where these documents are located, and that he has access to them.

    If his questions indicate there are gaps in those documents and/or procedures, and/or the training and onboarding process, this is a very different kettle of fish that will require management getting their act together.

    You also need your actual manager to do their job and manage Carl.

  51. RebelwithMouseyHair*

    It strikes me as rather odd that the new tasks are falling to the new guy. Obviously, these new tasks may be mind-numbing and OP doesn’t want to handle them, but I would have thought that the new guy should be given the tasks that OP is very comfortable with, which are presumably easier, while OP then takes on the new stuff, and leverages her greater experience to work out the best way to tackle it.
    Whenever I had a colleague to help with my workload, I had a similar relationship in that I had to explain the basics and provide guidance as necessary, without being that person’s supervisor or having any power over her (which suited me just fine). I would give them the easier stuff at first, keeping the tough stuff for myself. Then I was perfectly comfortable pointing the colleague in the right direction when they got stuck.
    The only exception to this was if they had experience in something that I didn’t (like the student who’d worked for Big Pharma before, obviously he got all the pharmaceutical and medical projects).

  52. Rainy Cumbria*

    One thing that might help nudge Carl towards making his own decisions would be to flip it back on him. When he asks a question, ask him what he thinks he should do, then give feedback on his answer if you need to. It might just give him the confidence to trust his own instincts.

  53. Squidlet*

    If this is Carl’s first job, it’s highly likely that he’s not used to, or expecting, a situation where there’s no right way to do something, and where context (which he doesn’t have much of) is so important. He’s probably expecting that there’s a right way, maybe another right way, and a bunch of wrong ways, to do something.

    It sounds like the issue is not with Carl or with the OP, but that this role/environment has inherent complexities, and that maybe more coaching or mentorship is required to get to grips with it. So in essence a management issue.

    It sounds actually very like my job, where there are dozens of methods, processes, and frameworks, and getting the right outcome is about knowing which to apply, when. But it takes a lot of learning and experience to get to that point.

  54. anonymous73*

    This is “teach a man to fish” situation. You need to help him help himself. Be honest when he comes to you with questions. “This isn’t a cut and dry scenario, you need to talk to X, Y, Z/look at this documentation/etc. and come up with the solution you think is best.” You have a right to be frustrated. Not just because you didn’t have “you” when you started, but because it sounds like he’s expecting you to hold his hand. I had this issue a lot when I worked in support. People would constantly come to me with questions when things were clearly documented. So I got into the habit of saying “What does the KBA say” and eventually they stopped coming to me first. It sounds like your job duties aren’t documented like that but the same applies. When he comes to you, ask him what he’s done so far, make a few suggestions and force him to work it out himself. That’s the only way he’ll learn and the only way you’ll get him to stop coming to you for every single thing.

  55. FloraPoste OP*

    Hi, OP here! Thank you Alison for the INCREDIBLY helpful advice and commenters for the equally helpful commenter suggestions! I am going to try:
    – Explaining explicitly that part of the job is figuring out things that won’t always have clear-cut answers, and that taking time to figure things out is completely fine.
    – Standing meetings, once a week.
    – Starting from a position of ‘what have you tried so far based on the knowledge you have? ‘ which seems to be key! And framing it as ‘guidance’ rather than answers – what are we trying to accomplish, and how does he think we could get there based on what he knows.

    And DOCUMENTING THINGS/making a cheat sheet. Some commenters have said that it sounds quite chaotic in my office. They are correct in some ways, and this is compounded by being a job that is more than most, I think, based on relationships with external positions in which the role-holder changes a lot (for context, we work in international advocacy).

    I am also going to talk to our joint manager, who gave me responsibility for supervision as a stretch role for me (there is not much upward mobility in our org and she thought formal supervision on my CV would be helpful when it comes time to move on). That this has also included full-on training is something I probably should have foreseen and prepared for, and that we definitely should have talked about already, but hopefully it’s not too late. I agree that both Carl and I need clarity at least on where the parameters lie for the sake of both our sanity and my workload! She is a pretty hands-off manager, and very supportive of autonomy, which I like for the most part (and it means I’ve been able to grow the role in directions which are interesting to me), but maybe this time it goes a bit too far. I told her that I was finding the situation a bit tricky and she said it would get better once he knows more, which… wasn’t particularly helpful!

    I hope Carl doesn’t quit because I think he will be great at the job once he’s more up and running, and he seems to like the substance of it. Fingers crossed we can make a lot of progress together without either of us being driven to distraction.

  56. I Don't Sing Along Thanks*

    This is great advice if there are a couple of ground rules. First, if the LW tells him he needs to figure certain things out on his own, it’s crucial that the LW then doesn’t turn around and change, criticize, and undermine everything they figured out on their own. What is the point of someone figuring out ways to make things work great, but it wasn’t what the LW would have done it so it is bulldozed without any consultation, undermining everything the new person did with everyone they work with. (this may have happened to me a LOT).

    Two, as some have pointed out, the things he needs to figure out on his own are able to be learned on their own with no guidance and is able to be learned on their own fast enough to fullfil the role *as it is now*, not as it was while the previous person was growing and changing the role over years.

    These two things make any job like this so frustrating and demoralizing.

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