I have an employee (my first), and I give them tasks to do. However, often they will do the task in a way that

  • officially meets the description I gave

  • but doesn't exactly do what I want, because I was thinking about it in a way that was implicit but obvious to me.

It seems to me that what is necessary is for us to "sync" with each other in a more refined way than we currently do. In particular, it seems like they are just "executing commands" rather than trying to understand what is needed and pursuing a goal.

In particular, it seems to me that it would be better for them to ask more questions to me and try to really understand what is needed. Instead what often happens is: they repeatedly redo a task after my feedback, taking a kind of trial and error approach.

I am unsure of how to improve the situation:

  • it seems like they are quite motivated to please me.

  • I am afraid that if I explain in detail how what they did doesn't meet my goal, it will just make them insecure, and they will just try again but now more nervously, rather than openmindedly trying to sync with me on what is actually needed.

  • I don't know how to explain the fact that I'd like them to really try to understand what needs to be done, rather than execute orders. This also seems like something that would easily be interpreted as criticism and just make them more insecure.

I am not sure whether I am even approaching this in the right way.

How do I get them to understand what I need, without overly micromanaging and make them think independently about what is needed to get to a goal?

  • 1
    This is a very difficult situation. Sometimes people are not a good fit for a job. Could you go a bit into detail, perhaps with an example (even a fictional one?). It makes a huge difference if you are talking about a programmer, a chef, a musician or the head of an entire department or someone in the public sector, maybe at a university. How much experience do they have? What did they do before joining your staff? Maybe you need to develop them, maybe all hope is lost. It's not really obvious from your post.
    – Raditz_35
    Jan 11, 2020 at 13:21
  • 2
    Raditz asked a lot about what your employee does, I'm also curious about you. Interpersonal Skills are behaviours you use when interacting with people, so I'd too like an example, one that focuses on how you gave your orders and what you thought was implied but the employee didn't pick up on. I'd also like to know what you've done to approach your employee when their first attempt wasn't really what you wanted, how do you give the feedback you've given so far, and why do you think that leads to several iterations instead of just 1 more try?
    – Tinkeringbell
    Jan 11, 2020 at 13:30
  • 1
    How lengthy are these tasks? Are they long enough that holding a quick daily standup meeting (Iike in Scrum) would be useful?
    – DaveG
    Jan 12, 2020 at 2:20
  • 3
    Do you want your employee to think independently or do you want them to know what you want without you having to bother telling them?
    – WendyG
    Jan 13, 2020 at 10:46
  • how old is the employee, what is her/his background ? Feb 19, 2020 at 9:47

3 Answers 3


I'm in the opposite situation as you. I have worked at two different places (with two different managers) and the first one would often blame me for my lack of initiative.

Here are some of the reasons I didn't take more initiative but the most important one is that: I felt like I wasn't allowed to.

The thing is, my manager seemed to have a very precise idea of want he wanted me to do, however, he didn't care to explain it to me in a lot of details.

So, the first time that happened, I did what I think was right and was surprised when my manager showed unhappiness because it wasn't what he had in mind. I blame this failure on poor communication and decided to ask my manager more questions so that I wouldn't fail again.

However, if me asking questions seemed to be the solution at first, it became clear pretty quickly that my manager wasn't very happy with the fact that I had so many of them. I felt more and more insecure about asking questions to my manager and I finally decided that I would rather not ask questions and fail than to ask questions that would lead my manager to be really unhappy with me.

Since I was now insecure, suggesting things became rather impossible and my manager quickly blamed me for my lack of initiative.

So, here are some suggestions on how to avoid discouraging your employee:

  • Whenever your employee asks you questions , do not look annoyed or make them feel like they are a burden for you. Do not do another task while they are talking to you because it would make them feel unimportant.

    If the timing isn't working for you, ask them to plan a meeting with you so you can answer their questions later (because you don't have the time right now). Asking them to send their questions using email might also work, but I would be careful with that because it often leads to less communication than a face-to-face meeting (and less communication means more uncertainty and grey area).

  • When giving a task to your employee, write down everything you want them to do. My manager used to assign me tasks by just talking in a rather long meeting and then they expected me to have remembered and understood everything. Even if I was taking notes, it never worked.

    However, I had other people assign me tasks by writing everything down and it worked much better. I would still need a meeting with them so that we can clarify points, but by having everything written down, I was sure to almost never forget something.

  • In my previous job, my manager used to let several weeks pass between two meetings. He would then get mad at me because the project wasn't going the way he wanted to. At my new job, I had some similar issues at the beginning, but the fix was rather easy: my manager simply planned a meeting with me every Monday. I would also communicate each day what I had planned for the day and, at the end of the day, what I have actually done (maybe I was stuck on an issue, maybe a more urgent task interrupted, etc...).

    This way, the lines of communication stay open. My manager always knows how things are going and if something isn't going the way it should, it can be detected (and thus fixed) really quickly.


I think this is somewhat of a Workplace SE question, and this will be somewhat of a Workplace SE answer, but here it is for what it's worth.

Aelis answered well from the employee's perspective. I'll add a teacher's perspective when dealing with uncreative students. The problem is similar.

It's important, if you want them to try different things and experiment, that you not unintentionally discourage that behaviour. As a person in authority, you set the tone in many ways, including your voice, expression, and attention – as Aelis said.

However, even more than that, those signals have to be authentic. I have many memories of poorly chosen questions where I told students to just try, because I value the process of discussion — but then I got frustrated when I realized their direction was way off where I was thinking they'd be and ended up shooting myself in the foot. "Hmm, OK, but not quite."

So you have to create situations where creativity is important and interesting to both of you. That begins with not putting them on tasks where the stakes for doing it "wrong" are high. That doesn't mean only pointless jobs, but jobs where there really are multiple ways to do it, including ones you haven't thought of or don't know about. It's hard to teach creativity when you limit it to different means of arriving at the exact outcome you had in mind.

Find things to give them for which there are many outcomes that can satisfy you and few that can disappoint you. Make sure it's hard to not do something you can receive positively. You could try giving problems you have and haven't solved yet. "How do I organize a thousand papers so I don't waste time shuffling through things so much? What would be a good system?" Low stakes for trial and error, but far from pointless.

Then the process and your reactions will be more congruent with what you say you want from them.

Creativity is a common enough problem when teaching English. Many students hate being asked to do creative work. They hate not having steps laid out for them, and they shy away from anything that might get a low grade whose cause isn't obvious. I hate grading that, too. So I don't make creativity the grade, but create a framework around it that I can grade.

For example, recently they had to write a new last stanza for "Do not go gentle into that good night" by Dylan Thomas, matching the poem's rhyme, meter, and repetition. Those three elements were marked, but what they actually said was not. Notice that the task is underspecified in that they must choose what they want for the content or "outcome", and there's no instruction they can turn to that will tell them what to do. They could even get all the technical aspects wrong — e.g. writing four new lines instead of keeping the last two because they didn't understand the pattern of a villanelle — and still have written something potentially interesting.

Now, my short-term goal is to teach those technical aspects, but my main goal is to develop an ability to read and enjoy poetry. The minor will serve the major, of course, but not if I let it take precedence. So I read, enjoy, and comment on what they choose to say, even if they get the technical aspects wrong. I can do that authentically because the grade is not tied to the creativity. I can even give them the benefit of the doubt and suppose that they intentionally chose wrong technical aspects because it was necessary in order to say what they wanted.

Later, when I want them to do creative things, I can point back to this moment. "Remember when you wrote a new final stanza for 'Do not go gentle'? You were still working on getting poetic meter right, but I liked how you added a sibling for the narrator. I didn't expect that and it was an interesting twist. Maybe you can add your personal touch to this assignment too."

Your situation is obviously more complicated, not least because you don't have the freedom to teach creativity as your main goal – you do indeed have a job for them to do and stakes if they fail. But this is a tack you can take till they're ready to take more creative approaches on regular tasks.


I agree with Euchris this is more of a Workplace SE question, and this is something of a Workplace SE answer. I've attempted to keep it within IPS SE guidelines and have it still be something of an IPS SE answer as well.

My position is similar to yours. I don't manage or supervise any employees, but I have a 'mentoring' task on my job description that's been there for a little over a decade. As a fairly technical person with a programming background working on a team of systems administrators, I'd been doing that job unofficially for most of the decade prior to that as well.

As a mentor, I don't select their tasks, set deadlines, do performance evaluations, or handle any paperwork associated with their employment. My mentor job is to guide them with what they need to do or learn to handle their tasks.

I'd like to have an easier to implement answer for this. What I try to do is talk with them about the problem they're supposed to solve at length, as long as they're able to tolerate. (If we ever actually covered the full topic, I'd end there, but when dealing with very junior employees, that never happens.) It's probably important to understand up front that if they haven't heard all of the concerns for the project they're working on, they will fail, and it won't be their fault.

Chances are good, no one person set them up for this failure, it's just life. There are only so many problems that are sufficiently urgent to tackle at this time, and they probably weren't perfectly suited for any of them. But the goal isn't for them to get it right the first time, it's to get it right with the assistance they can get by the deadline they have.

So they'll make a first attempt, and come to you with that attempt. Sometimes, it will be overly literal like you're struggling with. Other times, it'll be something "out in left field" which seems like complete insanity. And then there are times when it'll be so far from what you expected that you can't even recognize it as an attempt to solve the problem they were given, until you have had some time to think about it.

Don't be discouraged. This was attempt one. It's real goal was to help enlighten you on what is needed to get their task completed. Whatever they bring you can help with this task. In roughly 20 years of mentoring, I've known immediately how to proceed from what they brought me to tell them exactly what they needed to do to get the job done without me having to spend more than a minute or two talking with them about it less than once per year.

Most of the time, however, it's been a lot less clear than that.

Based on your question, you're seeing multiple obvious failings with their solution, and they're all things that you haven't actually talked with them about. Because they weren't discussed, you can't reasonably be upset with them about them. Although, that said, even if they were things you'd discussed, being visibly upset frequently isn't conducive to maintaining the communication that you need to do your job.

So talk with them about the situations their product will be used in. Ask them to do most of the work here. "Imagine if" the various base situations happen, and ask them to list various possible outcomes. As much as feasible, get them to explain how what they've provided doesn't meet the needs that you have.

You haven't really talked about what type of work they're doing. But the sort of brainstorming one does in test driven development to come up with the test cases for software can be used for more things than software development. You maybe can't use automated testing to evaluate those tests, but you can still come up with tests, or rather have them come up with tests.

The biggest frustration I've had with this approach is some people are literal enough that they still won't see their issues. Once when I was working with someone who saw me as his counterpart in my organization, so he wasn't looking to me for any guidance, I found myself unable to get him to really follow through on any thinking about what if something didn't go according to plan, until I verbally walked him through one particular failure use case.

At this point, he basically gave up and admitted that his program wouldn't work for that case. I tried talking with him about how to make it fail more gracefully, but he just dismissed it as too much work. Any further attempt I made to discuss it was returned with the assertion that I wasn't his boss.

I'm still not sure what I could've done better in that case. I'd been asked to work with him because his code was generally seen to be too fragile, and his boss hadn't been able to get through to him.

Most of the time, though, the people I've worked with have been much easier to help see the issues with what they'd first submitted as a solution to the problem they were given to fix. Getting them to notice the problem without me explaining it to them has generally been much more conducive to getting them to move from recognizing that there is a problem onto fixing it. If I tell them exactly what the problem is, there tends to be a significant lag period before they even acknowledge my message.

I work in corporate for a very big company, so the vast majority of my mentoring has been of people who are not located at the same site that I'm at, so I haven't really had the privilege of being able to drop in on these people and check on how they're doing. I mean, I can send them an instant message easily enough, but that generally doesn't work as well as a traditional 'water cooler' discussion.

Of course, if you are at the same work location as they are, 'water cooler' discussions might be an option. But it's something to be careful about. As somebody who is actually their boss, this can be a bit delicate - there's a fine line between a boss checking on how their employee is doing and a boss who is interrupting their breaks to nag them back to the grind stone. Unfortunately, as somebody who hasn't actually been somebody's boss, I don't feel like I can properly advise you on how to do that dance.

At the beginning of the assignment lifecycle, one can encourage some creativity by suggesting a brainstorming session, once you've handed out the assignment but while you're still talking about it with them. They haven't really had a chance to think through the full assignment yet, so you can't expect them to have a full strategy on how to solve it yet, but you can ask them about their ideas of how to proceed to coming up with a strategy.

I tend to do this with my boss when I'm getting assignments. I do it on my initiative, because I find it frustrating to find I've gone a completely wrong direction on a project. I also tend to do it with my boss when talking about the assignments my coworkers have that I'm going to need to mentor them on.

This is more about figuring out what kind of project result would be acceptable than coming out with a concrete plan.


Attitude is important; they're not doing this to annoy you, so keep calm.

Explain as much of the problem as you can when you give the assignment or they're asking for help, and after they've produced a solution, try to get them to run through scenarios to show where it fails, so they understand they can do that.

Also, when giving the problem at first, try to get them to talk about their initial ideas for how to possibly solve it, to reinforce that you're interested in their ideas rather than just having them be your hands.


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