I am currently the manager of a team of 15 people. In two weeks' time I will leave this job for a totally different one, in a different sector and a neighbouring city.

At my current job, I have one member of staff (professionally qualified) who has a very challenging personality. Although highly intelligent, she seems to have no awareness of how she comes across to people; and she comes across as dismissive, presumptuous and condescending most of the time. She's a know-it-all in the worst kind of way.

Among her more irritating traits is the tendency to reply to brief announcements or requests, delivered to the whole team via email, with very lengthy (500-1000 words), structured emails, outlining what she sees as every possible objection anyone on the team could have to it and detailing every aspect of the request/announcement she thinks could go wrong. She typically sends these within hours of receiving my email, putting into question her time management skills. (Luckily though, she doesn't usually "Reply All".) Prior to a recent conversation she and I had over a more inflammatory missive, she seems to have been unaware that nobody else was responding in this way, and indeed that few of the objections she anticipated ever came to pass, and never seriously. I think she misinterprets idle chatter, and the usual mild criticisms of one's boss, as expressions of deep dissatisfaction on the part of her colleagues.

I know that she has ambitions to move into management, and I also know that the team would revolt if she managed to do this, given her personality flaws. I am sympathetic to her though, because I know she is professionally frustrated. I believe she continues sending me these emails because she wants to show me she has the chops for management -- unfortunately, it shows me the opposite.

Before I leave, should I take her aside and tell her this? Would this help her, or be a waste of time? She has a history of missing the point, and at this stage (she's about 40) she's unlikely to change. But I also feel she has a right to know what is holding her back.

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    Comments are not for extended discussion; this conversation has been moved to chat.
    – Jane S
    Jun 7, 2016 at 21:35

11 Answers 11


Before I leave, should I take her aside and tell her this? Would this help her, or be a waste of time? She has a history of missing the point, and at this stage (she's about 40) she's unlikely to change. But I also feel she has a right to know what is holding her back.

It's a waste of time.

In your comments, you indicated that you have talked with her about her behavior in the past. Hopefully, your annual reviews of her also reflected your feelings and she hasn't been rewarded for behavior that you consider inappropriate. (Annual reviews are an important time to provide feedback on work and behavior as well as career growth - both good and bad).

Hopefully, you tried to coach her up, but unfortunately it didn't sink in. That happens. Not everyone really wants to hear the truth about themselves, particularly when it's not all positive.

Either way, unless she herself asks for some constructive feedback, it's too late to do anything about it. Feedback on the way out the door carries far less meaning. And feedback to someone not ready to accept it is just hot air.

If she does ask for your feedback, this is your opening to be very honest. Consider having a lunch or coffee offsite and making it clear that you feel she has lots of potential but has one area to work on. And if you get the sense that she isn't hearing what you are saying or becomes defensive, just stop. You'll have done what you can.


If your goal is to help her develop professionally you should already be bringing this up with her.

It sounds like you haven't. It is incredibly likely she will feel betrayed and view your inability to discuss this with her prior to leaving as a sign of your poor management skills. Particularly if you tell her, "oh those emails you write that are long? I don't read or value them. Actually they make you look bad, but I never told you even though I know you have management ambitions!" If I was doing something I felt was valuable for a long time only to have my soon to be ex-boss tell me "this was a waste of time" I'd be really frustrated with them.

Whether you were a bad manager is immaterial, she will almost assuredly think that. It's only normal - you have apparently been feeling she does this poorly for months (years?) and only when you were about to leave felt she should know.

I would only recommend doing this if you take a negative reaction as a given and start off with an apology. "I really should have brought this up before, but I did not, and am sorry, but wanted you to know..."

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    Better late than never? I don't agree that she would feel betrayed. Most of us have flaws that we never see and our friends and family knows but don't share. We ourselves know people that have flaws and we don't mention it. That guy picking his nose. That girl with too much ego. It's only nice that he is actually sharing it.
    – Mr Me
    Jun 6, 2016 at 13:33
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    @MrMe the overwhelming majority of people will react negatively to their manager telling them, "this thing you've been doing for a long time is a complete waste of time and counterproductive" only after that manager decides to quit their job.
    – enderland
    Jun 6, 2016 at 13:40
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    I agree with this answer, but it still is likely better to tell her than not.
    – user45590
    Jun 6, 2016 at 14:38
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    These are helpful comments. Just to clarify, I have addressed the emails before as unhelpful and not a productive use of time. I've never addressed them from the perspective of them being a hindrance to her development, because it is an assumption on my part that that's why she's sending them.
    – JK39
    Jun 6, 2016 at 14:43
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    @enderland before this goes any further, I think it's worth you knowing that your aggressive style coupled with not checking whether the key fact - whether or not this has been addressed before - was the case may hinder you. But you are a valued mod and I hope things will improve!
    – Rob Grant
    Jun 6, 2016 at 20:35

In my opinion, you should do your best work until the last hour in your job, so the fact that you will leave in two weeks does not make (much) difference.

That said, the main question should by:

What do you want to accomplish?

It does not look as if the behavior of the employee is causing concrete problems, so with respect to the goal of getting work done, there is no need to to anything.

Another goal would be to help the person. That is a noble goal (and may, indirectly, help your old employer, by avoiding problems down the road). However, unwanted help is rarely a good idea.

So you might try the following:

Casually tell the employee that you have some feedback to offer before you leave. Something like

Hey, X, I noticed a few things about your work that I think you could approach differently. If you are interested, I'd be glad to talk to you about it. Would you like to sit down together with me before I leave?

Wording to be adjusted accordingly, of course.

The key point is that you are offering observations/advice, not giving an order. If she is interested, then maybe your observations will help her. If she is not interested, I think you should drop the matter.

As the saying goes: "You can lead a horse to water, but you can't make it drink".

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    If part of your work is to help people and you can't do it in two weeks, then only having two weeks left makes a difference.
    – user8365
    Jun 6, 2016 at 14:20
  • @JeffO: True, but the question is "Should I tell the employee", which is probably doable in two weeks. If it turns out further work is needed, then the two weeks could become a problem. But that's a different question :-).
    – sleske
    Jun 6, 2016 at 15:05
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    I always thought the saying was "You can lead a horse to water, but you can't drown it because it's WAY bigger than you and would totally just run off." You learn something every day, I guess...
    – mHurley
    Jun 7, 2016 at 21:32

Look at it from this perspective: what would you do about this if you were not about to leave?

The way you frame this, it seems like your report wants to grow professionally, which is good, but has serious obstacles in her personality. This sounds like something you as a manager should address. At the bare minimum, you should explain to her what is holding her back and assess together with her whether she wants to work on these problems or not. If yes, then you should help her as much as is reasonably possible. If not, it would make sense to point out to her that she likely won't advance in her career aspirations. That may well be a trade-off she is willing to make. And then at least she knows what is holding her back.

(Of course, she may simply refuse to listen.)

Now, that's what you should be doing as a manager if you stay on. What changes about this now that you are about to leave?

I'd say that little changes. You still need to do your day-to-day job. You will still manage right up to the day you leave. This would argue that you should hold at least the first part of this conversation with her. And then hand this over to your successor, along with everything else you will hand over.

Now, of course this is not going to be a comfortable discussion. But it's still part of your job. If you don't do this now, then your successor will need to do it - just like everything else you might decide not to do now and leave piling up for your successor. When you handed in your notice, did anyone tell you that you could now stop doing the unpleasant parts of your job for the last two weeks?

An exception might make sense if you already know who your successor is going to be and if you think that he or she will do a better job about this than you could - for instance, if that successor already has a good relationship with your problematic report.

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    I agree. The time to address this was while you were her in manager. I was once leaving and my manager at the time gave me some advice in which he was critical of the type of experience I already had and suggested I seek that out at my new place. I'm sure he meant well, but why was he not providing exposure for me of that kind while I was working for him? There was nothing stopping him, in fact I was often asking for that kind of work and not getting it, and it was a big part of why I left. I still remember what I feel was misguided advice. Jun 6, 2016 at 16:00
  • The advantage of leaving soon is that you can be a more frank with people than you normally would, as a bruised relation because of someone taking your well meant feedback the wrong way doesn't matter as much. Of course one would hope the risk of that is small, but anyway I'm more careful with people I know I'm going to work with for years to come. Jun 7, 2016 at 7:26

I believe it is a human trait to help each other. It is nice to do it. Probably you will sleep better, if you are a good person.

If you have insights that could help her, why not sharing them? Tactfully, of course.

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    I think this is likely to attract downvotes, because it's not much of an answer. You may want to choose to delete it to avoid that. Jun 6, 2016 at 14:59
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    I think it's as much of an answer as any other one here, maybe it's not got a lot of extra words to pad it out, but it puts forward a valid argument very succinctly. Jun 6, 2016 at 15:42
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    @AmyBlankenship OP asks "Should I help an employee?" and I answer "Yes, it is a nice thing to do". If you really need logic/reasons to be a nice person then I'm glad I don't know you ;)
    – Mr Me
    Jun 7, 2016 at 14:22
  • I like this answer. It's the right of the manager to be tactful, sensitive... and so on, but if you've got good intention, why not? The conversation is likely not easy, but I feel it is the result of poor communication up to now. However, if he decides to take action (and not the easy way out), I hope he would be wise enough to let go of his/her prejudice. Jun 9, 2016 at 6:01

What do you have to lose if you speak with her ?

If she doesn't listen or doesn't understand what you say, then at least you tried.

If she does listen and understand, that maybe she will try to change her attitude.

Anyway, try to give her a good talk, with a clear "I want to help you" at first.

Try to give her some tips about how to be better etc... and explain how what she is doing is wrong.

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    I would turn this around: what do you have to gain by speaking to her? Probably nothing, unless you would enjoy having a flaming row with her. (I assume that you are not selecting your own replacement as manager, of course). Two weeks from now she's not your problem any more - unless you do something in the next two weeks that makes her your problem, at least until the lawsuit / industrial tribunal case that she starts is finished.
    – alephzero
    Jun 6, 2016 at 22:50
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    @alephzero "Two weeks from now she's not your problem any more" she's still his problem at the moment. As a good manager, he has to do everything to deal with that problem before he goes away. Leaving that to the next guy is not really professional.
    – Gautier C
    Jun 7, 2016 at 6:12

This person is not likely to change this behavior over-night since she doesn't have the personality tendency to behave differently. It is important that someone point out this flaw, but you're not going to be able to follow-up and provide any useful feedback in only two weeks. She really needs an ally to help her through this.

If you're able to get cooperation from another employee, who could take over this process of helping this person, you should consider it. Talk to her first and see what she thinks. Suggest getting help from someone else in the company.

Just pointing out this flaw without any intention of helping with a solution (sometimes people need professional help), could hinder your relationship. Basically, you'll be burning a bridge.

  • I am testament to the right kick-in-the-arse at the right time can help the most hard-headed person improve.
    – Tony Ennis
    Jun 8, 2016 at 13:43

Do it.

It's the right thing to do. Let her know the consequences of her actions.

For her sake, try to make this a two-way conversation. Ask her what she is hoping to achieve by writing these lengthy E-Mails, and listen to her response.

I recall doing something similar when I was part of an organization that had a different culture than what I embraced. My work was appreciated, but the different perspectives kept my advancement in the company slowed. In essence, I do believe that the reason I wrote some of the E-Mail content that I did is that I was hungry for more communication. I felt like I wasn't quite on the same page in some ways, and I was trying to close the gap. I rather ceased this action when I invested quite a bit of time in an E-Mail that I was told wasn't read because it was too long, and I attempted some other communication methods which ended up working better.

If your issue is the length of time that she writes, and expects you to read, about plans of possible futures, then explain to her how much many managers appreciate brevity. Explain that if there is any benefit whatsoever in such planning, she can probably communicate it with a simple bullet point list of possible concerns/threats, and she can effectively look on top of things with a simple statement about being readily able to elaborate on any of those topics.

As Joe Strazzere's answer points out, your efforts could be fruitless. Still, just plant the seed. Let her take care of nurturing the seed and letting it grow. (To become less analogous, I'm saying, let her decide how much the advice will affect her life.) But if you don't even give her the information that you know she needs, that decision pretty effectively prevents the possibility of good things being able to possibly happen. Let her have the chance, and let her decisions determine what good does or doesn't happen.

I will even go on to predict that you will probably not find the conversation very satisfying. However, you may help her to realize some other perspective. There may be results in a short time (days or weeks), or maybe down the road (months, years, decades). In the end, the insight you share may help her a great deal. However, it sounds like you won't be around to see it. If you end the conversation without any apparent good, accept that likely and expectable conclusion.

Still, even if you aren't likely to feel the immediate satisfaction of known success, do the right thing. Try to help people. Do the action that has the most chance of being good for her. You're less likely to do this (reach out to her) after you leave, so now is the best foreseeable time to do this.

  • Totally agree that communication is kind of lacking here... However, it's not only "for her sake", but also "for the manager's sake". A manager who don't understand his/her subordinate will have difficult time managing people Jun 9, 2016 at 5:44

Looking at it from a different perspective, this person clearly has ambition and is trying to make themselves look better to other people (even if they're failing). They would likely be much more open to advice than say, someone that hates their job and is just doing this because they are an awful person. You are also already in a managerial position, so they're likely to take advice from you on how to be a good manager much more readily.

You don't have to be super blunt about it. It's certainly possible to break it gently and pose it as advice. You may have to do some 'real talk', but you don't have to be harsh about it, because they do seem to have good intentions.


I agree with the other comments that the last 2 weeks on the job is rather late to be doing this, however...

Rather than bringing up the emails at all I would recommend just mentioning to her as a bit of feedback that "soft skills" are very important if she wants to progress her career and see if you can recommend some people management courses or even better if your company provides training get her signed up for some.

The emails are a symptom not a cause so rather than addressing the symptom go to the cause. They need to learn how to communicate and work with other people effectively. For all we know those emails would be great if sent to the right audience, without seeing them we don't know. The key skill is being able to send the right message to the right people and that is what the person you are describing needs to learn.

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    This feedback is too vague to be acted upon. If she is unaware that these emails are a problem, she'll not connect "soft skills" to "don't waste your manager's time" or whatever message it is you want to get across.
    – meriton
    Jun 7, 2016 at 12:06
  • @meriton Not at all. See the paragraph I just added.
    – Tim B
    Jun 7, 2016 at 13:44

While I understand how you feel, you have another consideration to make.

You are a short-timer. Anything you say, will be seen under that light.

Be that as it may, if you say anything at all to the employee, you could make a huge mess including any liability for the company and yourself. However, there is something you can offer and stay safe.

Talk with HR gingerly and briefly and let them take on the mantle. They may ask the legal department for guidance. Keep in mind that managers are in the firing line. Your being a short-timer makes any approach you make suspicious. Something as significant as you are describing should not be done in a vacuum. Remember that your are trying to help and couch your approach as a genuine offer and not a criticism. You may find that HR would advise you not to say anything at all and that will be the end of it.

Do not write up your concerns without being asked to. Present your concerns to HR as an honest concern and something you are willing to do, not as a retaliation, but as a help for the employee and company. Again, be brief so that HR understands the problem and do not go into details that could be seen as being slanderous. Let HR drive this one. Otherwise, stay out of it.

Leave it as that. Nothing more. Let HR take on the challenge if they want to. If HR asks for your help, then give it, however, still limit your comments and put it in the most helpful light you can including simple suggestions to illustrate your willingness to help the employee and the company equally.

Remember, this can be as much a reflection of you as the employee. Often, these things go badly. So please keep that in mind.

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    This is awful advice. Bringing HR in will only send the message this employee is an intractable problem and needs to be put on a PIP, stunting the employee's career very effectively. There is zero reason to get legal involved. What's going on is strictly a management issue and the problem behaviors merit constructive guidance, not punishment. Jun 6, 2016 at 17:53
  • @EsotericScreenName I guess you missed Otherwise, stay out of it. I did not say involve legal. I said talk to HR and see if they want to approach the issue. HR might ask their legal department for guidelines. My advice is to hand it off or leave it alone. Saying something now on your own is just very bad advice.
    – closetnoc
    Jun 6, 2016 at 19:15
  • "Let HR drive this one." You give no reason why HR would be more qualified.
    – TOOGAM
    Jun 7, 2016 at 21:05
  • @TOOGAM Actually, I do. The manager is a short-timer and therefore anything they might say to the employee could be a liability and reflect poorly on the OP. It could be seen as retaliatory. I also mention to limit the comments to HR and to couch any comment as a means to help the individual. Anything said should be said in a positive light if at all. I also say twice that it is likely better not to say anything. If the employee has issues, then it would be found out with the new manager. That would be better all-round. Cheers!!
    – closetnoc
    Jun 7, 2016 at 21:19

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