I share an employee with a difficult boss

A reader writes:

I’m a program manager in a nonprofit and supervise one employee, our program associate. She’s great. Very productive, efficient, intelligent, and in general a pleasure to work with. She’s been with the organizaiton about 2 years and is eager to advance in her career. (This is her first full-time paid position after college.)

About four months ago, she started working half-time in another department due to budget cuts in my office. Her new supervisor has a reputation for not responding to emails, being a micromanager, and just being a difficult person to work with. Everyone in the office knows how she is, and my supervisee knew it before she accepted the 50% position in that office.(Granted, she would have gone to part-time if she hadn’t accepted the job.)

However, now my program associate cc’s me on emails to her other boss in which she says that she feels like she doesn’t have enough job responsibility, isn’t being allowed to work on specific tasks in her job description, asks to go to meetings that she feels that she’s being excluded from, etc. I don’t disagree that she should be working on this things, but her emails come across as not just assertive but quite demanding. Frankly, I feel that when she cc’s me, it may give the appearance that I’m condoning the emails when I’m not.

My supervisee ccs me because she and I have a good relationship and I think she feels like I should be in the loop. I haven’t asked her to stop cc’ing me, but maybe I should. I’ve sometimes tried coaching her through other strategies for dealing with her boss (such as aying, “I’m eager to work on XX project. What can I do to prepare myself,” etc). I’ve also reminded her that it can take time to get to know a new boss and figure out the best strategies for working with him/her. I’ve told her that once this busy time of year passes in in a few weeks that may be a better time to advocate that she be brought up to speed on the other projects she thought she’d be working on.

I’m not sure what else I should do, if anything. My direct supervisor is the head of the organization, so I feel like if I go to my boss for input, it just escalates the whole issue. Should I ask to not be put in the middle or should I be doing more to look out for my program associate’s best interest? Ultimately, I want her to stay with the organization. It would be a loss of my program if she decided to move on because of her frustration with her other boss.

The other boss might be a bad manager, but your employee doesn’t sound like she’s helping herself either. I would do three things, and maybe four:

1. Talk to your employee about how she’s handling the situation. Point out the following:

a. The tone of her emails to her other boss is coming across as demanding, not assertive. Explain that no matter how frustrated she might be, she needs to keep her tone professional when talking to coworkers, and especially to her boss, and that sending a slew of demanding emails is likelier to undermine her position and reduce her credibility than to get the outcome she wants. Give her specific suggestions about how to word things differently.

b. She can’t force the other boss to do what she wants. She can make her case for it, but ultimately she may not get what she wants. This probably isn’t going to be the last difficult manager she has in her career, and she needs to figure out how to deal with it professionally and productively. At some point, arguing for the same thing over and over is both pointless and potentially combative, and the more productive way to handle it is to think, “Okay, this is the situation and it doesn’t look like it’s changing. What do I want to do from here?”

2. Ask her why she’s cc’ing you on the emails she’s sending to the other boss. Hear her out, but let her know that it’s not appropriate and ask that she stop. Unless something truly involves her work for you, she needs to handle her relationship with the other boss independently.

3. Talk to your own manager, the head of the organization. Give her a heads-up that your employee is unhappy and frustrated with the other 50% of her job and explain why. Don’t present this as “I’m asking you to intervene,” but rather as “I want you to be aware of this, because it may come to a head at some point … and by the way, I really don’t want to lose Jane because she does great work.” (On the other hand, maybe you do feel she should intervene — and if that’s the case, it’s fine for you to make the case for that.)

This conversation is appropriate for you to have, both because you’re part of the organization’s management team and because it’s affecting one of your employees. You mentioned being concerned that talking to her will escalate the issue, but frankly it sounds escalated enough already that your manager should be aware of it.

4. This last one is optional, and without knowing the personalities involved, I’m not sure if it would be constructive to do or not, but you might want to talk to your coworker — the other manager — as well. After all, she knows you’ve been seeing all those emails, so it wouldn’t be crazy to talk to her about what’s going on.

However, don’t go into that conversation accusing her of anything or with a tone that says you’re there to advocate for Jane. Just tell her you’ve noticed Jane feels frustrated and ask what her take is. It’s possible that you’ll get some insight that might change your perspective on this. After all, Jane’s complaints — that she feels she doesn’t have enough responsibility, isn’t being allowed to work on specific tasks in her job description, and wants to go to meetings that she’s being excluded from — are all things that could have legitimate reasons behind them. (For example, for the sake of argument, maybe the manager feels that Jane wants more responsibility than she believes is reasonable for someone at Jane’s skill level or in her position, isn’t going to give her tasks X, Y, and Z until she’s first mastered A, B, and C or until the department’s busy season is over and she has time to train her on them, and doesn’t invite her to high-level meetings because it’s not appropriate for her job.) Or maybe not. But it might be worth talking to her about what’s going on, since you manage half of Jane’s time and are interested in retaining her.

Ultimately, though, it’s up to (a) the other manager to decide she manages Jane, (b) the head of the organization to decide whether she wants things done differently, and (c) Jane to figure out how she wants to respond to the situation, with the understanding that she can’t force things to change.

{ 26 comments… read them below }

  1. Ask a Manager* Post author

    Clearly everyone is over at the “share your worst holiday work story” post, because I cannot remember the last time a post had zero comments an hour after being published. I should have known better!

    1. Jamie*

      You set up a party over there, you may as well have poured the drinks and loaded the virtual buffet table!

      I’m curious if the job responsibilities are similar in both positions. Is it possible she’s not performing as well for the other manager because it’s a different skill set that’s needed – hence hitting the wall with responsibility?

      Either way – I think Alison laid it out beautifully. You need to tell her to cc you when it’s relevant to your department and appropriate – and otherwise it’s a separate deal.

      Is it completely separate though? Are you her main manager, or does she have one? I have some people reporting to me for projects and I will get involved with their career development as it pertains to what they do for me – but it’s a coordinated effort with their manager who at the end of the day the person still reports to.

      So I guess I’m just wondering if ambiguity of how this is split is confusing her, hence the weird ccs to you?

      1. The IT Manager*

        I wondered that too. Is it clear to “Jane” that she only works for you part time and you have nothing to do with her work in the other job or does she think you’re still her supervisor even if these new tasks don’t fall in area?

      2. KellyK*

        Yeah, that’s a good point. I’ve been in the position of having multiple “bosses”: your supervisor who assigns you to projects, evaluates your performance, etc., and one or more project managers who assign you specific work on those projects. If the employee is thinking of the LW as her “main boss,” that may be why she’s ccing.

    2. Ariancita*

      Ha! I haven’t even read that one yet. Now it sounds interesting… But want to say: excellent excellent advise. This is really helpful for me as well as I feel a similar situation (not exactly the same, but similar) brewing in my department and now I know how to handle it. Thanks!

  2. Janet*

    I was nervous about being the first comment!

    I have some sympathy for the employee because I have had a non-responsive boss in the past and if you’re young and female, it’s tough to find that balance of being assertive and being overly demanding. If you’re too tentative, it’s easy to get bulldozed or ignored but if you’re too forceful, you’re not minding your place.

    I imagine it’s very frustrating for her to want to do more and have the time and ability to do more and have those requests go unanswered over and over again. I also wonder if she’s a little terrified that if she isn’t busy, she’ll be forced into part-time or cut completely if money has already been an issue in the past.

  3. The IT Manager*

    I kind of don’t know what to say. My first thought was “what an awful position for Jane, the program associate, to be in.” I’ve never heard of something quite like this. It sounds like its set up as two separate part time jobs except it’s for the same organization so the boundaries are unclear. Is she going to get two seperate perfomance reports each year? How weird would it be for her to get a good one from you and a poor one from the other boss?

    I’m a project manager in a matrixed organization and I have some people assigned to my project part time, but they all have a direct supervisor in addition to their various PMs. In a situation like Jane’s, they could go to their own supervisor to get asisstance and I would not be involved.

    If awful boss was instead her full time boss (if you had left and awful boss replaced you), she’d be on her own so I do think its great you’re trying to help her.

    1. K*

      This isn’t a totally unusual set-up in some fields. Law firm associates, for instance, might work for any number of partners, some of whom love them and some of whom are trying to phase them out. It has downsides, but the upsides usually come about when you can transition into working more with the people who like you (and who you click with), which doesn’t sound like a possibility here.

      1. The IT Manager*

        I’m curious how this works. What happens if one of the partners fire an associate in a fit of anger? This sounds very unwieldy and confusing.

        1. K*

          Interesting question. I don’t know what happens if a partner fires an associate in a fit of anger (oddly enough, I’ve never heard of it happening, which is weird because you hear about all kinds of bizarre behavior in law firms), but in theory the rest of the partnership could overrule that partner if they wished. In practice, that might be why for all the weird and abusive things law firm partners can do, that’s not usually one of them.

          It may be unwieldy, and often is, but it actually arises out of a logical principle: law firms are jointly owned by the partners because they can’t, like other companies, be owned by non-lawyer shareholders (that would constitute unauthorized practice of law). So the joint owners of the business get to decide how it’s run, and that includes supervision of employees. And since associates are hired with the expectation that they may, if things go well, become partners in 7-9 years, they’re supervised by the partnership as a whole in anticipation of that role.

          In smaller law firms, that’s fine. In today’s mega-law firms (which the original rule were never really designed to account for ), where you might have hundreds of partners, I think associates tend to be brought into smaller practice groups and the partners in that practice group practically make all decisions for them. If they work in more than one practice group and one stops working out, they can try to switch to another one and if another partner likes them well enough that can work too.

          Personally, I’m an associate at a relatively small firm (about 20 lawyers). At that size, it works okay. I don’t have a direct supervisor, per se, but there is a management committee that handles overarching supervision and things tick along.

          1. The IT Manager*

            you hear about all kinds of bizarre behavior in law firms

            That’s why I asked because I’ve heard stories.

            Also learned something new – I didn’t really understand that only lawyers could “own” law firm.

    2. Ariancita*

      It can be this way for staff in academia. They have percentage efforts, so they may have a part time job with one team/faculty member (say 15% effort as an RA) and then another percentage effort for another team/department (say 85% effort). I’m not sure how it’s handled with evaluations, but I imagine that they get two separate evaluations which both go to HR.

      1. fposte*

        Yes, in my branch of academia this isn’t at all uncommon; the two jobs often are paid out of different budget lines, even (though they get reblended come pay time). It’s therefore no problem for one job to end if another’s still going on (though if they were actually fired for doing something horrible that might be a little weird in the building–the manager would be likely to inform the other supervisor in that case).

    3. Judy*

      We’re that way too. I have a manager who is the software manager. But the work I do is really for one of three project managers, that have MEs, EEs, SEs, etc assigned to their teams. So the person who does my evaluations does not have a stake in the projects, he’s just in charge of the “competency” of software, so he’s very focused on the technical process of writing software rather than the delivery of the projects. Can be interesting. Especially when priorities from the different project managers are in conflict.

      1. The IT Manager*

        That’s the same for me. My compentency manager has nothing to do with my projects, but she’s the one who does my evaluations. She has a background in training so she’s focussed a lot on me being properly trained for the job. (I am new so do need the training). But I do know if I am having problems with the senior PMs on my team, I can go to her and she will go to bat for me because she’s my supervisor and my career/actions, etc is her responsibility.

        That’s why I feel for the associate here; although, maybe she’s better off than if the awful boss was her full time boss. At least she gets a reprieve for half her time.

  4. JLL*

    Question for the OP- is she your direct report and just doing some work in that department, or do you both have equal authority? I agree with Alison, although I feel a bit for this employee, who is in a bit of a no man’s land.

    She feels she’s being actively hampered by one direct boss, and the other direct boss that she does have a good working relationship with, does not want to get involved, but doesn’t want it to go up, which is where it probably should, if said boss is as bad as you suggest their reputation is. If s/he has a rep for not responding to emails, she’s probably cc’ing you as a “witness,” not as a co-signer.

  5. Lanya*

    I don’t think it’s good for one employee to have two direct supervisors unless those supervisors communicate well, and frequently. I have been in situations where my two bosses were not keeping track of the workload they were each giving me. I would always ask what my priority should be…but since both of their priorities were different, it didn’t help me much.

    1. businesslady*

      it also gets difficult when the employee likes one boss (or the tasks associated with one boss) more than the other.

  6. COT*

    My first job out of college was an Americorps-type position at a nonprofit. I split my time equally between two distinct departments and supervisors. For the most part it was no problem; I got to enjoy a big range of tasks and team styles. It was a little challenging balancing priorities and time, but it was a good experience.

    Both of my managers were good overall, but one of them was not very good at onboarding new people to her team (not just me–every new employee or intern). A few weeks in, I had yet to be trained in her department or assigned any work from her, and my other boss didn’t really need 40 hours from me. Being new to the organization I really appreciated that my (better) boss intervened and pushed my (negligent) boss to get me going on that team. I wouldn’t have known how to effectively ask for it myself at that point in my career. Navigating internal politics doesn’t come naturally to me.

    I think your employee wants to do a good job for her new supervisor and just doesn’t understand her place on the team nor how to go about addressing the problem. Alison’s advice is good: coach your employee, but also address the issue with the other supervisor or your director. It might help for you, the other manager, and your employee to have a sit-down meeting to coordinate duties and workload. This might be an opportunity for you to gently advocate for your employee, vouch for her talents, and demonstrate how to ask for more work… without it becoming a long email chain.

  7. Anonymous*

    I’ve had several “split” employees in the past, and it worked out fine. The other manager and myself split it out by days, so there was never really a question of overloading. We’ve found it’s a great way to give our staff a chance to build their resumes up.

    So far, we haven’t had any issues with someone liking one boss and not liking another – but if they were unhappy, I suppose they could leave and we’d hire another employee or they could go PT for one boss.

    1. fposte*

      Yes, it works really well for us–as in the OP’s situation, it means that I don’t lose a great employee that I don’t have full-time money for. But I’d be deeply perplexed by an employee who cc:ed me on emails to the manager of her other job–to me it would be like she were waiting tables on the weekend and cc:ing me on her emails to her restaurant manager.

  8. Lulu*

    Ugh, I’ve been on the other side of the situation in the past, and it was no fun: I was assigned to assist 3 teams that of course sat in completely different areas. So the managers that I did not sit near felt like I wasn’t doing the job properly, despite the fact that they were the ones that inevitably skipped our scheduled 1:1 meetings, ignored emails, and would just not show up for work (and not give me a heads-up or put it on their calendars), or give me anything significant to do beyond occasionally make a binder. I was under the impression that I was split evenly 3 ways, but since the guy I sat nearest was also the only one who tried to get me involved with the team or interact with me on any level (in addition to the proximity issue), he logically got more of my services.

    I made a lot of effort to work with the others’ idiosyncracies, but everyone obviously had different levels of expecations of all of our roles. When review time came, the guy who’d become my primary manager warned me that despite his desire to give me MORE responsibilities on his end, the others were saying I was not able to to my job (whatever they thought that was). It was awful, especially since he left soon after and I still had to work with the guys who hated me.

    Which is all a long way of saying, managers who share an employee should make a point of talking to eachother about their expectations, and are very clear with the employee about them as well. Especially if someone in the mix is known to have potential issues.

    I agree your associate’s cc’s may be her way of indicating that she’s feeling a little powerless and desperate about the situation, and feels that she may end up being further marginalized if she can’t recruit anyone to step in – for all she knows, the other supervisor’s assignments could suddenly become most/all of her job. Particularly if she was used to such a convivial partnership with you, trying to find ways to work with someone more difficult may have been quite a shock, especially when there’s a large discrepancy between how she had been operating and what the new person wants her to do. If she’s also both young and highly ambitious, it’s true she may also have some unrealistic assumptions about the scope of her job since it sounds like up until now, she hasn’t had to deal with much in the way of roadblocks. Definitely disabuse her of the notion that her current tactics are the best way to handle the situation, regardless – maybe if you can reassure her that you and the other manager do communicate about her work, as well as make it clear what the reporting structure is (if it’s not already), it will help mitigate things. After that, it really is up to her how to handle her frustration and whether she wants to continue working this way, assuming nothing changes in that regard.

    1. Lulu*

      Sorry for the novel! Obviously, this touched a nerve ;) I’ve just witnessed so many poor work situations that could have been avoided by having better communication and clarity…

  9. Not So NewReader*

    As I read through you question. OP, I got the picture of a sinking ship sending out an SOS.

    It could be that she is drowning at the other job and she is sending you the email version of SOS. By giving you the play by play, she at least has left someone with documentation of what is going on.
    It sounds like her complaints cover lack of training, lack of assignments and not being included in activities of that department.

    Uh. That is some pretty serious stuff. I know if I got caught “wasting” employee talent I would have been called on the carpet big time.

    Granted her solution to email you copies of everything is not really a solution. She may not know where else to turn for back up. And just because someone is treating her poorly that does not give her license to use whatever tone of voice she wants. (Are the cc’s OR bcc’s?)

    Does the other boss actually have work for her to do? Has work dwindled down so much that the other boss is struggling to keep busy? This could be an inroad to a conversation that puts your subordinate in a work area that she is needed for the other half of her time. Maybe this other boss does not actually need her.

    Conversely, if the situation is that dire that she wants to quit then could she just work part time for you until things pick up?

    Who has authorization to fire this woman? Both of you? What happens if you disagree on firing? (These are good questions for your boss.)

  10. Mtnlaurel*

    I am in a similar situation myself. I am, like the employee, working with someone who should be working with me but instead works around me. She ignores emails and plans events that directly involve a space that I manage without giving me information that I need to make my space accessible to clients. She is not my boss and we don’t share the same boss, because the corporate structure has us answering to 2 different managers. In my case I blame the organization for not having thought through how integral our two jobs are. It seems like the writer’s employee is calling for help and the advice here is excellent: offer help, but be clear about what communications are appropriate to be cc’d on. From the sound of the situation, speaking with the other manager may be helpful but it also might be fruitless. When I have to confront my colleague I find that she changes her tone, gives me the information I need, but in a spirit of appeasement and not cooperation. The cycle of not being in the loop repeats itself soon enough. If this colleague were my boss, I would have looked for a new job a long time ago.

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