Hello all-

I posted about my situation early on in my job here, and I wanted to provide an update of sorts and request some advice on the situation. I've been in the role for nine months now. Small not-for-profit, not a very old organization. My predecessor left in an ugly scene and I was brought on three months after that. My #2 and my current boss became very close during my predecessor's departure - I've been told that my #2 and boss talked regularly behind my predecessor's back in the runup to her ouster. So, a somewhat toxic situation when I came on, but I did my best to manage it effectively.

Here are the two problems I face today - 

1. Boss is a bully - wants everything their way, very particular and specific, very demeaning in public situations. I am seeking the demeaning boss podcast to review, and I've also read a lot of what Mark has said on other posts about being thankful that I'm in a position to control my reaction. I'm on board with that - it's a hard pill to swallow but it's very real (Horstman 9).

2. #2 continues to talk with my boss behind my back, just as she did with my predecessor. They aren't very secretive about it - very often my boss knows things she just wouldn't know otherwise. Often times when my boss is frustrated because she doesn't understand something I'm doing, she'll call #2, talk with her about it, and then at midnight that night send me a completely missing the boat nasty-gram email that I then have to sweat and walk back (rather than just calling me directly and getting the answers). As to the direction of the contact, I think my boss instigates the contact in this situation, but I have the feeling that my #2 relishes the opportunity to be connected at the top.

One more important factor here - my current boss term limits out at the end of the calendar year, and the new guy and I have a good strong understanding of how things will be in the new regime. So, I can see the light. 

My only real questions are whether anyone has any general advice about the situation, and then secondarily whether I should address the communication issue between my #2 and my boss. My trust in my #2 has really descended to a low point in the situation and I find myself somewhat at a loss as to how to approach her about this (or whether I should at all).

Love Manager Tools, love the empowering nature of the content, have been thinking for a while that it was time that I posted the situation here. Appreciate your help in advance.

JDPM311's picture

Hi Execdir,

If your term limits at the end of the calendar year, e.g. approx. 1 month, and you don't see yourself maintaining this role going forward, then I would say save yourself the trouble and forego the conversation with your #2.  When you say, "I see the light", I take it that means that you won't be maintaining your current role, but I may be reading wrong.


In the event that you continue in your current role, the only thing you can do is to have the tough conversation with #2.  A few key points in that conversation would be trust, communication, etc.  I mean, you can't constantly be getting second guessed by your #2 and then have them going behind your back up the ladder with their doubts.  The #2 clearly has their own agenda in mind.  Should you continue to have a manager-direct relationship with the #2 and that continues, you can obviously base some performance reviews/decisions on that type of behavior continuing, however, it seems your boss may continue to intervene in that sort of a situation.


I think MT has a podcast to the effect of "My direct skips me" that addresses this situation, where the manager is left out of communications directly involving their boss.  I actually received this kind of feedback from MY boss, though I wasn't omitting her maliciously, as it seems your #2 is.  I was mistakenly under the impression that I was "handling things for her" so she didn't have to worry about them.  I got a nasty email saying that I needed to CC her on comms. to anyone that was a director-level or above and have complied ever since.   I wouldn't suggest going that route, but that's the conversation in a nutshell, and then you apply positive or negative feedback to behavior after setting that type of expectation.


Good luck!