Hi All –

I have been a long time member of the M-T community and am posting under a new account for this topic. And I have an interesting dilemma that I would appreciate some advice and insight on.

I recently completed a performance review with my supervisor. I have been in my position for two years and she has been my supervisor for the last 12 months. It was everything I could ask for recognition of what I accomplished in quality and quantity, generating new clients, accolades for the relationships I have built, kudos for the talent I am hiring and developing, affirmation I am on the radar of executive management, acknowledgement that I am her strongest performer and the like.  It was an A-Letter day…… with the exception of one thing.
She has very much put me in the driver’s seat to improve my relationship with one of my peers named “Bob.” She is couching at as “a challenge” and really honing in on how it will stretch me to be able to work well with future executive teams. She is right, it will. She acknowledges that it is not a fair challenge but that she expects more out of me (compared to him anyhow). 
Bob and I are peers relative to pay and status (although he would disagree on the latter). We both report to the same supervisor, neither of us is in the others chain of command, and we have different responsibilities. I am a division head. Bob is a special assistant to my boss. His hiring predated both our boss and me.
I was not intending to discuss “Bob-issues” during my performance review. My boss brought it up and I was surprised that she stated a number of things that, while I may have thought them, I would have never shared them with her. I will share a couple of the statements which may provide some back drop are: She is aware that Bob tried to jade her negatively regarding me when she was new. She is aware that Bob is an insecure person . She is aware that Bob is conflict avoidant and has refused to engage me regarding our issues despite my overtures.  She is aware that Bob is very sensitive to having his decisions questioned and that he has made some bad ones. While there are some times where I could have been more sensitive to Bob, her observation is that often times she is surprised at his reaction when she can see nothing inappropriate or edgy about the interaction. She is aware that she and Bob have some friction (I was aware this and have tried to stay away from it).
I was surprised and a little flattered that she would trust me to be so open like this (has me wondering what she has told Bob). It was encouraging to me that she was so aware (and that she recognized some of the things that I was doing to try and improve the relationship AND that Bob was “into avoidance”). When I discussed the situation with one of my mentors last spring, their question was what my boss was doing about it. My take (at least this is what I have been telling myself to keep it in the positive) is that my boss would rather lean on me a little bit harder than to run the risk of bruising Bob’s ego because she knows I will respond better.
It does take two. I arrived from a different region of the company with more management and supervision experience than Bob and knowledge of more product lines. I also arrived with a little bit of an up-and-coming reputation. Bob is about 15 years my senior. Bob did not offer himself as a resource to me; nor did I recognize him as one.  In short (and Bob has told me this on so many words), it is important to Bob that I agree with him and look up to him – one of his complaints about me is that I have never come to him with a problem. While I engaged with my other peers quickly and they engaged with me, I spent an awful lot of time with Bob initially. There have been a couple things that have diminished my trust and respect with him but I believe that I have kept my own counsel on it. My workload had been such this last 9 months, that I have not had a lot of time to stop by and chat. At the same time, he has never reached out and been in my office no more than 10 times in the last 2 years.
I relish the challenge of improving my relationship with Bob and the confidence that my boss has in me that I can do it. It is likely that I will learn a lot and be able to apply a lot of it as I move up within the organization.  I am a little perplexed that I feel that my boss is having me carry what seems like a lot of  her water on this because of her relationship with Bob.
Here is the other side of the dilemma and the one that is really bothering me. On several occasions, my boss has mentioned that Bob grew up with only sisters, has 5 daughters, and he is comfortable with his interactions with women and has to do it all the time. (For clarity, I am a woman). Bob is a member of a faith where men hold superior roles to women in both family and society (note: I do not manage by faith, make generalizations about people of specific faiths, and work well with many members of Bob’s faith.) My boss bluntly brought this up during my review and stated that it is likely that he has some problems with confident women.  The connection is that for me to be successful in this challenge,  it may require me to stoop, ego-inflate, and subjugate myself beyond what I think may be reasonable– in this case to appease someone who has gender related ideas which probably do not belong in the repertoire of an effective manager in the first place. My opinion is that the latter is her job.
I appreciate that with ability and position come responsibility and challenge. I am toying with some ways to make this work. Yet, it feels to me like I am being asked to do something that is a little far reaching to the norm and that my boss may be laying a little too much on me so that she can avoid. In the end, my job is to help my boss achieve her goals and one of her goals is people getting along. Yet, this does not feel quite right to me.
From an outsider point of view, do you see additional questions I should be asking? Or thoughts on how I might approach this? Or just thoughts?  It’s a topic that covers all the awkward workplace stuff expect politics. Then again, perhaps I am making this a bigger deal than what it is. My humble thanks in advance for your insight.