Dear Liz,

I guess this is a relationship question, but it’s work-related. I worked for a terrific boss at my last job and since I moved on to a new company we’ve become close friends. I love my new job and I’m really glad that my old boss and I are now such helpful advisors to one another. The only thing that kind of bothers me is that I can give her really frank, meaningful advice on her job now, whereas when I worked for her I always felt there was a wall up, where I could maybe gently suggest a change in a process, but never push too hard. Is this normal? I greatly admire this friend, but am I right to be slightly irritated that she didn’t listen to me so seriously when I gave her great advice while working for her?

Yours,
Tracey

Dear Tracey,

I understand your feelings, but don’t be too hard on your old boss/new friend. There are a number of barriers to ideal, authentic communication that were in place while you worked for her but that have disappeared since you changed jobs. For one thing, you were already friendly with her when you two worked together. Try to imagine the conflict she may have felt, wanting to hear your great advice, but possibly being wary that other team members would see you as a ‘teacher’s pet’ or fault her for taking her leadership advice from a subordinate. Also, she may have been barred by company policy or her own standards from certain relevant bits of information with you, whereas nowadays the two of you can talk freely as friends about everything that’s on your friend’s desk and on her mind at work. Be happy that you’ve reached a more fulfilling and useful level of conversation with her. And if you want to, some evening over a glass of wine, you can ask her, “Am I giving you better advice now that I don’t work for you, or was it just the boss-subordinate relationship that made it harder for us to advise one another back at XYZ Corp?” I betcha she’ll fill you in, gladly.

Cheers,
Liz