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I'm an in-house attorney and manage most of the outside counsel for my company. I've recently had two experiences that have put me in a bind as it relates to my boss. I'd like some input on what obligation I have to share feedback from third parties with my boss about her behavior; how I should react to it in the moment; and whether I should adjust my behavior to comport with it.
In one case, my boss and I have been teaming up negotiating a resolution to a pending dispute. At one critical juncture, our outside counsel asked if there was any way we could have the next meeting with the other side without my boss present. I said I doubted it, because she was committed to being there, but asked why. She said that the other side's counsel didn't like my boss, thought she was rude, combative, and didn't treat the other people on my company's team (including our outside counsel) with respect. Our lawyer believed that the negotiations could suffer if my boss was there. I asked our outside counsel if she agreed with the other side's assessment, and after a brief pause, she said no, but she thought it would be helpful to avoid future conflict if she wasn't there. I thanked her for the honest feedback and said I'd get back to her.
In another case, our outside counsel seemed stubbornly resistant to copying my boss on e-mail, despite my boss' repeated request to be copied. Because it kept turning into my job to forward the e-mails along, I asked the outside counsel why he didn't copy my boss. He said he wished he could just work with me, because everything became emotionally-charged and took twice as long when my boss got involved, but he understood the request to copy her and would do so. I said that would help a lot.
At this point, I haven't shared any of this feedback with my boss or anyone else. I'm afraid that if I shared it with her directly, it would come across as attempting to manage her (I don't disagree with the feedback, by the way), and it would only hurt our company's relationship with these very good lawyers. That said, both lawyers indicated that my boss' presence on the team was hurting our company's effectiveness, and that seems like the kind of information that shouldn't go unheard - even if she doesn't want to hear it. Any suggestions?
I don't envy you
You're in a difficult position here, and I don't see a smooth way out (others may have better wisdom to share, though). Based on your description of your boss, she's probably not going to be open to hearing this kind of thing ("emotionally-charged", "combative", and "didn't treat the other people [...] with respect" don't sound like things that would be said of someone open to feedback from their directs). If you had a truly excellent relationship, you could consider a bit of peer feedback on particularly egregious things ("Hey Sue, I don't know if you realise that when you tell the other side's lawyers that they'll want to grow eyes in the backs of their heads, it makes it harder for me to negotiate a settlement"), but... yeah. You'll just end up the target of some "combativeness" yourself.
Perhaps if you could describe actual behaviours that your boss is engaging in that you're characterising negatively, someone might be able to provide more specific guidance on how to defuse it in the moment, or deal with it with your boss afterwards.
Alternately, is there anyone else in the organisation you could bring this sort of concern to? I don't like the idea of going around one's boss, but if its causing problems for the organisation and driving away good outside counsel, it's the kind of thing that I'd want to know about, if I was your boss's boss (or other very senior person in the organisation). It isn't something you just go blabbing to the first person in an expensive suit, though -- you'll need to have a solid pre-existing relationship with this person, and be confident that they'll handle it in a discreet and mature way (such as observing a couple of these sessions involving your boss directly to see the extent of the issue).