I have been in my new job for about five weeks now with a very small service-providing firm of only about 10 employees. I am a director-level employee and report right to the COO.
Our COO is new in his role, but not new with the company. I get the feeling he does not have a lot of leadership experience, and he certainly has never led at this level before now. The issue is that he feels the need to share drama about his ex-wife, his two teenage daughter's antics, and his current wife's hatred of his ex-wife. This sharing goes on and on when it occurs -- and it occurs during meetings occasionally, where it is totally inappropriate and wastes valuable time. Once in a while, we leave the office together at the end of the day, and I actually have stood outside waiting to walk to my car while he finishes another tale. He does this over-sharing with everyone, not just me.
I know I need to say something, but I do not want to appear insensitive. How do I tell this guy to back off without making it seem like I am cold and heartless? I am comfortable initiating the conversation, but unsure of the approach.
When you want to address someone’s problematic behavior in the workplace, you have two choices: Address a specific instance on the spot when it happens, or address your big picture concerns in a conversation at another time.
It’s usually much easier to address it on the spot. Saving it for a bigger conversation later tends to make it feel much more serious, and that’s something that can be particularly sticky when (a) you’re new to the job, and (b) the person you’re taking issue with is your boss. Because the reality is, those two factors make this a situation where you need to proceed with much more caution than you otherwise would – especially him being your boss.
So the next time he starts over-sharing about his personal life, speak up in the moment. If at all possible, do it in a kind way, not with an overtly critical or serious tone. For instance:
Boss: “You won’t believe what my ex-wife has done now! This morning, I had an outrageous phone call from her!”
You: “Not something I should know! Sorry you’re dealing with that, but can we talk about the software bugs that just got reported?”
Do this a few times, and he may start to catch on.
Alternately, you can have a separate conversation with him about the pattern itself, saying something like, “Bob, I really enjoy working with you, but I want to tell you about something that’s troubling me. When you share details about your ex-wife and other personal problems, I feel uncomfortable, especially when we end up spending a lot of time discussing it. I so enjoy working with you aside from this, and I thought you might not realize how often it’s coming up.”
The problem, though, is that he’s doing this with everyone and because you don’t have an established relationship with him because you're new, you risk standing out as the one unfriendly person on the team who’s shutting him down. Are you willing to take that risk? That’s something you’d want to decide before you tackle this. You might decide that if he’s unprofessional enough to hold that against you, he’s not a manager you want to be working with anyway – but this is a decision you want to make ahead of time so that you’re not caught off-guard afterwards by negative repercussions.
One last option: If you have a good rapport with someone above your manager, you could consider talking discreetly with them about the problem. But you'd want this to be someone you trust to handle it sensitively, not just report to your boss that you complained about them.