Ask a Manager: Old work drinking buddy now new boss

[minoanmiss]

My new boss is someone I used to drink on the job with

At a previous job, when I was young and dumb, I joined in with two other “rebel” coworkers, Rachel and Monica, to drink on the job. Daily. Usually meeting at one of our cars in the parking lot as we laughed and disparaged the company. Completely unprofessional and stupid. I left that job and eventually so did the other two.

So now, 10 years later, I have a great job at a great company that just hired a new manager for my team and it is … Monica! *cringe*

Do I say anything to her? Part of me wants to get out in front of this and say I don’t do stupid things like that anymore! Is she going to assume I’m a bad employee? Is she going to be awkward around me? Is she going to get rid of me fearing I may tell stories that undermine her? Or do I pretend it never happened unless she brings it up? Just hope she has forgotten? We are not and have never been friends.

It was 10 years ago — she’s probably (hopefully!) changed a lot in that time and will realize you might have too. And after all, she was part of it along with you! So at least as an initial approach, I’d leave the topic alone, don’t mention it, and focus on demonstrating through your conduct now that you’re not the person you were then.

If you get the sense that it’s going to be A Problem, you might need to address it more directly — and either way, if you want to say something, you could say in private at some point, “I’m a little embarrassed of what you know of me from 10 years ago and want to assure you I have a very different approach to work now” — but start by acting as if of course neither of you are those people anymore and see how things go.

Comments

[minoanmiss]

Oh my God if I were LW I would be scared shitless. People in the comments were quite reassuring but I honestly don't see any reason Monica won't fire LW tomorrow to keep her secret.

[angelofthenorth]

I would be thinking that if there's a nice HR person, having a quiet chat with them might be an idea, so if she does try to sack LW, HR have a heads up.

[mirlacca]

I wouldn't mention it. LW is assuming that she's grown up over the past ten years, but Monica hasn't? Let it go. If Monica says something, she could always say, "Oh, I quit doing that years ago." And leave it at that.