Hi! long time listener, first time caller.

I’m going to be transitioning into a management role on my current team, and was wondering what advice you have for managing people who were once your peers. Particularly if some of those people have had a longer working career than you. I expect there to be some discomfort, but I want to minimize the awkwardness and show support as much as possible!

Hello caller. First, congrats on the promotion!

Emma: This is great and huge and we’re so excited for you. Go out and buy yourself a new pair of boots to celebrate.

Andy: Manager boots!

Emma: We both completely understand why you’re a little intimidated by the transition from teammate to manager. I myself have been absolutely flattened by the pressure to perform for the friends I started managing — not to mention the people I didn’t get along with. “Sunday scaries” were never a thing until I started managing my peers.

Andy: There are a lot of feelings swirling around, and right now, you feel like everyone’s focal point — your team members who are excited you got the job; the people who were rooting for someone else; the people who wanted the role and didn’t get it; the people who are skeptical of your authority, experience, style, vision for the future.

You’d have to be a Teflon robot not to internalize some of that energy. I have to very consciously remind myself: I was the one they picked for the job. This means that, regardless of years in service or other qualifications, I belong in this role and I am ready for it.

Emma: I don’t love the idea of you tip-toeing around or pandering to the people who have a longer tenure or more experience. It’s counter-productive. We discussed this in one of our earliest issues of The Bent: Your job as a manager isn’t to outperform your best people — it’s to make it so your best people can be even better. Set your sights on that future and you’re going to ride out any initial discomfort just fine.

Andy: Yes, this kind of general, presumed discomfort isn’t something I recommend trying to solve head-on. You can hear how cringey that moment could be: “I know you have many more years experience in the field, and I appreciate that I’m super green. It can be scary that I have no clue what I’m doing. Right?” Even the best rendition of this conversation doesn’t breed hope.

The Good Boss Scorecard is my go-to when I want to win trust and show my team that they can believe in me. I show up consistently, doing what I say I’m going to do.

Emma: Save your gently confrontational conversations for the things that are concrete and that you can actually have a point of view on. A great example is removing obstacles — a core component of the Good Boss Scorecard. Since you’re upleveling within your own team, you’re already deeply familiar with the issues you’re facing — you’ve heard the raw, unfiltered frustrations of your teammates, and you’ve experienced your own. But when you are the boss, you also sometimes gain perspective about why things are so hard to change, or what limitations you have for changing them. I like to be really honest with how fast I can solve these problems.

If I could snap my fingers and change this immediately, I would. The reality is that there’s one annual budget review. If we don’t carve out the budget during that time, we don’t have the budget. So, our next shot is in June. It’s still months away, but it’s also the fastest we can get it.

Andy: Love it. That statement does so much: affirms the want, provides context, sets expectations. The same formula works for managing my good buddies. I like to put it all out there in our first 1-on-1:

We’re friends. And now, I’m also your manager. I’m new to this and I’m going to do my best. I can predict that there will be times when I have to do things as your manager that I wouldn’t do as simply your friend — talk about your performance, not tell you about some news that I get a few weeks advance on. I’ll do my best. What questions do you have?

Emma: Generally, friendships between bosses and reports can thrive when there’s mutual respect — of the work, of each other’s boundaries, of the insights and advice you provide each other. We got a message on Instagram after last week’s newsletter from a reader who said she was “besties with her manager,” who she “respected the hell out of” and who’s her “constant champion.” Amazing!

I think it’s a much taller order to stay friends with someone whose performance or behavior at work is not great. I’ve never pulled it off.

Andy: Yeah, maybe now as the boss, something that was charming or just fine about your friend is part of your job to manage. They were always late or goofing off — fun as a friend, maybe. Not so fun as a manager. Straight talk helps here, too:

You’ve been late to the last three staff meetings. What’s up with that?

Emma: Some of your friendships will not survive this transition. Usually the new manager comes across as the villain of this story — the one ditching her true pals to chase empty corporate glory. This is not reality. She’s just trying to find and follow her path.

Andy: It’s just true that the shifts in the workplace may cause shifts in your relationships. My aim in any role I take on is to be a human being in it. To that end, I’ve gotten much better at being honest and direct about where the two relationships overlap:

I have some pretty crappy news. As your friend, I wish I could change it. And as your manager, it’s my job to deliver it.

If your friend/report is mature enough to understand that your relationship can be two things at the same time, then you have room to continue to grow the relationship in this new world.

Emma: Managing is hard and scary. You’re going to grow a lot, and that takes support. If your friend/reports can provide that support, I believe you’ll remain friends. If they don’t, and you can find it in your boss or your co-managers or the CEO of your company, well then…

Andy: Unless you are both growing in the same direction at similar enough paces, you may grow apart. Shout out to my best friend in middle school who wanted to walk around during lunch just talking while I was still adamant on working up a pretty intense brow sweat at the wall ball courts. We weren’t the same anymore. So, on we went in two different directions. That’s healthy and natural, and it’s best to authentically go after what you want, rather than trying to keep a relationship alive like the DNA in the amber-trapped Jurassic Park mosquito.

Emma: Send us a note in a month or two, caller. We definitely want to hear how it’s going!

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