You now manage your peer. Awkward.

A friend Slacked me this conundrum after a re-org — managing a former peer. I laugh-cried because it’s one of the awkward situations that so many of us go through, and still tricky no matter how seasoned you are. So I hope this edition resonates with my fellow managers, soon-to-be managers, or peer-turned-direct-reports.

The Situation

We recently had a re-org and I now manage a larger team. It is generally a good move, but one of my new direct reports is someone I used to be peers with. We’re friendly. We’ve vented about our old manager together. He knows what I make. He’s very smart and a solid performer so I’m sure he feels slighted by this change. It’s all weird. How should I approach this?

My Take

Ah the awkward yet flattering milestone of managing a former peer.

This transition is genuinely awkward, and if you didn’t feel a pang of discomfort, I would be worried you were a monster. It means you’re taking the relationship seriously and you’re empathetic! Take the points where you can get them.

Here’s the thing: the dynamic has to change. The longer you delay resetting it, the worse it gets. The good news? You can do this without blowing up the friendship (and maybe even strengthening it?), but it takes some intentional moves upfront.

1️⃣ Have a conversation early (like, now)

Don’t let the weirdness linger. Have a direct, honest conversation — not a big dramatic “things are different now” speech, but a clear acknowledgment. I personally like to lead with positive intent and not making any assumptions about how they are feeling.

“I value our relationship and I want to be intentional about how we navigate this transition together. Let’s talk about how things might shift.”

Name the new dynamic out loud. It makes it less weird, not more. Share your intentions — you don’t want to micromanage, you want to maintain open lines of communication, and you value their perspective.