When You Start Leading the People You Used to Work Beside: Managing the Awkward, the Hard, and the Hurt.

One minute you’re grabbing coffee and talking about weekend plans with your work bestie. The next? You’re sitting in a meeting… and she’s giving you the cold shoulder over your new workflow plan.

Welcome to one of the most emotionally charged and under-talked-about career realities out there: becoming the leader of your friends.

I’ve been there. And out of all the tough things I’ve had to navigate as a leader, this one hit the hardest. Not because it was the most complicated—but because it was the most personal. Let me tell you: it’s not all high fives and “so proud of you” messages. Sometimes it’s the silent treatment. The shift in tone. The moment you realize your old lunch crew is now going without you. I’ve watched others go through it too, and it never seems easy. Looking back, I can see that all of us—me included—had unspoken expectations about how our work relationships would evolve. But those expectations weren’t aligned. And they definitely weren’t realistic.

Not everyone is going to tell you that leadership can feel lonely. But it can feel especially isolating when the very people who used to have your back suddenly see you as “them” instead of “us.”

At First, It Feels Fine… Until It Doesn’t

When you first step into a leadership role, especially if you were promoted from within, your friends at work might be thrilled for you. Genuinely happy. Supportive. Celebrating.

But then the dynamic shifts.

You have to make a decision they don’t like. You have to hold the line. You start seeing things from a bird’s-eye view they’re not privy to. And suddenly, you’re not “one of us” anymore.

You’re the boss. You’re the one who’s changed.

Except… you didn’t. You grew. You stepped up. You said yes to responsibility. But let’s not pretend that doesn’t cost you something. Because it does.

Leadership looks different now. Sometimes it means sitting at the table alone—and owning your seat anyway.

The Emotional Whiplash Is Real

What no one prepares you for is the emotional toll of leadership when friendships get tangled in the mix.

You’ll question yourself: Did I make the right call? Did I explain it well enough? Was I too cold? Too direct?
You’ll take things personally, even when you know you shouldn’t.
You’ll feel guilt for enforcing standards or giving tough feedback.
And when people take things personally, and act hurt or distant, it stings. Deeply.

I’ve felt personally attacked for doing my job. I’ve cried over decisions that were necessary but hard. I’ve been frozen out for putting the whole of a team and program ahead of one person. I’ve been both the respected leader and the misunderstood “bad guy”—sometimes on the same day.

It’s also true that not every friendship falls apart. Some people do get it. They understand the shift, respect your new role, and continue to root for you even when they don’t agree with every decision. I’ve had the privilege of leading people who remained true friends—people who saw me as a whole person, not just a position. Those relationships still mean the world to me. So no, it’s not always doomed. But when it does go sideways, it’s the emotional punch you didn’t see coming that makes it so hard.

Can You Be Both Boss and Friend?

Let’s be honest: it’s tricky.

Yes, you can still care deeply about the people you lead. You can still be warm, approachable, compassionate. But the friendship can’t function the way it used to.

Because leadership isn’t about making everyone happy. It’s about being in service of something bigger: the mission, the team, the clients, the vision. And sometimes that means making hard calls that disappoint people you care about.

So no—you can’t always have it both ways. Not if the friendship depends on you never having a say on how they show up at work, their performance, behaviour and role. Not if it relies on you saying yes, being agreeable, or putting the friendship before the work.

But what you can have is integrity. Clarity. Respect. And yes—genuine connection. Just a more evolved version of it.

So What Do You Do?

You lead. With heart. With honesty. With boundaries.

You normalize that yes, it might feel awkward.
You name it if it so that it makes sense to you and others.

What does it mean to name it?
It means you don’t pretend everything’s the same when it’s clearly not.
It means you step into the discomfort with honesty and humility, rather than avoiding it and letting tension quietly build.

Here’s how you can do that:

Acknowledge the shift
Whether it’s in a one-on-one or a team setting, you can gently call out that things have changed:
"I know the dynamic between us looks a little different now. I’m aware of it, and I care about how we move forward together."

Connect with shared values
Remind your team (and yourself) that you're still in it together, just in different roles:
"I’m here to support the team, and that hasn’t changed. What’s shifted is my responsibility to make decisions that serve the bigger picture—even when they’re hard."

Invite open dialogue
Sometimes just giving permission to talk about it can ease the tension:
"If any of this feels weird or tricky for you, I’m open to talking it through. I want to lead in a way that’s and open and respectful."

Set new expectations
If you're sensing confusion or resentment, it’s okay to clarify your changed roles:
"I value our past connection, and I still care deeply about working well together. But my role now means I have to look through a wider lens. That might feel different, and I want to be upfront about that."

Naming it doesn’t mean over-explaining or apologizing for being in charge. Your investment in yourself to step into leadership is something to celebrate - not apologize for.
But naming it, calling it out can just mean making space for honesty—before assumptions and unspoken resentment take root.
Stay grounded in your values and the reason you stepped into leadership in the first place. Don’t twist yourself into a pretzel to keep everyone comfortable.
And when things get tense or you feel hurt—because you will—get support. Remind yourself that having feelings doesn’t mean failing.

Final Truth?

Sometimes you outgrow relationships when you grow into your leadership and your career.
Sometimes people project their own stuff onto your success. Be aware of that, but don’t take it on - not your problem.
Sometimes leadership costs you closeness—but it earns you clarity.

You’re not here to play small in order to stay liked.
You’re here to blaze trails. To lead well. And to keep your heart intact while doing it.