The Cool Boss Trap: Why Being Liked Might Be Killing Your Team

Let’s talk about the trap of trying to be the cool boss.
I’ve been there. I’ve slid right down that hill wanting to be fun, approachable, super flexible — and let me tell you, it doesn’t do you or your team any favors.

It ends up eating your time, draining your energy, and costing way more money than you realize. And ironically, it doesn’t even create the awesome, high-performing team you’re hoping for.

The Pendulum Problem

Here’s what typically happens (in big companies, small teams, every industry — I’ve seen it across the board):

You start out wanting to build a great culture. You want to be approachable, fun, someone your team actually likes. Maybe you even want that story for your next LinkedIn post:

“This person messed up, but I still believed in them, and now look how amazing things turned out.”

Or the TED Talk opener, right?

But then performance starts to slip. Accountability fades. You catch yourself thinking:

Maybe it’s me. Maybe I’m not being the leader I should be.

You crack open another leadership book. You remember how well this person interviewed, how great they were when you first hired them. You start second-guessing.

And because performance is slipping, your trust starts slipping — not just in them, but in yourself. So what happens next? You overcorrect. You swing hard the other way:

• More rules.

• More structure.

• More micromanaging.

• Or you stop delegating altogether because it feels safer to do it yourself.

This constant swing is exhausting. It’s expensive. And it absolutely crushes momentum.

So How Do You Avoid the Cool Boss Trap?

If you know me, you know I love keeping things super simple and actionable.

The first place to look?
👉 Set clear expectations.

That’s it. Not fancy. Not groundbreaking. But it’s the single biggest thing that keeps you from bouncing between being everyone’s buddy and becoming the resentful micro-manager.

And yes — you can still be friends with your team.
When I check in with my VA, we spend half the time talking about her farm animals. My husband’s managed teams where we’ve gone to concerts and birthday parties with the people he leads.
It works because expectations are clear.

If you skip that?

• Performance dips.

• You avoid tough conversations.

• Trust evaporates — in them, and in yourself.

But when expectations are defined, it becomes so much easier to handle missed KPIs or project hiccups. You can say:

“Hey, we talked about getting this done by [date]. Looks like that didn’t happen — help me understand what’s going on.”

You can be direct and kind, without feeling like a jerk.

It also stops you from overcompensating for people who aren’t right for the role. You rebuild trust in your hiring and leadership instincts, instead of always doubting yourself.

Put It Into Practice

Want to break free of the cool boss trap? Here’s your simple gut check:

✅ Ask: Does my team know exactly what success looks like right now?
✅ Spot: Where might you be avoiding tough conversations or letting things slide?
✅ Reset: Pick one area to clarify expectations this week. Keep it direct and simple.
✅ Use it: Let that clarity guide kinder, easier accountability talks.

Want more practical team + leadership strategies?
Shoot me a message on LinkedIn or email info@auxosvs.com — I’d love to answer your question in an upcoming episode or blog.