Chill Bosses Never Win: 3 Leadership Lessons from Rippling's COO Matt MacInnis

Chill bosses never win.

I know that's not a popular opinion. We're in an era that celebrates "laid-back leadership" and "psychological safety" and "bringing your whole self to work." And those things matter. But somewhere along the way, we confused being humane with being soft.

Matt MacInnis, our COO and CPO at Rippling, doesn't make that mistake.

I recently listened to him on a podcast, and it crystallised something I've believed for a long time but hadn't quite found the words for: the best leaders aren't chill. They're intense, demanding, and deeply invested in their people's growth. And that combination, not in spite of the intensity, but because of it, is what builds exceptional teams.

Here are three lessons that stuck with me.

1. "Be intense. Be good. Be respectful. But do not be chill."

This is the standard at Rippling. And it's a deliberate choice.

Chill sounds nice. Chill sounds like a place where people aren't stressed, where the vibes are good, where everyone gets along. But here's what chill actually means in practice: accepting sub-par standards. Letting things slide. Choosing comfort over excellence.

Chill is the enemy of great.

Being intense doesn't mean being a tyrant. It doesn't mean shouting or belittling or creating fear. It means caring deeply. It means having high standards and holding people to them. It means not accepting "good enough" when great is possible.

You can be intense and kind. You can be demanding and supportive. You can push people hard and still have their backs.

What you can't do is be chill and build something exceptional. Pick one.

2. Withholding feedback is selfish

This one hits hard because it reframes something we often dress up as kindness.

We tell ourselves we're being nice when we don't give someone tough feedback. We're protecting their feelings. We're keeping the peace. We're being a "good" manager.

But here's the truth: when you withhold feedback, you're not protecting them. You're protecting yourself.

You're prioritising your own comfort, avoiding an awkward conversation, dodging potential conflict, not wanting to be the bad guy,over what your people actually need to hear to grow.

That's not kind. That's selfish.

The kindest thing you can do for someone on your team is tell them the truth. Tell them where they're falling short. Tell them what great looks like. Give them the chance to close the gap.

Yes, it's uncomfortable. Yes, they might not like it in the moment. But a year from now, five years from now, they'll thank you for caring enough to be honest.

The managers who changed my career weren't the ones who made me feel comfortable. They were the ones who made me better.

3. Success teaches more than failure

We're obsessed with failure in business culture. Fail fast. Embrace failure. Learn from your mistakes.

And yes, failure teaches you things. But Matt made a point that I think gets overlooked: you learn more watching excellence than dissecting disasters.

When something fails, you learn what not to do. But when something succeeds you learn what right looks like. You see the standard and you understand what's possible.

Study the wins. Study the people who are operating at a level above you. Figure out what they're doing differently. That's where the real lessons are.

"Good teams get tired, and that's when great teams kick the good team's asses."

This is the line that stuck with me most.

Everyone starts strong. Everyone's motivated at the beginning of a project, a quarter, a year. The difference between good teams and great teams isn't how they perform when they're fresh, it's how they perform when they're exhausted.

Good teams fade. Great teams find another gear.

That's not about working longer hours or grinding people into dust. It's about building a culture where intensity is sustainable. Where people are so invested in what they're building that they dig deeper when it gets hard.

You can't manufacture that. You can't mandate it. You can only create the conditions for it by being the kind of leader who's intense, who gives honest feedback, who celebrates excellence, and who never, ever settles for chill.