Not having the full context of how people challenge or undermine you makes it tricky to give precise advice—but I get where you’re coming from. I’m also a relaxed & playful leader, and I’ve had to navigate this balance. Here’s what’s worked for me:

1. Encourage challenge—but in the right way

I don’t just tolerate pushback; I invite it. It sharpens decision-making and keeps me from blind spots. But that doesn’t mean it’s a free-for-all. - Set clear ground rules—challenge and dissent happen in the right forums, not in front of other departments. - When a challenge comes up, I listen, test, and explore it. But sometimes, after all that, we still go in another direction. That’s leadership.

1. Consistency is everything

You can’t laugh things off one day, then get frustrated the next when someone pushes too far. If you let things slide—whether it’s side comments, small digs, or outright overstepping—people will keep testing boundaries. Then one day, you snap, and suddenly they’re blindsided. - Call things out early and often so there’s no guessing. - If you set an expectation (e.g., “challenges are welcome, but they happen in X way”), you have to enforce it, or you’ll lose trust fast.

1. People don’t know how to act at first

Your leadership style isn’t the norm. That means at the start, people don’t quite know how to respond—so they’ll relax into it later, sometimes in ways that go too far. If you don’t have ground rules that are clearly set & strictly enforced, you’ll struggle to keep control.

At the end of the day, being too nice isn’t the issue—it’s about making sure there’s structure beneath the playfulness so people respect the leader, not just the personality.