You know that skeptic in the meeting—the one who seems to poke holes in every new idea just when you’re trying to build momentum?
Don’t roll your eyes. That person might just be the most valuable voice in the room.
Over the years, I’ve noticed a pattern across teams and leaders: the folks who push back the hardest, ask the most pointed questions, and seem slow to jump on board? More often than not, they’re not doing it to be difficult.
They’re doing it because they care.
This really clicked for me while working with a leader who took time warming up to my process. He questioned everything. Dug into the details. Wanted to be part of every step.
It would’ve been easy to write him off as resistant. But his skepticism wasn’t about control or ego or obstruction. It was about investment.
Skeptics are skeptics because they care.
I’ve seen this play out time and time again, from strategic plans to leadership programs to culture development.
They’re not challenging ideas just to stir the pot. They’re pushing because they’re deeply committed to getting it right. They see the risks. They want it to work. And they care enough to say so.
It’s not always comfortable. It’s not always efficient. But it’s incredibly useful.
In my work—especially in facilitation and team coaching—I’ve learned not to quiet the skeptics, but to invite them in. Their questions sharpen our thinking. Their doubts reveal blind spots. Their concerns help us build something stronger.
The trick is knowing the difference between a skeptic and a cynic:
A skeptic asks hard questions because they want it to succeed.
A cynic asks hard questions because they’ve already decided it won’t.
So I make space for the skeptics. I ask what they’re seeing that others might not be. I involve them in building the solution.
Because when someone is brave enough to voice concern, it usually means they care enough to help make it better.
The next time you encounter a skeptic on your team, remember: that voice isn’t an obstacle to progress.
That voice might just be the one that helps your idea fly.
What skeptical voice in your organization might be worth a second listen?
Looking to increase the cohesion, trust, and impact of your leadership team? Reach out and let’s discuss The Compass Team Experience and how I can help.
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