How to Spot Cynicism and Protect What You’re Building

We've all done it (I’ve made the mistake more than once).

We hire someone who looks perfect on paper — sharp, experienced, maybe even a little scarred. The kind of person who's weathered some storms and lived to tell the tale. And at the time, it feels like a good thing. We tell ourselves that's exactly what our company needs: Someone seasoned. Someone who won't get starry-eyed at the next shiny object. Someone who knows how hard this can be.

And then, a few months in, we realize that's exactly the problem. They have seen it all. And they no longer believe in anything new.

They may walk in with experience, but it comes wrapped in layers of distrust and doubt. They've been burned, and now they're on the lookout for smoke. It might look like wisdom, but it's really just wariness. And over time, that cynicism seeps into the culture you’re trying to build.

So let’s talk about why we’re drawn to cynics in the first place, why they rarely deliver what we hoped for, and how to tell the difference between someone who’s ready to build alongside you and someone who will hold you back.

Why We're Drawn to Cynics

Let’s start with empathy (because most cynics didn’t start out that way).

They were probably like many of us in the beginning: hopeful, ambitious, genuinely eager to do meaningful work. But somewhere along the way, something broke their belief. Maybe it was a bad boss, a culture that promised more than it delivered, or just the constant churn of change with no real growth.

So, they did what many smart people do when they get hurt — they armored up.

From the outside, that armor can look like maturity or experience. They’ve got stories, they speak with confidence, and they don’t get overly excited. They come off as grounded, rational, maybe even wise. But spend a little time with them, and it becomes clear that they’re not grounded. They’re detached.

In reality, cynics don’t trust leaders because they’ve seen too many fall short. They don’t believe in your vision because they’ve seen too many collapse under pressure. They nod in meetings, but you can sense that they’re looking for what could go wrong instead of what could go right.

And here's where we need to step in. Because cynicism often looks like competence, but what you’re actually getting is someone who’s pulled back. Not because they’re assessing risk, but because they’ve stopped believing change is worth the effort. And when that mindset enters your company, it doesn’t just stall progress. It reshapes the culture around it.

The Cultural Cost

Here’s the hard truth: Once cynicism finds a way into your company, it starts changing how everyone shows up.

It’s never just the cynic it affects. The distrust and doubt they bring in spreads. Your people start holding back, say less in meetings, and stop offering bold ideas because they don’t want to look naive. So they stay quiet. And before you know it, optimism becomes something to be embarrassed about.

Over time, the entire team gets more cautious. People do what’s required, but not much more. They’re still competent, but they’re not engaged (and they’re definitely not going the extra mile) because they stop believing their effort will make a difference.

And once it sets in, it’s hard to reverse. A cynical team isn’t just hard to lead. It’s impossible to scale.

You can’t build a resilient, high-performing company without people who believe in what they’re doing. And when belief goes missing, everything else gets harder — execution, progress, growth.

Cynicism will slow you down. It doesn’t stay with just one person. It spreads to everyone around them and changes the culture in ways that are hard to see until it’s already happened.

Cynicism masquerades as wisdom, but it is the farthest thing from it.

Stephen Colbert

5 Ways to Protect Your Company

Cynics interview well. Why? Because they sound grounded and experienced, like they’ve seen enough to know what matters. And we think, “Finally, someone who gets it.”

But they carry their experiences like evidence that nothing good lasts, and they’re just waiting to be proven right. So how do you protect your company? How do you make sure you’re not bringing in the wrong people?

Here are a few ways I believe you can protect your company from cynicism:

1. Ask better questions: The right people, the ones who’ve grown and still hold onto belief, talk about what they’ve learned, not just what went wrong. They own their part, they reflect, and they move forward. Cynics stay stuck in the story. So dig deep by asking questions like: What did you take away from that failure? What would you do differently now? Keep in mind, you’re not just looking for experience. You’re looking for perspective.
2. Hire for humility and growth: We’ve all been wrong before, and we’ve all been hurt. What matters is how we handle it in the moment and how we choose to move forward afterward. So in interviews with candidates, ask: When’s the last time you changed your mind? When and how did you rebuild trust after it was broken? If they can’t name an example, or they dodge the question, it’s a sign they haven’t moved on. You’re not looking for perfect, but you are looking for someone who’s open and self-aware.
3. Look for realistic optimism: You want people who still believe things can get better because they’ve seen it happen. They know what dysfunction looks like, but they haven’t given up. They’ve worked through hard things and still want to build. That’s not naive — that’s earned belief. Cynics can’t see that because they’ve already decided it’s not worth the effort.
4. Stay consistent: People who’ve been let down before aren’t listening to what you say —they’re watching what you do. If you’re clear one day and vague the next, they notice. If you talk about culture but tolerate the wrong behavior, they notice. Over time, every little inconsistency adds up. And if you want people to really buy in, they need to trust that what you say actually sticks.
5. Call it out early: You can’t just ignore it and hope for the best when someone checks out. The sarcasm, the passive-aggressive comments, the resistance — it’s contagious. When you see it, say something. Directly, respectfully, and without dancing around it. Some people can re-engage. Others can’t. But either way, you’re responsible for protecting the culture you’re trying to build.

Remember, every person you bring in, especially your senior leaders, shapes what your company becomes. So choose people who still believe. Who genuinely are excited not just about what you're building but about rolling up their proverbial sleeves and partnering with you. Who’ve been through the hard parts and are still willing to lean in and run with you. That’s how you build a collection of teams that work great together.

Choosing Belief

Let’s not pretend founders are immune to cynicism. We’ve been burned too. Co-founders have backed out. Investors have ghosted us. Launches have flopped. We know betrayal, exhaustion, and disappointment.

And yet, we choose to build anyway.

That’s the heart of it. Not that we haven’t been hurt, but that we still believe it’s worth doing. That belief is what allows us to keep moving forward when things get hard. It’s what helps us stay focused, make decisions, and keep building even when the setbacks pile up.

So yes, hire the scarred. They’ve learned from the hard stuff and come out stronger. But steer clear of the cynical. They’re not building anything — they’re bracing for disappointment. And that’s not the mindset that helps you build a great company.

You can only build something enduring with people who still believe it’s possible. Who show up with hope and run alongside you with pleasure, not because it’s easy, but because they’ve decided it matters. That willingness to keep going, to stay open, to keep trying — that’s who you want running beside you. That’s who helps you build the future that you envision. Those are the kinds of colleagues you need to have if you're going to have any fighting chance of turning your vision into reality.