Your Employees Should Challenge You

The Leadership Lie No One Wants to Admit

Here’s a hard truth no one wants to say out loud: most leaders don’t want to be challenged. They say they do—“My door’s always open!”—but what they really mean is, “Come in, agree with me, and leave.” But great leadership isn’t about collecting a team of yes-men and patting yourself on the back for how “collaborative” you are.

It’s about building a team that will call you out, ask tough questions, and push you to think harder. Leadership isn’t just about guiding others—it’s about being willing to get uncomfortable, to let your employees hold up the mirror and show you where you’re falling short. Because here’s the thing: if your team isn’t challenging you, they’re not just letting you down—you’re letting them down, too.

The Ego Trap of Leadership

Leadership is a breeding ground for ego. Titles, corner offices, and LinkedIn kudos can lull you into thinking you’ve got it all figured out. But the second you believe you’re the smartest person in the room, you’ve lost.

Great leaders know their job isn’t to have all the answers—it’s to create a space where the best ideas rise to the surface. And spoiler alert: those ideas won’t always come from you. Sometimes, they’ll come from the junior analyst who points out the flaw in your grand plan. Or the team member who’s gutsy enough to say, “I think we can do better.”

The question is, do you have the humility to listen? Or does your ego slam the door on the conversation before it starts?

Why Pushback is a Gift

When your employees challenge you, it’s not a sign of disrespect—it’s a sign of trust. It means they care enough to speak up, even if it’s uncomfortable. And isn’t that what you want? A team that’s invested enough to question the status quo, to push for better, to demand more?

Pushback forces you to confront your blind spots, question your assumptions, and refine your ideas. It’s not just good for you—it’s good for your business. Because the best solutions don’t come from one person dictating from on high. They come from the messy, collaborative process of testing, questioning, and iterating.

The Silent Team is the Real Red Flag

Here’s the thing: if no one on your team is challenging you, it’s not because you’re always right. It’s because they don’t feel safe. Silence in the workplace isn’t a sign of harmony—it’s a warning sign.

Maybe your team is afraid of retribution. Maybe they’ve seen others shut down for speaking up. Or maybe they’ve just decided it’s not worth the effort to fight against your immovable opinions. Whatever the reason, a silent team isn’t a strong team. It’s a disengaged, disempowered group of people just waiting for the clock to hit 5.

How to Encourage Pushback Without Losing Control

If you want your employees to challenge you—and trust me, you do—it starts with creating an environment where they feel safe to do so. Here’s how:

1. Check your ego. You’re not infallible, and your team knows it. Stop pretending otherwise.
2. Model vulnerability. Admit when you’re wrong. Share what you’re learning. Show that you’re open to growth.
3. Ask better questions. Instead of saying, “Does everyone agree?” try, “What am I missing?” or “Where could this go wrong?”
4. Celebrate dissent. When someone challenges you, thank them. Even if it stings. Especially if it stings.
5. Follow through. If someone raises a valid concern, act on it. Nothing kills trust faster than asking for feedback and ignoring it.

Leadership Isn’t About Being Comfortable

Great leadership isn’t a spa day. It’s a gauntlet. It’s about being willing to hear what you don’t want to hear, to question what you thought you knew, and to grow in ways you didn’t think you needed to.

If your direct reports aren’t challenging you, it’s not because you’re perfect—it’s because they don’t feel they can. Fix that. Build a team that will push you, question you, and make you better. Because when your team challenges you, it’s not a threat to your authority. It’s a gift.

Leadership isn’t about having all the answers. It’s about creating a space where the best ideas can thrive—even if they weren’t yours to begin with. So, embrace the discomfort. Invite the challenge. And remember: the strongest leaders aren’t the ones who demand silence—they’re the ones who demand better.