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Fail Forward: Why Smart Leaders Celebrate Mistakes

Mentorship moments, scientific insight, and team culture

Jason Dyer

Thought Leadership

Article

Team reflecting during a meeting

A young person I mentor recently asked me what makes someone a strong manager. My answer was simple: good managers make room for mistakes. They expect them. They build the culture around learning—not punishment—so their teams can try, adapt, and grow.

I remember learning this the hard way myself.

Early in my career at Leo Burnett, I was working on the McDonald's Happy Meal business. During a review meeting with the creative team, I was asked for my thoughts. Being young, I gave my personal opinion on each idea—what I liked, what I didn't. The account lead stopped me midstream and said, pointedly: "We're not here for your personal preferences. We're here for strategic alignment." It was a blunt correction, but it was necessary. I learned that my role wasn't to speak as myself, but as the voice of our target customer, grounded in the brief we developed. That mindset shift stuck. And today, I still coach clients to evaluate work based not on what they prefer, but on what will resonate with the people they serve.

This is what failing forward looks like. Not just making mistakes, but learning from them, sharing those lessons, and using them to get better.

After all, trial and error is the engine of progress. The scientific method is built on it. So is innovation. Test, learn, iterate. It's how startups pivot. It's how teams evolve. It's how great leaders build companies that last.

But learning from failure isn't just an individual practice—it's a cultural one. Teams grow faster when they can talk openly about what didn't work. Great managers set that tone: no shame, no blame, just shared insight. That kind of culture turns isolated missteps into collective momentum.

James Joyce once wrote, "A man's errors are his portals of discovery."

That holds true for teams as well. If you create a space where people can learn out loud—without fear—you accelerate the learning process.

So this week, whether you're leading a team or starting something new, remember: the fastest way forward isn't to avoid every mistake. It's to make the right ones and learn from them together.