If you follow leadership advice at all, you’ve heard the same encouragement by now: Don’t shy away from failure; squeeze every drop of learning out of it. Plenty of books preach the power of iteration, how to fail better, and even how to chase failure outright. But few tell you what to do once you’ve caught it.
The courage to fail gets you “in the room where it happens” or where problem-solving, iteration, and innovation take place. How you handle setbacks with your people is what sets you apart.
I’ve watched the Global Leadership Summit (GLS) for several years now, and every year I look at the speaker lineup before I look at anything else. One of this year’s speakers is Ryan Leak, and among his core ideas is that you can’t grow by protecting yourself from failure.
He regularly tells audiences to chase failure instead of avoiding it, to take the risk before they feel ready, and to treat failed attempts as part of the process rather than as proof they should stop. It’s a great message and one that I can relate to for personal reasons.
In this space, I’ve told my story about leadership at Prologis, so I won’t retell it in detail here. The short version is that I accepted the board’s invitation to fill the role of CEO during the 2008 financial crisis, and I didn’t have the luxury of feeling ready.
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I had to make decisions without knowing whether they’d work, and I had to say, “I don’t know” out loud to people who needed me to have answers. I was living Ryan’s message in real time. Growth doesn’t begin when you avoid “I don’t know” moments. It begins when you stop protecting yourself from failure.
I’ve always been comfortable with numbers, and during that crisis, I learned that competence with data would only get me to a certain point. I had to become more transparent and more visible—a more accessible leader. That meant getting comfortable with vulnerability in front of people. You don’t level up by collecting more authority. You level up by becoming more trustworthy.
That’s the difference between chasing failure and surviving it well. It’s tempting to treat resilience as a solo sport—yours to survive and explain later. But I stood in a room full of people who shared my concerns and skepticism, and the numbers alone weren’t going to win them over. Trust would.
Courage gets you in the room when you have to face the results. What gets you beyond the room is whom you choose to be once you’re there—slower to speak and quicker to listen. If Ryan’s talk at GLS this year gets you thinking about your own version of failure and the culture that supports it, I hope you’ll ask yourself this question and sit with the answer: “How will I show up for the courageous people facing setbacks with me?”
