There’s a saying that often floats around in entrepreneurial circles: “Fail fast, fail often.” While the origins of this phrase are up for debate, its lesson is clear. Failure isn’t just an inevitable part of leadership. It’s one of the most defining. How a leader reacts to failure (their own or their team’s) can reveal their true character and shape the trajectory of their future success.
But here’s the thing: writing about failure and leadership can quickly sound like a series of cliches. We’ve all heard the platitudes about “learning from mistakes” and “rising stronger.” But there’s a deeper message about what truly separates those who lead with integrity and vision from those who crumble when things go wrong.
When failure strikes, leaders face a choice. They can own it, adapt, and come back stronger. Or they can point fingers, wallow in resentment, and stall out. The decision often happens in an instant, but its impact can last a lifetime.
Great leaders take ownership of failure, even when it’s not entirely their fault. Why? Because owning failure builds trust. When a leader says, “This didn’t go as planned, let’s discuss what we’ll do to fix it,” they inspire confidence. They create a culture where the team feels safe to take risks, knowing that mistakes are part of growth, not reasons for punishment.
When leaders blame others, they erode trust. Pointing fingers, whether at the team, external circumstances, or bad luck, signals an unwillingness to reflect and adapt. Over time, this creates a toxic environment where innovation dies and progress stalls.
“Fail fast, fail often” isn’t about being reckless. It’s about embracing experimentation and accepting that not every idea will succeed. Failing quickly means you can pivot sooner, learn faster, and ultimately get to a better solution.
This idea requires two things:
Humility: The willingness to admit when something isn’t working.
Agility: The ability to adapt and try again without becoming paralyzed by setbacks.
Elon Musk is a great example. From continual iterations of experimentation and failure at SpaceX—including multiple RUDs (rapid unscheduled disassembly in rocket speak)—to the challenges Tesla faced in scaling production and support, he’s built companies on the idea of learning through failure. Musk doesn’t see failure as an end point. He sees it as feedback. A necessary step on the path to success.
To handle failure effectively, leaders need more than optimism. They need a process. Here’s a simple approach that works (notice I didn’t say it’s an easy approach):
-Recognize the failure and what it means. Be transparent with your team.
-Reflect on what went wrong without assigning blame. Focus on systems and strategies, not personal shortcomings.
-Identify key takeaways. What worked? What didn’t? What’s worth trying again?
-Adjust your approach based on lessons learned.
-Recommit to the goal with a renewed focus and determination.
Failure doesn’t only teach leaders how to solve problems. It shapes their emotional intelligence (if they allow it). Leaders who’ve faced setbacks tend to have more empathy and patience. They’ve had to overcome multiple failures themselves, so they know how challenging failures can be for their teams.
When leaders normalize failure, they create cultures where people aren’t afraid to take risks or push boundaries. That’s where breakthroughs happen.
The mark of a true leader isn’t perfection. It’s how they handle failure. Whether they embrace it as a teacher or fear it as an enemy. The choice of owning mistakes, adapting, and persevering defines not just their success, but the success of everyone they lead.
The next time failure arises, ask yourself: Will I let this moment shape me for the better? Will I lead my team through it with grace and determination? Will we learn from this failure?
The answers will set the course for everything that follows.
Photo by David Trinks on Unsplash
Grandpa Bob Encouraging Leadership 
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