For all the talk about innovation and risk-taking in leadership, many organizations still send a different message: Play it safe.
Too often, we celebrate only the wins—reinforcing the belief that success is about getting it right rather than about pushing boundaries, learning, and growing. Yet, in a world that demands agility, the leaders and organizations that will thrive are those that reward the try—not just the perfect outcome.
This is a principle that Carla Harris, a senior advisor at Morgan Stanley emphasizes in her work and wrote about in her book, Lead to Win. Carla and I met at a conference for alumni of Harvard Business School’s women on boards program. As Carla shared with the women in the room, “People need to know that effort matters, that taking a swing is valued—even if they miss.” And yet, too often, women as well as men hesitate to take risks—not because they lack ability, but because they fear what will happen if they fall short.
The problem? Most of us are wired to avoid failure. We fear looking incompetent. We hesitate to take risks because we don’t want to be wrong. We assume everyone else has things figured out while we alone are second-guessing ourselves.
But here’s the truth: No one has a monopoly on intelligence. No one has it all figured out. The best leaders—and the boldest innovators—are those willing to make a bet on themselves, even when success isn’t guaranteed. And they don’t just do it once. They do it often.
Derisking the Try
As I explored in The Courage Gap, many people hesitate to take action not because they lack ability or the knowledge to act. Rather, because they overestimate the cost of failure and underestimate the risk of inaction. They wait for certainty, but certainty never comes.
So how do we make it safer for ourselves and others to try?
- Celebrate effort, not just results. When failure is punished, people stop experimenting. If we want teams to take smart risks, we must reward well-intentioned attempts—even the ones that don’t succeed. As Amy Edmondson’s research on psychological safety has shown, the best teams aren’t the ones that make fewer mistakes; they are the ones that talk about them openly and learn.
- Extract the lesson, leave the baggage. Leaders should model what it looks like to “fail well.” That means sharing their own missteps, normalizing failure as a source of growth, and helping others reframe setbacks as stepping stones rather than stop signs.
- Affirm potential. In a follow up conversation, Harris shared with me, “I try to tell people what I can see of them.” Leaders who do this empower their teams to take bolder action. When people doubt themselves, they don’t need empty reassurance—they need someone to remind them of what they’re capable of.
Many professionals hold themselves to an impossible standard, assuming that anything less than perfect isn’t valuable. But in environments where innovation is key, perfectionism isn’t an asset—it’s a liability. It stifles risk-taking, slows execution, and keeps people from sharing ideas until they are fully polished (often missing the window of opportunity).
As Harris points out, “Your ideal of perfectionism may not align with what your organization actually values.” If speed, adaptability, and innovation are what drive success, then failing fast and learning faster will always be more valuable than getting it “perfect” the first time.
Make a Bet on Yourself
At the heart of all this is courage—the courage to take a swing, to make a bold ask, to apply for the job you’re not fully qualified for, to raise your hand for the big project, to share an idea that might not land.
If you’ve prepared to the best of your ability, you can silence the inner critic that says you’re not enough. You may fall short, but you’ll know you gave it your all. And that is how confidence is built—not by waiting for certainty, but by stepping forward in spite of uncertainty.
So, the next time you hesitate, ask yourself: What if I bet on myself?
Because the leaders who make a real impact—the ones who shape industries, transform teams, and leave legacies—aren’t the ones who played it safe.
They’re the ones who dared to try.
Dr Margie Warrell is a keynote speaker and leadership advisor who helps people close the gap between where they are and where they want to be. Her new book is The Courage Gap: Five Steps to Braver Action.