In this special compilation episode of What If?, Leslie Grandy revisits moments from past conversations with leaders, founders, investors, executives, and coaches who have all had a close relationship with failure—and have learned to think about it differently.
Failure is often treated as evidence that something, or someone, was not good enough. From school onward, many of us are trained to connect failure with inadequacy, punishment, or shame. So we learn to play smaller. We avoid risk. We compress our thinking. We look for certainty before we move.
But creative leadership requires a different relationship with failure.
It requires the ability to test assumptions, take intelligent risks, listen deeply, adapt quickly, and stay curious long enough to understand what went wrong.
This episode brings together insights from previous What If? guests including Kelly Smith, Marcelo Majonchi, Kelly Breslin Wright, Chuck Garcia, Chris DeVore, and Sean Atkins, each offering a different perspective on what failure reveals and how leaders can use it to grow.
Together, these voices explore:
Why failure is often misused as a label when an outcome simply did not match expectations
How leaders distinguish between high-quality failure and failure that comes from ignoring what they already knew
Why prioritizing business performance over human wellbeing can become a failure that stays with a leader
How product builders learn from lack of product-market fit
Why failure should be expected when teams are building something that has not existed before
How resilience, adaptability, and risk tolerance become leadership muscles
Why admitting “I don’t know” is not weakness, but a necessary part of learning
How great teams normalize experimentation without lowering standards
Why startups often fail when founders lack a strong feedback loop between what customers say and what they build
How failure can sharpen judgment when leaders are willing to interrogate it instead of defend against it
Across these conversations, one theme becomes clear: failure is only useful when it is examined.
It is not enough to reframe failure as growth and move on. The real value comes from owning it, questioning it, and understanding the pattern it reveals.
Was the assumption wrong?
Was the customer feedback ignored?
Was the team moving too fast to notice the risk?
Was the leader trying to appear certain instead of staying curious?
Was the failure actually a stumble—or was it a signal?
The leaders featured in this episode do not romanticize failure. They do not suggest that every failure is automatically noble, productive, or necessary. Instead, they show that failure becomes meaningful when it creates better judgment, stronger resilience, clearer communication, and a more honest relationship with uncertainty.
Because creative leaders are not the people who avoid failure.
They are the people who know how to learn from it without letting it define them.
Reflection question:
What failure are you ready to examine more honestly, not to relive it, but to understand what it can teach you?
Comments
Nothing yet. Say the first thing.
Sign in to join the conversation.