Why How You Lose As A Leader Matters As Much As How You Win

Building great organizations requires wins. Let’s be clear about that from the start. Without wins, you don’t have an organization - you have a support group.

But here’s what changes when you step into leadership: your losses become public property. When you’re an individual contributor, you can fail quietly, learn privately, move on. That bug in your code? Fix it before anyone notices. That presentation that bombed? Iterate for next time. Your failures are yours to manage.

When you’re leading transformation in teams, the physics change entirely. Your failures are watched and dissected, with or without you knowing exactly what is being discussed. They become water cooler conversations and organizational folklore. This isn’t about celebrating failure - that confuses activity with progress. This is about recognizing that losses are inevitable, and how you handle them becomes organizational DNA.

I learned this the hard way with many (many) failed projects and ideas. I make it a point to be public about these failures, laying out to the team where my thinking went wrong, showing the flawed assumptions, owning the disruption it caused.

The response? Team members talk about the trust this approach built.

That’s the paradox. Leaders who can’t admit obvious failures think they’re protecting their authority. They’re actually destroying trust. Everyone can see when something isn’t working. Pretending otherwise doesn’t make you look strong; it makes you look delusional or dishonest. Sometimes both.

There’s this pressure to be “too much” of everything as a leader - too confident, too certain, too polished. But the leaders who own failures publicly are criticized for being “too vulnerable,” “too open.” Here’s the thing: that vulnerability, when paired with actual wins, creates something powerful - proof that falling down isn’t fatal.

The most infuriating leaders aren’t the ones who fail. They’re the ones who fail and then gaslight everyone about it. Who pretend the strategy that clearly didn’t work was actually successful “from a certain point of view.” Who make their teams question reality rather than question their decision.

Kind Versus Nice in Victory and Defeat

This difference between protecting ego and protecting trust brings us to a critical distinction that shapes how we handle both victories and defeats.

Nice leaders celebrate wins loudly and bury losses quietly. They smooth over mistakes, avoid uncomfortable conversations, keep everyone feeling good about themselves. They’re the ones who say “great job everyone” when half the team knows it wasn’t. When failures surface, they blame the team that executed their flawed strategy, the market that didn’t respond to their mistimed launch, anyone but themselves.

Kind leaders do something harder. They celebrate wins generously - giving credit widely and specifically. But they own losses personally and publicly. They say “I made this call, here’s where my thinking was flawed, here’s what we’re learning from it.” When you have power, this admission isn’t weakness - it’s redefining strength. You’re dismantling the myth of infallible leadership, the toxic idea that authority means never being wrong.

This is where privilege enters the equation in ways we don’t talk about enough. Who can afford to take public ownership of failure? Usually those with enough wins banked, enough social capital, enough alternatives if things go sideways. The senior director with a track record can admit failure more safely than the new manager still proving themselves.

This creates an obligation. If you have the safety net to fail publicly, you must model how to fall and get back up. Not for your own growth - for everyone watching who can’t afford to take the same risks.

The arithmetic is actually simple. Your wins create permission to show your losses. Your losses create permission for others to take risks that lead to wins. But if you only show wins, you create a culture where people hide losses until they become catastrophes.

Real kindness in leadership means making people uncomfortable with truth rather than comfortable with fiction. It means telling your team their idea has fatal flaws rather than letting them waste six months on it. It means challenging the senior executive dismissing junior voices, even when that executive writes your performance review. It means using whatever privilege you have to amplify those who can’t speak as safely as you can.

Building Organizations That Can Win Because They Know How to Lose

These individual acts of courage and accountability compound into something larger - they become the foundation of organizational resilience.

The strongest organizations aren’t built by people who never fail. They’re built by people who fail instructively and create cultures that can metabolize failure into fuel. Not the fake “fail fast” culture where people celebrate any failure as learning. That’s just incompetence with better PR. I’m talking about teams that reflexively ask “what did we learn?” because they’ve watched leaders model that question about their own mistakes.

Here’s what I’ve observed: wins create momentum, but how you handle losses creates culture.

Every time you stand up and own a failure, you’re doing several things simultaneously:

• You’re making it safer for someone else to take the risks that lead to wins
• You’re demonstrating that recovery is possible
• You’re showing that learning matters more than looking good
• You’re building a team that can handle reality rather than requiring fantasy

The ratio matters. You need enough wins to have credibility. Nobody wants to follow someone who fails constantly and owns it beautifully - that’s just transparent incompetence. But without visible losses and recovery, you’re not building an organization that can innovate. You’re building a performance theater where everyone pretends nothing ever goes wrong.

Your real community - in leadership and in life - isn’t the people who only see your wins. It’s the ones who’ve watched you fail spectacularly and stick around to ask, “What did we learn?” instead of “I told you so.” The best ones do it with humor, making the medicine go down easier. They’re the ones who, when you’re about to make the same mistake again, remind you of last time and save you from yourself.

These are the people who make organizations antifragile. They’ve seen losses handled with grace and learning, so they’re willing to take bigger swings. They know that failure isn’t career-ending if you own it and learn from it.

Organizations that only know how to win are brittle. When they eventually lose (and they will), they shatter. They look for someone to blame, someone to fire, someone to sacrifice to maintain the illusion of constant success.

Organizations that know how to lose - because they’ve watched leaders do it with accountability and grace - can take bigger risks, fail harder, recover faster, and ultimately win bigger. They don’t waste energy on coverups or blame games. They put that energy into learning and adjusting.

The hardest truth? The most successful leaders I know and respect aren’t those who never failed. They’re the ones who failed instructively, publicly, and then used their recovery to light the path for others. They have impressive win records, but what distinguishes them is how they turned their losses into organizational assets.

Remember:

• Your wins give you permission to show your losses
• Your losses give others permission to take risks
• Public accountability for failure is as, if not more, powerful than any success story
• Choose kind over nice, especially when owning mistakes
• Your privilege to fail safely creates an obligation to fail instructively
• The ratio matters - you need wins, but losses teach culture

Make a decision. Own the results. Build something that can win because it knows how to lose.

Because in the end, organizations aren’t built on the fairy tale of constant success. They’re built on the human reality of falling down, getting up, and being honest about both.