Getting Better at Getting Better

Every leader has their list of the decisions they wish they could redo. This is particularly true now given the violent market swings in both directions in the past few years.

Maybe you hired executives assuming you’d achieve larger scale than you actually reached; now you sense you have the wrong team. Maybe the layoff you did was too small and you aren’t moving fast enough. Maybe your big strategic bet isn’t working and you’d be better off declaring it a failure and reallocating resources.

But as you think about fixing these mistakes, something holds you back. Somehow the risk-reward seems off. Because in the short term the problems probably aren’t existential…but the proposed solutions are definitely painful.

Let’s go back to the layoff example because it’s the most agonizing one I can think of. Maybe you cried when you told the company some teammates were being let go. You told them you were sorry about letting them down. You swore you would never make that mistake again.

But what happens when you realize you didn’t cut deep enough the first time? It’s not existential because you’re not about to run out of money. But you know in your heart the company is too big and slow. How do you tell the team you need to do another layoff without seeming incompetent as a leader…and even worse, like a liar?

It’s incredibly painful to imagine standing in front of the team and telling everyone you made a mistake on something so consequential. It can feel like an assault on your ego and identity as a leader.

In reality, embracing the pain of admitting our mistakes is a leadership superpower that can have compounding benefits for the organizations we lead.

The first and most obvious benefit is we learn the lessons of our mistakes. The bigger the mistake and the more public the admission, the less likely we are to make that specific one again.

The second benefit is counterintuitive. The experience of making, admitting, and ultimately fixing big mistakes makes us more bold. We learn that the world doesn’t end very often. We learn that our organizations are more resilient than we think. We learn that we are more resilient than we think. So we try bigger and bolder things and don’t wait so long the next time before calling them failures.¹ We get better at dealing with the ego and identity blows that come from admitting our mistakes. This starts to build on itself.

But the true compounding benefit comes from the impact on the culture. Remember, as the leader, your team watches everything you do. If you act like you have all the answers, your team will too. But if they see you trying things, taking accountability when you screw them up, and getting back up to do it again…they will do that too. The culture will begin to reward boldness, truth-seeking, and speed of learning.

Your company will make better mistakes and learn better lessons. The feedback loop will get faster. The company will get better at getting better.²

None of this is easy. But the cruel reality is that the choice is not between getting better and staying the same. Our markets are too dynamic for that. You’re either getting better at getting better…or you’re on the decline.

Greg LeMond, the Tour de France winning cyclist, has an amazing quote: “It never gets easier. You just go faster.” He was talking about training but he could have been talking about startups.

Embrace the pain. You will build an organization that is honest, decisive, and resilient.

You won’t make it easier. But you will set the pace.