You can learn a lot about an organization by watching what happens in the first few seconds after someone gets something wrong. With basketball season underway again, I’ve been painfully reminded of one of the best examples I’ve seen.
Last March, in the Elite Eight, my Duke Blue Devils men’s basketball team were up by two points with seconds left when Cayden Boozer had a pass deflected, and UConn hit the three that ended Duke’s season.
Afterward, Cayden owned the turnover.
Then he said he'd ruined his team's season.
His teammate Dame Sarr pushed back right away. So did Coach Jon Scheyer. Dozens of moments had brought the team to that final possession, and one play didn't decide a season.
Nobody pretended the turnover hadn't happened. They just refused to let it become the whole story.
That response took seconds. In many organizations, the opposite takes years.
The list everyone knew about
Some years ago, I worked with an organization where everyone knew about the list.
No one could show it to you. It wasn't in a system or a file. But the rumor mill was clear: if you'd made the wrong mistake in front of the wrong leader, you were on it. And once you were on it, you didn't come off. It even had a nickname.
The list was real enough to shape careers.
It came up, quietly, in conversations about promotions and stretch assignments. It decided who got the benefit of the doubt and who didn't.
This was an organization with a long memory. Its leaders were deeply tenured. That meant the people who saw your mistake often had a say in your next opportunity, sometimes years later. Some of the most talented people eventually left for places where they could start fresh. Others stayed, kept their heads down, and stopped volunteering for anything that might go wrong.
The ones who stayed remembered, too. They carried old wounds, and sometimes, without meaning to, they passed those wounds on.
Memory isn't the problem
Remembering is normal. Organizations should learn from what went wrong. The problem starts when memory stops being about the lesson and starts being about the person.
And it’s noticeable. People see when a capable leader is sidelined for something that happened years ago. They remember the colleague who was embarrassed in a meeting for getting something wrong. They learn what's actually safe long before anyone explains the culture to them.
Then they adjust. They stop raising the concern. They stop challenging the assumption. They stop taking the thoughtful risk the organization says it wants.
What looks like alignment may actually be learned caution. And a team that has learned caution can't give you the candor, creativity, or initiative you need to move forward.
What great sports teams already know
Great sports teams make more mistakes in a game than most leadership teams make in a year, and they do it in public. So the best of them build habits for handling mistakes on purpose. A few are worth borrowing.
They review the play, not the player. Film sessions are specific: what happened, what we saw, what we'll do differently. The conversation is about the decision, not the person's worth.
They practice the next play. Athletes train to reset quickly, because dwelling on the last mistake makes the next one more likely. Leaders can build that same reset into how teams debrief.
Teammates speak up for each other. What happened with Cayden wasn't only the coach's job. A teammate stepped in first. Strong cultures expect peers, not just bosses, to keep a mistake in proportion.
Correction is expected, so it isn't a verdict. On good teams, feedback is constant and normal. Because everyone gets coached, being corrected doesn't mean you're on the outside.
None of this happens by accident. Teams train for it. Organizations can too.
Accountability still matters
This isn't an argument for looking the other way. Dishonesty, misconduct, and serious harm carry real consequences, and they should. Repeated errors need to be addressed directly, not tolerated in the name of being kind.
But letting things languish is its own failure. When a mistake is never really addressed, it doesn't go away. It hardens into a reputation, then into a rumor, and eventually into a list.
Accountability says, this happened, and you're responsible for it. It doesn't say, this is all you'll ever be. The healthiest organizations deal with mistakes clearly and early, so they don't have to keep dealing with them for years.
What it actually takes to change
More than once in my career, I've been asked to help rebuild a culture from the ground up. I can tell you what didn't work: new values on the wall, a training day, a memo announcing a fresh start. People had heard it all before, and they waited to see what leaders would actually do.
What worked was slower and more specific. We had to agree on what we expected of each other, including how we'd respond when someone got it wrong. Then we had to carry that into everything that teaches people the real rules: how leaders are developed, how new people are welcomed, who gets hired, and who gets promoted.
That work looks different in every organization, because every organization's memory is different. But one thing doesn't change. Leaders go first. A team will believe it's safe to recover from a mistake when they watch someone senior own one, learn from it, and keep their seat at the table.
One question to sit with
Is there someone in your organization whose old mistake still comes up whenever their name does?
If a name came to mind quickly, your culture is already telling you something.
Cayden was responsible for a play. He wasn't responsible for a season. And he was still their teammate.
The best organizations know how to say that, and mean it.
Your culture is already teaching people what happens after a mistake.
The question is whether that lesson is building trust, candor, and growth, or caution, quiet, and a list no one admits exists. A confidential conversation can help surface what your organization may be reinforcing without intending to, and what it would take to change it.
Cassandra Shepard is the founder of Shepherd + CO, a boutique strategic advisory firm. She works with senior leaders navigating the intersection of enterprise strategy and advanced leadership. www.cassandrashepard.com