Questioning "What went Wrong?"
- Mike Bensi
- Jun 16
- 2 min read

Sports are pretty easy once the game is over.
A quarterback throws an interception late in the fourth quarter and suddenly everyone becomes an expert.
"He never should have thrown that pass."
"How did he not see that defender?"
"The right decision was obvious."
It's easy to say that when you're sitting on the couch watching the replay for the third time.
What makes sports interesting is that players don't get the benefit of hindsight. They have to make decisions in real time with incomplete information, pressure, distractions, and uncertainty. Sometimes they make great decisions and get a bad result. Sometimes they make poor decisions and get lucky.
The outcome doesn't always tell the whole story, and the same is true in leadership. Most leaders I know have experienced at least one moment when a situation didn't turn out the way they hoped. An employee leaves unexpectedly. A customer chooses another direction. A hire disappoints. A business relationship ends poorly.
That's usually when the replay begins. We revisit conversations, decisions, and moments looking for the clue we missed. We tell ourselves we should have acted sooner, asked more questions, or recognized what was coming.
The challenge is that hindsight has a way of making yesterday's uncertainty look like today's certainty. And in the process, we often start judging the quality of our decisions based solely on the outcome.
The goal isn't to avoid learning from painful outcomes. The goal is to learn the right lesson by:
Improve your judgment. Take time to reflect on what the situation can teach you. Ask yourself what information you had at the time, what information you missed, and what questions you might ask differently in the future.
Strengthen your systems. Don't rely solely on instincts or good intentions. Consider what processes, expectations, checkpoints, or safeguards could help you identify issues sooner and reduce risk going forward.
Move faster where you need to move faster. Not every problem needs an immediate response, but many leaders wait too long hoping a difficult situation will resolve itself. When patterns become clear, address them directly rather than allowing them to linger.
But don't let one disappointing outcome convince you that helping people, trusting others, or acting with integrity was the mistake.
Sometimes the lesson is not that you led poorly. Sometimes the lesson is simply that leadership involves making good decisions without ever being guaranteed a good outcome.




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