Why Leaders Who Have Failed Make Better Decisions, According to Jason Osborn

In a recent LinkedIn post, Jason Osborn explores the often-counterintuitive idea that leaders who have experienced failure are better equipped to make sound decisions than those who have never faltered. Osborn argues that a leader’s past stumbles, rather than hindering them, provide invaluable lessons that shape more effective leadership.

Osborn highlights that leaders who have navigated the consequences of poor decisions possess a unique understanding of risk. He states:

“They know the real cost of being wrong. Leaders who’ve failed have felt the consequences firsthand. That experience makes them weigh risk differently.”

This firsthand experience, according to Osborn, transforms caution from a potential impediment into a form of ‘earned wisdom.’ This perspective suggests that true leadership development is not about avoiding mistakes, but about learning from them.

The Humbling Power of Failure

A key theme in Osborn’s post is how failure cultivates humility and a more grounded approach to decision-making. He points out that untested confidence can lead to significant blind spots, whereas failure instills a more rigorous process for evaluating choices.

As Jason Osborn notes:

“Failure teaches that confidence isn’t the same as being correct. So they build in checks. Ask more questions. Seek outside perspective.”

This emphasis on seeking external input and implementing checks suggests a shift from relying solely on intuition to a more data-driven and collaborative decision-making process. Osborn contrasts this with leaders who haven’t failed, suggesting they might rely more on theoretical confidence rather than tested judgment.

Recognizing Patterns and Building Resilient Teams

Early Warning Systems

Osborn further argues that leaders who have experienced failure develop a superior ability to recognize warning signs. Having gone through the ‘fallout’ of a past mistake, they become more attuned to the subtle patterns that can precede disaster. This ‘pattern recognition,’ as he calls it, is a direct byproduct of having lived through it.

Fostering Openness Within Teams

Another significant point made by Osborn is that failure fosters an environment where team members feel safer challenging their leaders. He suggests that failure humbles leaders, making them more receptive to feedback and less defensive about their decisions. In contrast, leaders who have maintained a perfect record may be more inclined to protect their ego and, consequently, may miss crucial dissenting opinions.

Osborn articulates this by stating:

“The leader who’s never failed is still protecting a perfect record. The one who has is just trying to get it right.”

This creates a more psychologically safe environment, enabling teams to provide the critical checks and balances necessary for effective leadership. Osborn concludes by posing a thought-provoking question to his audience: “Success teaches you what worked once. Failure teaches you what to watch for every time after. Which has taught you more?” This prompts leaders to reflect on the true value of their experiences, suggesting that the lessons learned from setbacks are often more profound and enduring than those from successes.