Leadership Development: Leading Through Mistakes

  • 7 mins read

Business leaders today are not exempt from making mistakes. While we like to believe their judgment is improving, certain behaviors make leaders vulnerable to error, such as mindset failures, delusions, mismanagement, and patterns of unsuccessful (or poor) behavior. Our wishful thinking, denial, and other forms of avoidance often prevent us from seeing their errors or the mistakes we make.

We live in a celebrity culture where leaders, and especially CEOs, are expected to be perfect examples. They are held up as icons. We don’t like to admit they have flaws or that the traits that make them special can also lead to failure.

We crave heroic leaders from whom we can look up and derive a sense of safety and security. However, we can’t do this when we see their flaws, so we contribute to the heroic myth and enable the leader to plunge full steam ahead, right or wrong. We must abandon this hero worship.

There is a fine line between right and wrong; leaders can swing back and forth like all humans. They can be great leaders or fallible human beings. When great leaders make mistakes, they realize they were wrong and take appropriate action.

So why don’t some leaders admit when they have made a mistake? The following areas need to be accessed for leadership development:

Fear of Mistakes

Fear of mistakes remains a common challenge for leaders today. This fear fuels our drive to avoid losing face at all costs. But the truth is, admission of error harms our credibility less than ongoing denial.

Social psychologist Adam Fetterman states, “When we do see someone admit that they are wrong, the wrongness admitter is seen as more communal, more friendly.” When someone promptly admits to being wrong, people do not think they are less competent.

Studies also reveal that some people are more willing to publicly acknowledge that their prior belief or attitude was inaccurate. The researchers called this a willingness to admit wrongness or WAW. In three studies, they created scenarios to measure WAW and found a correlation with agreeableness, honesty/humility, and openness to experience.

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What is a Meaningful Mistake?

Being wrong requires accepting that our understanding may be limited, out-of-date, or simply fallible. This requires intellectual humility. Social and personality psychologist Mark Leary states, “Intellectual humility is simply the recognition that the things you believe in might be wrong.”

In today’s complex world, this is not always easy. Even great leaders can fall into any of the five common blind spot categories:

1️⃣ Experience

2️⃣ Personality

3️⃣ Values

4️⃣ Strategy

5️⃣ Conflict

Great leaders recognize and acknowledge that they have cognitive blind spots. They also carefully examine and choose their convictions. When they identify errors, mistakes, or new understanding, they promptly admit it.

Meaningful Mistakes in Organizations

The practice of making meaningful mistakes can be mastered as a corporate culture. This requires support from leadership: proper mindset and models. In Being Wrong: Adventures in the Margin of Error (HarperCollins 2010), author Kathryn Schulz describes two models of wrongness:

Pessimistic model: errors are dangerous, humiliating, distasteful, and un-fun. 

Optimistic model: errors are a surprise of bafflement, fascination, excitement, hilarity, and delight. 

With the second model, innovation is more likely to occur. This culture is highly agile, adaptable, and productive.

Leadership and Meaningful Mistakes

No one is immune from making a mistake. However, by taking appropriate action, we can avoid making matters worse.

To be sure, mistakes vary in degree, but when we make an insensitive comment, send a message without having all the facts or considering how it will be received, or publicly berate a subordinate (or colleague), we must promptly acknowledge our mistake and make amends. It’s time for a good apology.

Bad v. Good Apology

A bad apology justifies or explains away our error. It paints a picture of why we did what we did or why we should be forgiven. Of course, trying to explain our actions is natural. But a bad apology rationalizes our error, even for the leader’s mistake.

A good apology has four elements:

Focuses on the other person(s) and how they have been affected by your mistake.

Takes responsibility. It acknowledges an error and remorse.

Makes amends. It addresses what can, is, and will be done to correct the mistake.

Builds trust. It communicates what you will do differently in the future.

Meaningful mistakes require reflection without obsession. A qualified coach can help you break the cycle of rumination and get back on track with productive self-reflection.

Employees and Meaningful Mistakes

When we feel responsible for an organization, and we’re confronted with the consequences of an employee’s mistake, we are quick to react with judgment and condemnation.

Peter Bregman, author of Leading with Emotional Courage (Wiley 2018), suggests that when you confront an employee with a past-focused question, such as, “What were you thinking?” they become defensive, and the mistake is reinforced. Instead, great leaders ask questions that focus on the future. Future-focused questions have numerous benefits:

▶ Allows the employee to acknowledge the mistake and the lesson learned.

▶ Allows the leader to guide the employee in identifying any other potential flaws in their thinking pattern.

▶ Builds trust: in the employee’s and leader’s competence.

Manage Your Response

While this sounds simple, we first need to learn how to manage our own emotional reactions when an employee makes a mistake. Bregman offers a few keys:

▶ When you experience an emotion, pause with curiosity. Take a breath.

▶ Ask yourself: “What is my desired outcome?” “What would I like my next action (communication) to achieve?” Be honest with yourself.

▶ Determine the actions (verbal or otherwise) that will most likely help you achieve your desired outcome. Often, you’ll find a conversation about the future, not the past.

▶ Ask your employees what they plan to do in the future in similar scenarios.

Of course, these actions require a willingness to tolerate all feelings. Bregman calls this “emotional courage.” And with practice, you can strengthen yours.

Lead Your Organization Through Meaningful Mistakes

Great leaders model ethical, wise decisions for all their employees. Part of the problem is our human tendency to blame. We perceive and react inappropriately to errors, mistakes, and failures. We either avoid blame or assign it, or we overact with self-criticism.

According to psychologist Saul Rosenzweig, we experience frustration and anger, often the triggers of the blame game based on our personality categories:

Extrapunitive: Prone to unfairly blame others

Impunitive: Denies that failure has occurred or one’s own role in it

Intropunitive: Judges self too harshly and imagines failures where none exist

These personalities influence a corporate culture. Extrapunitive responses are common in business; you don’t have to look far to see them. To be sure, some mistakes are blameworthy. But you want to use your energy more productively to build organizational resilience and bounce back from mistakes.

Listen and communicate. Never assume you have all the information until you ask probing questions.

Reflect on both the situation and the people. We’re good at picking up patterns and making assumptions. Remember, however, that each situation is unique and has context.

Think before you act. You don’t have to respond immediately or impulsively.

Search for a lesson. Look for nuance and context. Create and test hypotheses about why the failure occurred to prevent it from happening again.

Make amends. Acknowledge responsibility for wrongdoing and take action to redress that wrong.

Make Amends

In Moral Repair (Cambridge University Press 2012), Margaret Urban Walker describes making amends as taking reparative action, but only action that prevents accepting responsibility for wrongdoing and that embodies the will to set right something for which amends are owed.

This is not unlike some of the steps in recovery programs, such as Alcoholics Anonymous. Translated loosely, for organizations, it might sound like this:

▶ We searched for who and how our organization has harmed, and we would like to do what we can to correct our mistakes.

▶ We accept full responsibility for our mistakes and will do what we can to correct this mistake.

▶ We will continue to monitor our attitudes and actions; when we are wrong, we will promptly admit it.

Making amends builds resilience for individuals and organizations. Leaders who can admit to their mistakes can make them meaningful. They can masterfully lead through mistakes.

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