How Leaders Learn From Mistakes

Leaders make mistakes like everyone else—but often with greater consequences. The good news is even the worst mistake can result in a new and improved leader.

When the wrong decision is made, or an approach that was advised against is taken anyway, the rush to judge an organizational leader is swift. Rivals of the leader to say, “I told you so,” while those who had faith in the leader express their disappointment.

The tendency to pounce when mistakes are made is understandable, but not wise—considering all there is to be gained in the recovery from a mistake. Three Training Top 125 leaders, and an expert, share how the mistakes they, their organizations, and others have made have allowed for growth and a renewed sense of purpose.

Mistake #1: Managing by the Numbers

We live in data-obsessed times, when computers allow us to measure nearly everything. In business, it is tempting for leaders to focus on metrics, rather than on nurturing their team. This is a short-sighted approach, says John Congemi, director of Employee Development for Training Top 125er MasTec North America, Inc.’s Utility Services Group. “For many, every action is a reaction to a number; and the only measurement of concern is the bottom line. I believe, and have personally witnessed, that energy spent building trust with employees will go further toward increasing business results than almost any other strategic effort,” he says. “I’ve learned through a partnership with trust expert David Horsager that a lack of trust is any organization’s single largest expense. Trust is quantifiable and can dramatically impact relationships, reputations, retention, revenue, and results at work.”

Congemi says the company learned last year through an employee engagement survey that it had some significant challenges with the level of trust employees had toward their leadership teams. “The issue, it turned out, was that employees desired more communication and transparency,” he says. “Not enough information was being cascaded to our field workforce.”

This year, Congemi says MasTec is making an effort to engage its workforce by emphasizing communication. The company is conducting town halls, in which its leadership team visits each market, or part of the company, to discuss the overall company vision, mission, and values, as well as answer any questions employees may have. In addition, MasTec’s Group president has started filming and sharing a video blog, allowing him to share updates on strategic initiatives directly with the company’s workforce. MasTec also implemented a quarterly newsletter, Connections, to share team updates and wins. Communication efforts now center around “creating a shared sense of purpose and an understanding around where everyone fits into the story, and most importantly, building trust!”

Mistake #2: Not Self-Empowering Employees Enough

A company’s leaders often will experience dissatisfied employees or department managers. It’s easy to step in and try to fix the problem for them, but that might not be the best approach. Training Top 125er SpawGlass has learned the value of empowering those with the challenges to work through the difficulties on their own. “One struggle is creating appropriate boundaries between making decisions and letting your people make decisions,” says Team Member Development Manager Charles Mogab. “One of our favorite anecdotes for leadership is to not take monkeys (problems) from your team. People will always come into your office and want to give you their monkeys. A leader’s job is to not take those monkeys, but to give them back to the person and follow up with them. Ask them questions, get them to think through the problem, or think about solutions they haven’t tried or thought about, but let them keep feeding their monkey. If you don’t, you’ll end up with not only a barrel of monkeys, but an office full!”

Mogab says part of the art of leadership is understanding how much room to give employees and managers to try and fail, and learn in the process. The challenge is knowing how much rope to give and when to pull back, so wrong decisions aren’t costly, he says. In addition to enabling learning and growth, empowering employees makes it possible for leaders to focus on long-term goals, rather than getting wrapped up in daily minutia. “Leaders must stay focused on their company goals and mission. They need to delegate, trash, move, or ignore the things that aren’t going to drive them to their goal,” Mogab says.

Understanding how to empower, rather than micromanage, is practiced in SpawGlass’ leadership training. “Our leadership development programs involve working on real-life examples, problems, and situations, so when people get back to their job, what they encounter is what they practiced in the program,” says Mogab. “The time spent in the workshop won’t make them an expert, but it can give them practice and build their confidence. It also gives them access to the infinite resources available in the company, and the confidence that it is OK to ask for help.”

Workshops that teach leaders how to most effectively help their employees succeed also provide a safe environment in which to fail. “It’s no different than a flight simulator,” Mogab says. “It’s OK to crash in the workshop; just learn how to avoid it on the job.”

Mistake #3: Not Delegating Enough

Hand-in-hand with not empowering employees enough to work through their own problems is an inability to allow others to pitch in. “When I assumed a management role for the first time in my career, I struggled with delegating,” says Heide Abelli, vice president of Business Skills and Leadership for global e-learning leader Skillsoft. “Until that point, I had been a highly successful individual contributor, but learning to delegate in my new role as a manager was challenging. I’ve always been a Type A perfectionist, and when I first started managing people, I had this nagging feeling that if I did not perform a task myself, it would not get done well. It took me a while to internalize that by not delegating, I was being disrespectful to my direct reports, and negatively impacting my team’s morale. Competent, hardworking, innovative people want to be challenged, and if their manager is unwilling to provide opportunities for development, they will find those opportunities elsewhere.”

One way to help leaders learn how to delegate is to offer them training modules that address that very challenge. Abelli says Skillsoft offers online coursework that allows leaders to focus on specific areas, such as delegation, that are weaknesses for them. “The course material is grounded in pragmatic, highly realistic business problems and situations,” she says. “Our library of leadership ‘QuickTalk’ videos provides leadership advice delivered by subject matter experts on a wide range of leadership challenges, and can be viewed anywhere/any time. Our short video simulations enable a leader to learn and practice leadership skills via realistic business situations.”

Mistake #4: Not Admitting Challenges

Abelli says that, along with delegation, another common leadership struggle she’s noticed is hesitancy to admit mistakes or challenges. She tells the story of a leader at her former company, who found herself judged harshly by her manager—not for struggling, but for failing to disclose that issue to him, and to the group, at a project meeting. She had come from a company where admitting mistakes was discouraged, so she needed to be re-trained to adopt an upfront approach.

“At the follow-up meeting, she reported significant progress, but made a point of acknowledging that there was still one set of activities in the task force’s project plan that still needed more work,” says Abelli. “The COO was pleased with the progress her task force had made, but even more pleased by her openness in the meeting with colleagues, and her ability to point out publicly that more work still needed to be done.”

Mistake #5: Lacking Self-Awareness

No matter how strong a leader is, each has strengths and weaknesses. Part of succeeding as a leader is knowing how to optimize what you do well and how to offset challenge areas. Top 125er Sitel believes it’s important to create leaders who know themselves well enough to know when they need greater help to improve. “Management styles are always unique and personal, but everyone has a tendency to lean into certain common themes. The key is to come to peace with the style you have, and play to that,” says Director of Learning and Development Jonathan Banman. “For a long time in my own career, I wanted to be recognized as a ‘hands-off’ kind of manager, especially as I moved up in the organizations I was a part of. I didn’t want to have a reputation as a meddler, or someone who was difficult to please and was always slowing projects down because of a demand for constant updates. What I came to eventually realize was that I wasn’t the kind of person who could just stay in the background and provide gentle guidance on occasion. I was an ‘in-the-weeds’ kind of individual who wanted to know what was happening, why it was happening, and how it was affecting all aspects of the system and project.”

Banman says understanding his desire for deep involvement in his team’s work has allowed him to be hands-on, while at the same time creating a positive work environment. “Once you understand, and accept, the kind of style you have and the person you are, the easier it becomes to gel with your team and drive great performance.”

Fortunately, coaching can help a leader understand how to take what others, or even they, themselves, perceive as a shortcoming, and tweak that style to become an effective leader. “Though we often say, ‘Leopards can’t change their spots,’ I’ve seen real success through immediate and sustained coaching,” says Sitel Vice President of Global Talent Brandyn Payne. As an example, she points to an executive whose management style alienated employees. “She had an intimidating personal approach that made her team feel like they couldn’t come to her with issues,” says Payne. “She literally had to practice smiling and making small talk. As you can imagine, she was not excited about this at first, but when it had an immediate impact on her team’s willingness to drop by and discuss projects, reach out to share progress, and so forth, she was won over! Now, she is well-known as an approachable leader in the company.”


  • Train leaders not to get so caught up in managing according to business metrics that they forget to think of their work team as individuals requiring development.
  • Rather than training leaders to take on every struggle of their team themselves, teach them to guide their employees to work out problems on their own.
  • Train even the most self-described Type A perfectionist leaders to share tasks with their employees. Learning to delegate gets the work done faster, and develops entire work teams in the process.
  • Create a corporate culture in which it’s OK to admit failure or challenges. Teach leaders that it’s better to be up front about struggles than to be too proud to admit areas where they may need help.
  • Help leaders become self-aware, so they recognize areas of strength to play up, and challenge areas to offset or improve.


By Judith Glaser, Chief Executive Officer, Benchmark Communications, Inc.; Chairman, WE Institute; and author, “Conversational Intelligence”

Once we make up our minds about someone, we set out to prove we are right. When we are addicted to being right, we are mastered by our Amygdala. We exhibit fight, flight, freeze, or appease behaviors. When we are addicted to being right, we are activating our “fight” behaviors, and we see the world through an I-Centric point of view. We are unable to see that others have valid points of view, and we move into more aggressive behaviors to sustain our power over others. Those who are on the receiving end of a person who is addicted to being right will feel attacked and likely react back, resulting in a highly unproductive relationship for revenue growth.

Try This

Being able to realize when your mind is “addicted” and being able to interrupt this behavior is vital to your success. Here are some tips that can help:

  • Build a movie in your mind about the interaction. You are the star and producer of that movie, and as the star, you can change the script.
  • When you realize you are at the fight stage, change the storyline.
  • Take a step back to analyze what you are doing and interrupt the pattern.
  • Imagine what would happen if this person really wanted to help you, and you them.
  • Imagine that they need to be valued, and to build a valuable relationship with you.

By now you know that “addicted to being right” is not going to lead to a productive conversation. You will need to build a new reality for that relationship to get rid of the distrust that has driven a wedge in your conversation and relationship.

Working on seeing this addiction before it gets the best of you— and your relationships—is vital to your success. Once you start to see the signs and signals that you are addicted, and have stopped listening without judgment, you can reverse the pattern by “ listening to connect.” You don’t need to give up your point of view. You do need to make space for others to have and share theirs. Remember, it is your movie. You are the star and the producer.

Lorri Freifeld
Lorri Freifeld is the editor/publisher of Training magazine. She writes on a number of topics, including talent management, training technology, and leadership development. She spearheads two awards programs: the Training APEX Awards and Emerging Training Leaders. A writer/editor for the last 30 years, she has held editing positions at a variety of publications and holds a Master’s degree in journalism from New York University.