Learning from Leadership Failures

Leaders have a particular condition that causes them to make mistakes… they are human beings. That’s not the worst part either; the worst part is that those mistakes can lead to failures. Worse yet, some of those leaders double up the failure by failing to learn from the mistake.

And that’s a terrible waste.

Authentic Leaders never waste a failure; they learn something from each one. They know that learning from leadership failures is one of the most valuable ways to grow as a leader. They understand that failure isn’t the end; it’s a stepping stone to future success when handled correctly. Here’s a structured approach that many Authentic Leaders use to learn and grow from leadership setbacks.

1. Acknowledge the Failure (Own It)

Take responsibility: Avoid blaming others or external factors. Owning your mistakes shows accountability and integrity.

Understand the impact: Reflect on who was affected by the failure (your team, organization, or clients) and how.

2. Analyze What Went Wrong

Identify root causes: Was it a poor decision, a lack of preparation, a communication breakdown, or something else? Tools like root cause analysis or 5 Whys can help.

Seek feedback: Ask your team, mentors, or stakeholders for honest input. Sometimes, others see things you missed.

3. Extract Key Lessons

Look for patterns: Have similar mistakes happened before? If so, it may indicate a deeper issue (e.g., rushing decisions, micromanaging, or failing to delegate).

Identify the leadership skill gap: Determine which leadership qualities (e.g., empathy, communication, strategic thinking) you need to improve.

4. Develop a Plan for Growth

Set learning goals: For example, if the failure resulted from poor delegation, commit to improving that skill by reading books, attending workshops, or seeking mentorship.

Apply the lessons in real time: Take proactive steps to prevent similar mistakes and implement changes based on what you have learned.

5. Communicate Openly and Transparently

Be honest with your team: Share what you’ve learned and how you plan to do better. This builds trust and shows your willingness to grow.

Encourage a culture of learning from failure: When leaders model openness about their own failures, it encourages the team to do the same.

6. Build Resilience

Focus on your mindset: Learn to see failure as feedback rather than defeat. Resilience helps leaders bounce back stronger after setbacks.

Maintain long-term vision: Don’t let one failure define your leadership journey. Keep the big picture in mind.

7. Celebrate the Comeback

Recognize progress: Once you have turned things around or successfully avoided repeating the same mistake, take time to acknowledge the growth.

Share your story: Talking about how you turned failure into a lesson can inspire and empower others on their leadership journeys.

Example in Action

Imagine a leader launches a major project that fails due to unclear communication and unrealistic timelines. By reflecting and gathering feedback, they realize they didn’t properly involve the team in planning. They then take steps to improve communication, adjust project timelines, and create a culture where team input is valued.

In leadership, failures are inevitable. But what separates great leaders from the rest is their ability to learn, adapt, and keep moving forward. What’s a leadership failure you have seen (or experienced), and what lessons came out of it?

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Learning from Failure

I am most certainly not a fan of failure. I have read a ton about failure and how beneficial failing can be. Things like, “failure shows you’re trying” and “failures are just stepping stones to success.”

Let’s be really clear about this absolute truth regarding failure… success beats failure every single day. If I’m succeeding then I don’t need to prove I’m trying. If I’m successful then I don’t need any damn stepping stones. I’ll just skip the stepping stones and make the leap to even greater success.

Given the choice, I’ll take succeeding over failing every chance I get.

But, no one succeeds all the time. Even people recognized as the best at what they do often endure frequent failures on their way to the top. Even at the top they continue to experience failure on occasion.

Ultimately, the difference between continual failure and eventual success comes down to learning from our failures. Learning from failure is a superpower that can help you grow, both personally and professionally. If you’re willing to learn from your failures, then you can make those failures temporary. If you’re not willing to learn from them, then buckle up because you’re in for a rough ride through life.

I’ll assume that you’re willing to learn from your failures and that being the case, here are some steps to help you make the most of setbacks and prevent them from becoming permanent failures.

1. Accept Failure: It’s a part of life, not a reflection of your worth. Don’t ignore it!

2. Analyze What Happened: Take a deep look and figure out what went wrong. Was it because you weren’t prepared, or was it something else?

3. Identify Key Lessons: Think about what you learned from the experience. Did you learn something about time management, resource allocation, or communication?

4. Adjust Your Approach: Use the lessons you learned to change your methods. Treat each attempt as a step forward, not an end.

5. Maintain a Growth Mindset: See failure as feedback. It’s not the opposite of success; it’s part of the journey. Stay persistent and keep going!

6. Take Responsibility Without Self-Blame: Own your part in the failure. Be kind to yourself and don’t be too hard on yourself.

7. Test and Experiment: Try again and see what works better. Use small experiments to test different approaches before committing fully.

8. Celebrate Progress: Celebrate even small steps forward to stay motivated. Appreciate the courage it takes to keep going, despite setbacks.

I can’t imagine failure ever being an enjoyable experience, but by using these ideas, failure can become a valuable learning experience that sets you up for greater success in the future.

Learning from failure is a choice, successful people make that choice; less successful people generally do not. Which one will you be?

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Failure isn’t final… unless you allow it to be.

There has been so much stuff written about failure that I hesitate to add to the pile. Motivational wisdom says that failure is part of success. Failing is a great way to learn. Failing just means you’re trying. It’s all great stuff.

Except, I’d prefer success without failure. I think there are more fun ways to learn than failing. And I’d especially hope people can tell I’m trying even if I’m not failing.

I do not like any part of failing, and I highly highly recommend you do everything you can to avoid it.

But, you knew there had to be a but, sooner or later you will fail. I know that because sooner or later, everyone fails. It’s my belief that it’s what happens after you “fail” that determines if it was really a failure. No matter how small the “failure” or how big, the simplest way to prevent it from really being a failure is to start again.

But starting over after a failure can be challenging. The good news is, it actually is also an opportunity for growth and improvement. I’m a big believer in the adage, “if at first you don’t succeed, try and try again.” But I only believe that if your next try includes a better plan.

Here’s how to develop a better plan next time.

1. Acknowledge Your Feelings

• Accept Your Emotions: It’s natural to feel disappointed, frustrated, or sad after a failure. Acknowledge these emotions rather than suppressing them. It’s even okay to be mad…for a short period of time.

• Reflect: Take some time to reflect on what happened. Understanding your feelings can help you process the experience and move forward.

2. Analyze the Failure

• Identify the Causes: Look at what went wrong. Was it a lack of preparation, a wrong strategy, or external factors?

• Learn from Mistakes: Identify lessons you can learn from the failure. Every setback has valuable insights that can prevent future failures.

3. Set New Goals

• Re-evaluate Your Objectives: Make sure your goals are realistic and achievable. Break them down into smaller, more manageable steps.

• Be Specific: Define clear, specific goals. This helps you stay focused and motivated.

4. Develop a Plan

• Create a Strategy: Outline the steps you need to take to achieve your new goals. Include timelines and milestones.

• Seek Advice: Don’t hesitate to ask for help from mentors, friends, or professionals who can offer guidance and support.

5. Stay Positive

• Maintain a Positive Mindset: Cultivate optimism. Believe in your ability to succeed and view setbacks as temporary obstacles.

• Surround Yourself with Support: Engage with positive, supportive people who encourage you to keep going.

6. Take Action

• Start Small: Begin with small steps to build momentum and regain confidence.

• Be Consistent: Consistency is key. Keep working towards your goals, even when progress appears slow.

7. Monitor Your Progress

• Track Your Achievements: Keep a record of your accomplishments, no matter how small. This helps you stay motivated.

• Adjust as Needed: Be flexible and willing to adjust your plan if things aren’t working out as expected.

8. Celebrate Small Wins

• Acknowledge Progress: Celebrate your successes, no matter how minor. This reinforces your motivation and commitment.

• Reward Yourself: Give yourself rewards for achieving milestones. This can boost your morale and encourage you to keep going.

9. Keep Learning

• Continue Learning: Always look for opportunities to learn and grow. You can do it through reading, taking courses, or gaining new experiences. Continuous learning is crucial.

Starting over after a setback is a process that takes time and effort. But in many ways it’s true that those setbacks can make the ultimate success even sweeter. These nine ideas can turn what you thought was a failure into a stepping stone for future success.

So step forward, step up, and succeed!

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Why Are You Hesitating?

There are many things that can limit a person’s ability to lead. Hesitating when action is required is one of the more common characteristics of weak leadership. 

 

There is rarely a perfect time to act. If you wait for that perfect time when all the stars are aligned and every conceivable obstacle has been removed then it’s likely you’ll never act at all. Sitting still makes it impossible to go anywhere so unless you’re already exactly where you want to be you better do something.

 

Some leaders hesitate because they are afraid of risk. Well here’s the deal…risk is mandatory if success and growth are your goals. The legendary Randy Gage (if he’s not a legend he should be) wrote a book in 2013 called “Risky is the New Safe.” The title pretty much says it all. I highly recommend this book if you’re struggling to take the leap of trying something new. It’s available on Amazon for under 10 bucks but it’s value remains priceless. 

 

The fact is the riskiest thing you can do in almost any situation is nothing. Yet nothing is what way too many people in leadership positions do when action is called for. That’s a direct path to failure.

 

Limited leaders also hesitate because they know that they need help yet they refuse to ask for it. They see acknowledging that they need help as a sign of weakness. Even the biggest most powerful trains sometimes need an extra engine to get going. Perhaps you need a boost too. It’s not a weakness to ask for help, it is in fact a sign of strength. If you need help ask anyone and everyone until you have the help you need to succeed.

 

Many failed leaders procrastinated past their window of opportunity. They may have convinced themselves that they were being patient. They were really hiding in their comfort zones waiting for the opportunity to pass. Their belief is that if you didn’t try then you cannot fail. They didn’t realize that their failure to try was their biggest failure of all. 

 

Patience is the acceptance that things can happen in a different order than you had in mind. When you don’t know what to do next just do the next right thing. The “order” of things will work themselves out if you keep doing the next right thing. 

 

Joseph Addison said “He who hesitates is lost.” He said that in 1713. I’m thinking life moved a little slower back then. Today that phrase might be updated to say, “if you even think about thinking about hesitating you have zero chance to succeed.”


Business and life in general move so fast these days that not only do you lose if you hesitate, you’re not even in the game. 

Are You Too?

The excuses I hear most often when someone can’t or won’t do something usually have the word “too” in them somewhere. As in, “I’m too busy.” Or “I’m too old to learn.” Or “I’m too important to do that job.”

 

Here’s what the most successful people would tell you…. no one is “too” for anything. 

 

I understand that sometimes we don’t want to do something. I also understand that sometimes we don’t have a good reason for not wanting to do it. I get that’s why we make excuses. 

 

But geez, if you’re not going to put any effort into doing the thing you don’t want to do at least put some effort into a better excuse. 

 

I remember the story about George Steinbrenner the long-time owner of the New York Yankees who passed away in 2010. A group was visiting Yankee Stadium and for whatever reason no one was available to show them around. Steinbrenner offered to do it himself. 

 

While attempting to lead the group across the field they were stopped by security. Mr Steinbrenner was informed he didn’t have the proper credentials to cross the field. The security guard directed him to take the group back up the long stairs and walk the long way around the stadium. 

 

The guard didn’t recognize the owner of the team. Rather than pull the “don’t you know who I am” card Steinbrenner dutifully lead his group all the way back up and around the stadium. He wasn’t too important to give a tour and he wasn’t so important that he felt the need to embarrass the security guard who was merely doing his job. 

 

George Steinbrenner wasn’t too important to do any job.

 

I recall years ago meeting a man who would become a good friend and mentor. He was already arguably the very best salesperson who ever lived. He had sold billions, yes billions, in life insurance yet I met him in a sales training program. He was well over 60 years of age at the time. I expressed a little surprise that someone of his “experience” would be in a sales course. He said, “well, intelligence begins with the knowledge that you’re never too old to learn.” 

 

He was in a sales training program to learn, one that I was going to help teach, yet that single sentence taught me more than I could ever teach him.

 

As for those who feel they are “too busy” I have very little sympathy for you. No one has more time than you! Everyone has 1440 minutes a day. The people who manage to get everything important done in that amount of time have simply stopped long enough to learn how to prioritize. 

 

They know what’s important and they know that most things aren’t important. They are never “too” to accomplish what they need to do to succeed. 

 

The most successful people don’t make excuses, they make things happen. They are never too busy, too tired, too old, or too important to do the things that less successful people simply don’t like to do. 


So…are you too?