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?

Preparing for the Future of Leadership

Change, it has been said, is one of the few certainties in life. While that’s always been true, the pace of change has never been more rapid. Think about it; much of the technology we take for granted today was considered impossible less than 20 years ago.

And it’s not just technology. It’s medical, it’s athletics, it’s societal, it’s literally every part of life.

Most recently, Artificial Intelligence (AI) has increased the pace of change exponentially. Improvements to AI arrive almost every hour. AI looks to be one of the most consequential changes to come along in years, maybe ever. Unless, of course, something else comes along in a few years that makes AI look like no big deal. (Before I could even publish this I received an update on something called “Synthetic Intelligence.” It far far surpasses AI capabilities in that it truly comprehends language. It can also explain it’s reasoning. Looks like it may not take even a few years for AI to be no big deal.)

All that makes it incredibly difficult to predict the future. Perhaps more than it’s ever been. But this much is certain; the increasing pace of change will bring with it multiple unexpected challenges and opportunities.

Leaders who prepare themselves for those future challenges and opportunities will simply outperform those who don’t. Not only will they benefit from that preparation, but their organization will also. It’s likely the people they lead will benefit most of all.

Being prepared for future leadership challenges requires a mix of adaptability, emotional intelligence, strategic thinking, and continuous learning. Here’s how you can stay ahead of the curve to continue leading into the future.

1. Embrace Continuous Learning

Stay informed about emerging trends in technology, business, and leadership.

Read books, take courses, and attend conferences regularly.

Follow thought leaders and engage in discussions to expand your perspectives.

2. Develop Adaptability & Resilience

Change is inevitable; practice leading through uncertainty.

Build resilience by learning from failures and bouncing back quickly.

Encourage a growth mindset in yourself and your team.

3. Enhance Emotional Intelligence (EQ)

Improve self-awareness, empathy, and interpersonal skills.

Build trust and strong relationships with your team.

Be open to feedback and practice active listening.

4. Master Digital & Technological Fluency

AI, automation, and remote work are shaping the future—understand their impact.

Learn how to leverage data-driven decision making.

Stay flexible with new work models (hybrid, gig economy, etc.).

5. Foster a Culture of Innovation & Collaboration

Encourage creativity and experimentation.

Build diverse teams that bring fresh perspectives.

Promote cross-functional collaboration and knowledge sharing.

6. Strengthen Decision-Making Under Uncertainty

Use scenario planning and risk assessment techniques.

Balance logic with intuition when making tough calls.

Learn to make decisions with incomplete information.

7. Lead with Purpose & Vision

Clarify your mission and communicate it effectively.

Inspire others by aligning business goals with meaningful impact.

Keep ethics and social responsibility at the core of leadership.

8. Develop Future Leaders

Mentor and coach emerging talent.

Create succession plans to ensure leadership continuity.

Empower others to take ownership and lead.

If you’re a regular reader of this blog, then you’ll know that over the last few months I’ve written extensively about many of these bullet points. Now we’ve put them together in a forward-looking post.

It requires effort to prepare for the future of leadership. The level of effort you put into any endeavor is completely within your control. The only question is, will you invest the time and make the effort today that’s required to be an effective leader tomorrow?

What do you say?

Developing the Next Generation of Leaders

I used to be shocked when so-called “forward-thinking” organizations couldn’t say who would be leading their organization in ten years. Worse than that, they had no idea who within their organizations would even be a good candidate. They were essentially “rolling the dice” on the future of their organizations every single day.

I’m not surprised by any of that these days because it’s actually very common. Many companies invest millions in new technology and products. However they invest precious little in developing their next generation of leaders. They hope for the best. They assume “when the time comes” that the next generation of leaders will show themselves.

When it comes to leadership, hoping and assuming are very poor strategies.

To build the next generation of leaders, organizations need a smart, long-term plan. This plan should focus on spotting, coaching, and empowering future leaders. Here’s a structured framework to ensure your organization has a strong pipeline of future leaders.

1. Identify High-Potential Employees

Not everyone is suited for leadership. Organizations should establish criteria to recognize employees with leadership potential. Look for:

Strong problem-solving skills

Emotional intelligence

Initiative and accountability

Ability to inspire and influence others

A willingness to learn and accept new challenges

Action Steps:

Use performance reviews and feedback to spot leadership traits

Encourage nominations from peers and managers

Conduct leadership assessments and regular 360-degree feedback

2. Provide Leadership Training and Development

Training should go beyond technical skills to focus on leadership competencies.

Action Steps:

Offer leadership development programs, mentorship, and coaching

Encourage participation in cross-functional projects

Provide soft skills training, such as communication and decision-making

3. Create Mentorship & Coaching Opportunities

Pairing emerging leaders with experienced mentors accelerates growth and fosters knowledge transfer.

Action Steps:

Develop a structured mentorship program

Encourage senior leaders to guide and support high-potential employees

Promote reverse mentoring to allow junior employees to share new insights

4. Encourage Real-World Leadership Experience

Leadership cannot be learned in theory alone—it must be practiced.

Action Steps:

Assign stretch assignments and leadership roles in projects

Offer job rotations to expose employees to different business areas

Provide opportunities to lead meetings, initiatives, or small teams

5. Foster a Culture of Feedback and Continuous Learning

Ongoing feedback helps future leaders refine their skills and adjust their approach.

Action Steps:

Implement regular check-ins and coaching sessions

Encourage self-reflection and adaptability

Provide access to executive leadership for open discussions

6. Align Leadership Development with Organizational Goals

Ensure that future leaders are prepared to drive the company’s vision forward.

Action Steps:

Clearly communicate company values and expectations

Develop leadership competencies that align with business objectives

Measure the impact of leadership development initiatives

7. Recognize and Reward Leadership Growth

Acknowledging leadership efforts motivates employees to develop further.

Action Steps:

Offer promotions or new leadership roles when ready

Recognize leadership contributions through incentives and public appreciation

Build a clear career progression path for emerging leaders

8. Create a Succession Planning Strategy

Leadership development should prepare individuals for critical roles in the future.

Action Steps:

Identify key positions and potential successors early

Build personalized development plans for successors

Review and update the succession plan regularly

By systematically investing in leadership development, organizations can build a strong pipeline of capable leaders who will drive future success. Long-term successful organizations know that the best time to develop their next generation of leaders is today.

If you leave leadership development to chance, then there is a good chance that your organization will lose potential leaders that one day you’ll wish were still on your team. I’m betting you really don’t want that to happen… so don’t.

Leading Across the Generations

Jimmy Johnson is a Hall of Fame American football coach. He coached the Dallas Cowboys to Super Bowl victories following the 1993 and 1994 seasons. He was known for getting the most from his players and was considered to be an excellent leader.

He was asked after winning his first Super Bowl what his “secret” was. His answer has stayed with me to this day. While the typical response at the time would have been some variation of “I coach all my players the same,” his answer was, “I coach all my players differently.” He said each of his players were unique individuals and it made no sense to treat them all the same.

They had different personalities, different goals, different ways of learning, and different challenges to overcome. He made the statement that leading everyone the same guaranteed that some of his team wouldn’t feel led at all. His answers were very insightful.

30 years later, his answers remain spot on. Yet many people currently in leadership positions still try to lead every member of their teams in exactly the same fashion. They believe “leading everyone equally” means they all must be led the same. That causes many of the personnel issues that those same leaders claim to hate.

So let’s take a look at what leading differently might look like. We can’t get to the individual level in a post like this, so instead we’ll look at different generations. A word of caution here: nothing frustrates me more than hearing someone say, “well ALL baby boomers want this,” or “all millennials do that.”

In my view, that’s not only incredibly wrong, it’s also insulting. As we examine the values of each generational group, please understand we are talking in generalities. There will always be exceptions—the kind of exceptions that make us all unique in one way or another.

Leading different generations effectively requires a solid understanding and recognition of their unique values, communication styles, and work preferences. It also requires true collaboration and genuine respect. Here’s a breakdown of what leadership should look like for each generational group.

1. Baby Boomers (Born 1946-1964)

Values: Hard work, loyalty, hierarchy, and personal sacrifice.

Leadership Approach:

Recognize their experiences and contributions.

Provide clear expectations and structured processes.

Use face-to-face communication when possible.

Offer opportunities for mentorship roles.

2. Generation X (Born 1965-1980)

Values: Independence, efficiency, work-life balance, and adaptability.

Leadership Approach:

Give autonomy and avoid micromanagement.

Focus on results rather than rigid processes.

Use direct, efficient communication.

Provide opportunities for skill development and career growth.

3. Millennials (Born 1981-1996)

Values: Purpose-driven work, feedback, collaboration, and flexibility.

Leadership Approach:

Offer meaningful work and explain the “why” behind the tasks.

Provide frequent feedback and coaching.

Foster collaboration and a positive work culture.

Leverage technology for communication and efficiency.

4. Generation Z (Born 1997-2012)

Values: Innovation, inclusivity, authenticity, and digital fluency.

Leadership Approach:

Encourage creativity and embrace new ideas.

Provide opportunities for skill-building and continuous learning.

Use digital tools for communication and collaboration.

Support work-life balance and mental well-being.

Cross-Generational Leadership Tips

Emphasize Common Goals: Align everyone around shared objectives.

Leverage Strengths: Utilize each generation’s strengths in teamwork.

Be Flexible: Adapt leadership styles to different preferences.

Encourage Mentorship: Facilitate knowledge-sharing between older and younger employees.

Foster a Culture of Respect: Encourage open dialogue and mutual appreciation.

If you’re in a leadership position and you’re still trying to lead everyone on your team the same way, then I’d recommend you stop that today. Do not lead your people the way you want to lead them; lead them the way they need to be led. If you’re an Authentic Leader, those two ways already align.

If they don’t, then use these ideas to align your leadership style with your people; it will be good for you and absolutely fantastic for them.

Powerful Habits of Successful Leaders

Successful leaders possess many characteristics and traits that contribute to their success. So many, in fact, that it is difficult to say exactly which characteristics a person must possess to be a successful leader.

I’d say integrity and judgment are absolutely essential, but it can become somewhat debatable after that. A characteristic that is very impactful for one leader may not play much of a role in the success of another. But, most leaders who have positively impacted their people share habits. These habits inspire trust, motivate teams, and drive results.

Here are some of the best habits of effective, successful leaders.

1. Clear Vision and Purpose

Habit: Define a clear vision and communicate it effectively.

Why it matters: A clear sense of direction helps align the team and focus efforts on shared goals.

2. Active Listening

Habit: Actively listen to others’ concerns, feedback, and ideas. Don’t interrupt or assume.

Why it matters: It builds trust, fosters teamwork, and ensures that leaders understand the needs and challenges of their team.

3. Consistent Communication

Habit: Regularly share updates, expectations, and constructive feedback.

Why it matters: Open communication minimizes misunderstandings and keeps everyone on the same page.

4. Emotional Intelligence (EQ)

Habit: Practice self-awareness, empathy, and emotional regulation.

Why it matters: Leaders with high EQ navigate interpersonal dynamics effectively, building strong relationships and maintaining a positive team culture.

5. Lead by Example

Habit: Demonstrate integrity, accountability, and hard work.

Why it matters: Teams are more likely to mirror the behavior of their leaders, creating a culture of excellence and accountability.

6. Decisiveness

Habit: Make informed decisions promptly and confidently.

Why it matters: Decisive leaders instill confidence in their teams and keep projects moving forward.

7. Adaptability

Habit: Embrace change and be flexible in the face of challenges.

Why it matters: Adaptable leaders can pivot effectively. This keeps their teams resilient in uncertain times.

8. Empowering Others

Habit: Delegate responsibilities and trust team members to deliver.

Why it matters: Empowering others fosters ownership and encourages professional growth within the team.

9. Continuous Learning

Habit: Seek feedback, stay curious, and pursue personal and professional development.

Why it matters: Leaders who learn and grow inspire their teams to do the same and remain relevant in a rapidly changing world.

10. Recognizing and Celebrating Success

Habit: Acknowledge achievements, big or small, and celebrate milestones.

Why it matters: Recognition boosts morale, motivates teams, and reinforces positive behavior.

11. Strategic Thinking

Habit: Look at the bigger picture and plan for the long term.

Why it matters: Strategic leaders anticipate challenges and opportunities, ensuring sustainable success.

12. Resilience

Habit: Stay composed and positive during tough times.

Why it matters: Resilient leaders inspire their teams to persevere and overcome obstacles.

We often tend to think of habits in a negative light, but these are all very positive habits. Leaders can inspire their teams and build trust by developing and practicing these habits. They will achieve lasting success. Which of these habits resonates most with you?

Earning the Right to Lead

One of the most common mistakes new leaders make is assuming that their position or title makes them a leader. It is as if one day they were individual contributors and the next day they were a respected leader. All because they have a new title or a position higher up in their organization.

But all the title or position does is give them the opportunity to earn the right to lead. It’s an opportunity that was available to them before they even had that position or title. They either didn’t realize it, or more likely, saw no need to earn the right to lead until they were actually in a leadership position.

But anyone who truly leads has earned that right by developing certain qualities and characteristics that inspire trust, respect, and commitment from others. They know that leadership is less about their title and more about the influence they build through their actions.

Here’s how you can also earn the right to lead.

1. Lead by Example

Integrity: Do what you say you will do. Consistency in your values and actions builds trust.

Work Ethic: Be willing to do the hard work. People follow those who demonstrate commitment. Never, ever forget that you’re leading by example, whether you intend to or not. It’s foolish to expect the people you lead to outwork you. You must show the way before you can lead the way.

Humility: Acknowledge your mistakes and remain open to feedback and learning.

2. Develop Strong Relationships Throughout Your Organization

Empathy: Understand and care about the needs, feelings, and challenges of others. Leaders who show empathy build deeper connections with their teams.

Active Listening: Pay attention to others’ input, showing that their opinions are valued.

Trust: Earn and give trust by being reliable, supportive, and respectful. We all have within us what I call a “credibility bank.” Every time we do exactly what we say we will, a small deposit is made into our credibility bank. Each time we fail to do exactly what we said we would do, a large withdrawal is made from that same credibility bank. That may not seem fair, but that’s the way it is. When your credibility balance goes too low, you lose the opportunity to lead.

3. Be Competent

Knowledge and Skills: Demonstrating expertise in your field and continuously learning builds credibility. When people know you’re skilled, they’ll trust your decisions.

Decision-Making: Be decisive but also thoughtful. Balancing analysis with intuition helps others to believe in your leadership.

Problem Solving: Leaders who can navigate challenges and come up with effective solutions gain the confidence of those they lead. And always remember, you are not the only one in your organization with good ideas. Listen to your team; your success as a leader depends on it.

4. Serve Others

Servant Leadership: Prioritize the needs of your team and help them succeed. When people feel you’re invested in their growth, they’re more likely to follow you.

Support and Empower: Encourage your team, give them the tools and freedom to excel, and celebrate their successes, big and small.

5. Communicate Frequently and Effectively

Clarity and Transparency: Be open about your goals, vision, and the reasoning behind decisions. Clear communication reduces uncertainty and builds trust. Information is the enemy of rumor. The more effectively you communicate with your people, the fewer productivity-killing rumors you’ll have to deal with.

Inspire: Share a vision that motivates others. A good leader knows how to articulate purpose and drive passion.

6. Build Credibility Over Time

Consistency: Leadership is earned through long-term behavior, not one-time acts. Be consistent in your character, values, and performance.

Accountability: Hold yourself accountable for your actions and the outcomes of your team. When things go wrong, accept responsibility; when things go right, share credit.

7. Adaptability

Embrace Change: Leaders must be flexible and open to new ideas. Being adaptable demonstrates that you’re capable of guiding others through evolving situations.

Resilience: Show strength in tough times. People look to leaders for confidence and direction when facing adversity.

8. Emotional Intelligence

Self-Awareness: Understand your own emotions, strengths, and weaknesses. Leaders who are self-aware make better decisions and manage relationships effectively.

Social Awareness: Recognize group dynamics, understand others’ emotions, and respond appropriately. This skill helps navigate complex interpersonal situations.

These are the qualities and characteristics that will help you earn the right to lead. By consistently embodying these traits, you build trust, respect, and influence. That ensures you have the commitment of the people you lead.

People in leadership positions who lack these qualities and characteristics can attempt to force the compliance of their people, but it’s unlikely they will ever have their commitment.

Learning to Lead

In our last post, we discussed why so many people who are promoted into leadership positions fail to actually lead. One of the big reasons is simply that they don’t know how to lead. And no one shows them. The vast vast majority of people in leadership positions never receive even one minute of formal leadership training.

So I suggested that if you find yourself with the opportunity to lead, you shouldn’t wait for your company, organization, or anyone else to teach you to lead. You should take the initiative and learn to lead on your own.

I received a bunch of feedback from people telling me that they couldn’t do that. In fact, they said there was nothing they could do. They were doomed to muddle through the best they could.

So let’s get something clear right from the start. There is ALWAYS something you can do. No matter what situation you find yourself in, no matter how you got there, no matter if you put yourself into that situation or you were put there by someone else, there is ALWAYS something you can do.

There is probably no more limiting belief in life than the belief that you are powerless over any situation in your life. If you buy into that belief, you will be unlikely to ever live your best life or come close to reaching your full potential.

You may need some help, it’s likely in fact. You could benefit from a mentor, coach, or close friend to help you strategize your way through whatever situation you’re dealing with. But never lose sight of this amazing truth: there is ALWAYS something YOU can do.

So, what does that something look like when it comes to learning to lead? That’s an interesting question because neither I nor anyone else can teach you to lead. I can share with you the characteristics of an Authentic Leader, I can offer ideas on how to develop those characteristics for yourself. I can even advise on more effective human relations approaches for dealing with people. But I can’t actually teach someone how to lead.

Using their own personality and skills, they must teach themselves the most effective way to lead others.

That will involve developing a range of people skills, characteristics, and attitudes. Here are some ideas to help you on this journey towards Authentic Leadership.

1. Self-Awareness and Self-Improvement

• Assess Strengths and Weaknesses: Understanding your own strengths and weaknesses is crucial. Tools such as personality tests, 360-degree feedback, and self-reflection can be helpful. Being 100% honest with yourself is vital here.

• Set Personal Goals: Identify areas for improvement and set specific, measurable goals to work on. Then work on them EVERY SINGLE DAY.

• Seek Feedback: Regularly ask for feedback from peers, mentors, and team members to understand how you can improve. Don’t be even a little defensive when accepting this feedback. If you’ve asked the right people, they’re legitimately trying to help you.

2. Learning and Development

• Education and Training: Take courses in leadership, management, communication, and other relevant areas. Online platforms, universities, and workshops offer valuable resources.

• Read Widely: Read books, articles, and case studies on leadership to learn from others’ experiences. Read constantly, read consistently, and never stop reading.

• Learn from Leaders: Study the behaviors and strategies of successful leaders in your field. Authentic Leaders lead by example; one of the best ways to teach yourself to lead is to closely watch those who already lead authentically.

3. Practical Experience

• Take on Leadership Roles: Seek out opportunities to lead, whether in your job, community, or other activities. Volunteer for projects or committees where you can practice leadership skills. Leadership is a skill that’s learned by doing, so do.

• Start Small: Begin with smaller leadership roles and gradually take on more responsibility as you build confidence and competence.

• Reflect on Experiences: After leading a project or team, reflect on what went well and what could be improved. Doing a “debrief” with yourself and a mentor or coach is crucial to self-improvement.

4. Develop Key Skills

• Communication: Work on both verbal and written communication. Effective leaders are good listeners and clear communicators.

• Decision-Making: Practice making decisions, both small and large, and learn to weigh the pros and cons effectively.

• Conflict Resolution: Learn techniques for resolving conflicts and managing difficult conversations.

• Emotional Intelligence: Develop the ability to understand and manage your own emotions and those of others. As I’ve said thousands of times, leadership is about people. People, including you, are emotional. To master leadership, you must master your emotions.

5. Building Relationships

• Networking: Build a strong network of contacts within and outside your organization. Networking can provide support, advice, and opportunities.

• Mentorship: Seek out mentors who can provide guidance and support. Being a mentor to others can also develop your leadership skills.

• Team Building: Learn how to build and maintain high-performing teams. This includes understanding team dynamics and fostering a collaborative environment.

6. Demonstrating Leadership

• Lead by Example: Model the behavior you expect from others. Integrity, accountability, and a strong work ethic are essential.

• Empower Others: Encourage and support team members to take the initiative and develop their own leadership skills. You don’t have to be at the top of your organization to begin the process of building more leaders. Start where you are and begin with whatever skills you possess today.

• Adaptability: Be open to change and willing to adapt your leadership style to different situations and team needs. No two people are truly identical. You’ll need to make adjustments early and often if you’re going to succeed as a leader.

7. Continuous Improvement

• Stay Informed: Keep up with trends and developments in your industry and in leadership practices.

• Adapt and Evolve: Be willing to change and improve your leadership approach based on new insights and feedback. Becoming an Authentic Leader is a journey. The moment you think you’re good enough, you’re no longer good enough. The moment you think you’ve arrived, you’ve missed the boat. Never never never stop evolving because when it comes to leadership, the last thing you want to be is good enough.

If it sounds like Authentic Leadership requires a lot of effort, you are correct. It absolutely does. But the rewards are beyond incredible. Helping someone is great. But, helping them become a leader means you’re also helping them help another person, someone you may never know. That’s phenomenal!

So I highly encourage you to make the effort. You will never regret that you did.