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?

How to Become an Agile Leader

If I were only allowed to give first-time leaders one piece of advice, it would be this. Always always always expect the unexpected. That’s because leading involves people, and people, no matter how well you know them, will surprise you.

Frequently.

Out of nowhere, they say something, do something, or don’t do something that you just didn’t see coming. Personally, that’s one of my favorite things about leading people. Even the most predictable people are, at times, unpredictable.

When you add all the other uncontrollable elements into the leadership mix, it can feel as if you’re always on the verge of outright chaos. Unless, of course, you’ve already descended into the realm of total chaos.

That’s why it’s so incredibly important that leaders consistently focus on developing leadership agility.

Leading with agility means being adaptable, responsive, and proactive in navigating change while keeping your team aligned and motivated. If you’re feeling like you’re on the edge of chaos, it’s very likely your people feel it too, and that can be a huge morale killer. You can’t afford to let that happen. Here’s how you can lead with agility and calm the stormy waters of surprise, whether it’s generated from your people or circumstances that seem to be beyond your control.

1. Embrace a Learning Mindset

View change as an opportunity rather than a threat.

Encourage continuous learning and innovation. Here’s the deal: if you’re in a leadership position and you’re not always learning, then you better be ready to always be leaving.

Be open to feedback, both good and bad, and be willing to pivot when needed.

2. Make Quick, Informed Decisions

Gather relevant data but avoid analysis paralysis. You will at times, maybe even often, be required to make decisions with less than complete information. Remember, no decision IS a decision; it’s a decision to do nothing, and that’s almost always a disastrous decision.

Trust your instincts while staying adaptable.

Involve your team in decision-making to gain diverse insights.

3. Empower Your Team

Foster a culture of accountability and trust. Everyone, including the leadership team, must be accountable for results. If even one person isn’t accountable, it doesn’t take long to lose all accountability within an organization.

Give your team the autonomy to make decisions and solve problems. If you’ve hired the right people, this should never be a problem. If you haven’t hired the right people, this won’t be a problem for very long.

Encourage cross-functional collaboration to enhance adaptability.

4. Stay Customer-Centric

Keep your focus on what your customers or stakeholders need. Focusing on your customers and stakeholders ensures you won’t get too far off track, no matter what level of chaos you’re navigating.

Be ready to shift strategies based on feedback and market trends.

5. Build Emotional Intelligence

Remain calm and composed under pressure.

Understand and manage your emotions while recognizing the emotions of others. Leadership is about people, and people tend to be emotional. If you forget that, it won’t be long before you’re a forgotten leader.

Communicate effectively, even in uncertain situations. It’s better to say “I don’t know” than it is to say nothing and leave your people wondering.

6. Create a Resilient Culture

Normalize failure as a part of growth and learning. There are few mistakes or failures big enough to prevent a person or an organization from bouncing back. Just remember to be kind to the people you see on the way up because you may see them again on the way down.

Encourage experimentation and reward adaptability.

Create a safe environment where people feel comfortable sharing ideas.

7. Leverage Technology and Data

Use digital tools to enhance decision-making and efficiency.

Stay ahead of industry trends and technological advancements.

Don’t wait and see; when new technology becomes available, use it as soon as it makes sense.

8. Be Ready to Pivot

Have contingency plans in place. Plans fail but planning always succeeds. Everyone seems to know that backup plans are important; not everyone seems to understand that you can’t have a backup plan until you have a plan to begin with.

Be willing to change direction the moment circumstances require it.

Final Thought

Agile leadership is about balancing decisiveness with flexibility, control with empowerment, and strategy with execution. The more adaptable you are, the more effectively you can lead through uncertainty and change.

Authentic, effective, and agile leaders take charge of change before change takes charge of them. As an agile leader, you can turn change and even uncertainty into a tool to help develop your people and your organization. All you need to do is always, always, always expect the unexpected.

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?

Recognizing the Importance of Recognition – Part Two

One of the leading causes of procrastination is lack of know-how. People delay starting a task or project because they don’t know how to begin. They also lack resources and don’t know who to ask for help, if they even have the courage to ask.

I think that’s also one of the big reasons why more people in leadership positions don’t give their people the recognition they often deserve. They know their people need and appreciate recognition, but they aren’t really sure what recognition actually is. They also lack an understanding of the various forms of recognition. So instead of providing their people with meaningful recognition, they provide themselves with the excuse of being too busy to recognize anyone.

So let’s provide some series “know-how” here so there will be no need for the “busy” excuse.

Providing recognition to your team is essential for fostering engagement, boosting morale, and reinforcing desired behaviors. Here are some tried-and-true suggestions for providing truly meaningful recognition to your people.

1. Tailor the Recognition

Know the Individual: Some employees prefer public praise, while others may value private acknowledgment.

Personalized Rewards: Consider their interests, preferences, and professional aspirations.

2. Be Timely

Recognize achievements as soon as possible after they occur. Immediate feedback reinforces the connection between the effort and the acknowledgment.

3. Be Specific

Highlight exactly what the employee did and why it mattered.

Example: Instead of just saying, “Great job,” say, “Your innovative solution to the customer’s issue helped us earn the sale on time and exceeded their expectations.”

4. Use a Variety of Methods

Verbal Praise: During meetings or one-on-one sessions.

Written Recognition: Personal notes, emails, or newsletters.

Formal Programs: Employee of the Month or annual awards.

Monetary/Non-Monetary Rewards: Bonuses, gift cards, extra time off, or experiences.

5. Celebrate Milestones

Acknowledge work anniversaries, project completions, or personal achievements.

Host celebrations for the team’s successes.

6. Encourage Peer-to-Peer Recognition

Implement systems that allow employees to recognize each other, such as a shout-out board or team kudos during meetings.

7. Leverage Technology

Use platforms or apps designed for employee recognition, where contributions can be celebrated company-wide.

8. Incorporate Into Culture

Make recognition a regular practice, not a sporadic event. Encourage leaders at all levels to model this behavior.

9. Focus on Impact

Show how their efforts contribute to the organization’s goals and impact the team.

10. Involve Leadership

Recognition from senior leaders carries weight. A quick message or handshake from an executive can leave a lasting impression.

Examples of Recognition Actions:

A surprise thank-you lunch for the team.

Highlighting an employee in a company newsletter or on social media.

Publicly sharing their achievements in meetings.

Offering professional development opportunities as a reward.

Recognizing team members doesn’t happen by accident. The key is consistency and authenticity. Don’t just say words that recognize people; mean those words. People can sense sincerity and they can also tell when you’re just going through the motions. People who feel genuinely appreciated are more likely to remain engaged and motivated.

But the best reason of all for giving your people consistent recognition is this: they deserve it. And if you’re an Authentic Leader, that is the only reason you should need.