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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How to Provide Constructive Feedback

If you’re in a leadership position, then you must know that the people you lead want to know some stuff as well. They want to know if they are doing what is expected of them. They want to know if they are meeting or exceeding expectations. They need to know if they’re not.

If you’ve hired the right people, then they have a strong desire to improve over time. They also need to know what “qualifies” as improvement. They want and need to know that what they are doing is worthwhile and makes a difference. They need, absolutely need, to know that they matter.

All of that information can only accurately come from the feedback given to them by you, their leader. If you’re an Authentic Leader, then all feedback, whether it’s feedback leading to corrective action, feedback for continuous improvement, or feedback for positive reinforcement, will be provided in a constructive manner.

Providing constructive feedback is a critical leadership skill that helps your team grow while maintaining motivation and morale. Every member of your team needs regular doses of constructive feedback. Here’s how you can do it effectively.

1. Be Specific and Clear

Vague feedback leads to confusion. Instead of saying, “You need to be better in meetings,” say, “I noticed in today’s meeting that your points were great, but they got lost because you spoke too fast. Try slowing down to ensure everyone follows your ideas.”

2. Focus on Behaviors, Not Personality

Avoid making it personal. Instead of saying, “You’re too careless,” say, “I noticed a few errors in the report. Let’s go through them together to see how we can minimize mistakes next time.”

3. Use the “Praise-Correct-Praise” Method (Sandwich Approach)

Start with something positive, then provide constructive feedback, and end with encouragement.

Example: “Your presentations are always engaging. One area to improve is the clarity of your key points. Maybe structuring them in bullet form could help. Keep up the good work—I know you’ll make it even better!”

4. Encourage a Two-Way Conversation

Feedback should be a discussion, not a monologue. Ask, “How do you feel about this?” or “What support do you need to improve in this area?” This makes them feel valued and involved in their own growth.

5. Provide Solutions, Not Just Criticism

Pointing out problems without offering guidance can be demoralizing. Instead of just saying what’s wrong, suggest ways to improve. “Your report has some missing data. Maybe setting up a checklist before submission could help.”

6. Give Feedback in a Timely Manner

Don’t wait too long. Feedback is most effective when given soon after the event. However, avoid giving feedback in the heat of the moment if emotions are high.

7. Adapt Your Approach Based on the Individual

Some people prefer direct feedback, while others respond better to a softer approach. Understanding how your team members receive feedback can make it more effective.

8. Remember, feedback isn’t always about improving.

Make sure a good percentage of your feedback is positive reinforcement. As Dale Carnegie said, “Be hearty in your approbation and lavish in your praise.” The people you lead crave your approval; make darn sure they get it whenever it is deserved.

9. Follow Up

Feedback is not a one-time event. Check in frequently to see if improvements have been made and recognize their efforts.

Weak leaders are often afraid of providing their people with consistent feedback. They see it as confrontational and they will do most anything to avoid conflict. But an Authentic Leader will tell you that providing well-thought-out, constructive feedback is anything but confrontational. It requires some effort to choose words that uplift rather than tear down. It sometimes requires practicing the feedback conversation beforehand. And it always requires listening and watching to determine if your message is being received.

The essence of leadership is influence. Providing consistent, constructive feedback to the people you lead is one of the most effective methods to influence them in a meaningful and positive way.

So do it!

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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.

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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?

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How to Improve Your Strategic Thinking

One of the many challenges for large, publicly traded companies is that they tend to run their businesses on a quarterly basis. They, of course, will deny this forever, but for many publicly traded companies, the most important quarter in the history of the company is whatever quarter they are currently in.

They have to “make the numbers,” or Wall Street will crush them.

That causes them to jettison a lot of long-term strategies in favor of short-term programs designed to achieve whatever quarterly results they had committed to achieving.

Surprisingly, the need for short-term programs at the end of a quarter most often comes from flawed long-term strategies developed earlier in the year. And better long-term strategies can only come from better strategic thinking.

Strategic thinking can be defined as the ability to analyze complex situations, anticipate future challenges and opportunities, and develop long-term plans to achieve specific goals. It involves a combination of critical thinking, problem-solving, and vision casting to make informed decisions that align with broader, long-term objectives.

Key elements of strategic thinking include:

Vision-Oriented – Focusing on long-term outcomes rather than just immediate problems.

Systems Thinking – Understanding how different elements interact within a larger system.

Analytical and Creative Thinking – Using data-driven insights while also considering innovative approaches.

Proactive Approach – Anticipating risks and opportunities before they arise.

Decision-Making Under Uncertainty – Navigating ambiguity with calculated risks.

Strategic thinking is a must for leaders, businesses, and even individuals who want to remain competitive, adaptable, and successful in achieving their objectives.

Leaders can improve their strategic thinking by developing a mindset that balances big-picture vision with practical execution. Here are key ways you can enhance your own strategic thinking.

1. Expand Your Perspective

Stay informed about industry trends, global developments, and emerging technologies.

Read widely—books, reports, and case studies—to gain diverse insights.

Engage with people outside your immediate industry to understand different viewpoints.

2. Ask Better Questions

Challenge assumptions by asking, “What if?” and “Why not?”

Use first-principles thinking to break down complex problems.

Regularly reflect on long-term goals and whether current actions align with them.

3. Develop Pattern Recognition

Analyze past successes and failures to identify trends.

Observe competitors and market shifts for early signals of change.

Use scenario planning to prepare for multiple possible futures.

4. Think in Systems, Not Silos

Understand how different parts of your organization interact.

Recognize bottlenecks, dependencies, and leverage points for impact.

Align resources and efforts to maximize synergy.

5. Make Time for Strategic Thinking

Block out time for deep thinking, away from daily firefighting.

Engage in brainstorming sessions with your team to explore long-term strategies.

Schedule regular reflection periods to assess progress and refine strategies.

6. Test and Iterate

Implement small-scale experiments to validate strategic decisions.

Use feedback loops to adjust course quickly.

Balance bold vision with flexibility to adapt to new realities.

7. Develop Decision-Making Discipline

Avoid analysis paralysis—focus on key priorities and take calculated risks.

Use data-driven decision-making while keeping intuition in check.

Learn from past decisions to refine future strategies.

All of this takes time. That’s where your mindset comes in. If you consider it a waste of time to block time on your calendar to think, then it’s unlikely you’ll do much, if any, of this. You will instead constantly be congratulating yourself for putting out one fire after another. If your mindset tells you that setting aside time to think and plan is a great investment of time, then you’ll likely prevent the fire in the first place.

Imagine what you can accomplish in the time you would have been firefighting. Whatever those accomplishments might be, I’ll bet they won’t include scrambling to achieve some goal at the end of a quarter or the end of a year. Because those goals will have already been met.

That’s a whole lot more productive and a whole lot less stressful way to lead an organization. But of course, as always, it’s your choice to make.

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Managing Resistance to Change

I have heard there are some people who are resistant to change. I’ve even met some of them. I can’t imagine why anyone but me wouldn’t fully embrace change at every opportunity. 🙂 I know so many people who need to change, and the funny thing is, those seem to be the ones most resistant to it.

Unfortunately, I am sometimes one of those people. As much as I’m usually a big continuous improvement guy, I can also at times be a “let’s just leave well enough alone” guy. I guess I like my changes in small doses. Never-ending change is especially hard to deal with.

Because I’m mostly an average person, it’s a safe bet that many of you feel like I do. If there is a well-defined purpose or reason for a change, then I can get onboard pretty quickly. But if it appears to be change just for the sake of change, I’m going to have a problem with it. I resist, and I can be damn good at it.

If you’re in a leadership position, you need to understand that each member of your team will respond to change differently. Some, like me, won’t always respond to change the same way. Change can be very emotional at times. That’s what makes it so hard.

And yet, as a leader, you know that improvement and growth, in any area, requires change. Change that you are expected to lead your people through. Even those people who resist the change.

Implementing change when your team, or part of your team, is resistant requires a strategic approach that prioritizes communication, involvement, and support.

Here is a proven step-by-step framework to help navigate resistance and drive successful outcomes from your next change initiative.

1. Understand the Resistance

Identify the root cause: Fear of the unknown, past failures, lack of trust, or feeling undervalued.

Listen actively: Have open conversations to uncover concerns and emotions behind the resistance.

2. Communicate the “Why” Clearly

People resist change when they don’t understand it. Explain the reasons for the change and the consequences of not adapting.

Use storytelling and real-life examples to illustrate the benefits.

3. Involve the Team in the Process

Give employees a voice in how the change is implemented. This increases ownership and reduces resistance.

Encourage feedback and make adjustments when possible.

4. Lead by Example

Your team will follow your actions more than your words. Show commitment to the change by embracing it yourself.

5. Provide Support and Training

Resistance often stems from uncertainty or a lack of skills. Offer training and resources to make the transition easier.

6. Create Small Wins

Break the change into smaller, manageable steps.

Celebrate progress to build confidence and momentum.

7. Address Emotional Concerns

Change isn’t just logistical—it’s emotional. Acknowledge fears and frustrations, and reinforce the positives.

8. Build a Coalition of Supporters

Identify influential team members who support the change and leverage them to influence others.

9. Be Patient but Persistent

Change takes time. Stay consistent in your message while being flexible in your approach.

10. Reinforce the Change

Once the change is in place, reinforce it through continuous communication, incentives, and integration into daily work culture.

The vast majority of changes within an organization will come with challenges. That doesn’t mean it has to be painful. Never forget that while you are managing resistance to change, you are still leading your people.

It’s when you slip into the dead zone of trying to manage your people along with the change that the change becomes truly messy and painful. It’s during times of change that your people really need you to lead. So manage the change but lead your people!

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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.

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