My Biggest Leadership Failure

Leadership is often seen as a position of authority that comes with experience, expertise, and confidence.

Sure, that’s true enough. However, I believe the best leaders aren’t just experts but also students.?Leadership isn’t a destination—it’s a continuous learning process.

The best leaders cultivate a beginner’s mind, the ability to approach every interaction, challenge, and opportunity with curiosity and openness. They recognize that everyone and everything around them has the potential to teach them something.

Everyone Is a Teacher: Lessons from Unexpected Sources

One of biggest mistakes leaders' make is assuming they can only learn from people at their level or above. In reality, leadership wisdom exists in unexpected places:

• A junior employee may have fresh ideas that challenge outdated processes.
• A customer may offer insight into your leadership impact from an external viewpoint.
• A competitor may reveal gaps in your strategy that need refining.
• A child may remind you that simplicity and curiosity are powerful tools in problem-solving.

Authentic leadership isn’t about proving what you know—it’s about seeking what you don’t and creating space for others to grow. Who in your daily life might be an unexpected teacher? What insight could they offer if you paid closer attention?

The Power of Observation: Leading by Watching, Not Just Acting

In a world that values action, leaders often feel the need to speak, direct, and decide quickly. However, some of the most valuable leadership insights come from simply observing.

I recall a time when I was newly promoted. We had a huge client meeting, and the morning of the meeting, my boss said he wouldn't attend (that’s another story!) He had prepared the presentation, and being on day two of the job was not a reason to reschedule. I went with his presentation.?

It was a disaster.

I barely had time to review the presentation in the taxi on the way to the meeting and I fumbled through it. Worse, it was the first day a new teammate witnessed my messiness and failure. I never recovered.?

Upon reflection, what if I went to the meeting with curiosity?instead of with someone else's script??

Understanding it’s normal to be nervous, I was 48 hours in, received no training, or support. Yeah, sometimes things are unfair.

I’ve been in plenty of “never been done before experiences” (it’s called life). The client was informed that?my boss wasn't coming and she'd be getting the new person. I could have used that time to build a relationship with her, rather than talk at her.? I could have asked her about the business challenges from the brief I received and got her talking.?

I could have tapped into my training and noticed that the vibe in the room changed quickly, but I was so busy “presenting” that I wasn't connecting. I was wrapped up in being the leader that I wasn't leading. My desire to look good meant I lost the ability to see the situation differently or recognize patterns.?

Sometimes, the most effective leaders say the least and notice the most.

Great leadership isn’t just about making moves—it’s about making the right moves at the right time.?

Now, you might be thinking that I am being hard on myself. Maybe. But I strive for excellence and the good news is I never made a mistake like this again. I offer you a challenge. In your next meeting, focus on observing instead of speaking. What do you notice that you might have missed before?

Expanding Your Leadership Education: The Thirst for Knowledge

Great leaders never stop learning. They actively seek new ideas, challenge their own assumptions, and continuously refine their skills. Some of my best insights came out of gospel choir practice or botanical formulation. Yes, I have diverse hobbies.?

• Read Beyond Business Books – Explore psychology, philosophy, art, and history for fresh leadership insights.
• ?Surround Yourself with Diverse Thinkers – Build a network of people who think differently from you. Include new or younger employees or those outside your industry.
• ?Ask for Feedback Often – you dont have to agree or implement, but hearing form your team, peers, and even competitors can reveal blind spots and innovative thinking.

You need to be intentional and make learning part of your practice and ensuring your leadership skills evolve with the world around you.

The Leadership Classroom Mindset: Applying What You Learn

I created a Leadership Learning Log in Notion. It is a repository that helps me remember all that I’ve absorbed. Sometimes I have a gut feeling that something is significant but I don't always know how I’ll use it. From quotes to concepts. It has served me well. Yes, this information is all google-able. But not with my IP and tagging so I can find it again.??

For the last 20 or so years, I’ve evaluated myself weekly. It’s how I learn from this brilliant brain and how I teach my brain to remember and apply what I’ve learned.?

• ?Weekly Reflection: What did I learn about leadership today?
• Integration: How can I apply this lesson in my work?
• Knowledge Sharing: Who else could benefit from this lesson?

Your Classroom is Everywhere. Are You Paying Attention?

The best leaders don’t just lead—they learn. And their education never stops.

The world around you—your colleagues, team, competitors, and challenges—is a constant classroom. Every conversation, experience, and setback is an opportunity to refine your leadership.?

Story time. What’s the best leadership insight you’ve learned from an unlikely source? I'd love to learn from your story. Drop it below.