July 22, 2026

Episode 289: The Blind Spots Holding Leaders Back

Leadership growth isn't always about discovering a new strategy. More often, it's about becoming aware of something that has been true all along.

In this solo episode, Dr. Darrin Peppard shares two defining leadership stories that changed the way he thinks about coaching, feedback, and personal growth. From a simple conversation with a superintendent that forever changed his communication style to a coaching experience that revealed the hidden system keeping a leader overwhelmed, this episode explores one powerful truth:

Awareness changes everything.

You'll discover why every leader has blind spots, why your team may see things you cannot, and why trusted coaches, mentors, and colleagues are so essential to continued growth.

If you're committed to becoming a more intentional leader, this conversation will challenge you to stop asking, "How am I doing?" and start asking, "What am I not seeing?"

In This Episode

  • Why one sentence from a superintendent transformed Darrin's leadership
  • The difference between our intentions and the experience others have with us
  • Why leadership breakthroughs come from awareness—not simply learning more
  • The coaching conversation that revealed the real source of one leader's overwhelm
  • How organizational systems become invisible over time
  • Why every leader has blind spots
  • The difficult truth about feedback and positional leadership
  • Why coaches don't exist to fix leaders—they help leaders see
  • How servant leadership can unintentionally become a bottleneck
  • The one question every leader should ask someone they trust

Memorable Quotes

"Learning adds information. Awareness changes perspective. Perspective changes behavior."
"Your staff knows what your blind spots are, but they may not feel it is okay to point them out."
"Leadership isn't about becoming perfect. It's about becoming more aware."
"Leadership isn't limited by what we know. It's often limited by what we don't yet know about ourselves."
"Sometimes the first condition we need to create is one where we can see ourselves more clearly."

Resources & Links

  • Learn more about Road to Awesome: https://roadtoawesome.net
  • Connect with Dr. Darrin Peppard on LinkedIn
  • Learn more about HeyTutor: https://heytutor.com/?utm_source=RTA&utm_medium=RTA&utm_campaign=RTA

Sponsor

This episode is proudly sponsored by HeyTutor.

HeyTutor partners with school districts across the country to provide high-dosage tutoring in mathematics and English language arts. Their comprehensive approach—including recruiting, training, scheduling, and managing tutors—allows educators to focus on what they do best while accelerating student learning.

Learn more by visiting the link above.

Connect with Darrin

If this episode challenged your thinking, I'd love to hear from you.

What's one piece of feedback that changed the way you lead?

Connect with me on LinkedIn or visit RoadToAwesome.net to continue the conversation.

If you enjoyed this episode, please subscribe, leave a review, and share it with another leader who could benefit from this message.

Darrin Peppard (00:00)

All right, everybody, welcome into the Leaning Into Leadership Podcast. This is episode 289. And as always, I am your host, Dr. Darren Peppard. Today it's just you and me. No guest. This is our normal midweek, mid month episode. So, no interview, just a conversation, and specifically a conversation about something I've been thinking a lot about lately. In fact,

It started because I was writing the newsletter for this week and as I sat down to put the words on the page, a memory from years ago came rushing back. It's funny how that will happen sometimes. You'll hear a phrase or you have a conversation or somebody asks you a question and something triggers a memory that you haven't thought about in years. And suddenly you find yourself right back in the moment. Well, that's what happened to me.

Before we dive into today's conversation though, I want to pause and thank the sponsor of today's episode.

Today's episode is brought to you by Hey Tutor. This is way too fucking slow. Okay, so let's try again.

Let's try that.

Okay, take two, here we go.

All right, everybody, welcome into the Leaning Into Leadership Podcast. This is episode two hundred and eighty-nine. Today it's just you and me. No guest, no interview.

Yeah.

Alright, we'll try that. All right, take three. Here we go. All right, everybody. Welcome into the Leaning Into Leadership Podcast. This is episode 289. And today it's just you and me. No guest, no interview, just a conversation about something I have been thinking a lot about lately. In fact, it's something that started because I was writing this past week's newsletter.

And as I sat down to put the words on the page, a memory from years ago came rushing back. You know, it's funny sometimes how that happens. You hear a phrase, you have a conversation, something triggers a memory that you haven't thought about in years. And suddenly you are right back in that moment. Well, that's what happened to me. Now, before we dive into today's conversation, I want to pause. I want to thank our sponsor for today's episode.

Today's episode is brought to you by my friends at Heytutor. As school leaders, we're constantly trying to create the conditions where every student has the opportunity to succeed. Sometimes that means improving instruction, sometimes it means strengthening culture, and sometimes it means providing additional support for students who need it the most. That is exactly what Hey Tutor does. Their high dosage tutoring programs in math and English language arts are aligned to your curriculum, your standards, and your students' needs. Better yet,

They handle the recruiting, hiring, training, and scheduling, and management of the tutors, giving teachers and administrators the capacity to focus on the work they need to do. If your district is looking for a proven partner to accelerate learning and support your staff, I encourage you to check out my friends at heytutor.com. Or get down there in the show notes and hit the link. It'll let them know you heard about them here. All right, here's where I want to go with this.

Years ago I worked for a superintendent and he said something that changed the way I communicate. The truth is he probably doesn't know. We had just finished up a leadership meeting. Nothing unusual. People were gathering up their stuff and some side conversations were happening. And as everybody headed back to their buildings, I was getting ready to leave as well. And he simply asked me, Darren, could you stay back for a minute? And he looked at me and he said, Darren, you say I disagree a lot.

That was it. That was the conversation. There was no lecture, no criticism, no embarrassment. Just, Darren, you say I disagree a lot. I remember standing there thinking, really? I do? Because I had absolutely no idea. And like, here's the funny part. He wasn't telling me I shouldn't disagree. That is not what this was about.

He was helping me understand the experience other people were having when they interacted with me. Think about that for a minute. There's a difference between our intentions and the experience other people have with us. I intended to contribute to the conversation. What others were experiencing, though, was someone who seemed to begin every response with disagreement. Those are not necessarily the same thing. And to this day, many years later.

When I catch myself about to say I disagree, which almost never happens, I stop because I still hear that superintendent's voice. I still hear that one sentence. I still go back to that one observation, that one moment, when the glass shattered.

Let me ask you something. Have you ever had one of those moments? Not a colossal failure, not a big public embarrassment, just one conversation where someone helped you see something that you couldn't see about yourself? If you have, you know exactly what I'm talking about. If you haven't, keep listening. I think every leader, every single leader needs to have one of those conversations.

I think one of the biggest myths in leadership is that growth happens because we learn something new. We read a new book, attend another conference, listen to a podcast. Now, don't misunderstand me. I love books. I love conferences. And obviously, I love podcasts. I hope you keep listening to this one. Learning matters, but I don't think that's where our greatest breakthroughs usually happen.

I think our greatest breakthroughs happen when someone helps us become aware of something that has been true all along. The difference is that learning adds information. Awareness changes perspective. And perspective ultimately is what changes our behavior. I saw this recently while coaching a school leader. When we first started working together, the conversation was pretty familiar. They said, I'm overwhelmed.

I just don't have enough hours in the day. I feel like I'm working all the time and I just can't keep up. Have you ever heard that? Maybe you've even said it. So I spent some time observing and watching and asking questions of this leader, trying to understand the work instead of just immediately trying to solve it. And after a while, I noticed something. Every decision went through this leader. Every approval.

Went through this leader. Every question went through this leader. Every little issue found its way to this leader. At first glance, you'd assume, hey, that's just part of the job. But then I asked a really simple question. I asked her, why does everyone have to ask you? And there was nothing but silence. Not defensive silence, thinking silence.

Eventually she said something like, I guess they don't. Exactly. You see, the system had slowly evolved until everyone believed the safest thing to do was just simply ask the leader. The fascinating part, that's not something she had realized that it even happened. It had just become the norm. And because it was a norm, it was just invisible. Boy, once we named it though, everything changed.

Not because we suddenly discovered some revolutionary leadership strategy, but because the leader became aware. Awareness is what unlocked the change. Awareness shattered the glass for her. Can I share what I think is one of the hardest truths in leadership? And I want you to sit with this one because it challenged me. It still challenges me. Your staff knows what your blind spots are.

But they may not feel that it's okay to point them out. Think about that. The people who experience your leadership every single day, they know things about you that you don't know. They know the habits you repeat. They know the expressions you use. They know the meetings that you dominate. They know the decisions that you won't let go of. Heck, they know when you unintentionally shut down a discussion. They know.

But it's the position that changes that relationship. The higher we move in an organization, the fewer people are willing to risk telling us the difficult truth. And it's not because they don't care about us, they do. But power changes conversations. Position changes conversations. That's why leadership can become so lonely. Not because people aren't around us, but fewer people are willing to hold the mirror up for us to see those things.

You know, people ask me all the time, why should I have a coach? Here's my answer. And it has nothing to do with coaches having better answers. The reality is you should have a coach because coaches see things that you can't. That's it. They aren't there to fix you. They're just help there. They are just there to help you see. Some of the biggest breakthroughs. God. Some of the biggest breakthroughs that I've experienced professionally didn't come. Son of a bitch.

They're there to help you see. Some of the biggest breakthroughs I've experienced professionally didn't come because someone gave me a new strategy. It came because someone asked me a question. They made an observation or reflected something back to me that I had never noticed. A leadership isn't about becoming purpose. God. Leadership isn't about becoming perfect. It's about becoming more aware. If I'm honest, I disagree.

wasn't my only blind spot. Early in my career, I thought being a servant leader meant saying yes to everything. I believed that the best leader solved everybody's problems. I believed accessibility meant availability. So I carried everything. Every decision, every issue, every crisis. Until eventually I became the bottleneck. I wasn't trying to control people. I was trying to help. But

That intention doesn't erase what the impact was. I had to become aware that what I thought was serving people was actually limiting their growth. And that awareness changed everything. Another glass shattering moment. So let me leave you with one question. Who is it in your life that has earned the right to tell you something you don't want to hear? Not somebody who wants to criticize you or someone who wants to complain.

I mean someone who genuinely wants you to become a better leader. Do you have that person? And maybe an even harder question. When was the last time you asked them? Not how am I doing, but what is it I'm not seeing? Because here's what I've learned. Leadership isn't limited by what we know. It's often limited by what we don't yet know about ourselves.

The leaders who continue to grow aren't the ones who have eliminated every blind spot. They're the ones who have created a life where people are trusted to hold up the mirror. And sometimes one simple observation, one quiet conversation, one sentence spoken with care can change the way you lead the rest of your career. I know because it happened to me. Now, if today's episode challenged you, I would love to hear your thoughts.

Connect with me on LinkedIn or visit road to awesome.net and let me know what's one piece of feedback that changed the way you lead. If you enjoyed today's episode, I'd appreciate if you'd subscribe, leave a review, and share it with another leader who might also need to hear this conversation. Once again, thank you to my friends at Hey Tutor for sponsoring today's episode. If your district is looking for a partner to accelerate student learning, make sure you check them out down in the show notes. Until next time, remember.

Leadership is the creation of conditions where people can do their best work. Sometimes the first condition we need to create is the one where we can see ourselves more clearly. Have a road to awesome week.