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July 22nd, 2026

Episode 289: The Blind Spots Holding Leaders Back

  1. Episode 289: The Blind Spots Holding Leaders Back Darrin Peppard 12:41

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 Dr. Darrin Peppard

Dr. Darrin Peppard is an author, leadership coach, consultant, and speaker focused on organizational culture and climate, and growing emerging leaders. Darrin is the best-selling author of the book Road to Awesome, and is the host of the Leaning into Leadership podcast. As a ‘recovering high school principal’, Darrin shares strategies and lessons learned from 26 years in public education to help leaders gain clarity, find joy in their work, and walk in their purpose.