June 17, 2026

Episode 283: Leadership Is the Intentional Creation of Conditions

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What if leadership isn't about carrying more?

What if the true responsibility of a leader isn't solving every problem but intentionally creating the conditions where other people can do their best work?

In this special solo episode of Leaning Into Leadership, Dr. Darrin Peppard reflects on a week of leadership coaching, keynote speaking, and executive development that led him to articulate a philosophy that has quietly guided his work for years.

Building on the response to his recent blog, I Thought I Was Helping - A Perspective on Servant Leadership, Darrin challenges traditional assumptions about servant leadership, delegation, coaching, and what it really means to support the people we lead.

Instead of measuring leadership by how much we carry, this episode invites listeners to rethink leadership through the lens of clarity, coaching, systems, intentionality, and growth.

In this episode you'll discover:

  • Why many servant leaders become trapped in the Cycle of Chaos
  • The difference between creating dependence and creating capacity
  • How coaching conversations create lasting leadership growth
  • Why systems and intentionality matter more than constant problem-solving
  • The leadership question that can transform every meeting and conversation
  • A new philosophy that connects coaching, ALIGN, leadership teams, and intentional leadership

Key Takeaways

  • Great leaders create conditions instead of collecting responsibilities.
  • Coaching is one of the greatest acts of servant leadership.
  • Every meeting, conversation, expectation, and decision creates conditions that shape culture.
  • Leaders escape the Cycle of Chaos when they stop doing everyone else's work and focus on developing people instead.

Memorable Quotes

"Leadership is the intentional creation of conditions where other people can do their best work."
"The Cycle of Chaos happens when leaders stop creating conditions and start doing everybody else's work."
"Sometimes the most servant-hearted thing we can do is ask another question instead of providing another answer."
"Maybe leadership isn't measured by how much we carry. Maybe it's measured by how much capacity we create in others."

Connect

If this episode challenged your thinking, share it with another leader, leave a review, and subscribe to the podcast.

For leadership coaching, keynote speaking, leadership retreats, and weekly leadership insights, visit roadtoawesome.net or darrinpeppard.com

Sponsor Spotlight:

This episode is sponsored by HeyTutor.

HeyTutor partners with schools and districts nationwide to provide evidence-based high-dosage tutoring support in Math and ELA while helping schools remain intentional about staff capacity and student support systems.

Learn more here: HeyTutor.com

Darrin (00:00)

Alright, everybody, welcome into episode 283 of the Leaning Into Leadership Podcast. This is our monthly midweek, mid-month episode of the show. And today will be a little bit different than some of our normal episodes. no guest, no interview, just simply a conversation. It's just me flying solo today. Over the last couple weeks, I have spent so much time traveling across the country. Last week alone,

four time zones in four days. And I've been working with corporate executives, with educational leaders, with leadership teams, and somewhere between all the airports, the conference rooms and the school hallways, I realized something. You know, I've spent years teaching leadership frameworks, the awesome framework, the cycle of chaos, the align framework, coaching, intentionality.

Leadership teams, clarity. And this week, for the first time, I think I felt like I could finally articulate a philosophy that has been underneath every one of those ideas. So in today's episode, I simply want to share with you that growing philosophy that has really percolated its way to the surface. Now, before we jump in, I want to take a moment.

And thank our sponsor for today's episode. This episode of the Leaning Into Leadership Podcast is proudly sponsored by Hey Tutor. And one of the things I believe deeply is that great leaders don't simply react to problems, they intentionally create conditions where people can succeed. That's exactly why I appreciate the work Hey Tutor is doing with school districts across the country. Hey Tutor isn't just a tutoring provider, they're a true educational partner.

Helping districts create the conditions for students to thrive through high-quality personalized learning experiences. With the National Student Support Accelerator Badge for high-quality tutoring, their programs provide targeted literacy and math support that closes learning gaps while giving students the confidence and skills they need to succeed. When leaders intentionally invest in the right systems and the right support, incredible things can happen. To learn more about how Hay Tutor is helping schools,

create those conditions for success, hit the link down in the show notes or go to heytutor.com and let them know you heard about them here on the Leaning Into Leadership podcast. All right, folks, let's dive into this conversation. And I'll start here.

A few days ago, I published a blog that I titled I Thought I Was Helping: A Perspective on Servant Leadership. And the response was incredible. There were a lot of comments that came my way. There were messages from principals and superintendents. I heard from some teachers and some leaders that were in completely different industries that

Essentially were saying, huh, I have not thought about leadership exactly that way. And there were also a couple of comments that disagreed with me completely. And that's normal. I don't take offense to those. I certainly didn't engage or respond or anything like that. But one person essentially said that the entire idea I presented in the blog was, quote, a bullshit excuse not to do your job. Interestingly,

I wasn't offended by that. I was actually kind of fascinated because I realized that we weren't disagreeing about delegation. What we were disagreeing about is what leadership actually is. And I think that is an important conversation. You see, for years I believed that being a servant leader meant doing whatever my people needed. If a teacher had a problem, I solved it. If an assistant principal was overwhelmed, I swooped in.

And took something off their plate. If a difficult parent conversation came up, I was right in the middle of it. I wasn't trying to control everything. I just genuinely believed I was helping. Then I was blessed to work with a leadership coach. Those of you who are longtime listeners to the show, you know that I had an incredible opportunity working with my leadership coach. Completely changed the way I led. I realized

By working with my leadership coach, that my job wasn't to do everything for everybody else. My job was to grow the people around me. And at first, that sounded a lot like delegation. But looking back, I realized it was so much deeper than that. It was a completely different definition of leadership. Now, this past week I mentioned it earlier, but I had the privilege of facilitating a corporate leadership summit. And during that summit,

One of the pieces that I did was working the C-suite executives through a model for coaching conversations. We paired up, and because of an odd number, I got to partner up with one of the C suite executives. And the one I actually got to partner up with was the chief operating officer. And he reflected on a conversation during our coaching conversation that.

he had had that ultimately helped to save an employee's career in their organization. And then I had him coach me through a leadership moment from years ago that still carries emotion from me to this day. Now neither conversation we had was about having a perfect answer. But ultimately both conversations I think were about creating the conditions for reflection, for ownership, and for growth.

The next day I keynoted the Leadership Academy in the state of Missouri. And afterward, one of the audience members stopped me to talk about servant leadership. They said that one statement I said really resonated with their thinking. And see, during the keynote, I said servant leadership isn't doing everything for others. It's empowering others to do for themselves.

A philosophy that I genuinely hold for a long time, something I truly believe. But as it turned out, this particular individual had done his dissertation on servant leadership. And we very much had the same philosophy. He said that many of the folks that are a part of their leadership academy, when they talk about servant leadership, they've realized that they have been carrying everyone else's responsibility because that's simply what they think.

Servant leaders are supposed to do. Ultimately, those leaders are exhausted. I would not be surprised if the respondent who said, Hey, that's a bullshit excuse to not do your job, isn't also exhausted. Now, later in the week, I got to spend two days coaching several leadership teams that I've been working with for well over a year. And our focus was on preparing for the new school year. And what's interesting is we

Spent very little time talking about logistics. Those are systems we've already built. Instead, we focused on instruction. We focused on coaching. We we focused on leadership. And a powerful, powerful piece that came out of that, that came from one of the members of one of the teams was focusing on being really intentional in those first couple weeks of the school year. Like really dialing in on

Creating experiences that allow teachers to focus on what matters most. Somewhere during that week, it really clicked with me. Leadership is the intentional creation of conditions where other people can do their best work. I wrote that down. I stewed on it. I thought about it. I wrote a blog, but didn't use that in there. But I just kept thinking.

And the more I thought about it, the more I believe it. Because if it's true, then my job when I was a principal wasn't to teach every lesson. It was to create conditions where great teaching happened on a regular basis. My job as a superintendent wasn't to solve every problem. It was to create conditions where my principals could lead confidently. My job today

Is not to tell leadership teams what to do. It's to create the conditions where they discover what they're capable of doing together. Think about how much changes when you adopt that philosophy. Suddenly coaching makes sense. Your systems will start to make sense. The aligned framework makes sense. Cycle of chaos makes sense. I mean, this is my thinking through the course of this week.

It all simply makes sense because the reality is the cycle of chaos happens when leaders stop creating conditions and start doing everybody else's work. We become firefighters instead of being architects. We become first responders instead of being developers. We become problem solvers instead of people growers. And the most ironic part of it all is we do.

All of that because we care so much. We want to help. We want to support. We want to serve.

But sometimes the most servant hearted thing we can do is ask another question instead of providing another answer. Sometimes the greatest act of leadership is trusting someone enough to let them struggle, reflect, learn, and grow. That's not abandoning people. That's believing in them. Takes me back to the people who I always identify as my greatest mentors. There are three.

My very first principal, the assistant superintendent who led human resources, who really helped me to learn so much about leadership, and then my leadership coach.

Each one of them gave me the space to struggle. But they pushed me to reflect. They pushed me to learn. And they pushed me to grow.

So maybe the question isn't what should I do? Maybe the better question is what conditions am I creating? Am I creating clarity or am I creating confusion? Am I creating ownership or am I creating dependence? Am I creating confidence or am I creating fear? Am I creating growth or am I creating compliance? Because every meeting that you lead.

Every coaching conversation you're a part of, every system you build, every expectation that you communicate. Heck, for that matter, every hallway interaction, every difficult conversation, every decision you make creates conditions. And people experience those conditions every single day. So maybe leadership isn't measured by how much we carry. Maybe it's measured by how much capacity we create in others. You know, I've spent

26 years in education and another five-year chapter of my life coaching leaders all over the country. I've shared a ton of frameworks over those years. Today, it's simply about sharing a philosophy that I believe is still evolving inside of me. Leadership is the intentional creation of conditions where other people can do their best work.

I'll say one more time. Leadership is the intentional creation of conditions where other people can do their best work. Now, if that idea challenges you, I want to ask you to wrestle with it. If you disagree with it, I want you to think about why. If it resonates with you, it's something I hope you'll carry into your next meeting, into your next coaching conversation, and into the next series of decisions that you make. Because I have a feeling this one idea

has the potential to change not only how we lead, but how the people around us experience our leadership. That's what I have for you this week, folks. Thank you so much for joining me for this special midweek edition of the Leaning Into Leadership Podcast. As always, rate, review, subscribe. Once again a big thank you to our sponsor, HeyTutor. Make sure you get down there in the show notes, click on their link and go check out their services and get out there.

Have a road awesome week.