Leadership Lessons - Pt 1

Delegate Until You're Uncomfortable, Then Do it Some More

I’ve started a list—something I may teach someday. When I’m in my 70s, I want to be able to look pastors and leaders in the eye and share what I’ve learned over the years. A few years back, I began compiling a list called “Things I’ve Learned in Leadership,” which now has about 20 entries. I imagine it’ll be much longer by the time I reach 70.

For my ReLeader community, I thought I’d start sharing some of these insights with you. Over the next several weeks, I’ll post different leadership lessons I’ve learned.

Let’s dive in—here’s the first one:

Delegate Until You’re Uncomfortable, Then Do it Some More

In my early years as Vice President at a small university, I learned leadership the hard way. There was no roadmap, no manual, and certainly no one to delegate to. I was trained in the school of "pull up your bootstraps and get it done yourself." That was my crucible—a relentless proving ground that forged my early leadership style. With only an executive assistant—one I shared with the President—I was practically a one-man show.

As the VP for University Advancement, I was responsible for everything fundraising. I developed fundraising strategies, established and cultivated alumni databases, created campaign materials, organized banquets, launched initiatives, and flew across the country to meet with major donors. Sometimes, after raising funds for a new project or renovation, I’d roll up my sleeves and step into work pants, tackling demo, laying tile, texturing, and painting walls myself if it helped stretch our budget.

This grind taught me resilience and built in me a relentless “get it done at all costs” attitude. And while I’m grateful for that tenacity and drive, there came a point where it wasn’t enough to sustain me as a leader—or to help others thrive under my leadership. I had to evolve. Moving to the next level required a shift: from a “get it done at all costs” mindset to a “delegate at all costs” approach.

When I transitioned into ministry as a campus pastor in 2011 and then as Lead Pastor in 2014, I carried the same “get it done at all costs” mindset with me. It’s an interesting dynamic because, on the surface, this trait seems invaluable. Who wouldn’t want someone on their team who’s relentlessly committed to getting things done? In many ways, it is a powerful trait.

But over time, I discovered a hidden limitation—a kind of glass ceiling over my potential. To truly step into the fullness of what God had placed within me, I had to break through this ceiling. That drive to do everything myself was holding me back from the growth, impact, and influence I was meant to achieve. It was only by shifting my approach that I began to unlock the greater potential God had prepared for me.

My Epiphany Moment

In April 2018, I got a call from The King’s University in Southlake, TX, offering me the role of university president. I was stunned by the invitation. I missed higher education deeply, and this role seemed tailor-made for me—all my degrees, including my doctorate, were in higher education and university administration. But I also loved ministry; Victory Church was where my heart was. The thought of leading both was exhilarating yet overwhelming.

That same day, I went to my pastor’s house for one of our regular workouts, and I shared my dilemma with him. I told him how crazy it felt to even consider leading a church in Oklahoma while also heading up a university in Texas. “How could I possibly do both?” I asked, half-expecting him to laugh at the absurdity of it all.

But he didn’t laugh. Instead, he looked at me and said, “Jon, you know what your problem is? You’ve only met the God of ‘or.’ But you’re about to meet the God of ‘and.’”

That one line changed everything. In a moment, he unlocked a new understanding of God’s limitless nature—one that didn’t box me into an either-or mindset but opened me to the expansive “and” of God’s calling. It was one of the most transformative moments of my life.

But it wasn’t going to be enough to just have a “one-liner” spoken over me. It was going to require transformative action that would thrust not just me, but a team of individuals into new heights of leadership.

Take the Step

As my start date with TKU approached, doubts crept in. I wasn’t sure if the members of my lead team were ready to handle the day-to-day responsibilities in my absence. Once again, my pastor’s words shook me awake. In one straightforward conversation, he made it clear that the issue wasn’t them—it was me. I was their lid. By always being in the room and leading every detail, I had unintentionally stifled their growth.

What we often overlook is that our presence as leaders can unintentionally limit the very people we’re called to develop. When we’re always the ones in charge, we become a ceiling over their potential, and they never get the chance to rise to the heights God has prepared for them. My pastor said to me, “Jon, once you get out of the way, they’ll blossom, grow, and lead in ways you’ve never seen before.” He was right. Over the next months and years, this lead team rose to the occasion. With my decision to step back, two things happened simultaneously: my own leadership capacity expanded, and so did theirs.

This change wasn’t easy. I was used to having my hands on everything, believing that effective leadership meant handling it all myself. But when I released control, it was as if new doors opened for both me and my team. Their skills sharpened, their confidence grew, and their ownership of the mission deepened. I began to see that one of the most impactful things I could do for my team was to trust them, empower them, and get out of their way.

If I hadn’t stepped into the role at TKU, neither my leadership nor theirs would have grown as it did. In truth, without room to expand, many of them might have sought opportunities elsewhere where they could fully lead. Sometimes we think we’re indispensable, but by clinging to that belief, we can end up holding others back from the roles God has for them.

Here’s the lesson: don’t wait until circumstances force you to delegate. Ask yourself, “Could God be waiting for you to release what you’re holding before He can hand you what’s next?” When we learn to entrust others with responsibility, we not only grow ourselves but open up space for others to thrive, too.

Effective leadership isn’t about doing everything yourself; it’s about empowering others to help carry the mission forward together. In the end, stepping aside doesn’t diminish your influence; it magnifies it. True growth comes when we let go and trust God to work through others as He works through us.

Delegate until you’re uncomfortable, then delegate some more.