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Enterprise or Entrepreneurial: Which Leader Are You?

Someone looked me in the eye recently and said, "You are not an entrepreneur." Another told me, "You are not a visionary leader." I'll be honest — both felt like a throat punch. A clear message that I wasn't enough.

Around the same time, I came across a piece by Steve Graves that named exactly what I was wrestling with. In "Enterprise vs Entrepreneurial: What Kind of Leader Are You?" he draws a clean line between two kinds of leadership every organization needs:

    Entrepreneurial leaders disrupt, motivate, pivot, and move fast — the kind of leadership an     organization never outgrows needing, whether it's declining or standing still. Enterprise     leaders, by contrast, bring order to the chaos: they unify siloed departments around a shared     purpose, pressure-test opportunities before chasing them, and streamline operations so     growth doesn't lead to burnout.

I've worked alongside entrepreneurial leaders my whole career, and they are remarkable. The ability to see a future no one else can see, and move toward it before anyone else will, is rare. True entrepreneurs are few, and they can take an organization somewhere unprecedented. But that gift comes with a price tag. A mentor once described it to me this way: "They make decisions that don't have feelings. If it works, great. If not, we fix it and move on." It isn't personal — it's just the cost of doing business. Can you build an organization on entrepreneurial leadership? You can, if enterprise leadership is standing right beside it.

Enterprise leaders bring two things to the table: strategy and execution. The ability to conceptualize a vision, build a strategy around it, and oversee the execution is a kind of leadership that shapes an organization from the inside out. Ironically, strategy and execution both complement and collide with each other. At their best, they work like a cog and a gear — fitting smoothly, creating efficiency, moving the mission forward. Out of sync, it's the same analogy with a very different result: grinding, conflict, miscommunication, misaligned goals. Most organizations settle somewhere on the line between the two extremes. The best enterprise leaders keep working to move the organization toward the healthiest point on that spectrum.

I know this firsthand, because I've lived it. Before I left Orlando for Tampa, I took a personality assessment — the pastor was simply instructed to have me take it. Years later, I learned the rest of the story. The results showed I was a dominant leader in strategy and execution. Our Founding Pastor was an entrepreneurial leader. The person who administered the test told him one thing: "If the two of you team up, you'll see remarkable results." We did — even as we added staff, even as the mission grew. The church went from 125 people to more than 14,000 on a weekend. The gear and the cog worked.

It wasn't without friction. Both leadership styles are strong-willed and dominant — that's what makes them leaders. A few principles kept it working:

Respect and trust each other. Neither style is greater than the other. Titles may signal hierarchy, but the way each leader uses their gifting deserves equal value and respect — that's what lets both be fully expressed.

Communicate constantly. Silence creates gaps. Gaps cause people to take initiative no one expected, make assumptions, and build stories that aren't true. Communication keep everyone focused and on goal.

Decision Clarity. The entrepreneurial leader should only make decisions at the level only they can make — anything below that breeds confusion. Enterprise leaders should do the same, while continually pushing decisions down to leaders under them who are ready for the authority and responsibility. That's what builds a culture of growing leaders.

Carry the culture together. The entrepreneur defines the culture and lives it out. The enterprise leader lives it out too — and holds others accountable to it along the way.

So which are you? Now do something with the answer. Find the leader on the other side of the spectrum from you — the entrepreneur if you're enterprise, the enterprise leader if you're entrepreneurial — and have one honest conversation with them this week. Ask where the gaps are. Ask where the trust needs rebuilding. Leadership like this doesn't happen by accident; it happens in the room, on purpose. Step in. Be that leader.