Three essential entrepreneurial skills for church leaders

This article previously appeared on Ministry Matters and Path1 / Church Planting from Disciples Ministries

Church planting, like any entrepreneurial endeavor, is inherently risky. You're attempting to build something that doesn’t exist, in a place that may not seem ready, with people who haven’t quite bought in. Developing key entrepreneurial skills can make the difference between endless headaches and spiritual breakthroughs.

In writing my book, The Progressive Planter: A Handbook for Ecclesial Entrepreneurs, I developed an assessment that examines the skills and leadership qualities often present amongst those who start churches and nonprofits. This article explores three of these skills: creative connectedness, powerful questions, and feedback loops.

There are three barriers to starting something new:

1. How do I come up with an innovative idea?

2. How do I overcome discouragement and negativity?

3. What if it doesn’t work?

Creative connectedness, powerful questions, and feedback loops are entrepreneurial skills that address each of these barriers.

1. Creative Connectedness: The Birthplace of Creativity.

Have you ever watched Jimmy Fallon’s “Wheel of Musical Impressions?” If not, it’s worth the YouTube rabbit hole.  In it, artists are asked to impersonate other singers while performing nursery rhymes or jingles. For example, you get to hear what it sounds like for Ariana Grande to impersonate Britney Spears singing “Mary Had a Little Lamb.” It’s terrific, of course. And where else will you find Alicia Keys impersonating Adele crooning the ABCs? That’s creative connectedness in action, or the ability to draw meaningful links between seemingly unrelated ideas.

As the biblical sage said, “there is nothing new under the sun”—at best, entrepreneurs bring ideas together in new ways. This is the secret to any creative endeavor. The ability to see and connect these ideas in a meaningful way is the birthplace of innovation.

It takes skill to combine disjointed ideas. This is what makes Jeni’s Ice Cream brilliant. Who else has been able to make ice cream with spinach and sell it for 12 dollars a pint? If I made ice cream with spinach, I'd have to pay someone $12 to try it. That’s because I haven't mastered the skills to make delicious ice cream. Creative Connectedness is not just about taking two things that don’t belong and mashing them together; it’s about doing it in a way that works.

Church planters need to take the time to master the skills of community organizing, theological integration, and leadership in order to offer theologically rich, fresh expressions of faith. Here are a few examples of where I’ve seen this in new church starts:

Evangelical + progressive

There is a growing movement of progressive evangelical churches that are rooted in inclusive, open-minded theology while embracing the belief that God wants us to share the Good News with new people.

Ancient Christian practices + postmodernism

The entire emergent church movement applied ancient practices with modern perspectives.

Nonprofit organization + church community

When we launched our church, I hoped to embrace the best of nonprofits with the best that churches had to offer. At times, especially in the beginning, people would wonder if we were a nonprofit or a church? But why not be both? Examples of this continue to pop up amongst church planting.

2. Powerful Questions: Overcoming Discouragement and Negativity

We’ve all heard it said: “There’s no such thing as a bad question.” But anyone who has worked with people, crafting visions or leading discussions, knows that’s not entirely true. Some questions open up new possibilities while others shut them down.

There’s a sitcom on FX about vampires and while most of the vampires are the traditional sort (they drink blood) one is an “energy vampire.” This comedic character lives off draining other people’s energy through tedious conversations, limiting questions, and perpetual negativity. If you’ve worked with people for any amount of time, it’s likely you’ve come across your fair share of energy vampires.

This was certainly Jesus’ experience. A quick survey of the Gospels will show that the Pharisees and religious establishment loved to ask limiting questions in an attempt to drain Jesus of his influence and confidence. For example, the Pharisees ask Jesus in Matthew 12:10, “Is it lawful to heal on the Sabbath?” This limiting question is designed to shut down the conversation and discredit Jesus’ ministry of healing. Like most limiting questions, it was rhetorical, and not meant for Jesus, but for those watching. This question would immediately cast doubt into the minds of those present. “Maybe Jesus shouldn’t heal on the Sabbath?!” they might think. But Jesus wouldn’t be hindered by their harsh remarks. He pushes back and ultimately forces them (and us!) to ponder what it means to truly love our neighbors.

Entrepreneurial leaders know how to ask powerful questions that can inspire and promote new opportunities, while successfully navigating the land mines of limiting questions.

This requires a mindset shift.

Let’s look at a few key mindset shifts that have to take place to ask better questions.

Asking powerful questions means moving from…

Scarcity to Abundance

Limiting question: “Do we even have enough people to do this?” Powerful question: “Who else could we invite into this work to multiply our impact?”

When churches operate from scarcity, they assume there’s never enough people, money, energy, or time. But Scripture reminds us that we follow a God of abundance. What is needed is often already present if we’re willing to put ourselves out there and ask for help. If everyone gives what they can, there will be more than enough to go around.

Fixed Mindset to Growth Mindset

Limiting question: “Are we even qualified to lead something like this?”Powerful question: “How can we grow into the kind of leaders this moment requires?”

A fixed mindset says you can only do what you’re already trained to do. A growth mindset trusts that you can learn, stretch, and evolve. Most church planters start the journey before they feel “ready.” And that’s okay. The only way to get there is to begin. A growth mindset is the belief that you can grow into the person you need to become and find the help along the way to make it possible.

In most endeavors, healthy leaders will figure out how to make it work, but only after they get started—so get started.

Survival to Impact

Limiting question: “What’s the option that will upset the least amount of people?” Powerful question: “What’s the boldest vision we can imagine for our community?”

Churches in survival mode try to minimize loss. They say, “Let’s do what keeps the most people happy.” The problem is that this approach rarely inspires anyone and seldom creates change.

How many decisions have you made this year because they caused the least amount of conflict? Powerful questions can help leaders break out of this tendency.

3. Feedback Loops: Turning Failure Into Growth.

The difference between the “fool” and the “wise” in the book of Proverbs has nothing to do with intelligence, professional experience, or credentials. No amount of accolades or degrees will make someone wise. The difference has everything to do with whether someone is open to feedback. A fool refuses to receive feedback, whereas a wise person is open and looking for it.

If you want to build something new, you have to listen well, iterate quickly, and avoid taking criticism personally. This is where feedback loops come in.

A feedback loop is a structured process where you seek input, reflect, adapt, and try again. It’s not about perfection—it’s about progress. Instead of seeing failure as something to avoid, feedback loops see failure as a small step towards new and better ideas.

Seeking and receiving feedback is a skill that wise entrepreneurs learn. After every event, program, or meeting, take time to evaluate what worked and what didn’t.

Final Thoughts

Creative connectedness, powerful questions, and feedback loops aren’t just business buzzwords. They’re spiritual tools—ways of seeing and leading that allow us to partner with God and other people in building something new. They are rooted in the belief that God is in the business of bringing new ideas to life, that people are naturally resilient and resourceful, and that you don’t have to have it all figured out.

You don’t need all the answers.

You need creativity that sees possibility.You need curiosity that asks bold questions.And you need humility to listen and adjust.

If you’re planting a church, leading a nonprofit, or launching a new ministry, these three skills will shape your thinking, dreaming, and acting.

I share additional ideas, resources, and examples of this work in my book The Progressive Planter: A Handbook for Ecclesial Entrepreneurs. This book includes a step-by-step approach to starting new ministries and over 60 resources and samples to help you implement what you’re learning.