ALWAYS ASK
The One Leadership Habit That Unlocks Money, Leaders, and Movement
The Smirk That Changed Everything
“Dave… you know who gets the money?”
I was sitting across from a mentor who would shape the way I lead for the rest of my life. Lyle Schaller had been called “the dean of church consultants.” He had written more than 50 books and served as editor to another 50. He had influenced thousands and thousands of church leaders. He was named the most influential religious leader in America.
And somehow, he showed up at the very first service when we started COMMUNITY.
If I needed to find Lyle, I knew exactly where to go—the local library. There he would be. Reading. Writing. Thinking. And graciously, always willing to make time.
I remember sitting with him one day, feeling stuck.
We had planted COMMUNITY to reach people far from God, and gratefully that was happening. But financially? It was very tight.
So I laid it all out for him. I explained that we were reaching people who were new to faith, new to church. Many were deep in debt. Generosity wasn’t yet part of their rhythm. I walked him through every obstacle, every barrier, every reason why raising money felt nearly impossible.
He listened. Then he smirked. Not smiled—smirked. And he said:
“Dave… you know who gets the money?”
He paused and said, “Whoever asks for the money.”
I thought he didn’t understand. So I explained it again—more detail this time. More nuance. More reasons.
Same smirk. Similar answer.
“Dave… you can make up whatever excuse you want. But it’s this simple: whoever asks for the money gets the money.”
That moment has stayed with me for years.
Because over time, I realized a couple truths:
Lyle was right, “Whoever asks…gets.”
That principle didn’t just apply to money. It applies to everything that moves the mission forward.
Jesus Already Told Us To Ask
What Lyle told me in the Naperville library, Jesus had already made clear. In Matthew 7:7–8, Jesus says: “Ask and it will be given to you; seek and you will find; knock and the door will be opened to you. For everyone who asks receives…” We’ve read and heard those verses before. But we often misunderstand them.
This is not a formula for getting whatever you want. This is not about manipulating outcomes. This is about a posture. Jesus is describing how the Kingdom works:
Ask…
Seek…
Knock…
These are not passive words. They are active. Courageous. Forward-moving. Jesus is inviting us into a way of living where we don’t sit back and wait—we step forward in faith. We engage. We initiate. We ask.
And embedded in His teaching is a principle that shows up in every area of life and leadership:
The one who asks is the one who receives.
The one who seeks is the one who finds.
The one who knocks is the one who sees doors open.
Not because they control the ultimate outcome—but because they positioned themselves for it.
A Leadership Problem We Don’t Recognize
Every time I meet with church planting leaders, I hear the same concern: “We just don’t have enough church planters.”
In the last several months, I’ve sat with hundreds of leaders across the United States, Europe, and Australia. Different denominations. Different contexts. They all share the exact same concern…
“Our pipeline of potential church planters has dried up.”
And the explanations for why follow quickly:
“Gen Z won’t settle for low-paying church planting jobs.”
“Young adults have been burned by the church.”
“We’ve already pulled from the youth pastor pool.”
Let’s be honest—the problem is real.
But I want to suggest something as a leader, a friend, and a coach:
The problem may not be what we think it is. The real problem is that we are reluctant to ask.
Because I can almost hear Lyle again. That same smirk on his face. “Dave… you know who gets the church planters?” And then the answer: “Whoever asks for them.”
The Courage Gap
If it’s that simple, why don’t we ask?
Because asking feels risky.
We’re afraid of rejection.
We don’t want to come across as pushy.
We assume people will say no.
We convince ourselves they’re not ready.
So instead of asking clearly, we… Hint. Suggest. Hope. Wait. And then we wonder why nothing changes. But here’s what I’ve learned:
The leaders who accomplish the most are constantly asking others for a commitment.
When you ask someone directly, you’re not pressuring them—you’re honoring them. You’re giving them the opportunity to step into something profoundly meaningful with their lives.
Application #1: Asking for Money
Let me take you back to a moment I almost missed when it comes to asking for money.
Years after that conversation with Lyle, I was at an Exponential global conference, talking with a friend. He had built a very successful business; scaled it and then sold it. He had the capacity to give at a high level. But that wasn’t why we were connected—we were simply friends.
We were talking about the mission—church planting, multiplication, the 16% mission and our desire to see churches become reproducing churches. And then he interrupted me: “When are you going to ask me for money?”
It caught me completely off guard.
Because I had never asked him for money.
Not because I didn’t believe in the mission. Not because he couldn’t help. But because somewhere along the way—I hesitated.
Maybe comfort.
Maybe assumption.
Maybe fear.
Whatever it was, it almost cost us.
I smiled and said to him, “I’m working on a proposal—I’ll get it to you.” (Which meant, I’m staying up late tonight in my hotel room to write the proposal and then I will give it to you.)
And I did!
I wrote out a clear vision—how his investment could help plant hundreds of more churches. I put language to what had been living in my heart.
The next day, I handed it to him and walked him through it. And as I did, he smiled. That same knowing smirk.
That moment led to a seven-figure gift.
But here’s what I can’t shake:
I almost didn’t ask! Not asking would have cost the mission more than $1,000,000.00!
And when I look back now at all those churches that have been planted around the world, there is an inflection point tied to that exact moment when I finally asked. God used that gift to accelerate the mission.
And I almost missed it.
In fact, God had to use him to ask me: “When are you going to ask?”
Application #2: Asking People to Plant Churches
But asking isn’t just about money.
In many ways, the greater hesitation is here: We talk about church planting. We celebrate it. We highlight stories. But we don’t often look someone in the eye and say: “I think God might be calling you to plant a church.” And when we don’t ask, something predictable happens - the pipeline of potential church planters dries up.
I believe we don’t have enough church planters because we’re not asking people to plant churches.
At Exponential, we’ve seen what happens when we do ask.
Every conference we have every done ends with a clear invitation. If God is calling you to plant a church or contribute in some way to a new church, come forward…we want to pray for you, commission you, and have you go with our blessing.
Every time we ask for people to commit to church planting at Exponential we see 10–20% of the people respond.
That is hundreds of people! And over the last twenty years that has now been thousands of people who have said “Yes” in response to the ask to plant new churches.
Some are taking a first step. Some are confirming a calling. Some are simply saying, “I’m available.” But they respond.
Why? Because someone asked!
Over the years, leaders like Ryan Kwon, Joby Martin, Jodi Hickerson, Derwin Gray—and many others—have taken steps toward church planting in moments like that. Not because we created the calling. But because we created space for it to happen.
Because we asked!
I was talking to Ryan Kwon and Jodi Hickerson both this week, who serve on the Exponential board. They recalled that moment during session #5 at Exponential, “It was like I was 85% there and when the ask was made it gave me the other 15% I needed to go for it.” Ryan told me, “Right before I went forward at Exponential I turned to my friend and said, ‘Geronimo!”
Here is my own video of the moment last March where nearly a thousand leaders came forward to be commissioned…
I’ve seen this not only at Exponential but also in my own home church. Let me take you back to the very first church we planted out of COMMUNITY. It wasn’t local. It wasn’t convenient. It was 1,000 miles away—in Denver, Colorado.
And we didn’t just plant a church. We asked people to go. Not vaguely. Not hypothetically. Not, “Hey, pray about it if you want.”
We looked people in the eye—people in our church in Chicago—and asked: “Would you move to Denver to help plant a new church?”
That’s not a small ask. That’s not incremental. That’s life-altering.
And yet… 35 people said yes!
Think about that. Thirty-five people. They didn’t just raise their hands. They reordered their lives.
They sold homes.
They left jobs.
They found new employment in a different city.
Some transferred colleges.
Others left family, friends, and everything familiar.
They packed up their lives and moved from Chicago to Denver.
Why?
Was it because everything lined up perfectly? Was it because they had been planning to move anyway?
No!
At least in part—it was because we asked. We gave them a clear invitation into a meaningful mission. We called something out of them. And when we did, something awakened. That’s what asking does. It doesn’t create calling—but it reveals it. It doesn’t manufacture courage—but it draws it out.
And I’ve seen that same dynamic play out again and again when we ask!
Where Did the Ask Go?
If we’re honest, somewhere along the way, we stopped asking.
We stopped asking students to consider vocational ministry.
We stopped asking young adults to give their lives to church planting.
We stopped asking leaders to go.
We replaced bold invitation with passive observation. And here’s what I believe:
God hasn’t stopped calling people. We’ve just stopped helping them hear it by asking.
The result? A shortage—not of calling, but of clarity.
A Deeper Truth: You Can’t Receive What You Don’t Give
This is where it all comes together.
Because asking and giving are inseparable.
We want people to give—but do we give them a clear invitation?
We want church planters—but do we ask them to step into that calling?
We want movement—but do we initiate it?
You can’t expect to receive what you’re unwilling to give.
If you don’t give the ask, don’t expect the response. If you don’t give clarity, don’t expect commitment. If you don’t give opportunity, don’t expect multiplication.
But when you give those things? People respond!
Always Ask
So let me ask you, where are you hesitating right now?
A conversation you’ve been avoiding?
A leader you need to call out?
A future church planter you need to invite?
A resource you need to request?
What might be waiting on the other side of that ask?
Because Jesus was not ambiguous…
Ask… and it will be given to you.
Seek… and you will find.
Knock… and the door will be opened.
Not always immediately. Not always easily. But consistently: The one who asks… receives.
So let’s bring it all the way back…
You know who gets the money? Whoever asks for the money.
You know who gets the leaders? Whoever asks for the leaders.
You know who sees people step into calling, resources released, and doors opened for the mission? Whoever asks!
So ask here is your assignment today. Literally do this today!
Ask God.
Ask boldly.
Ask people to give.
Ask people to go.
Because what God wants to do next— might be waiting on the other side of a simple, courageous ask.
You know who gets…? Whoever asks!
Bro, this is such good stuff. It inspires me to do something I naturally have done, but for some reason have let slide.
By the way, you’re pretty good at this writing stuff. Maybe you should consider writing a book! 😀