What I Learned From Executive Pastors at Some of America’s Largest Churches
After our 2026 Large Church Gathering in Chicago, I wanted to put a few of my takeaways on paper.
Every time we go into a Gathering, we wonder, “Do we have the right people in the room? Will the conversations be helpful? Will every leader leave recharged?” And every time, it’s awesome to see how God brings the right church leaders together.
Here's what stuck out to me after the gathering:
1. The humility in the room
This group represented churches ranging from around 5,000 to 20,000 in weekly attendance. These are leaders who could walk into a room thinking, “We’ve got this figured out. We know what we’re doing.”
But instead, they showed up with humility.
Everyone came ready to learn from each other. There were several churches in the room that most church leaders would recognize, and their leaders were just as willing to say, “Here’s what we’re trying to figure out.”
I’m always grateful and a little amazed by that kind of openness.
There’s something powerful about being in a room with experienced leaders who are willing to talk honestly about what they’re facing. Leadership can get isolating, especially as your organization grows and the decisions get more complicated. Having people around you who understand that weight matters.
2. The questions are changing
We covered a lot in Chicago, including staff culture and health, the complications of multisite ministry, the tension between central leadership and campus autonomy, and how decisions get made when you have 10, 15, or 20 campuses.
We also talked about how church is changing.
Several leaders shared that while attendance may be going down in some areas, engagement is actually up. They’re looking at the data in real time and asking what the future of gathering, discipleship, and the weekend experience looks like.
Those conversations reminded me how important it is for church leaders to keep asking questions. Ministry continues to change, and the questions leaders are carrying today aren’t always the same ones they were carrying five or ten years ago.
These leaders were willing to talk about what they were seeing, compare experiences, and learn from what was happening in other churches.
3. Some of the best conversations happen between sessions
Some of the most meaningful conversations at a Gathering happen over lunch, at dinner, or during open time.
Two leaders realize they’re dealing with the exact same issue and start comparing notes. Someone hears an idea they can take back to their team. A question they’ve been carrying for months suddenly feels a little clearer.
I love watching those connections and lightbulb moments happen.
One thing we heard over and over again in Chicago was how helpful it was to get out of the day-to-day and spend a couple of days working on the ministry instead of always working in it.
That feedback always encourages me because it’s exactly why I wanted to start these Gatherings in the first place. I wanted to create space for church leaders to step away, have honest conversations with people who understand what they’re carrying, and go home better equipped to lead.
I share these reflections partly because it’s helpful for me to put pen to paper and process what I’m learning from these rooms. But I also hope they remind you that you’re probably not alone in what you’re carrying.
Sometimes getting out of the day-to-day and sitting across the table from leaders who are in your shoes can change the way you see what’s in front of you. Those conversations can stick with you long after you’re back home.
Our LeadingSmart Gatherings are a great space to do that. You can check out our upcoming Gatherings here.
Listen to the Full Conversation
In this episode of The LeadingSmart Podcast, Holly and I share more of our takeaways from the 2026 Chicago Large Church Gathering, including what surprised us, the conversations leaders were having, and a few behind-the-scenes moments from our time together.
More on LeadingSmart Gatherings
LeadingSmart Gatherings are curated, high-trust environments for senior church leaders to think strategically, build meaningful relationships, and leave with practical tools they can implement immediately.
These are not conferences. They are working sessions designed for leaders who carry complex responsibilities.
Each three-day experience creates space for honest conversation around topics like staffing, succession, governance, culture, and growth with peers who understand the weight you carry.
See what LeadingSmart Gatherings are open for registration here.