A one-on-one is a 45- to 60- minute intentional conversation between two people, held for the purpose of building a public relationship.

One-on-one’s are how we started this church, asking people in coffee shops and at storytelling shows if they’d be game to talk for 45 min or an hour. We had a ridiculous goal. Like, Rebecca was gonna have 800 one-on-ones in 6 months. (She probably hasn’t had that many in her life — or maybe she’s approaching it now, 8 years later.) Anyway: they work. They work to create connections, to deepen relationships, and to build power.


Sunday night, April 21, 2024, we launched a campaign of one-on-one’s with a more reasonable, but ambitious, goal: 100 one-on-one conversations among Gileadites before September 15th. Our goals? To build community, deepen the relationships we have, and find new connections.


There are two ingredients you need for one-on-ones. Courage and curiosity.

Start with curiosity. If you don’t think the other person is worth 45 min of genuine interest, you can skip it. For some folks, that curiosity comes more easily than others, but you can definitely cultivate it. Often, when people first think about doing one-on-ones, they get nervous about “what am I gonna say?” But good news: the assignment is more like, “how hard can I listen?”


Curiosity in a one-on-one can include:

  1. having some go-to starter questions in your back pocket. H/t to the crew on April 21, who liked “What brought you to Chicago?”

  2. listening deeply for one thing you’d like to know more about and asking a follow-up question based on that. H/t to the crew who appreciated Jill’s asking further “why” questions (eg, “Why did you come to Chicago the first time?”)

  3. listening deeply for something you wonder about in what they’re saying and asking that — a meaning-making question or one about what motivates them (eg, “How’d you get interested in that?”)

  4. listening deeply for a point of connection, in yourself or with someone else in the congregation. (“Have you talked to Lucas? He’s our bread hoss.”)

It takes courage to ask someone to meet up in the first place, to ask them to remind you of their name, for their phone number, to give 45 minutes of their time, to ask good questions, and to share some of your own story authentically — because this isn’t a one-way interview.


Steps (it’s simple: you’ve had coffee before!)

  1. Book it. Set a place and time.

  2. Honor your time and plan: stop at 45 or 60 min. REALLY.

  3. Take a selfie and tag Gilead on social media. The next time either one of you is at church, your beer or tots are on us!

  4. Ask if there’s anyone else they think you should connect with (and pass on your recs to them). Aka, The Bump.