Most pastors don’t struggle with generosity because they don’t know what to say. They struggle because they’re uncomfortable saying it, and the discomfort won’t go away no matter how many times they rework the message.

You’ve softened the language. Delayed the ask. Framed it carefully. Maybe you’ve told yourself the congregation just isn’t ready, or the timing is off, or a better on-ramp is coming next season.

None of it is working. And you know it.

The awkwardness isn’t a confidence problem. It’s not a theology problem. It’s a design problem, and it has one very specific cause.

You’re Talking to Everyone at Once

Every Sunday, your room holds multiple kinds of people:

• Someone exploring faith for the first time
• Someone who has given automatically for twenty years
• Someone who is spiritually engaged but financially stretched
• Someone who is financially capable and almost completely disconnected from generosity as a spiritual practice

You stand up and talk to all of them. With one message.

That’s where the mismatch begins.

When a message is designed to reach everyone, it ends up vague enough to apply to all of them and specific enough to reach none of them. The person who needs vision walks away with guilt. The person who needs a concrete next step walks away with inspiration they don’t know what to do with.

The awkwardness you feel isn’t your conscience. That’s your instinct telling you the message didn’t find anyone.

Generosity Isn’t One Conversation

This is the part most pastors haven’t fully accepted yet.

There is a version of the generosity conversation for someone who has never connected their faith to their finances. They need an entry point, not a challenge. Something that makes a first step feel possible rather than just convicting.

There is a version for someone in the middle. They’re giving something, but loosely. No real practice. No clear why. They need to understand what a next step looks like and why it matters now, not someday.

There is a version for someone who is spiritually and financially all-in. They don’t need to be persuaded. They need to be deployed. They need to know their generosity is accomplishing something specific, not just keeping the lights on.

Same topic. Completely different messages. Most pastors deliver one.

The Question That Changes Everything

Before your next generosity moment — from the stage, in a letter, at a campaign kickoff — ask yourself this:

Who am I actually talking to right now?

Not “Who’s in the room?” in a general sense. Specifically. Who is the person this message is designed to move? What do they need to hear? What would make this moment produce a step rather than a feeling?

That one question changes everything about how you communicate. Your illustrations shift. Your language tightens. Your ask gets specific. When you know who you’re talking to, vagueness disappears, because you’re no longer hoping someone responds. You’re designing for a person. That person takes a step.

The conversation stops being awkward when it stops being generic.

This Is a Design Decision, Not a Communication Adjustment

Naming who you’re talking to isn’t a homiletics tweak. It’s a structural commitment.

It means you can’t walk into a generosity moment with a message built to cover all your bases. You have to choose. Who is this for? What are they ready to hear? What does movement look like for them right now?

When You Choose Wrong

You’ll read the room wrong sometimes. You’ll build for someone in the middle and discover the room is full of people who haven’t started. That’s a data point, not a failure. You can adjust.

The alternative — aiming at everyone — guarantees you consistently reach no one.

What Designing for Someone Actually Produces

When the message is built for a specific person, something shifts in the room. The right people lean in because the message sounds like it was written for them. Because it was. The others still hear something that feels more real than a message that tried to be everything to everyone.

Specificity produces credibility. Credibility opens people up.

Before Sunday

Pull up your next generosity communication.

Ask the question. Who is this for? Don’t answer it vaguely. Name the person. What do they need to hear to take a specific next step?

Then rebuild the message from that answer.

If you can’t name who you’re talking to, you don’t have a message yet. You have content. There’s a difference.

The Cost of Getting This Wrong

Every generosity conversation that misses is more than a missed financial moment. It’s a missed formation moment.

The awkwardness you keep feeling is your instinct telling you something isn’t landing. That instinct is right. When you keep overriding it — softening the language, delaying the ask, defaulting to inspiration without direction — you aren’t protecting people from pressure. You’re protecting yourself from a design decision you haven’t made yet.

And the person who was ready to take a step? They left without one.

Design for someone. Say something specific. Make the ask. The awkwardness disappears when the message finds the right person.

Want to work through who you’re actually talking to in your next generosity moment? Reply to this post or reach out at gavin@gavinadams.com. This is one of the fastest problems to fix when you’re willing to make the design decision.

Quotes to Share

• “When you design for everyone, you reach no one. Pick a person. Build the message from there.”
• “The awkwardness in your generosity conversations isn’t a confidence problem. It’s a design problem.”
• “If you can’t name who you’re talking to, you don’t have a message yet. You have content. There’s a difference.”

Helping You Add More Intention To Your Mission,
Dr. Gavin Adams