It’s the time of year when church leaders are starting to see lots of red—and it isn’t always early Christmas decorations! Lots of churches have deficits they need to close by year’s end. I have been there many (MANY) times.

Sometimes, these gaps are relatively small. All you need is to remember to ‘double December’ and take a breath. (If you don’t know what this means, read this.) Other times, the gap is wide enough that you need to make the need known and stir up some end-of-the-year generosity. Here’s a quick guide on all the ways you can do that, and there’s a bunch more in Giving Up. And of course, you’ll be sending out that end-of-year appeal letter, and I’ve got you covered there, too.

However, there have been a few years when I needed to make house calls at the end of the year. Once or twice, this was because something had gotten really out of whack in the budget due to something no one could’ve anticipated. Most of the time, though, it was because we were headed toward a new challenge—a building campaign or some other ‘big growth moment’, and I needed ‘a few good donors’ to step up and lead the charge.

Recently, I was at a conference and a young pastor asked me to ‘role play’ this sort of conversation. There was lots of enthusiasm for it in the room, and I was surprised to learn how few head pastors have sat across a kitchen table and had this sort of talk with a big donor.

I’ll walk you through my approach to this conversation, sharing some tips from my experience. But it all boils down to this: be their pastor.

Ground Work

Any time I have approached someone in my congregation with considerable means, it’s always been in the context of a relationship. This shouldn’t feel like some sort of out-of-the-blue, who-are-you-again? moment. I know them and they know me. I know their family and they know mine. We have a shared history and we can swap stories.

It may not be possible for you to be chummy with everyone in your congregation, but there should be some sort of baseline that establishes that your interest in them is about more than their checkbook.

I also never want to blindside anyone with a conversation like this. If I am going to be visiting the house of some of my big givers, it’s always preceded by lots of communication to the whole congregation. I will have published where we stand with our yearly giving, I will have spoken frankly about the need in my sermons, and (in the case of a capital campaign or other project) I will have all the relevant materials readily available. Talking to someone about a big donation is a tough enough thing to do—you don’t want to be trying to explain all the details at the same time.

But that mass communication still isn’t enough. I will always send a personal (hand-written!) letter to the family I plan to visit. I will talk about how grateful I have been for their support and I will let them know I will be in touch soon to set a time to meet. That way, they are expecting me and they know what’s headed their way.

Set the Table

As far as the meeting goes, I usually meet with people in their homes. I find that coffee shops and restaurants are distracting and noisy and they impose an artificial timeline. Nothing is worse than ending a meeting and then needing to wait around for another 30 minutes trying to pay the bill. People are comfortable in their own homes and meeting them on their turf reminds them of the relationship we share. I am their pastor—pastors visit people in their homes.

I try to make sure that both partners are present at the meeting, if the donor is married. Everyone’s first ‘out’ in a meeting like this is, “Well, I’ll have to talk to my wife about this.” Besides, a big decision like this should be shared equally—both spouses should hear everything firsthand from me. As their pastor, I do them a disservice if I intentionally exclude and create an information imbalance as they pray and discuss their commitment. As far as bringing my own wife to the meeting, that’s a case-by-case decision based on our relationship with the family.

I’m always on time and I’m always prepared. This should be obvious, but I feel the need to write it here because some pastors just haven’t dealt with big-time professionals before. In general, your big donors are folks who got where they are because they are professionals. They may love you to death, but in a meeting like this you need to meet them on their terms. Any documents you put in front of them should be clear, concise, and polished. Like I said before, if you’ve laid the ground work, you shouldn’t need to use much—you aren’t here to brief them on every detail of the situation—but it’s good to have information on hand as questions arise.

Coffee Talk

The meeting should last about half an hour. Remember: these people are professionals. They appreciate directness and they don’t enjoy feeling like their time is being wasted.

Still, you should take the first half of the meeting to talk about family, share stories and pictures, and just generally ‘check-in.’ It’s good to re-establish your friendship and it’s also a gentle reminder (for you and them) that your first and only real intention is shepherding them as people. If these donors are people with considerable means, they are being approached regularly to donate. But you have a different and privileged relationship—you are their pastor.

This is also an important step as several times I have walked in the door with all my papers and plans intact only to discover in this ‘coffee talk’ time that there were serious pastoral issues that needed attention. I was so thankful I had taken that moment to check in with them; I shifted gears, put my notes aside, and was present and available to them.

Down to Business

Once the casual conversation has died down, it’s best to get straight to the point: Here’s why I wanted to meet with you today. Of course, a little humor always helps ease any discomfort here. If this is a new experience for you, there’s also nothing wrong with being transparent about that, either.

But the point is to be direct. Remember those appeal letters I showed you? Same thing here. Don’t beat around the bush—lead with the need. Present them with the facts of the matter in a general way: We’ve got a big deficit that we need to close by the end of the year…We’ve got a capital campaign coming up and I need some giving leaders to step up as an example for everyone else…You get the idea.

Answer any questions they have, but try not to get bogged down in the details. Once they’ve understood the need, remind them how grateful you are for everything they have done. You aren’t there because they’ve been neglectful and now you are here to collect. You are there because they are part of your core, part of your team—they are the ones you’ve counted on and who have come through.

Then give them (on paper!) some straight-forward guidance for their involvement. (Note: this only applies for fundraising for an upcoming project, not closing a budget gap.) For me, this is a document with clearly defined levels of gifts and commitments with real dollar amounts. I go over that, and I direct them to the levels I’d like them to consider (probably those top categories, if you know what I mean). It’s important both to narrow this down to give a sense of the commitment you think they can meet and to give them some options. You don’t want them to feel trapped.

Now this is the most important moment of the meeting. I ask them my one big question: Would you be willing to pray about the possibility of committing to this project?

Don’t Ask for Money

Did you notice that I didn’t ask them for money? I asked them to pray. Now, I’ve had some push back on this from folks who wonder if this isn’t manipulative, asking a question that only has one real answer. But my response to this is pretty simple: When is it ever wrong to ask your people to pray?

I don’t ask them to pray about it to guilt trip them into anything. I am asking them to pray because that’s my job and I don’t want any confusion on this. I am not the one who controls their giving, and I am not here to pressure them to give. There is no biblical precedent for pressuring or cajoling people into generosity. The model again and again is presenting the need, making a clear path for involvement, and then asking for prayerful, purposeful, commitment.

This is also what sets you apart from everyone else asking for their money. By asking them to pray, you remind them that you are not someone asking for a handout, and you don’t work for an organization that will shrivel up without them. This isn’t a moment for them to decide between giving to you or to a mission organization or to their college athletics booster club. This is a moment for them to consider what sort of faithfulness God is calling them to in their finances. The church is never ‘just another nonprofit.’

Shut Up and Leave

Once you’ve asked them to pray about this, be quiet. Let that awkward silence build. Don’t let yourself backtrack or hedge your words. You want this to be a weighty moment for them. You want them taking this seriously. So shut up.

They may respond in a number of ways, but I’ve never heard someone say No, they weren’t willing to pray. Sometimes there are a few more questions that come up—go ahead and answer but return to the question at hand. Sometimes they will tell you more about their current financial situation and why they won’t be able to make the kind of commitment you might be expecting. Listen to them; you need to know their hearts. If it sounds like you’ve misjudged what they might be able to do, scale back and point to other options. But regardless, remind them that you are only asking that they would pray together over the next few days.

Once you’ve done that, you’re done. Say a quick prayer of thanks, asking God to bless them—and please, please don’t use this as any opportunity to lay on guilt—then let them know that you will be calling them sometime within the week to follow up. This allows them to anticipate the next step in the process.

I’ve had dozens of these conversations over the years, and all I can tell you is that it takes some practice. It won’t always go smoothly. But my point is that once you realize it isn’t your job to ask for money, you are freed from fear. You are freed to fulfill your role as their pastor, even in this practical matter of giving. Approach it as you approach every other part of your ministry: as a chance to build up the kingdom of God and to build up his people.