I knew I needed to reconnect.

I told myself that for weeks — and didn’t do it.

I talked myself out of it, over and over. Too much time had passed, I reasoned. Showing up now to ask for a gift would feel presumptuous. I could have called. Instead, I decided I needed to see Bill in person — one more excuse to stall.

Finally, I drove out. Palms sweating, I walked up to the door of his processing plant, rehearsing what I’d say. I found Bill and thanked him for his past generosity. Later, I mentioned it had been almost a year and a half since we’d talked. He looked genuinely surprised — he thought they were still giving. He surprised my by handed me a check for $10,000. Years ago, while raising money for a Christian homeless shelter in Grand Forks, North Dakota, I met a donor named Bill I hadn’t talked to in eighteen months. Bill and his family ran a potato operation outside town. They’d given over $10,000 a year to our work with people experiencing homelessness. I knew I needed to reconnect. I told myself that for weeks — and didn’t do it.

I talked myself out of it, over and over. Too much time had passed, I reasoned. Showing up now to ask for a gift would feel presumptuous. I could have called. Instead, I decided I needed to see Bill in person — one more excuse to stall.

Finally, I drove out. Palms sweating, I walked up to the door of his processing plant, rehearsing what I’d say. I found Bill and mentioned it had been almost a year and a half since we’d talked. He looked genuinely surprised — he thought they were still giving. Before I left, he handed me a check for $10,000.

I almost missed his generosity

Relief is too calm a word for what I felt. It was sheer joy.

Feeling brave, I called another donor, Mike, that same week. What he said back has stayed with me for years: “Dave, I was praying about who to send $7,500 to. You are an answer to prayer.”

Relief is too calm a word for what I felt. It was closer to joy.

Feeling brave, I called another donor, Mike, that same week. What he said back has stayed with me for years: “Dave, I was praying about who to send $7,500 to. You are an answer to prayer.”

Weeks of avoidance. Two gifts, both waiting on the other side of a fear that had nothing to do with the donors and everything to do with what was going on in my head.

If you’ve lived some version of this — stalling, rehearsing, finding one more reason to wait — you’re not bad at fundraising. You just never trained for this part, and you’re doing it scared.

What you’re actually afraid of

The fear of asking is rarely about the money. Most ministry leaders can talk for an hour about their program’s impact without hesitating once. Put a dollar figure and a person’s name in the same sentence, though, and something locks up.

We are taught not to talk about money. It is disrespectful or nosy to have conversations about people’s finances. So many Christian leaders get stuck in their own brains instead of letting the donor guide the discussion.

I can almost always hear them ask the same questions in their mind:

Will they say yes? Will they see this as greedy, asking again so soon? Am I doing this for the right reasons, or to keep the program funded and my paycheck coming?

I’ve sat across the table from dozens of ministry leaders stuck at exactly this point, staring at a number that feels too big to say out loud. Almost always, they’re comparing their bank account to their donor’s. We assume donors see money the way we do — scarce, guarded, a big deal to give away.

It’s rarely true. Generous people have more reasons and more ways to give than you’d guess. Money means something different to them than it does to you. Stop putting donors in a box. You don’t actually know what a gift will cost someone until you ask.

Write this on a sticky note:

Think of the Trust Bridge — awareness, belief, trust, partnership. If you’ve done the work of the earlier weeks in this series — real stories, real outcomes, people treated like people instead of prospects — the donor is already standing at the threshold by the time you get to the ask. They already believe. They’re already trusting you with their attention, maybe their prayers, maybe their name on your list.

The ask doesn’t introduce a transaction into the relationship. It opens a door that’s already half-open and says, “Here’s how you walk through.”

A donor who’s followed your work, prayed for your program, told their spouse about the family you helped last spring — isn’t waiting to be left alone. They’re waiting to be invited. Your silence doesn’t protect them.

What to actually do this week

Reframing helps. It won’t send the email on its own. Here’s what will:

• Call it an invitation, not an ask — even just in your head. Before you write or say anything: I’m inviting someone into work they already care about. Small shift. It changes your tone on the call.

• Be Memorable.

  • Thank the donor: And share how they have impacted your program in the past: “Thank you for your gift that helped Stacy and her kids find a new home.”

  • Be specific when you ask: “We are currently $8,000 short of covering the tutors for next semester.”

  • Share with them a concrete next step: Then, specify the next step: “Would you consider making a gift of $500 this month?” A vague request results in uncertainty, while a specific one leads to a interaction between trusted friends.

• Make the smallest ask first. Don’t wait for the six-figure conversation to practice courage. Send one email today to one donor for one modest thing. Size matters less than the fact that you did it.

• Decide in advance what “no” means. It’s not a verdict on your worth, your program, or your calling — it’s information about timing. No is just the first few letters of “not yet.” Not at this time.

• Debrief every ask, win or lose. What did you notice? What would you change? It’s a skill you’re building, not a test you’re passing or failing.

• Rehearse with one person — a board member, a spouse, a fellow leader. Say the ask out loud before you say it to the donor. The number gets less terrifying every time you hear yourself say it.

None of this makes the ask comfortable. It makes it possible. That’s a fair trade.

What Scripture already knew about this

Nehemiah wanted to rebuild the wall around Jerusalem. He had no resources of his own — the wood, the funding, the permission belonged to a foreign king who held his life in his hands. Scripture says he was “very much afraid” before he asked (Nehemiah 2:2). He prayed first. Then he asked anyway — specifically, naming exactly what he needed and from whom.

The wall got built because a frightened man asked a hard question out loud.

I think of that every time I remember what Mike told me. I hadn’t set out to be anyone’s answer to anything — I’d just made the call I’d been avoiding.

That’s often how it works. Someone’s already praying about what to do with a gift. Your ask is what connects their obedience to your need.

Stewardship isn’t just what you do with money once it arrives. It’s whether you were willing to ask for it in the first place, on behalf of people who are counting on you to.

The door is still open.

Somewhere right now, a donor who believes in what you do is waiting — not to be left alone, but to be given a way in. Every ask you’re avoiding is a door someone else wants to walk through.

You’re asking them to say yes to something God is already doing.

And you might be the answer to somebody’s prayer, the way I turned out to be Mike’s.

Send the email. Make the call. Sit across the table and say the number. The mission was never funded by leaders who felt ready. It was funded by leaders who were afraid and asked anyway.

What’s the ask you’ve been avoiding? Hit reply and tell me. Sometimes the fastest way through the fear is saying it out loud to someone else first.

Dave Sena is the founder of Bold Leading, where he works with faith-based nonprofit leaders on fundraising strategy and donor relationships that sustain meaningful mission work.

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Forty names. People I knew of — a name on a donor report, a face from an event two years ago — but had never actually spoken to. Jim Holdman, a seasoned fundraiser I was learning from, challenged me to call every name on my top forty list. He warned me not to pay attention to all the reasons I would have for not calling.

On my third call, a woman named Carol picked up, and I could hear the pause. I hear it on almost every first call — that beat of silence where the person on the other end is thinking, Why is this person calling? What do they want? I introduced myself, then rushed to say thank you before the silence stretched any longer. I could still hear the hesitation in her voice. She had no idea who I was or why I was calling.

I thanked her for a gift she’d made the year before, then waited and asked how she’d first gotten connected to the organization. She was surprised by the question — and then appreciative.

It took four minutes.

I grabbed a napkin to dry my hands, said a quick prayer of thanks, and decided to make another call.

I’ve since pulled the reports on what happens after these calls. The pattern holds: We often get a donation within a week — even though I rarely asked for one. I just called, introduced myself, and said thank you.

That’s what I remind myself of when the fear or the procrastination sets in. I pick up the list and make the next call.

The System

Jim’s challenge wasn’t just “call people.” It was a system—and that system made it sustainable.

Each week runs two tracks at once. Early in the week, you call ten people to schedule a real conversation — a coffee, a phone call, a short visit — for the following week. Later in the week, you follow up with the ten people you scheduled last week: either have the actual conversation or close the loop if it didn’t happen.

So, week one, you’re only scheduling. Week two, you’re scheduling ten new conversations and following through on week one’s ten. Week three, same thing, rolling forward. Within a month, you have a standing rhythm of donor contact that doesn’t depend on you feeling brave that day — it depends on the list you made three weeks ago.

I wish I could tell you the fear goes away

It doesn’t.

I have not changed.

Skip a week, and the excuses don’t stay the same size. They get bigger. The system exists precisely so you don’t have to out-willpower the fear every single time; you just have to follow the list.

Why the Call Still Matters

Most people find your organization on their own — a friend mentions it, they see a Facebook ad, they land on your website.

That’s self-directed discovery.

When someone responds to an email, shows up to volunteer, or answers a request, they’re doing more than just discovering you.

They’re raising their hand.

They’re telling you, in the only language most donors have, that they want more contact — not less.

Most nonprofits read that hand-raise and respond with more automation. A system deserves a person on the other end. That’s what the phone call is for.

Two Calls Worth Making This Week

If you’re calling a current donor:

• Pick up the phone and lead with thank you — no ask, no update, just gratitude.

• Ask how they first got involved with your organization.

• Ask what excites them most about the work right now.

• If the “I don’t have time” voice shows up before you dial, dial anyway. That voice is never right about how the call will go.

If you’re calling someone you’ve met but who isn’t yet a donor:

• Remind them where you met — be specific; it’s the difference between a call and a cold call.

• Tell them you’d love to host them, and invite them in to see what your organization actually does.

• Offer a real next step: a tour, a volunteer shift, an open house.

• The same rule applies — shut the excuse down and dial.

It’s Simple. It’s Also Hard.

Fundraising means fighting through the voice that tells you not to call. It means carving out time from a day already full of urgent things for something merely important. We don’t see donors the way we see the people our programs serve. But they both have needs. They both need time.

When you pick up the phone, you open a door. When you listen to the voice that tells you not to, the door stays shut — and a donor who wanted to partner with you never gets the chance to help change something.

Pick ten names this week. That’s the whole system, to start.

If you want help building a fundraising rhythm that actually fits how you’re wired, that’s the work I do at Bold Leading.

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A slingshot only works one way. You pull back. The stone goes nowhere until tension loads against it — the rubber stretched tight, the rock held still, everything in your arm screaming forward while your hand drags the opposite direction.

The backward pull isn’t the delay before the launch.

The backward pull is the launch.

I didn’t know that for thirteen years.

Thirteen years in a small mission. I thought it was where I’d landed. I didn’t know it was where God was loading the stone. I knew so little then — about leadership, about Christian leadership, about what it actually costs to shepherd people.

So I paced.

I prayed for God’s providence in the dark, lost whole nights to concern and to my own ignorance, certain that nothing but His hand was going to cure how little I understood.

I remember the excitement of victory in those years.

David was not just a shepherd. He was a worshipper.

David knew long nights of tough prayers and worship before he ever faced the giant. Anointed in a back room, then sent right back out to the sheep like nothing happened. Hidden. Held. Drawn back. Then God sent him — and a shepherd’s stone dropped a giant the whole army feared.

I don’t know about you, but I think about David watching over sheep by himself, his thoughts and prayers to God. Sometimes that sounds simpler.

As an Executive Director, you have meetings, noise, and disappointment. Frustration can feel like our only meal when you are striving to make things better for the people you serve, your staff, and community.

One Step forward and five back.

Joseph spent years looking like a man going backward — sold, framed, forgotten — and every inch of that descent was God loading the stone. In the Bible and in history, there is a time of preparation. We see it as a lack of optimal performance. God sees it as us learning to lean on Him.

“You intended to harm me, but God intended it for good.” — Genesis 50:20

It was the aim. It was God inviting us to rely on him and his timing.

Jesus said it plainest:

“Unless a kernel of wheat falls to the ground and dies, it remains only a single seed. But if it dies, it produces many seeds.” — John 12:24

Burial looks like the end of the story.

It’s actually the planting.

Descent before ascent.

Down before up. Back before forward.

The danger isn’t the pullback.

Don’t quit early. God has a way of launching and surprising us. One day, you will be talking and realize that the future has arrived.

For years, I wondered what it would be like to be a million-dollar mission. I prayed for God to prosper us more than the $350k in revenue we received over decades (so my treasurer reminded me at every board meeting).

Then one day, driving to work, I realized we were a million-dollar mission. That is when I knew I needed to act, pray, and rely on God, and that the future would be the present.

So don’t quit. Expect the most from God.

Look at King Jehoash. Elisha told him to strike the ground with arrows. He struck three times and stopped. The prophet was furious — five times, six times, and you’d have finished Aram for good.

But he stopped too soon. The striking felt pointless, so he let go before God was done drawing him back (2 Kings 13:18-19).

That’s the warning hidden inside the promise. The danger was never the pullback. The danger is letting go early — settling for three when God was loading you for six.

From inside those thirteen years, the prayer and the pacing and the not-knowing felt like a holding pattern, not a slingshot. But the launch came.

Bold Leading is my tentmaking now — my way of giving back to the people still learning, still leading in the dark the way I was. Being the VP of Men’s Programs during the day is my ministry.

None of it would preach if I hadn’t first been the man pacing the mission floor, ignorant but praying.

The thirteen years weren’t the wait before the work. They were the draw that sent the stone. God was shaping me.

In our lives, there is a rock that will slay every giant.

When we rely on Him, we can slay giants.

If you’re in the pullback right now

The small post. The obscure season. The years that feel like they’re curing nothing but your patience.

Don’t read it as God forgetting you. Read it as God aiming at you.

“Though it linger, wait for it; it will certainly come and will not delay.” — Habakkuk 2:3

Don’t let go early. The further back God draws you, the further forward He intends to send you.

GRIT: The field wasn’t obscurity. It was preparation for launch.

Praying to the Giant Slayer.

Father, thank you for your providence. What the world views as obscure, you see as hidden. What others see as forgotten. You see as forged by fire. Thank you for shaping me to fly. You are shaping me to be a giant killer.

For the one reading this in their own small field right now — tired, hidden, wondering if the years are curing anything but their patience — steady their hand. Don’t let them release early. Don’t let them settle for three when You’re loading them for six.

Give them the patience to hold the tension until the launch, and give them the grit to rely on and trust you.

We’re not forgotten. We’re aimed. Send us when You’re ready.

Amen.

If this resonated with you, Bold Leading exists to help nonprofit leaders stay grounded in their mission while building the organizational capacity to sustain it. Whether you’re navigating the jump from practitioner to executive or just trying to reclaim your calendar, there’s more at boldleading.com.

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Instead, one of them stood up and told us his wife had taken him back. Thirty years of marriage — nearly destroyed by alcohol, nearly lost for good — restored. Another man described the night he almost didn’t make it home at all. He was smiling when he said it.

I almost missed it the story of a man restored back to life and his wife of thirty years.

Not because I wasn’t in the room. I was. But my brain was somewhere else — somewhere between the next project due Friday, the fall campaign email I hadn’t finished, and the donor who’d left a voicemail I still hadn’t returned. Physically present. Mentally fractured.

That’s not multitasking. That’s context switching. And it’s one of the biggest joy stealers in ministry.

I Started as a Chaplain

I came into this work through the front door — sitting with men in crisis, walking with them through recovery. I became a program director, then an executive director of a staff of five.

We grew. Five staff became thirty-five. In a town of 90,000 people, we were serving nearly 1,000 men each year. The mission was working.

And then the budget started staring me in the eyes.

Payroll. Capital needs. Facility costs. Grant deadlines. The financial engine that made all the program work possible suddenly needed someone to run it — and that someone was me. The shift wasn’t gradual. It was abrupt. One season, I was living inside the programming. Next, I was scrambling to raise the funds.

I know I’m not the only one. Many of us entered nonprofit leadership through the work itself — as chaplains, counselors, program directors, and community organizers. We were good at the mission. Then the mission grew, and the job description quietly changed beneath us.

The Enemy Disguised as Productivity

For years, I called it multitasking. I thought it was normal — running from a staff meeting to a donor call to a grant application to my inbox, all in the same afternoon.

Now I know what it actually was: context switching. I have learned it is controllable. I just needed some rules and guard rails.

The research is detailed — every time your brain shifts from one task to another, it pays a toll. You’re not doing two things at once. You’re doing two things badly, one after the other, with diminished capacity each time.

But the deeper cost isn’t cognitive. Its presence.

When you’re bouncing all day from program prep to grant writing to donor email to opening mail, you arrive at the end of the day having touched everything and finished nothing. Worse, you can end up sitting in a room where a man’s marriage is being restored and miss it entirely because your mind is still three tasks behind.

What Wednesday Night Reminded Me

The celebration service exists for one reason: to stop and name what is actually happening. Men who were once homeless, addicted, estranged from their families — standing up and saying this is what eighteen months looks like. This is what rescue looks like.

A thirty-year marriage restored causes tears and a deep appreciation for God and his grace. The impact is hard to write well in the impact section of a grant proposal. But it is exactly why the grants exist. It is exactly why the payroll matters. It is the whole point.

And I was in the room when it was announced — halfway thinking about the next thing I had to do.

"Martha, Martha, you are anxious and troubled about many things, but one thing is necessary. Mary has chosen the good portion, which will not be taken from her."
— Luke 10:41–42

What I’ve Learned to Do Instead

I am not perfect at this. But managing demands on my calendar has been the key — not working harder or faster, but working in a way that matches how the brain actually functions.

I have created guard rails on my time to give me margin:

Stack similar tasks together. Answer email in bursts rather than reacting to every notification. When you batch similar work, you stay in one mental mode longer and spend less energy on the switching cost.

Find or Protect two to three-hour blocks for big work. Grant writing, strategic planning, and major donor correspondence — these need sustained focus. Treat those blocks like appointments. Look at your schedul regularly to see if you can move meetings to find a two hour block to write and do focus-thinking tasks.

Keep meetings to three days out of five. Meeting-heavy weeks fragment everything else. Two protected, meeting-free days change what actually gets done. This is hard but a great goal. If you can, protect either the morning or afternoon. Don’t let people fragment these days.

Put witnessing time on the calendar. Program visits. Celebration services. Client testimonies. If they’re not scheduled, they get crowded out by whatever is loudest that week.

The Joy Is Still in the Room

The man who stood up Wednesday night and talked about his marriage — that’s why I work in a Christian nonprofit. That’s why the mission grew. That’s why the budget matters.

The joy was never in the multitasking. It was always in the room. We have to be present enough to receive it.

Have you experienced the shift from doing the work to funding the work? How do you stay connected to why it matters? I’d love to hear from you in the comments.

If this resonated with you, Bold Leading exists to help nonprofit leaders stay grounded in their mission while building the organizational capacity to sustain it. Whether you’re navigating the jump from practitioner to executive or just trying to reclaim your calendar, there’s more at boldleading.com.

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Dan and his wife gave to our events every year through sponsorships. Reliable. Consistent. I assumed he was happy.

One morning at breakfast, I asked him something I’d never asked before: Does giving this way actually satisfy you?

I expected a yes.

He said no.

So I asked what he’d prefer. He said: What if we met a few times a year, you told me what the mission actually needed, and maybe I funded that?

Dan became one of our largest donors. He funded studies. He invested in the work itself. All because someone asked one question and got quiet enough to hear the answer.

Here’s what I’ve learned since: Dan was carrying a question for years that he never said out loud. And almost every donor on your list is doing the same thing right now.

The Questions That Stay Silent

Donors rarely say what they’re wondering. They won’t push back. They’ll give you every signal the meeting went well — and walk away uncommitted.

Not because they’re dishonest. Because they’re human. The questions that matter most stay silent, and if you want to be responsive instead of just polished, you have to learn to hear what isn’t being said.

There are five of them.

1. “Is this leader actually okay?”

Donors are observant — many have spent careers reading people. They notice exhaustion. They sense anxiety. They can tell when someone is running a program they love while carrying more than they should.

You don’t have to pretend everything is fine. Donors don’t need fine. They are aware that things are not perfect — they’ve spent their working careers in the trenches too.

Name what’s hard, then name your plan to get through it. There’s a confidence that comes from telling a donor here’s the barrier in front of us, and here’s how we’re working through it. That’s not weakness; it’s command of the situation.

You’re not asking donors to fly the plane over your problems. You’re inviting them to join the journey through the barriers. When they see that you’ve already mapped the way forward, they don’t see someone drowning — they see someone committed and resilient enough to be worth backing.

2. “Will my gift actually matter?”

They won’t ask, because they don’t want to sound cynical. But they’ve given before and felt nothing — no proof, no story, no line connecting their check to any outcome.

The story isn’t decoration. It’s the answer. One recent, specific story. Not an aggregate. One person. Something real.

3. “Am I the only one giving?”

Donors don’t want to be the lone believer. If they sense the organization runs on one or two relationships, it stops feeling like a movement and starts feeling like a dependency.

You don’t need a massive base to answer this. You need evidence of breadth — a recent new donor, a growing list, a community of givers. That signals their trust isn’t a solo bet.

4. “Will this leader still be here in two years?”

This one is personal in a way the others aren’t. Donors give to people, and people leave — they burn out, pivot, move on. A donor who’s lived through that carries the scar.

You can’t promise you’ll never change course. But you can show durability — through consistency, through how you talk about the long game. The leader who describes the mission ten years out as if they’ll still be in it answers this question without ever raising it.

5. “Can I trust what I’m being told?”

Not is this person untruthful. Something deeper. They want the raw truth. Are these impact numbers measured, or just hoped for? Does what I’m hearing in this room match what’s happening on the ground?

Show your work. Share the real numbers. Actual learnings. When you say here’s what we tried, here’s what it taught us, here’s what we changed — you let a donor behind the curtain of your commitment to change lives. They’re not just hearing the polished outcome; they’re watching you do the work and improve at it.

That kind of honesty is rarer than donors expect. And they notice it immediately.

The Shift

Stop preparing around what do I need to communicate. Start preparing for the question this person is most likely carrying.

A first-time prospect is usually wrestling with question five. A longtime supporter who’s gone quiet is probably at question two. A foundation officer is almost certainly on question three.

When you know which question is live, you shape the whole conversation to answer it — not by addressing it head-on, but by telling the right story and showing up the right way. Donors give when they’ve resolved something internally — when trust tips into action.

This is exactly what Dan was waiting for. He’d been quietly stuck on question two for years. Not a better pitch — a better question.

Why Most Fundraising Never Gets Here

Here’s the hard part. Reading donors this way isn’t a talent you either have or don’t. It’s a system — a repeatable way of knowing who’s carrying which question, and building the conversations that answer it before you ever make the ask.

Most organizations don’t have a repeatable, learnable method. They have a calendar of asks and a spreadsheet of hopes. Every donor meeting starts from zero. Every relationship lives in one person’s head. And when that person leaves, the giving walks out the door with them.

This is the work I do with executive directors. I call it the Connected Fundraising Framework — a structure that turns scattered donor relationships into a repeatable engine: which question each donor is carrying, what conversation answers it, and how to move them from awareness to partnership. It gets the system out of one person’s head and into the organization — down to the mechanics of how you prepare for a meeting, what you put in front of a donor, and how you follow up so nothing falls through.

It’s the difference between hoping your donors trust you and building the conditions where they actually do.

You already know how to read people. You’ve done it for years — in program work, in pastoral conversations, in volunteer relationships. That attentiveness isn’t separate from fundraising. It is fundraising. The Framework just gives it a structure so it scales past you.

The Faith Piece

Not a fundraising verse — a description of what good relationship work looks like. Insight that draws out — the opposite of manipulation. Understanding what someone is carrying, and creating the conditions where they can think clearly, feel safe, and decide from their own values.

When you meet with a donor, they want to know what’s in your heart. And they’ll often reciprocate — sharing their own purpose in giving. When two people partner in a way that honors shared values, trust wins. Your mission moves forward. Lives are changed.

Start Here

Schedule a meeting this week with a donor you haven’t seen in a while. Before you go, ask yourself one question: What is this person wondering that they haven’t said? If you’re unsure, pick two of the five and aim to answer those. Then listen and adjust. People would rather you be authentic and awkward than polished and performative.

That’s how trust funds the mission.

If you’re tired of every donor relationship depending on you personally — and you want a system that makes Connected Fundraising repeatable across your whole organization — that’s exactly what I help executive directors build. Book a 20-minute discovery call, and I’ll show you what it looks like in an org like yours.

Book a Discovery Call

P.S. — Want a taste of how the Framework works in practice? The Two Folder System is the exact setup my major gift officers use to walk into a donor meeting prepared and walk out with a clear next step — what to put in the donor’s hands, and what to keep for your own follow-up. It’s the simplest piece of Connected Fundraising you can put to work this week.

Dave Sena is the founder of Bold Leading, where he helps faith-based nonprofit leaders install the fundraising systems and donor relationships that sustain meaningful mission work. Subscribe to Trust Funds the Mission at blog.boldleading.com.

You got into this because of the people

Maybe it was a recovery program that you watched change lives. An after-school ministry that kept kids off the street. A food pantry that you started in a church basement because the need was right in front of you and you couldn’t look away.

You didn’t get into this to write donor emails.

You didn’t feel called to manage a giving database or plan a year-end appeal. You felt called to the work — the real work — the part where something actually changes in a person’s life.

And now here you are, trying to figure out fundraising.

Not because you love it. Because the program you love won’t survive without it.

I want to start there — with that tension — because I think it matters more than most fundraising teachers acknowledge.

You’re not a reluctant fundraiser because you’re failing.

This week I want to give you that reason.

The mistake most program leaders make when they start fundraising

When ministry leaders step into fundraising for the first time, most of them make the same mistake: they try to become someone they’re not.

They watch a polished development professional run a donor event. They see the smooth ask, the cultivated relationships, the practiced storytelling. And they think: I need to learn how to do that. I need to become more like that.

So they build systems. They read books. They set up an email platform and write a newsletter. They create a donor database and a communication calendar. They do everything “right.”

And then they wonder why it still feels hollow. Why donors aren’t responding the way they expected. Why the whole enterprise feels like it’s running — but not alive.

Here’s what’s happening: they built a skeleton without a heartbeat.

Every organization needs a skeleton

Let’s be clear: the systems matter. The skeleton is real and necessary.

A donor who gives and never receives a thank-you doesn’t feel cherished. They feel forgotten. An ask that arrives six months after the last communication doesn’t feel like relationship — it feels like an ambush. Consistent communication, timely acknowledgment, clear impact reporting — these things are not optional. They are the structure that makes trust possible at scale.

You need the skeleton.

But here’s what I want you to understand:

“The skeleton is not what makes donors stay.”

The heartbeat is what you already have

The heartbeat in fundraising is the part that can’t be automated. It’s the specific, human, unrepeatable moments of genuine connection that no system can produce on its own.

And here’s the thing about program leaders: you are already full of heartbeat material.

You know the people your program serves. Not as statistics — as human beings.

You know their names. You know what they were like when they first walked in and what they’re like now. You’ve sat with them in hard moments. You’ve seen the thing your donors are funding actually happen, up close, in real time.

And most program leaders don’t realize they’re carrying it.

“That is the single most powerful asset in fundraising — and it’s already in your hands.”

When a donor hears from someone who runs the program — not a communications staff member, not a form letter, but the actual person who is doing the work — something shifts.

The message isn’t just information. It’s testimony. And donors who receive testimony don’t just stay. They deepen.

What this looks like practically

You don’t have to become a different person to fundraise well. You have to learn to bring the person you already are into the donor relationship.

A few places to start:

Tell a fresh story. You don’t need a library of rehearsed testimonials. You need the fresh story that captures the essence of what your program does — told in your voice, with real detail, from your own experience. Those stories, shared consistently and personally, does more work than a hundred polished appeal letters.

Let donors into what you’re carrying. Program leaders often think donors want to see polish and confidence. What donors actually respond to is honest leadership. Write one honest update a quarter — not about what’s going well, but about what’s hard and why you’re still doing it anyway. This is where trust is built.

Use the skeleton to make room for the heartbeat. Set up the systems — the thank-you process, the communication calendar, the giving acknowledgment — so that they run without requiring your full attention. Then use the time you free up to make personal contact with your top supporters. A phone call. A handwritten note. An invitation to come see the program in person. These moments are what the systems are protecting space for.

Don’t wait until you need something. The donors who stay for decades are the ones who hear from you when you’re not asking for anything. A brief note in April — not tied to any campaign, just sharing something meaningful — is worth more than ten well-crafted appeals. It says: you matter to me even when I don’t need your money.

A word about the discomfort

If asking for money still makes you uncomfortable, it is real and necessary.

The discomfort usually isn’t about the money. It’s the intrusive thoughts that show up the moment you sit down to write an appeal or pick up the phone. The ones that tell you that you’re asking for money for yourself — not for the people you serve. Or that the number feels too big, too much, too bold for someone who got into this to help people, not to ask for things.

Those thoughts feel true. They’re not.

But consider what you’re actually doing when you invite someone to fund your program.

“You’re not begging. You’re not performing. You’re extending an invitation to participate in something that matters.”

The people who give to your program are not doing you a favor. They are becoming part of the work. They are co-laborers in something they couldn’t do alone. And you are the one who gets to offer them that — because you’re the one who built it, who tends it, who believes in it.

“Each of you should give what you have decided in your heart to give, not reluctantly or under compulsion, for God loves a cheerful giver.” — 2 Corinthians 9:7

The cheerfulness on the giving side often starts with the confidence on the asking side. When you believe in what you’re inviting people into, the ask becomes an act of generosity, not desperation.

The systems keep the lights on. The relationships keep people coming back.

“The systems keep the lights on. The relationships keep people coming back.”

Build the skeleton. You need it. But don’t stop there.

Bring the heartbeat — the real you, the one who knows why this program exists and what it costs and what it produces — into your donor relationships. That is the part no consultant can give you. It’s the part you already have.

And the way you’re wired — close to the work, close to the people, close to the mission — is exactly the foundation that lasting donor trust is built on.

I’d love to hear from you: what’s the hardest part of fundraising for you right now — the systems side, or the relationship side?

Reply and tell me. I read every response.

If this is landing for you, subscribe at blog.boldleading.com for weekly reflections on funding the work you’re called to do.

And if you’re ready to build both the skeleton and the heartbeat in a way that actually fits who you are, let’s talk.

Dave Sena is the founder of Bold Leading, where he works with faith-based nonprofit leaders on the fundraising strategy and donor relationships that sustain meaningful mission work. Subscribe to You Didn’t Sign Up to Be a Fundraiser at blog.boldleading.com.

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