3 Eerie Truths About Major Gift Fundraising (And What to Do About Them)

We are entering the spooky season, so I'm sharing frightening truths about major gift fundraising.

They are actions I see fundraisers doing - or not doing - much too frequently.

Or mindsets that are blocking connection-based fundraising success without them even realizing it.

The good news? Every single one of them is something you can change.

Eerie Truth #1: All Those Cultivation Efforts May Not Be Moving Toward an Ask

You've invited the donor or prospect to events (maybe every event!). You've shared the newsletters, sent the annual report, and provided plenty of organizational updates. 

Maybe you've invited them for coffee or a tour.

Your database shows lots of activity. You're doing a GREAT job keeping in touch. Or are you?

Being busy with reaching out isn't the same as building relationships.

I often see executive directors and major gift fundraisers checking all the cultivation boxes, sending "check in" emails, and doing everything they've been told they're supposed to do.

But here's what moves the needle to deepen the connection between the donor's values and the work of you organization:

• Discovering WHY your mission is deeply meaningful to this person, couple or family.
• Understanding WHAT MATTERS most to them?
• Learning WHAT THEY IMAGINE their philanthropy can accomplish, this year or for a lifetime.
• Determining HOW they became curious about the impact of your work and why they wish to be more involved.

If you can't yet answer those questions, you might have a wonderfully documented cultivation plan without being any closer to knowing the prospects or donors, what motivates them, and why they give. And that's ghastly!

Cultivation isn't about how often you communicate. It's about what you're learning and how the relationship is growing.

And that requires curiosity. Listening. Being willing to set aside your agenda and discover what matters to the person sitting across from you.

🪄 Try this relationship "alchemy" instead

Before your next donor meeting, forget about what you want to TELL them for a moment. Think about what you'd love to LEARN about them. Prepare two or three thoughtful, open-ended questions that invite your donor to share more about themselves, their values, and their connection to your mission.

Getting curious before you get strategic can change everything.

Eerie Truth #2: Your Donor May Be Ready to Give. But You've Never Actually ASKED.

Oh, this one!

You've been cultivating a donor for months. Maybe even years.

It's all so friendly. 

You know they're interested in your organization. They respond to your emails. They attend your events. You've had some wonderful conversations about the work you're doing.

And yet, you keep cultivating. Another coffee. Another update. Another invitation to an event.

Because you're waiting for the PERFECT moment to Ask.

You're waiting until you're absolutely certain they'll say, "Yes."

But here's the dreadful truth: Sometimes, the person who isn't ready for the Ask isn't the donor. It's YOU.

I've coached too many fundraisers who are so worried about damaging a relationship that they avoid having the very conversation that could deepen it. They don't want to seem pushy. They worry about feeling awkward. They're afraid of hearing "No."

And I understand that.

But consider this: If you've taken the time to understand your donor, what they value, and how they want to make a difference, an Ask doesn't need to feel like a high-pressure sales pitch.

The Ask is an invitation to make something meaningful possible.

And your donor gets to decide whether that invitation is right for them! Of course, I'm not suggesting you rush out and Ask every donor in your portfolio tomorrow. 

Sometimes a donor genuinely needs more information, more connection, or more time. That's why we pay attention to donor signals and have meaningful conversations along the way.

But there's a difference between recognizing that a donor isn't ready and assuming they're not ready because YOU feel uncomfortable.

 🪄 Try this relationship "alchemy" instead

Think about a donor you've been cultivating for some time. 

Ask yourself: Am I waiting because the DONOR needs more time, or because I need more confidence?

If you have a strong understanding of what matters to them, consider opening a conversation about an opportunity that aligns with their values. You don't need a perfect script. You need a thoughtful invitation and the confidence to have an honest conversation.

Eerie Truth #3: You Got the Gift. And Then You Became a Ghost and Stopped Building the Relationship.

This one might be the most spine-chilling of all.

Think about the time and effort we put into securing a major gift.

The research. The meetings. The conversations. The cultivation. The proposal. The Ask.

And then... YES! The supporter makes a wonderful gift!

You celebrate. Your organization celebrates. Maybe you "ring the bell." You send a lovely thank-you. Perhaps the donor receives a personal call from your CEO or board chair.

And then? You're off pursuing the NEXT gift.

Your donor gets added to a stewardship schedule. They'll receive the annual report, perhaps an impact update, and an invitation to your next event. But a personal note or further communication from you? DEAD SILENCE.

So what happened to the relationship?

The gift isn't the finish line. It's the beginning.

I often say: "The thanks for the last gift is the handshake for the future gift." And I believe that with all my heart.

Stewardship isn't simply reporting back about how funds were spent. And it certainly isn't just making sure the donor receives the "appropriate number" of thank-you letters and updates.

Stewarding is caring for and deepening the relationship between the supporter and the organization's work. It's helping donors see the difference their generosity is making, in ways that matter to THEM.

It's staying curious about their interests, their experiences, and their evolving philanthropic goals.

And it's remembering that someone who has just made a significant commitment to your organization may be MORE interested in being connected than they were before they gave!

Think about it... They've just invested in something important to them. Don't you think they might want to stay involved, learn more, and see what happens next?

And yet, the donors who have said YES to our impact promises often receive less personal attention than the ones we're still trying to engage.

Now THAT'S petrifying.

🪄 Try this relationship "alchemy" instead

Look at the major gifts you've received over the past six months. 

Choose one donor and ask yourself: What have I done since their gift that has strengthened our relationship?

Not what communications they've received. Not whether their thank-you letter went out on time. What have YOU done to help them feel more connected to the mission they care about?

If the answer is "not much," there's your next opportunity. A personal call. A meaningful update. A thoughtful question. An invitation to see their impact firsthand.

Not because you want another gift tomorrow. Because you value the relationship.

The Good News? None of These Eerie Truths Has to Stay Hair-Raising.

Here's what I love about major gift fundraising.

You don't need a perfect portfolio, a flawless cultivation plan, or an elaborate stewardship program to build meaningful donor relationships. 

You need to be intentional. You need to be curious. And sometimes, you need a little courage.

Get curious before you get strategic.

Learn what matters to your donors, rather than simply filling their calendars with activities. Pay attention to their signals, and have the courage to invite them to make a meaningful gift when the time is right.

And when they say YES, don't disappear into the next solicitation. Keep showing up.

Because major gifts don't happen simply because someone has money to give.

They happen through trust, meaningful conversations, shared values, and relationships that continue to grow.

One Last Question

Take a look at your portfolio right now. Which of these three eerie truths might be showing up in your own fundraising? And more importantly, what's ONE thing you could do differently this week?

You might be surprised by what happens when you do.

Happy Halloween! 🎃