Money Questions: Your Key to Bigger, Faster Major Gifts

Stop guessing. Start asking with purpose.

Let’s blow up another outdated idea:

Donor cultivation isn’t about polish, perfection, or perks.

It’s not about sending charming updates, complimenting their kids, or waiting patiently for the mythical moment they’re “ready” to give.

And it’s definitely not about making donors feel like heroes in the hopes that they’ll reward you with a gift.

Real cultivation is about clarity, consent, and trust—and it starts with you.

Yes, YOU.

If that feels like a relief—if it makes you exhale, smile, or tear up a little—you’re not alone.

Because let’s be honest: fundraisers have been asked to do the impossible with too little for too long.

We’ve been taught to be miracle-workers, people-pleasers, and emotional labor machines—all while staying invisible.

Enough of that. You matter in fundraising.

The sooner you own that, the sooner you’ll move more money to your mission with less stress and way more confidence.

Cultivation Is About You (No, Really)

Donor cultivation is about you being clear and confident in what you need to know to ask a donor for a bold, values-aligned, personally meaningful gift.

Every (and we mean every) cultivation interaction should serve one purpose:

What do I need to know before I can ask them for their most significant gift?

That answer is your Money Question—the guiding purpose behind the conversation.

And let’s be clear: if you don’t know what your money question is, you’re just… hanging out. Building a relationship without direction. That’s fine for friendship. But you’re here to raise money.

No more meaningful contacts for the sake of checking a box. No more donor meetings that don’t move you closer to the ask.

Why Money Questions Work (and Feel Good)

Money Questions are the game-changer in Values-Based Major Gifts. They help you uncover what matters most to your donors—their values, giving priorities, and decision-making styles—so that you can confidently invite them to give in a way that feels powerful and personal.

When you lead with a Money Question, you’re doing two things:

• You’re making the donor feel seen, not sold to.

• You’re gathering the insight you need to ask them for a transformational gift—sooner and more effectively.

Let’s take it a step further: when you get your Money Question answered, you win.

Even if the rest of the conversation is about their dog or their latest trip to Italy.

You’re still moving the relationship forward with purpose.

You’re still getting closer to the ask.

Examples of Powerful Money Questions

Here are a few questions we use again and again in Values-Based Major Gifts coaching:

• What do you want your giving to make possible? (informs what you’ll pitch)

• How do you decide what to give, when, and how? (informs your timing and planning)

• What gift do you dream about giving—but haven’t made yet? (informs your ask amount or strategy)

These aren’t “tricks.” They’re tools.

They open the door to meaningful conversation—and more importantly, they give you the information you need to plan a strong ask.

Fundraisers Tend to Drift Away from the Money. Let’s Change That.

We’ve coached and managed hundreds of fundraisers. And here’s what we’ve seen: brilliant, mission-driven people slowly drift away from the actual fundraising part of their job.

Why? Because it can feel easier to focus on:

• Sharing updates

• Talking about volunteer opportunities

• Building rapport

• Sending newsletters and hoping they’ll stick

All good things—but not enough.

As a fundraiser, you are here to move money.

And every donor interaction should get you one step closer to a bold, joyful, direct ask.

This Fall: Plan with Purpose

If you’re heading into fall with 50, 150, or even 500 donors in your portfolio and no clear cultivation plan—don’t panic. But don’t wing it, either.

Start with your Money Questions.

Go through your donor list and ask:

• What do I already know about each person?

• What don’t I know yet that I’ll need in order to ask for a significant gift?

• What questions will help me fill those gaps?

Then, make a plan to get those questions answered—one interaction at a time.

Want Support to Build or Level Up Your Major Gifts Program?

If you have:

• Individual donors who give each year

• Someone (or a small group) who can focus on building relationships

• A desire to raise more money this fall—without guessing

We can help.

You don’t need:

• A full-time Major Gift Officer

• A pipeline of billionaires

• A gala or golf tournament

You just need a clear path, a solid plan, and a team like ours in your corner.

We’ll help you:

• Identify which donors you’re already connected to

• Define the money questions you need answered

• Map out your cultivation actions

• Script your asks (yes, really!)

• Practice them with you until they feel easy and natural

We’re accepting 2 more Values-Based Major Gifts clients this fall.

If that sounds like something your team needs, email us here.

TL;DR: You’re a Fundraiser. Own It. Celebrate It. Lead With It.

You’re not just building relationships for the sake of it.

You’re building trust that leads to bold, personal, transformational giving.

And Money Questions are how you do that—with purpose, precision, and power.

Want our list of 50+ Money Questions to get started? Send us an email —we’d love to send it your way.

Here’s to clarity, ease, and your juiciest ask season yet.