The way we think about asking for money is all wrong.
Hate asking for money? You’re not alone. And you don’t have to do it the way you think.
I get it. Sometimes the thought of asking someone for money can make your palms sweaty and your stomach churn.
Maybe you’ve convinced yourself you’re just “not good at it.”
Maybe you’ve even thought about finding a different career path.
But what if the problem isn’t you?
What if the problem is the way we’ve all been taught to think about “the ask”?
So many people in fundraising (development staff, board members, executive directors, etc) have been taught that fundraising is about convincing people to part with their hard-earned cash. That it’s about having the perfect pitch, overcoming objections, and closing the deal.
We’ve been told that fundraising is about convincing people to part with their hard-earned cash. That it’s about having the perfect pitch, overcoming objections, and closing the deal.
No wonder it feels awful.
We absolutely have to ask for money, but it doesn’t have to feel like begging.
The best fundraisers have conversations. They listen. They connect people with opportunities to make a difference in areas they already care about.
When you recommend your favorite restaurant to a friend, are you “selling” them on it?
Of course not. You’re sharing something meaningful that you think they’ll enjoy.
That’s exactly what a great ask feels like.
At the most basic level, all you have to do is show donors a compelling menu of options and invite them to choose the one that looks most compelling to them.
You’re not convincing. You’re not persuading.
You’re simply presenting opportunities for them to solve problems they already want to solve.
“But Michael, that sounds too simple.”
Well …
Simple? Yes. Easy? Not always.
But it’s a whole lot more effective (and enjoyable) than the arm-twisting approach most of us learned.
So how do you transform your approach?
Start with their interests, not your needs.
Before you ever mention money, understand what lights them up.
What problems keep them awake at night? What change do they want to see in the world?
Share stories, not statistics.
People give to people, not percentages.
Tell them about Maria, whose life was transformed by your after-school program. Show them what their gift makes possible in human terms.
Present options, don’t push solutions.
“Based on what you’ve shared about your passion for education, here are three ways you might consider getting involved…”
Notice how different that feels from “We need $10,000 by Friday”?
Make it about partnership, not transaction.
You’re not taking their money. You’re inviting them to join you in making something amazing happen.
There’s a world of difference between those two mindsets.
Want to know a question that can change everything?
It’s not, “Will you give?”
Nope. How about:
“What would it take for you to feel great about supporting this work?”
Then stop talking. Listen. Really listen.
You’ll be amazed at what happens when you give people permission to create their own giving experience.
And you don’t have to transform your entire approach overnight. This week, try just one thing.
Can you block out 30 minutes to have a genuine conversation with a donor?
Don’t ask for anything. Just listen. Ask about their story. Find out why they first got involved. Learn what they hope to see happen.
That’s it. No agenda beyond connection.
When you stop trying to extract money from people and start helping them express their values through giving, everything changes.
The conversations become energizing instead of draining.
The relationships become authentic instead of transactional.
And yes, sometimes the money follows.
Not because you’ve become a better “asker,” but because you’ve become a better partner in their generosity journey.
The ultimate goal of fundraising is to unleash more generosity.
And that happens through connection, not coercion.
What conversation will you have this week?
-Michael
