The Best Questions to Ask Major Donors – And Why They Matter So Much

You already know this: Successful major gift fundraising isn’t really about making a pitch.

It’s about listening.

It’s about drawing out your donor’s story, learning what’s important to them, and finding the alignment between their vision and your mission.

That’s why questions are one of the most powerful tools in your toolbox.

When you show up with a genuine spirit of curiosity, your conversation becomes something deeper. More meaningful. More memorable — for you and for your donor.

Don’t Lead With Your Project

It’s tempting to begin a donor conversation by diving right into your campaign or initiative. After all, you’re excited — and your project is worthy.

But when you start by asking your donors to talk about themselves, you immediately change the energy.

Instead of presenting something to them, you’re inviting them into the conversation.

You’re signaling that you care — not just about a gift but about who they are as a whole person.

And that opens the door to real connection. 

It’s how you switch from transactional fundraising to relationship fundraising – don’t talk about money first. 

Your Questions will Guide the Conversation.

Remember, this is “Discovery.” You’re trying to discover how enthusiastic this prospect is about your work. 

And you want to determine whether they may be a serious prospect. 

So, discovery means you are simply asking questions. You’re encouraging your donor to reflect on why they care about your work. 

Hopefully they will begin to reconnect with the values and experiences that have shaped their generosity. Remember all giving starts with a personal connection to your work, and it’s your job to find it out.

Your questions help you understand what they want to accomplish by giving..

Here are three categories of questions that we use often — and you can too.

1. Questions That Invite Personal Storytelling

These are the kinds of questions that help your donor reflect on their life, their values, and the moments that matter to them. You’ll be amazed at how much you can learn from a simple conversation like this. 

And remember, to always use permission! Begin the questions with “if I may, may I ask you about . . . “

• I’d love to know where you grew up and went to school. 
• How did your early experiences shape your outlook?
• What do you like to do in your spare time? 
• What causes are you involved in?  And why?
• Are you traveling or vacationing this year? 
• What are you most proud of that you’ve done or experienced?
  

These questions don’t just build rapport. They start to uncover what your donor really believes in – the “why” behind their giving.

2. Questions That Invite Insight and Involvement

Asking for advice is one of the easiest and most effective ways to bring donors closer. It makes them feel included, respected, and valued.

Try these prompts when you want to deepen the relationship and invite their perspective:

• We’re considering a new approach to [project/initiative]. I’d love to know your opinion about it.
  
• Can I get your insight on a challenge or issue we’re working through?
  
• What would your ideal version of this project look like?
  
• Who do you think we should involve in this effort?
  
• How would you approach this if you were in our shoes?

One of my favorites? “Tell me more about that.” It’s simple — but it shows that you’re listening and truly care about what they have to say.

3. Questions That Explore Philanthropic Interests

These questions help your donor articulate their giving priorities. With these questions, you hope to find out their “Donor Story” – why they believe so deeply in your organization’s mission and why they support it.

 These questions can easily open up a Gift Conversation. 

• I’d love to know what causes are closest to your heart.
• What kind of impact would you most like to have through your giving?
  
• How do you decide which organizations to support?
  
• Why have you chosen to invest in our work in particular?
  
• What aspect of our mission speaks to you most?
  
• Would you be interested in knowing more about this aspect of our mission? 
• Would you like to know how you can help? 

You don’t have to force anything. Just stay open, be warm, and let the conversation unfold naturally.

When donors feel seen and heard – and listened to –  amazing things can happen.

Why This Works

When you ask the right questions — and truly listen — your donor begins to feel like a partner, not a prospect.

They’re not just giving to a cause. They’re helping shape it.

That’s what makes these types of major gift conversations not only productive but deeply rewarding.

Takeaways for Your Next Donor Visit

Here’s what I hope you’ll carry with you into your next donor meeting:

• Your job isn’t to do all the talking — it’s to invite a real, heartfelt conversation.
  
• Use thoughtful questions to bring out their personal values and discover what they deeply believe in. 
• The more you understand your Donor’s Story, the better you’ll know how to inspire them.
  
• And the ask? It becomes easier, more natural — and more joyful for both of you.
  

BOTTOM LINE: 

As always, we’re here to help you deepen relationships, raise more major gifts, and succeed in your next capital campaign. 

If you’d like our support in crafting your donor strategy or training your team, reach out — we’d love to partner with you.