Questions for a Discovery Interview

Here are some starter questions for interviewing someone about how they give and why they give.

What’s best is if you stay in the moment with your interviewee shaping your next question based on the answer you just heard and asking follow ups. Best is if the interview actually turns into a lively conversation where your interviewee turns loose and starts telling you freely the behind-the-scenes story of their giving.

Also, some of the questions I’ve included are too personal for some people, so keep reading your interviewee’s mood and comfort level. And tell them upfront…

“It’s okay to say ‘pass’ anytime you want, and then I’ll just go right to the next question.”

Favorites
Now I’m going to begin with my two favorite openers which are also very simple questions. I like asking each of them more than once because I like to hear lots of stories, so I’m giving you variations here:

What’s a time when you gave money to a nonprofit and loved it?

Would you tell me another satisfying experience with giving?

Would you tell me another time when you made a donation and it was meaningful to you?
Any other times come to mind?

And…

What’s one of your worst experiences with giving?

Would you tell me about another time when you were unhappy about giving?

Would you tell me another time when you gave money and in the end didn’t feel good about it?

Any other times come to mind?

You can have a rich and rewarding interview just asking about best and worst experiences. But there’s lots more to get curious about so here are a bunch more questions to play with if you like:

What do you like and not like?

What inspires you to give? Is it the cause? The person asking you? The mood you’re in? How you’re doing in your life? How you’re doing financially? A mix? Something else?

What’s the pleasure you get from giving? Is it different depending on the issue or nonprofit?

How do you like to be asked? Do you like small talk first? Do you want to get right to the point? Do you want someone to give you a presentation? Do you prefer a conversation? Do you need Q&A time? Do you want the person to start by asking you what you’re interested in?

What questions do you want answered about a nonprofit before you make your decision?

Do you want someone to ask you for a donation or do you prefer to figure out your giving on your own?

Do you prefer a one-on-one ask or do you prefer to go to an event and make a donation as part of that?

How do you like to be thanked for a donation? A card, a phone call, a premium? Do you want your name printed in the nonprofit’s newsletter or posted on their website? Do you like to be thanked in different ways depending on the size of the contribution you make?

How is giving a way of saying publicly what you believe in and what matters to you? What’s it like for you to be seen by others for what you believe in?

How do you respond when someone is putting too much pressure on you to give? Do you wait them out politely? Do you say something about it? Do you get mad?

How often do you say yes to making a donation when you really want to say no? What are the circumstances?

Have you ever wanted to ask for your money back?

Tell me a time when you were asked for money and didn’t feel pressured, in fact you felt it would be perfectly okay to say no? How about another time like that?

What’s been your most surprising experience with giving?

Strategy

In what ways do you think strategically about giving? Are there priorities or perhaps a social change strategy you use to guide your decisions?

Do you prefer to give to advocacy or to direct services? Or both?

Do you prefer to give locally, nationally, internationally? A mix?

Do you give mostly with your head or your heart? Or both?

What matters most to you about giving? The cause? The people? The leader? Knowing someone from the organization personally? Having a personal connection to the cause? How well they spend their money? Their reputation? The percentage of their budget they spend on fundraising?

Do you like to just write a check? Do you like to get personally involved? Are you more likely to write a check, or a bigger check, once you’ve gotten personally involved? Are you more likely to get involved once you’ve written a check?

Do you generally continue giving to an organization once you start? What’s the longest period of time you’ve given consistently to the same organization?

Do you like to give to lots of organizations? Do you prefer to give larger gifts to a small number of nonprofits?

How often do you give the basic members amount? How often do you give more? What makes you decide to give more?

Do you have set plan you follow for the year? Do you give spontaneously in the moment when someone asks you? Or both?

What are your thoughts about planned giving, things like wills and living trusts?

How has your giving changed over time? Have you always had the same approach to giving or has it shifted and developed? What are the reasons you’re giving has stayed the same, or what are the reasons it’s changed?

Family and friends

How is your giving similar to that of your parents and siblings, and how is it different?  How much are you influenced by them?

How are you and your life partner similar or different in your giving? How much do you influence each other? Do you do joint giving? If so, how do you make your decisions?

What about your friends? How much are you influenced by them? Do you like giving to the things they give to? How much does their opinion matter? If they give to an organization does that increase its credibility in your eyes?

How do you teach your children about giving? Do you talk with them about it? Do you wait for them to ask questions? Is it something you want them to figure out on their own as they grow up? Do you give them money specifically for making donations?

What was your first experience with giving money? What did you learn from that? How did it influence you? What about other formative experiences?

Special Bonus
Here’s a great fall back question in case you get stuck. It’s something I learned in my coaching training.

But it’s something I like to throw in even if I’m not drawing a blank, because the answers I get to this are among the most revealing and interesting:

“What question should I ask you next?”

And a variation:

“What am I missing? What do you want to tell me that I haven’t asked about yet?”

These are a lot of questions, but there are a zillion more that you can ask, and lots that you’ll come up in the moment during your interviews.