What’s one of the best things you can do to increase your chances of closing a major gift?

Listen.

Fundraising and sales experts alike will tell you that we need to do far more listening and far less talking when working with prospects. Most of the time, if you get them talking, they’ll tell you exactly what their needs are and how you can fill them.

You need to fuel that conversation with some good questions to get it rolling.

But thinking up a handful of questions is the easy part. The real artists of conversation excel in their ability to follow up and build upon questions to really dig deep into a topic with someone and get them talking.

That takes a whole lot more planning.

Until you’ve mastered that skill, it’s good to have a series of questions preloaded and ready to go.

Good news! I’ve gone ahead and done that for you.

The beauty of this technique is that it really doesn’t matter so much if you get a short, one-sentence answer to a single question because you’ve already got your follow-up question ready to go, which will keep the conversation moving and help you learn about your prospect.

Each series of questions is intended to be asked in order. Once the conversation has some momentum, you can go off-script and ad-lib a bit.

Let’s get to it!

Learn about their background

  1. Where did you go to college?
  2. What did you study?
  3. What brought you to that field?

Pro-tip: If you’re unsure if they went the traditional university route, find a new way to phrase this. It would be rude to assume they went to college.

  1. Where did you grow up?
  2. What brought you to this area?
  3. Would you ever want to move back to your hometown?

Question 3 should give you some really useful information on WHY they choose to be in your community rather than “home.”

  1. What do you do for work?
  2. How long have you been there?
  3. What’s been your biggest accomplishment this year?

You probably already know many of the answers to these, but that’s not the point.

  1. Enough about work! What do you like to do on weekends?
  2. How old are your kids?
  3. Are you planning any trips with them soon?

Learn about their dreams

  1. What’s the next big goal for you? Retirement? Start your own business?
  2. How long do you think you’ll be at (their company)?
  3. Do you like the role you’re in now?

These may touch on the personal, so be sure you’ve got a good feel for your rapport.

  1. Are you a traveler?
  2. What’s the best place you’ve been to?
  3. What’s the best meal you’ve had while traveling?
  4. Where do you want to go next?

A personal favorite conversation of mine:

  1. What would you do if you didn’t have to work anymore?
  2. Think you’ll ever go for it and do that?
  3. What’s stopping you?

Learn about their interest in your program

  1. Where do you see this community in 20 years?
  2. What do you think is the biggest hurdle to reaching that goal?
  3. What role will you play in that, you think?

It may not be specific to your organization, but it helps you understand their interests and goals in philanthropy.

  1. How did you first get involved with our organization?
  2. What drew you to the cause originally?
  3. What did you think of (the program you just ran)?

Everyone likes being asked their opinion.

  1. What other nonprofits do you admire?
  2. I love their work as well. Have you ever attended one of their events?
  3. What got you involved with them?

This will help you start to put together a pattern of what/why they support.

Now that you’ve got the conversation rolling, you should be able to ad-lib and start to really get at the heart of their needs/desires. Let them do the talking and keep on listening!