asking thoughtfully

Alfie Kohn, the awesome education and parenting expert says this over and over as a sort of golden rule of parenting.

I would argue that it’s great advice for any person in any relationship, but especially for fundraisers looking to connect with donors.

When you’re talking, you’re focused on yourself, your talking points, your accomplishments, what you’ll say next…etc.

When you’re talking, you’re making assumptions about your listener based on yourself, your values and what you think they want to hear—or what you want them to know.

But when you’re asking, you’re opening yourself up to your donor. You’re still talking, but you’re acknowledging that they have something to give you. Asking requires humility and empathy.

Yes, you want donors to give money, but the money isn’t the most important thing. The connection is. And when we’re asking thoughtfully for money, we need to truly ask, not beg, or badger our donors.

When we ask for money, it needs to be about them and the change they can make with their investment, not about us as individuals.

Yes, asking is hard. Asking for anything, money, advice, help. We’re opening ourselves up and we’re in a vulnerable place if we ask our donors:

  • “What do you think of this program?”
  • “What do you think we should do to address this new challenge?”
  • “What did you think of the last event?”
  • “Can you help?”

There’s a chance that they might say something that you don’t want to hear, or that they might have an idea that you can’t or won’t use. They might say no. And that’s okay. You need to be ready for all of that.

It’s better to have questions to ask, and learn more about your donors, more about your work (or at least their perception of it), than to assume you know how they feel, what matters to them, and what they want.

Think about how you can talk less at your donors, and ask more. This is something you can do across your donor base, for every single person who gives. You can use donor surveys, social media and personal phone calls.

Asking thoughtfully often will bring your donors closer to you, it will make you better in your work, and it will make it easier to ask for money when you (and your donors) are ready. It also gets them in the habit of hearing you ask. It’s one way that you show you care. Ask thoughtfully. The smart folks at Storycorps have a great list of questions to help you.

And as much as asking is important, sometimes questions aren’t the answer. Sometimes, asking too many questions is the problem.

In my work as a fundraiser and as a mentor (and trainer of mentors), I’ve learned the value of silence. Sometimes the best thing you can do is lean into that silence. It’s tempting to ask one question, then another in a bid for connection, but sometimes you need to embrace the awkwardness of the moment. Ask a question, then wait.

And wait.

If nothing happens, embrace the awkwardness, and the silence. Sit with it. Name it. Acknowledge that making new connections is hard, and ask for help. It can be as simple as:

  • “Sometimes, it’s hard to know what to say.”
  • “What would you like to talk about?” or even,
  • ”Wow, this is awkward!”

Identifying this experience can be critical to building trust, especially in the early stages of a relationship that can pay dividends of connection and investment down the road. So ask more, talk less and see how you strengthen ties with your donors.

donor surveys

Marcy Stengel

Marcy Stengel

Director of Development and Communications at Capital Region Sponsor-A-Scholar
Marcy Stengel has more than 17 years of experience working for mission-driven organizations as a fundraiser, event planner and communications professional. She has worked for organizations and causes within education, media, environmental policy and public health. She is one of the few people out there who likes asking people for money, and wants others to find comfort and confidence in asking as well. She believes that philanthropy makes our communities stronger and our world a better place. She lives in upstate NY with her husband, son and their spry rescue dog.