When walking to school with my son, I've learned how to engage him in meaningful conversation. Many of these skills can be translated to keeping donors engaged.
man and boy walking

I walk with my eight-year-old son to his school everyday. It’s a new routine for us, one that started just a couple of weeks ago. He and I have 15 minutes to ourselves every weekday morning. No siblings. No screens. Just my boy and me. 

Every morning, my son asks me the same question. Every. Single. Day. 

“So, what should we talk about?”

Sometimes, I have an answer all lined up and conversation flows. Sometimes, it’s surprisingly hard and my mind goes blank.

I’ve paid attention over the last couple of months as to the best way to respond to my son. I’ve paid attention to what “works” to engage him for those 15 precious minutes. How do I get the most out of our conversations?

Here is what I do.

1) I ask him questions about himself. I ask him about his favorite subject in school. (Math.) I ask him what he did during recess yesterday. (Basketball.) I ask him about the funniest part in Dog Man. (When the titular character is framed by the Fleas for a robbery he didn’t commit.)

2) I flatter him. I use the time to remember small things he did that made me proud. He waited so patiently for a package – a birthday present – that was late to arrive in the mail. He practiced his reading (in two languages!) with enthusiasm and vim. He exhibited great self-control during his most recent fight with his brother (but not the one before that). I recount these small-but-important details, and he lights up. 

3) I tell him stories. I tell him stories about when he was a baby, about when I was his age, about when his mother and I met. He listens. He asks questions. He loves every second of it. 

4) I give him problems to solve. We practice multiplication. We play a convoluted version of license plate poker. We play “Would You Rather” and “Who Is,” a game that tests his knowledge of our family tree. I give him challenges. He rises to them.  

5) The best walks, however, are the walks where HE starts telling stories.  When I ask the right questions, give him the right challenges, or share the right memories, he begins to overflow with things to say. I’ve learned that asking him “Who got in trouble yesterday?” is a cheat code for conversation. The story tells itself. 

All of these lessons directly apply to the fundraiser. Sometimes, I think we make fundraising (and donor retention specifically) more complicated than it needs to be. 

We’re just having general conversations with people with whom we want to form deeper relationships. The best ways to do that: 

  • Ask them questions. Ask them about their values, their hopes, and their dreams. 
  • Flatter them. Tell them they are awesome. Be a storehouse of memories – stellar examples of your organization in action – and give donors the credit. 

  • Tell them stories. Paint a vivid picture for them. Draw them into the narrative by making it real. 

  • Give them a problem to solve. Whether it’s recruiting people for a committee, engaging your board, or finding a speaker for your next event. Donors love to help.

  • Get them to tell their stories. There are lots of ways to get donors to open up. The Donor Connection Survey, a subject for another time, is my favorite one. Constantly be on the lookout for ways that they can share their narrative. 

Then, all that’s left to do is listen and let the relationship bloom.

Reader interactions

3 Replies to “Fundraising While Walking to School”

  1. Loved this ! practical for both professional and day to day life!
    I think the key in both worlds is to creat a dialog and not monolog.
    sending it to my partner, sisters and co workers 🙂


  2. Beautiful story. Very touching. Great analogy.


  3. looks good nice work



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