Walk a Mile in Your Donors' Shoes (A Fundraising Essential!)

Your success depends on walking a mile in your donors' shoes. Here's what that really means.

Brett here:

When I was a middle school English teacher, I struggled for years.

At first I tried to do everything the way my peers did.

Eventually I took inspiration from my 6th grade art teacher, Mr. Brown.

Mr. Brown was known for doing things differently. For example, if you wanted to use a stapler for a project, you had to give him one of your shoes. You'd get your shoe back when you returned the stapler.

This was in the 1980s.

Would it fly now? Hmm, well...

But you get the idea. And I did too.

So I started to mix things up in my own classroom. I thought about what it was like for my students, who had to sit in desks all day long. School wasn't their job (you get to apply for a job) or their hobby. It was an obligation. Many of them didn't want any part of it.

One of the first changes I made was to the passing out and collecting of papers. I instituted what I called Pass Attack and Collect Attack (then, later: Seat Attack, Desk Attack, vocab videos, daily thoughts, collaborative novels...).

For Pass Attack, I'd place a stack of papers at the front of the room. Then I'd say, "Ready... go!" and time the students as the first person in each row (column?) dashed to the papers, counted out enough for their row, raced back, and passed out papers to the rest of their row. I'd stop the timer when all students at the back of the class raised their paper in the air to indicate their row was done: everyone had their papers. Collect Attack was essentially the same thing in reverse. All of this was recorded on a white board for each of my three 90-minute Literacy blocks. Crucially: there were prizes involved.

Some students did not like the chaos that followed, but to my knowledge most of them very much did. It got them moving. It was different. Did I mention there were prizes?

This was me trying to walk a mile in my students' shoes.

Bit by bit, I made other changes along these lines, and my teaching got better. My students were happier. They and their parents expressed more gratitude. This was the way.

Over time, I've come to see it's the same in fundraising.

Your success, too, depends on whether you...

Walk a mile in your donors' shoes

There are at least 2 kinds of walking in your donors' shoes:

1.) The kind where your mind "walks" in their shoes when you're writing for your donors.

This including things like:

• personalization ("Dear Reader")
• segmentation ("As a monthly donor, you know...")
• YOU language (make sure you're talking to me)
• framing (make sure you're talking to me about something I care about)
• authenticity (try to sound like an actual person with real feelings, not like a corporation, a committee, or an AI: too smooth and vague and perfect)
• storytelling (show the urgency and the stakes in your appeals; show the impact in your stewardship; don't forget to include me, your donor, in the story)

2.) The kind where you're doing all the things as a donor would: signing up for your own newsletter (or equivalent), making a donation yourself, and keeping track of what experiencing your own donor journey feels like.

This includes things like (below: less-than-ideal examples we found, so you can get a sense of how it might be for you if you haven't tested your own donor journey for years or someone else set it up before you arrived at your org):

• evaluating your sign-up experience; hopefully with more feeling than this...

• evaluating your email follow-up experience; hopefully with more heart than this...

• evaluating your confirmation experience; hopefully with more humanity than this...

It's still early in the year.

It's a great time for this resolution:

In 2026, I will walk a mile in my donors' shoes.

Get in the habit of asking yourself:

What should I be feeling here, ideally?

What am I actually feeling here?

Why am I feeling this way?

What needs to change?

Would I open this?

Would I read this?

Would I donate?

Once you start walking a mile in your donors' shoes, it's so much easier to figure out how best to write to your donors and how best to ensure a rewarding (for everyone) donor journey experience.