by Barbara Barron | Posted February 4th, 2026 | Subscribe to this newsletter
I’d like to start by reposting a piece by the great Seth Godin:
It’s difficult to write directions.
A user interface, a map or a recipe all require empathy.
That’s because the person writing it knows something the reader doesn’t. In fact, that’s the only reason to do it.
But because instructions exist to bridge this gap, we benefit by understanding and focusing on the gap. The instructions aren’t there to remind you of how to do something. They serve to help someone who doesn’t know, learn.
Here’s a useful way to begin:
Assume less.
Yes, the person reading your recipe knows what a knife is, but do they know you keep your mustard in the food cabinet, not the fridge?
List every step you could imagine, and then list some more.
Once the overdone, step-by-step instructions exist, begin removing them. The interface for your induction cooktop probably doesn’t benefit from having icons so obscure they’re meaningless, but it also doesn’t need every step for boiling water enunciated in capital letters.
In my experience in reading instructions, it’s easier for the user to skip over steps that are too complete than it is to try to guess what the person writing the directions had in mind.
You can – and should – give him a follow at his blog.
I read this article by Seth, and a little light went off.
I have been writing this blog for over nine years. Many of my articles are big think pieces designed to debunk myths or invite us to work in new and better ways. Others are what my web manager calls “hand-holdy” ones. These are the pieces that take a reader step by step through a new process or offer specific ways to refine one. My piece “How to Write A Good Welcome Letter for Parents” was first published in August 2018 and continues to be the most read and shared article yet.
Similarly, but even earlier, in September 2017 in the first month of my business, “How to Get Rid of the Terrible Thank You Letter” was published. That one is also very popular.
Both are good examples of the “hand-holdy” piece. They help guide someone new to this work or someone looking to revamp their work. Step. By. Step. They get a lot of eyes because advancement pros share them with new trustees or new members of the team. Love it.
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Invisible steps
When I read Seth’s piece, it made me think about all the steps that are invisible to me – and likely to you if you’ve done this work for a while. It’s the invisible stuff that trips us up every time, whether we are writing an appeal or welcoming new families or offering orientation to new trustees.
We naturally and innocently make assumptions about what others already know. Seth’s point is that it is better to be more specific and allow the reader or learner to skip over the steps they know — rather than leave them guessing, because we’ve assumed.
So, I’m thinking about how to help someone new and maybe a bit tentative to ask for a gift.
I can show you how to do that. We can practice until you get comfortable with my method and can then customize it to fit your style. But writing out the steps? Not so easy. And that’s precisely because there’s so much that is unique to each circumstance. I can tell you, for instance, that it’s helpful to start the conversation by asking how their early experience has been at the school.
But the step I may have missed for you is how to ask for the meeting itself.
Or – after they’ve shared about their child’s early days and how things are going for their family – you might need to know how to steer the conversation to the school’s giving program and what you hope they will consider.
Or even trickier for many, how to ask for that gift. Or how to ask and then wait. Or ask, wait, and then ask how you can follow up if they want more time to think about your request. (That happens a lot.)
It is after that meeting that you get the chance to do great cultivation work. That’s where it all begins.
The day I purchased my first personal computer, the sales guy loaded the giant boxes (yep, it was back then) into my car and said, “This is where the sale actually begins.”
So maybe Seth’s recipe analogy falls apart for us here. Maybe step-by-step instructions, as good as they can be, and as complete and even obvious as Seth urges, aren’t enough. Instead, we ought to talk this out, practice the different parts until we are so comfortable with the goal of the conversation (which is not only to secure the gift), that we can be fully and totally in the moment with these good people who’ve come to meet with us and hear our request of them.
I do agree about the empathy. When we put ourselves in the shoes of the people we are asking to support our schools, we have a far better chance of seeing it from their perspective. We can slow it down. Ask better, more thoughtful questions about them and what is important to them. We can be clearer about our hopes for them as engaged members of our community.
This kind of coaching is something I love to do and have done with big success for many clients. We all need to keep our donor skills sharp. It’s the only thing that we as human beings can truly do far better than AI. If you could use a walk-through session, do reach out.
Thanks for everything you’re doing.
Barbara Barron
[email protected]
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BARBARA BARRON is one of the most respected and highly sought-after independent advancement professionals in the country, having worked with dozens of schools in every corner of the United States.
She has raised over $20 million for schools where she served as the Director of Development. Barbara is a New York Times bestselling author, speaker, and presenter who currently advises dozens of schools in various capacities. She is considered a thought leader in the world of advancement, with her writing widely shared by professionals in development offices worldwide.
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