October Does Not Have to be Scary
Okay so I have to tell you about this mailing list.
Not long ago I pulled one for a year-end mailing. A few hundred people. Not a big list. It took me way, way longer than it should have.
I have been doing this for almost thirty years. I know where the buttons are. And I am sitting there clicking screen, screen, screen, going what is happening right now. Everything I needed was in there. I just could not get to any of it.
Here is the part that made me mad. The fundraiser in me knew exactly who needed to be on that list and why. The operations person in me could see that the system was the only thing in the way. Every hour of clicking is an hour nobody spent on the phone with a donor.
And I thought, oh, this is October. This is exactly October.
The Letter gets all the attention.
If you are a development director or an ED right now, you know what October looks like. The letter is being written. The list has to get pulled. The board wants a number. And everyone is kind of crossing their fingers that the database plays nice this year.
It is also the month somebody finally opens an AI tool at work on purpose. And what do they ask it to do first? Write the letter. Of course they do. I would too. The letter feels like the big scary thing and that is what everyone says AI is for.
So the draft comes back in like four minutes. Amazing. And the list still takes forever. And the thank you letters still pile up on somebody’s desk the second week of December. And nobody got any time back.
I have started calling this the efficiency plateau, which sounds fancy, but really it just means you got faster at the same stuff and you are still drowning.
And can I say something as someone who has written a LOT of appeal letters? The prettiest ones do not always win. What works is saying it more than once, actually knowing your people, and a list you trust. The letter is kind of the least of it. Every year I watch teams pour their best hours into the copy and then lose the gift in the follow up, because the follow up lives in a system nobody has time to fix.
Where it actually saved me.
This year I found myself working in a database I had never touched. Never. Not too long ago I would have been buried in manuals and support tickets and quietly panicking that I was supposed to already know this.
Instead I made a project in my AI tool and basically trained it to be my tour guide for that one system. I ask it how do I do this thing, it tells me, I go do the thing. I do not have to learn the whole database. I just need to get out what the work needs.
It did not write anything for me. It just got me unstuck, which is the thing I actually needed. That is the pattern I keep seeing everywhere. The writing is rarely what is slowing a development office down. It is the stuff underneath the writing.
One More Story.
Years ago I ran annual giving and advancement services at a school, and they had no manual for their database. So I wrote one, because I am a syllabus girl and I need to know how things work or I lose my mind.
Fast forward, someone who had just started working there told me my manual is still there. STILL THERE. Somebody probably should update it. But I was so tickled, because I made a thing that people actually kept using, long after I left.
That is what I want for your appeal this year. Something that sticks around after the person who knows how it works moves on.
So here is what I would do.
Go find every note from last year’s appeal. The sticky notes, the email thread, the spreadsheet with tabs nobody remembers making. Throw all of it in and ask for a checklist. Then save that checklist somewhere you will actually find it next October, which, real talk, is the hard part. The reason this matters is that most appeals live in one person’s head, and that person is not always there next year.
For thank yous, give it a count of gifts by type and size. No names. You do not need names for this. Ask for a few templates you can make your own, so January is not a pile. A thank you that goes out in three days and one that goes out in three weeks are not the same thank you, and the donor can tell.
And think about whatever blew up last year. The list that would not pull. The segment three people defined three different ways. Tell it what happened and ask if this is a one time thing or a thing that is going to keep happening, and what the smallest fix is. If it keeps happening, it is not a people problem. Something underneath is broken.
Most of the fires are reruns.
Stuff catches fire at year end. It just does. But so much of it is the same stuff from last year, and you already know how that episode ends.
So point the tool at what keeps breaking, and let the letter be the fun part.
And if the thing that keeps breaking is bigger than one October, that is exactly what a Fundraising Operations Audit is for. We find what is in the way and you leave knowing what to do first.
Oh, and yes, that is me in the witch hat. If you know me at all, I am usually a very pleasant person. It is a costume. Mostly.
If you want to set up a project like the one I use, the Put AI to Work workbook walks you through it, including what is safe to put in and what never leaves the building.
Erin Peshoff is the Founder of Vivid Operational Advisors. She has spent thirty years inside nonprofit operations, helped raise over $100 million for institutional missions, and built Vivid around the operating discipline most strategic engagements skip.
