Hi Reader,

Crazy to think, but in the early days of AI, I nearly gave up. 😭

Maybe you’ve been there. I'd open a chat window, type something like "write a fundraising appeal for a nonprofit", and stare at whatever came back, feeling a little deflated.

It was generic. No real ask, no sense of the client I worked with, no gratitude. My voice, lost in a sea of bleh. I remember thinking this was supposed to save me time, but instead I was rewriting it from scratch.

For a while I chalked it up to the tool not being good enough. It took working through a tricky campaign for a client where the wording for a transformation gift had to be exactly right before I understood what I was doing wrong.

I wasn't giving it anything to work with. I was handing it one sentence and expecting it to somehow know the client's mission, the donor's history, the tone we'd built over months of strategy meetings.

It was no wonder it kept handing me back the most average version of a nonprofit appeal it could produce.

I knew I had to change how I used the tool. Before asking for a draft, I started feeding it everything I knew: who the donor was, what they cared about, the specific ask and the number behind it, details from the case for support, and three words for the tone I wanted: warm, direct, never transactional.

The first draft, with better ‘context’ in front of it, was closer to something I could send than anything I'd produced in months of typing quick one-liners.

It’s where it started to click for me. AI hadn't gotten better overnight. I had gotten better at working with it. Same tool, same person typing. The only thing that changed was the context I put into the conversation before asking for anything back.

Here's the part I continue to see most of us miss about writing AI prompts: it can’t read your mind. It reads a context window, meaning everything you've told it in that conversation, and nothing else. Give it a one-line instruction, and it fills in the blanks with the most average, generic version of what a nonprofit appeal "should" sound like.

Give it your context. Share your numbers, your voice, your donor, your goal, and it starts sounding like you.

Think of it like onboarding a new team member. You'd never hand them a single sentence on their first day and expect a polished donor letter back. You'd give them background on your organization, a sample of past work, the campaign goal, and the tone you're aiming for. AI needs the same briefing every time because, unlike a person, it doesn't carry your organization's history into the next conversation. It only knows what's in front of it right now.

A simple way to think about what "context" means for a fundraising prompt is to list out who you're writing to (a lapsed donor, a monthly giver, a board member), what you want them to do, what's true about your organization's mission and voice, and one concrete detail, like a number or a story, that makes it real. Four ingredients, and most generic AI output is missing at least three. Here’s an example to try out:

[I'm writing a renewal email to a donor named [Sarah], who's given [$500] a year for the past three years but hasn't renewed this year. The goal is to get her to renew at [$500] or increase to [$750]. Our mission is to help families facing food insecurity build long-term stability, not just get through the week. Our tone is warm and direct, never guilt-driven. This year, our food bank served [40%] more families than last year because of rising grocery costs. Please write a 150-word email making the case for her to give again.]

That's the new formula, shared in one paragraph instead of only one sentence.

Keep in mind this is not about outsourcing your judgment. You still decide what goes in the letter, what to cut, and whether the tone is right before anything reaches a donor's inbox. Context simply means the first draft AI produces is closer to what you'd send, rather than something you must fight with for an hour.

Open your last AI-generated draft that fell flat. Before revising the wording, rewrite the prompt that produced it. Include your campaign goal, one real donor or beneficiary detail, and three words that capture your organization's tone. Run it again and compare the two side by side.

Want to know what to include in that context, or would you like a second pair of eyes on a prompt before you rely on it for a big campaign? Hit reply! I read every response and am always happy to help you build a better brief.

See you in two weeks!

Link 💜

Effective AI prompts are the difference between generic output and fundraising gold. Some great ones in here. ​

For the wannabe developer in you! Anthropic (Claude peeps) offers more on context but engineering this time.

Prompt ✨