AI in Advancement

a practical guide for CAIS development teams

Working with AI

Compare it to the help you actually have

Not the world’s best grant writer, but the help available to you at 4 p.m. on a Thursday with a deadline. (Ethan Mollick)

Treat it as a thought partner

Think out loud with it. Bring half-formed ideas and let it help you work out what you think. You bring the judgment and make the final call.

Find the jagged edge

It’s excellent at some tasks and surprisingly weak at others, and the line isn’t where you’d guess. The only way to find it is to try.

Spend the time on people

The point is more time for relationships, and better preparation for them. It should never replace them.

Every school has to decide where its privacy line is

There is no single right answer here. Some schools only use AI with public information. Others share de-identified data. A few have enterprise agreements that cover more. What matters is that you decide on purpose, as a team, and write it down.

Three things to do first

  • Know your plan. Consumer, business and education plans handle data differently. Check whether your conversations can be used for training, and turn that off where you can.
  • Strip what you don’t need. Names, emails, addresses and contact notes rarely matter for analysis.
  • Decide your line together. Agree what can be shared, and with which tool.

De-identifying a CRM export, step by step

  1. Export

    Pull only the fields you need from your CRM.

  2. Remove names

    Delete names, emails, phone numbers, addresses and free-text notes.

  3. Swap the IDs

    Replace each CRM ID with a new random ID. The same person keeps the same new ID across every gift.

  4. Analyze

    Bring the cleaned file to your AI tool and ask your questions.

  5. Match back

    Use your private key file to reconnect results to real people, on your own computer.

your CRM export

Name CRM ID Gift
Jordan Alder 48213 $250
Priya Okafor 51907 $1,000
Jordan Alder 48213 $500

what the AI sees

Donor Gift
A7F2 $250
K9Q4 $1,000
A7F2 $500

Let the AI build the tool. The latest flagship models can write a small program that runs entirely on your own computer. It anonymizes a file before you analyze it, then puts the real names back when the results return, so donor details never reach anyone’s server or the cloud. Ask your AI tool to walk you through building one.

It only knows your school if you tell it

AI knows nothing about your mission, your voice, your families or how you do things. The single biggest improvement most people can make is to write that down once and hand it over every time.

Keep a short context document and paste it in, attach it, or save it in your tool’s project or custom instructions feature. Most major tools have one. Update it each year as priorities change.

Talk instead of type. Voice transcription makes it easy to give rich background. Right after a meeting, talk through what happened for two minutes, then ask the AI to organize it.

Let the AI interview you. You don’t have to write the document from scratch. Ask the AI to interview you, one question at a time, and turn your answers into a draft.

try this 
I want to create a context document about my school's advancement work that I can give you at the start of future conversations. Interview me one question at a time about our mission, voice, constituents and this year's priorities. When you have enough, draft the document and tell me what's missing.
a context doc outline 
# About [School Name]

## Who we are
[Grades, size, location, founding story in 2–3 sentences]

## Mission
[Your mission in plain words]

## Our voice
- [How you sound, e.g. warm, direct, a little playful]
- Words we use: [...]
- Words we avoid: [...]

## Who our people are
[Alumni, current parents, past parents, grandparents,
trustees: what each group cares about]

## This year's priorities
1. [Annual fund goal]
2. [Campaign or project]
3. [Key events and dates]

## An example of our best writing
[Paste a short piece you're proud of]

## How I'd like you to work with me
- Ask me questions when you need details.
- Don't invent facts, names or numbers.
- Tell me if something sounds generic or pushy.

Where AI is strongest for advancement work

Open any card for ideas and a starter prompt. Each prompt assumes you’ve shared your context document first.

Differentiation

One story, shaped for every audience
  • One campaign update rewritten for alumni, current parents, trustees, grandparents and young alumni
  • Appeal letters in several tones for different segments
  • A long impact report turned into a social post, an email and a one-page summary
try this 
Here is an update about [project]. Rewrite it three ways: for alumni (memory and belonging), for current parents (what it means for their child now), and for trustees (strategy and numbers). Keep each under 150 words, in our voice. Don't add facts that aren't in the update.

Analysis

Patterns in data you already have
  • Retention and lapsed-donor patterns: who stopped giving, and when
  • How reunion years move alumni giving
  • Which appeals and channels actually work
  • Common themes across survey or event feedback comments
  • Its broad knowledge of how other organizations work, applied to your situation (verify what it tells you)
try this 
Attached are two de-identified files: donors and gifts. First, describe what's in them and flag any data quality issues. Then tell me: which donors gave regularly before 2024 but not since? How does alumni giving change in reunion years? Show your work so I can check it.

Visuals

Maps, charts and timelines that make the case
  • A heat map of constituents by zip code to decide where to hold regional alumni events
  • A capital project timeline, from first conversations to ribbon cutting
  • Board-ready charts from a spreadsheet
try this 
Using the zip codes in this file, make a map showing where our active alumni donors are concentrated. Then suggest three cities for regional gatherings next year and explain why.

Events & logistics

Homecoming, reunions and everything in between
  • Master checklists and timelines so nothing slips through the cracks
  • Volunteer roles, run-of-show documents and day-of schedules
  • Invitation and follow-up sequences for each class
try this 
We're planning Reunion Weekend for [date] with classes ending in [X]. Build a planning timeline working backward from the event, with owners as blanks I can fill in. Then list what usually gets forgotten.

Grants & writing

From messy notes to a strong first draft
  • Grant narratives built from meeting notes and voice memos
  • Summarizing long RFPs to decide whether to apply
  • Ideas and angles for personalized thank-you notes
  • Annual report narratives and board communications

For anything personal to a donor, use AI to spark ideas and approaches, then write it in your own words. A note that builds a relationship should come from you.

try this 
Here are my notes and a voice-memo transcript from three meetings about [program]. Organize them into an outline for the [funder] proposal, matched to their criteria (pasted below). Mark anything I still need to find out.

Visit prep & strategy

A thought partner before the big conversation
  • Briefs and talking points for donor visits, using only information you choose to share
  • Role-playing a difficult conversation before you have it
  • Stress-testing a plan: “Argue against my plan”
  • Meeting summaries and action items from a transcript
try this 
Here is our plan for [campaign or event]. Act as a skeptical trustee and argue against it. What are the three weakest points, and what questions would you ask me?

The good stuff happens in the back-and-forth

do

Have a conversation

The first answer is a starting point. Say what’s off, add what’s missing, and go a few rounds. A one-line request gets a one-line-quality answer.

do

Run an adversarial pass

Ask it to argue against your plan, read your proposal as a skeptical program officer, or find what you’re missing. You don’t have to take every critique.

do

Go big, then prune

Let it generate a lot early on. Then do a pruning pass: what is essential to the goal, and what can go without losing quality? The result is usually stronger and more compact.

do

It’s not like using Google

Search finds things. AI drafts, critiques, role-plays and reasons with you. If you’ve only used it to look things up, you’ve barely started.

watch for

Confident and wrong

It can invent sources, dates and statistics, and sound sure about all of them. Verify anything you’ll act on or publish.

watch for

Removing the human

Your judgment, taste and relationships are the point. If you just go where it tells you, you get generic work, and you lose the skills that make you who you are.

More on these techniques: Moving Beyond the Basics, The Power of an LLM Debrief, and Don’t Let the AI Handle It.

Tools and resources

Assistants

  • Gemini

    Built into Google Workspace, so a natural fit for Google schools.

  • Copilot

    Built into Microsoft 365.

  • ChatGPT

    Widely used, with a free tier.

  • Claude

    What I use in the session demos.

Helpers

  • Handy

    Voice transcription, so you can talk instead of type.

  • LLMFeeder

    Browser extension that turns a web page into clean text to paste in.

  • liteparse

    Converts PDFs to text. Use the OCR option for scans.

Learn more

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