When I started in this trade 61 years ago, my tools were a legal pad and a portable typewriter. The clickety-clack rhythm of those keys was the soundtrack of early direct mail.

     Then came dictation—a revolution in time-saving —as Jerry Huntsinger and I toyed all through the 90’s and into the early 2000’s with the primitive magic of Dragon NaturallySpeaking the early voice-recognition software.

   Fast-forward to today,  my path has  gone from legal pads, to typewriters, dictation Microsoft Word and now to  the age of AI and ChatGPT.

  For those of us who’ve seen it all, from paper cuts to predictive text, AI tools like ChatGPT are a leap perhaps as monumental as the Gutenberg press or at least as Diet Coke. I’ll admit, I approached it cautiously—equal parts skeptic and explorer. But now, I consider ChatGPT a marvelous companion. It doesn’t replace the creativity, grit, or experience that fundraisers bring to the table, but it sure can make the day-to-day grind easier and the work product better.

     For those who fear it, loathe it, or embrace it, I wanted to share some prompts I’ve used in my drive to create better copy.  These I’ve found helpful—and hope you will too. Whether you’re crafting appeals, building cases for support, or just looking for inspiration, they are designed to  spark ideas, save time,  and check your work while leaving plenty of room to bring your own brilliance to the job at hand.

     I’ve attempted to organize the prompts I use most often into functional areas such as checking the readability of my work, setting the tone of voice and style of the copy, creating narrative for different personality traits and donor identities, and converting a piece of copy created for one purpose , let’s say a direct mail appeal, for use as an email appeal, or a Facebook carousel, Instagram post, or Tik-Tok script.

WARNING: This is a long post ‘cause there are prompts for lots of situations.  So, scroll to the categories that most interest you.  OR…you can download this post here and read at your leisure.

      Here goes.

READABILITY

1. “How long would it take the average adult in the U.S. to read this passage?”
   • Calculates the time it would take an everyday reader to get through the text, helping to figure out if the writing is short and sweet.
2. “Is there anything in the passage (or the entire letter/email/whatever) that feels like fluff or doesn’t add value?”
   • Spots parts of the text that might be padding or off-topic, making sure every word pulls its weight.
3. “How does the layout of this passage stack up? Any tweaks to make it easier on the eyes or user-friendly?”
   • Suggests adjustments like bullet points, shorter chunks, or visuals to make the content more scannable and appealing.
4. “Is the information in this passage lined up in the right order? If not, what should come first?”
   • Checks if the key points hit readers front and center or if the flow needs a little shuffling.
5. “What vibe or tone do you get from this passage?”
   • Gives honest feedback on the mood and style to ensure it fits the audience like a glove.
6. “Is there anything in this passage that feels like it doesn’t fit the tone we’re going for?”
   • Calls out language that sticks out like a sore thumb, ensuring a consistent voice.
7. “Does anything in this passage seem like it might confuse the average Jane or Joe?”
   • Flags sections that might be too highfalutin or leave readers scratching their heads.
8. “Can you point out any parts of this passage that use passive language?”
   • Highlights sentences where the action feels buried, so you can cut to the chase and make it snappier.
9. “You’re an advocacy organization [ or X] writing a guide on voter registration or [X]. Where would a call to action fit naturally in this passage?”
   • Finds smooth spots to slide in calls to action without sounding pushy.
10. “If you were trying to trim the fat, what words or sections would you cut from this passage?”
    • • Pinpoints spots to pare down, making the text lean and clean.

11. “Where would you add some breathing room in this passage?”

• • Suggests adding white space to make the content easier to skim and easier on the eyes.

12.“Is there anything in this passage that sounds forced or like you’re overselling it?”

• • Identifies wording that might feel unnatural or like it’s laying it on too thick.

GRAPHICS

     When graphics/images are called for AI makes it easy to quickly create appropriate images.  You may chose to use the AI-created image or use it as a guide for searching stock photo databases. Here are some sample prompts for creating an image using AI tools:

General Imagery

1. “Create an image of a serene beach at sunrise, with soft pastel skies and gentle waves lapping at the shore.”
2. “Illustrate a bustling city street at night, with glowing neon signs, crowds of people, and reflections on wet pavement.”
3. “Design a magical forest scene with glowing mushrooms, towering trees, and a sparkling river running through.”
4. “Generate a snowy mountain landscape with a cozy cabin nestled in the foreground, smoke curling from the chimney.”

Thematic Imagery

1. “Draw a futuristic cityscape with sleek skyscrapers, flying cars, and glowing holographic billboards.”
2. “Create a vintage-style poster of a 1950s diner, complete with a jukebox, classic cars, and chrome accents.”
3. “Illustrate a fantasy battle scene with knights in shining armor, a fire-breathing dragon, and a stormy sky.”
4. “Generate a minimalist art piece of a lone tree in the middle of a vast desert under a starry night.”

Specific Concepts

1. “Create an image for a petition campaign featuring a diverse group of people standing in front of a state capitol and signing a huge petition mounted on a tall easel. “

1.  “Create an illustration of a superhero flying over a cityscape at dawn, with their cape billowing and holding a basket of groceries for the food bank.”

 

2.    “Illustrate an educational diagram showing the life cycle of a butterfly with vibrant colors and clear labeling.”

3.    “Generate an image of a diverse group of people working together funky nonprofit  office space, showcasing collaboration and inclusivity.”

 

Whimsical/Creative Ideas

1. “Draw a cat astronaut floating in space with a galaxy backdrop and Earth visible in the distance.”
2. “Create a surreal image of a floating island with a waterfall pouring into the clouds below.”
3. “Illustrate a dreamlike scene of a hot air balloon shaped like a giant teacup, floating over a lush valley.”
4. “Generate an image of a fairytale castle on a cliff, surrounded by colorful flowers and sparkling fireflies.”

     These type of prompts can be customized based on your specific needs or preferences for the image.

BIG FIVE PSYCHOLOGICAL TRAITS

     Here are sample prompts tailored to crafting writing or imagery in alignment with the Big Five psychological traits that the behavioral scientists at DonorVoice rely on for critical parts of their work.  And remember you can get your file matched for Personality at DonorVoice

Openness to Experience

High Openness:
“Write a whimsical story in a highly imaginative and descriptive tone, incorporating metaphors and colorful, creative imagery.”

“Generate an abstract image with bold, unexpected color combinations and surreal elements, such as floating objects and impossible geometries.”

• Low Openness:
  “Compose a straightforward and factual report with a logical, no-frills tone, sticking to established norms and conventions.”

“Create a simple, realistic image of a tidy suburban neighborhood with clearly defined lines and traditional aesthetics.”

Conscientiousness

• High Conscientiousness:
  “Write a methodical and professional email in a polite, structured tone, emphasizing responsibility and attention to detail.”

“Generate an image of a neatly organized workspace, with symmetrical arrangements and minimal distractions.”

• Low Conscientiousness:
  “Write a casual, spontaneous blog post in a free-flowing tone with scattered ideas and less focus on strict structure.”

“Create an abstract image of a messy artist’s studio with splashes of paint and creative chaos.”

Extraversion

• High Extraversion:

“Write a lively, enthusiastic fundraising pitch in an upbeat, persuasive tone, full dynamic language.”

“Generate an image of a vibrant street festival, with dancing crowds, bright lights, and cheerful expressions celebrating victory for the X Campaign.”

• Low Extraversion (Introversion):

“Compose a reflective, introspective essay in a calm and thoughtful tone, focusing on internal experiences that come from saving nature.”

“Create an image of quiet forest glade with moss, a small stream, deer and a serene atmosphere.”

Agreeableness

• High Agreeableness:

“Write a warm and empathetic letter in a kind and reassuring tone of Alice Munro, focusing on collaboration and mutual understanding.”

“Generate an image of a community garden where people of all ages are planting flowers and helping each other.”

• Low Agreeableness:

“Craft a strong, assertive critique in a direct and matter-of-fact tone in the style of Ernest Hemingway, highlighting clear problems without sugarcoating.”

“Create an image of a lone figure climbing a rugged mountain, emphasizing individual determination.”

Neuroticism

• High Neuroticism:

“Write a dramatic monologue in an anxious and emotionally intense tone, capturing feelings of uncertainty and vulnerability.”

“Generate an image of a stormy sea, with dark clouds and crashing waves evoking a sense of tension.”

• Low Neuroticism (Emotional Stability):
  “Compose a calm and reassuring instructional guide in a confident, composed tone, focused on solutions and stability.”

“Create an image of a tranquil lakeside at sunset, with soft reflections and a serene ambiance.”

     These prompts align content creation with the nuances of each trait, helping writers and designers adapt to their audience’s psychological preferences or desired themes.

TONE AND STYLE

      You can create effective prompts for writing in the tone and style of specific, well-known authors.  Each author has distinctive features in their voice and style.  Take a piece of copy you’ve written in your own style and tone and then view it again through the lens of a famous author.  Or give the details of your appeal or whatever message and then request it be written in the style of whatever author you choose.  Below are some of my favorites with a description of the tone and style each produces.

Ernest Hemingway

• Prompt:
  “Write a short story [or re-write the attached appeal]  in the tone of Ernest Hemingway. Use simple, concise sentences, emphasize action over description, and convey deep emotion through understatement. Focus on themes of courage, loss, or human resilience.”
• Example Output:
  A man sits in a small boat, staring at the sea. He feels the weight of the fish on the line, his hands blistered from the struggle. The sun burns, but he does not flinch. He waits.

Toni Morrison

• Prompt:
  “Write a character-driven scene in the style of Toni Morrison. Use poetic, evocative language to capture the complexity of identity and heritage. Incorporate elements of folklore, spirituality, and the weight of history in the dialogue and setting.”
• Example Output:
  The house spoke in creaks and whispers, holding secrets in its wooden bones. Alma sat by the fire, her hands weaving tales as her children listened. The stories were hers, but they belonged to something older, deeper.

Alice Munro

• Prompt:
  “Write a short narrative in the style of Alice Munro. Focus on the quiet complexities of everyday life, using richly detailed settings and nuanced character interactions. Let the story unfold with subtle twists and revelations about the past.”
• Example Output:
  The kitchen window overlooked the field, where the corn grew tall and restless in the wind. Margaret washed the dishes, her hands steady, though her thoughts weren’t. She hadn’t seen Dan since the morning he left without his lunch.

Raymond Carver

• Prompt:
  “Write a scene in the tone of Raymond Carver. Use sparse, plainspoken language and focus on small, intimate moments between characters. Let the subtext of their emotions and relationships speak louder than the dialogue.”
• Example Output:
  He poured the coffee and slid the mug across the table. She didn’t look up. The sound of the clock ticked between them.
  “You working late again tonight?” he asked.
  She nodded, still not meeting his eyes.

Mark Twain

• Prompt:
  “Write a humorous anecdote in the style of Mark Twain. Use colloquial language, sharp wit, and a touch of satire to highlight the absurdities of human behavior.”
• Example Output:
  There’s nothing so terrifying as a man with a plan and no sense. When Cousin Joe decided he’d teach the mule to fetch water, we all took bets on how long it’d take the mule to teach him instead.

AGITATING AGITATORS

Perhaps you want to emulate the tone and style of a particular person in your organization or its stakeholders.  AI will help you immensely.  In case Kevin transforms his threat to abandon his post for a new reality of tropical beach combing we have that contingency covered.

 

Kevin Schulman

To write in the style of Kevin Schulman from The Agitator, you’ll want a tone that is direct, thought-provoking, and laced with a touch of skepticism about the status quo in nonprofit fundraising. His writing often challenges readers to rethink conventional practices while grounding arguments in data, behavioral insights, and actionable advice.

Here’s an example of a prompt to emulate his style:

Prompt:
“Write an article in the style of Kevin Schulman from The Agitator [include a link to one of Kevin’s posts]. Use a direct, conversational tone to challenge conventional wisdom in nonprofit fundraising. Incorporate behavioral science insights and offer actionable advice for improvement. Ground your argument in evidence, but don’t shy away from using rhetorical questions to provoke thought and critique outdated practices. Focus on helping organizations rethink their approach to donor engagement.”

Example Output:
Title: Why “Thank You” Emails Are Killing Your Donor Retention

Let’s cut to the chase: most “thank you” emails suck. They’re generic, impersonal, and filled with empty platitudes like, “We couldn’t do it without you!” But here’s the kicker—these hollow gestures do more harm than good. Why? Because they signal to the donor that you see them as a checkbook, not a person.

Behavioral science tells us that identity drives behavior. Donors give because they see themselves as helpers, advocates, changemakers. So, when your email doesn’t reinforce who they are—or worse, makes them feel like just another cog in the machine—it’s no surprise they don’t give again.

Here’s a better way: craft your “thank you” around the donor’s identity. Did they give to help children? Show them how their gift aligns with that purpose. Did they support you after a natural disaster? Make it clear they’re heroes in times of crisis.

Donors aren’t walking wallets. They’re people with values, stories, and motivations. If you don’t tap into that, no amount of “we’re grateful” will save you.

Roger Craver

To write in the style of Roger Craver from The Agitator, adopt a conversational yet authoritative tone. Roger blends humor, sharp critique, and a deep understanding of the nonprofit sector. His writing often calls out inefficiencies, challenges readers to embrace innovation, and conveys a sense of urgency.

Prompt:
“Write an article in the tone and style of Roger Craver from The Agitator [copy a link from a Roger post]. Use a conversational and witty tone to address inefficiencies in the nonprofit sector. Incorporate sharp critique of outdated practices and highlight the urgency of adopting new strategies. Blend humor and pragmatism to engage the reader and inspire action.”

Example Output:
Title: “Your Data Isn’t Broken—Your Thinking Is”

Let me guess: you’re convinced your nonprofit has a “data problem.” Your CRM isn’t up to snuff. Your reports are a mess. And if only you had better tools, your donor retention would skyrocket, right?

Wrong.

Here’s the truth: the biggest barrier to your success isn’t your data; it’s your thinking. The nonprofit world loves shiny new toys—AI this, analytics that—but all the tech in the world won’t help if you’re stuck in the Stone Age when it comes to strategy.

Take donor retention. Everyone talks about it, but few actually do anything meaningful to improve it. Instead, we drown donors in generic appeals, then scratch our heads when they leave. And here’s the kicker: we knowwhat works. Behavioral science has shown us time and time again that personalized, identity-based engagement is the key. So why aren’t we doing it?

The answer is simple: it’s easier to blame the tools than to rethink the system. It’s easier to send 10,000 emails than to craft 1,000 meaningful ones. But guess what? Easier doesn’t cut it anymore.

If you want to stay relevant—and solvent—you need to stop treating donors like numbers on a spreadsheet and start treating them like people. Yes, that takes effort. Yes, it requires rethinking your processes. But the alternative is clear: obsolescence.

The choice is yours. Just don’t blame your CRM when donors walk out the door.

DONOR IDENTITIES

We discuss Donor Identities a lot in The Agitator  because we know the one-size-fits-all approach to fundraising and donor engagement is thin gruel when it comes to truly nourishing your fundraising program.   Here  are tailored prompts for creating messages or content that resonate with the specified donor identities:

Nature Lover

Prompt:
“Write an engaging email for a donor who identifies as a nature lover. Use evocative language to celebrate the beauty of the natural world and emphasize the importance of protecting it. Highlight how their support helps preserve landscapes, forests, or natural landmarks for future generations.”

Wildlife Lover

Prompt:
“Craft a heartfelt social media post aimed at wildlife lovers. Focus on the importance of protecting endangered species and their habitats. Use compelling imagery and stories of specific animals to inspire empathy and action, emphasizing how their support directly helps wildlife thrive.”

Conservationist

Prompt:
“Compose a persuasive appeal for donors who see themselves as conservationists. Use factual, action-oriented language to highlight environmental challenges like deforestation, pollution, or climate change. Frame their contributions as vital to creating lasting, measurable impact on the planet’s health.”

Parent

Prompt:
“Write a letter to donors who are parents. Use a relatable and emotional tone to connect their love for their children with the importance of leaving a better world for the next generation. Show how their support ensures a safer, healthier future for kids everywhere.”

Caregiver

Prompt:
“Draft a compassionate email for donors who are caregivers. Use empathetic language to recognize their nurturing nature and commitment to helping others. Highlight how their generosity supports vulnerable individuals, reflecting their personal dedication to care and support.”

Victim of Disease

Prompt:
“Create a sensitive and empowering message for donors who have been affected by disease. Acknowledge their personal experiences and show how their contributions help fund critical research, support patients, and bring hope to others facing similar challenges.”

Example of Putting an Identity  Prompt to Work…..

Draft a compassionate email for donors identified as Caregivers. Use empathetic language to recognize their nurturing nature and commitment to helping others. Highlight how their generosity supports vulnerable individuals, reflecting their personal dedication to care and support.”

ChatGPT Draft:

Subject Line: Your Compassion Creates a Ripple of Hope

Header: Your Care Makes a Difference

Body:

Dear [Donor’s Name],

Every act of care, no matter how small, has the power to change a life. As someone who knows the unique challenges and joys of caregiving, you understand this truth better than most. Your compassion, dedication, and selflessness light the way for those who need it most.

Because of you, [Organization Name] is able to provide vital support to vulnerable individuals who might otherwise feel alone. Whether it’s offering a warm meal, a safe place to stay, or a helping hand during a difficult time, your generosity ensures we can be there for them—just as you have been there for those in your life.

Caregiving is a profound act of love, and your support extends that love to countless others who are struggling. Together, we are building a community where no one feels forgotten and everyone has a chance to thrive.

Thank you for making the world a kinder, more compassionate place. Your commitment inspires us every day.

With deep gratitude,
[Your Name]
[Your Title]
[Organization Name]

P.S. If you’d like to see the impact of your support in action, visit [link to success stories or impact page]. Your care changes lives.

SOCIAL MEDIA

Some organizations are fortunate enough to have social media specialists.  Most aren’t.  So, if you have to prepare the direct mail appeals, the email appeals and also deal with social media, you’re gonna  love AI.

Here’s how you can adapt that caregiver-themed appeal into formats for Facebook carousels, Instagram posts, and TikTok scripts:

Facebook Carousel Prompt

Prompt:
“Convert the caregiver appeal into a Facebook carousel ad. Break the content into 5 slides, each focusing on a key message: (1) recognition of caregivers, (2) the impact of their care, (3) how their donations help, (4) a heartwarming story of someone impacted, and (5) a call to action to give or learn more.”

Example Content:

1. Slide 1 (Visual): A caregiver helping an elderly person or a child.
   Text: “Caregivers like you change lives every single day.”
2. Slide 2 (Visual): Close-up of hands clasped in support.
   Text: “Your compassion extends beyond your loved ones, reaching vulnerable individuals in need.”
3. Slide 3 (Visual): A safe shelter or meal being provided.
   Text: “Your generosity ensures we can deliver vital support when it’s needed most.”
4. Slide 4 (Visual): A smiling person helped by the organization.
   Text: “Meet Maria: Thanks to donors like you, she found hope and stability during a tough time.”
5. Slide 5 (Visual): Call-to-action button with a heart icon.
   Text: “Be the light for someone in need. Donate today [link].”

Instagram Post Prompt

Prompt:
“Transform the caregiver appeal into an Instagram post with a single compelling image and a short caption that conveys empathy and impact. Include hashtags relevant to caregiving and community support.”

Example Content:
Image: A caregiver with a person they’re helping, with warm lighting to evoke hope.
Caption:
“Caregivers make the world a kinder place. 💕
Your compassion doesn’t just touch your loved ones—it creates ripples of hope for those in need. Together, we can provide meals, shelter, and support to vulnerable individuals.

Join us in making a difference. Link in bio. 🌟

#Caregivers #CompassionInAction #CommunitySupport #MakeADifference”

TikTok Script Prompt

Prompt:
“Convert the caregiver appeal into a TikTok video script. Keep it under 30 seconds. Use an empathetic voiceover, compelling visuals of caregiving and community support, and end with a call to action to donate or learn more.”

Example Script:

Visuals: A caregiver helping a child with homework, someone assisting an elderly person, and a warm meal being served.

Voiceover:
“Caregivers are the unsung heroes of our world. 💙
Your care doesn’t just change the lives of your loved ones—it extends to those who need it most.

Because of you, we can provide meals, shelter, and a helping hand. Together, we’re building a community of hope and compassion.

Join us and make an impact today. Click the link to learn more.”

Text Overlay:
“Your care changes lives. 🫶 Donate now [link].”

Prompts to Make Your Fundraising Life Easier and Your Work Product Better

Here’s a brief summary of some prompts you should play with to get a feeling of how to work with AI.  Remember, working with ChatGPT or any of the AI tools is best done treating the AI like a sidekick, tossing out different ideas and trying different approaches.  It won’t bite.  It won’t take long vacations. Nor ask for the weekend off. And it sure as hell won’t steal your job.

1. For Crafting Donor Appeals

• “Write a warm, persuasive donor appeal focused on [specific cause]. Highlight the emotional impact of their support and include a clear call to action.”
• “Draft a thank-you letter for donors who gave in response to [specific campaign]. Use a tone of deep gratitude and show how their contributions made an impact.”

NOTE:  Get yourself a copy of Lisa Sargent’s Thankology and then you’ll have the makings for the best Thank You prompts in the whole wide world.

• “Write an appeal that speaks to [specific donor identity, e.g., nature lover, parent, caregiver]. Highlight their unique motivations and values.”

2. For Tone and Style Adjustments

• “Rewrite this donor appeal in a conversational tone, inspired by Raymond Carver’s style: direct, engaging, and thought-provoking.”
• “Analyze the tone of this appeal and suggest adjustments to make it more empathetic and donor-centered.”

3. For Specific Audiences

• “Create a compelling message for Baby Boomers, emphasizing legacy and long-term impact.”
• “Draft a social media post aimed at younger donors, using a fun, engaging tone that highlights immediate results.”

4. For Storytelling

• “Develop a narrative around [specific donor or beneficiary]. Use vivid descriptions and emotional language to create a connection with the reader.”
• “Write a story in three parts: the problem, the solution (enabled by the donor), and the impact.”

5. For Digital Fundraising

• “Write a Facebook carousel ad with five slides for [campaign focus]. Each slide should emphasize a key message and end with a call to action.”
• “Draft a TikTok script that explains [cause] in under 30 seconds with an emotional appeal and a call to action.”

6. For Operational Efficiency

• “Create an FAQ section for [specific campaign], with concise answers to donor questions in a warm, professional tone.”
• “Identify redundant or unclear content in this donor appeal and suggest edits to make it more concise and impactful.”

7. For Testing and Refinement

• “Test this donor appeal for readability. Are there any words or phrases that could be simplified for better understanding?”
• “Suggest alternative opening lines for this appeal to grab the reader’s attention.”

Why Prompts Matter

Good prompts don’t replace good fundraisers. They amplify your creativity, making it easier to turn ideas into action. And when you’re juggling campaigns, meetings, and deadlines, having a starting point can be the difference between spinning your wheels and hitting your stride.

So, for the skeptics: don’t think of ChatGPT as a shortcut; think of it as your assistant. For the enthusiasts: keep pushing it to make your work better. And for the rest of us, somewhere in between—let’s keep experimenting, improving, and sharing what works.

Got a favorite prompt of your own? Share it with us.  Please send to RogerCraver@gmail.com or place it in the Comments section this Post.

 We’re all in this together.

Roger

P.S.  The prompt for the image at the opening of this post was:  “Create an image that goes with this blog post.”