Using ChatGPT as a fundraising strategist
The robots have the answers
Today’s article…
…is some light relief from all the ROI related chat.
We hope you love the momentary diversion.
I (Caroline) have been checking in with AI (mostly to help me with first draft funding applications).
The results were frankly horse-shit.
Generic sentences, wrong information in the wrong place, too much repetition of the words ‘program’ and ‘organization’.
It’s highly possible that I’m not doing it right and that there are genuinely helpful ways of involving large language model AI tools in our work (I did have ChatGPT write a decent covering letter once).
But not for me, not yet anyway.
I won’t give up completely though. I know that this is the trajectory of the world and that it’s important to stay engaged.
On the theme of AI, it is almost a year to the day that I asked ChatGPT for support with my trust fundraising practice.
If it’s capable of planning a romantic weekend away for fellow fundraiser Andy King, then it should be able to glean / collate / steal sufficient information to help me with my trust fundraising right?
Below, you’ll find my original 2024 prompt (plus ChatGPT’s answers), my subsequent iterations, followed by the 2025 version.
Has the response changed or is it completely the same?
Is it better?
Is it worse?
Should we be worried?
All will be revealed…
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Using ChatGPT as a fundraising strategist
The robots have the answers
by Caroline Danks
I think all of us are curious about how technology is going to impact our jobs, so I asked ChatGPT for some ideas.
Spoiler – they’re not entirely shit…
Version 1 - May 2024
Caroline: Give me twenty ideas to help me raise more money from charitable trusts and foundations
ChatGPT: Of course! Here are twenty ideas to help you raise more money from charitable trusts and foundations:
1. **Research and Targeting**: Invest time in researching potential trusts and foundations that align with your organization's mission and goals.
2. **Personalized Proposals**: Tailor your proposals to each trust or foundation, highlighting how your project aligns with their specific areas of interest and priorities.
3. **Build Relationships**: Cultivate relationships with trustees and foundation staff through networking events, meetings, and regular communication.
4. **Impactful Storytelling**: Use compelling stories and case studies to illustrate the impact of your organization's work and how their support can make a difference.
5. **Clear Budgets and Plans**: Provide detailed budgets and project plans to demonstrate how their funding will be used effectively and efficiently.
6. **Highlight Successes**: Showcase previous successes and outcomes achieved with the support of other trusts and foundations.
7. **Demonstrate Sustainability**: Emphasize your organization's long-term sustainability and how their funding can contribute to lasting change.
8. **Offer Recognition**: Offer recognition opportunities such as naming rights, donor acknowledgment in publications, or invitations to special events.
9. **Collaborative Partnerships**: Explore partnerships with other organizations to strengthen your proposal and demonstrate collaboration within the sector.
10. **Engage Board Members**: Leverage the connections and influence of your organization's board members to introduce your cause to potential funders.
11. **Grant-Writing Workshops**: Host workshops or webinars to help other nonprofits in your community improve their grant-writing skills, positioning your organization as a resource.
12. **Demonstrate Capacity Building**: Show how their funding can support capacity-building initiatives within your organization, such as staff training or infrastructure improvements.
13. **Provide Regular Updates**: Keep funders informed about the progress of funded projects through regular updates, reports, and impact assessments.
14. **Seek Multi-Year Funding**: Request multi-year funding commitments to provide stability and continuity for your organization's programs and operations.
15. **Highlight Match Opportunities**: Encourage trusts and foundations to consider matching grant opportunities to leverage their support and inspire other donors to contribute.
16. **Host Site Visits**: Invite trustees and foundation representatives to visit your organization's facilities and witness your work firsthand.
17. **Utilize Technology**: Utilize online platforms and tools for grant applications, reporting, and communication to streamline the process for both parties.
18. **Offer Flexibility**: Be open to discussing flexible funding arrangements that accommodate the unique preferences and requirements of different trusts and foundations.
19. **Acknowledge Donor Preferences**: Respect and accommodate donor preferences regarding anonymity or specific conditions attached to their funding.
20. **Express Gratitude**: Express genuine gratitude for their support, demonstrating the impact of their generosity and the value they bring to your organization's mission.
By implementing these ideas, you can enhance your organization's fundraising efforts and build stronger partnerships with charitable trusts and foundations.
Thanks, ChatGPT!
These ideas are ok and they make sense.
But they’re generic and US focused.
There’s no sense of which activity to do first, which to go all in on and which to experiment lightly with.
*The bit where I panicked a little about imminent robot replacement*
Version 2 - May 2024
Caroline: “Give me twenty ideas to help me raise more money from charitable trusts and foundations including examples and case studies”.
The response was similar but with an example from a named trust / foundation for every tip.
‘The Bill and Melinda Gates Foundation hosts annual events to build relationships with supporters’
My mind was blown on seeing that the software was capable of pulling specific examples as requested.
Once I’d had a sit down and a cup of tea (and by ‘tea’ I mean ‘luxury hot chocolate with a splash of amaretto in it’), I relaxed a bit.
There was still no context, nuance or specificity.
What sort of events do the Bill and Melinda Gates Foundation host?
How do they define ‘supporters’?
How can I even begin to use this as an example in my own charity?
Version 3 - also May 2024
My third and final iteration of the question:
Caroline: “Give me twenty ideas to help me raise more money from UK charitable trusts and foundations including examples and case studies”.
I got twenty similar tips without the examples, bar this at the bottom:
“The National Literacy Trust partnered with several UK trusts and foundations to launch a pilot literacy program targeting disadvantaged communities. Through tailored proposals highlighting the alignment with each trust's funding priorities, they secured significant support for the initiative. Impact reports showcasing improved literacy rates among participating children and families further strengthened trust relationships, leading to continued funding and expansion opportunities”.
Version 4 - 2025 edition
Caroline: “Give me twenty ideas to help me raise more money from UK charitable trusts and foundations including examples and case studies”.
Absolutely! Here's a list of 20 practical ideas to help you raise more money from UK charitable trusts and foundations, with examples and case study-style inspiration where possible. These are a mix of strategic, tactical, and relationship-focused ideas tailored for someone like you—an experienced trustee with marketing background looking to grow fundraising.
🔎 STRATEGY & TARGETING
Create a “Top 20 Trusts” Focus List
Focus on trusts that match your cause and size.
Example: A small mental health charity focused on young people created a hit list of 20 mid-sized UK trusts that specifically supported early intervention in mental health and secured 6 grants in a year.
Use 360Giving + Charity Commission Data
Mine publicly available grant data to find funders supporting similar causes.
Tool tip: Use GrantNav to search past grants.
Segment Your Projects
Break down your work into fundable themes (e.g. youth work, homelessness, disability).
Case: One youth charity packaged its mentoring scheme as a standalone project and received a £25k grant from The Henry Smith Charity.
Develop a Multi-Tier Funding Pyramid
Align small/medium/large trusts with specific levels of need.
Example: Large trusts fund core costs; smaller ones fund equipment or volunteer costs.
Use a Rolling Trusts Calendar
Plot deadlines 12 months in advance to manage capacity and avoid last-minute rushes.
Tip: Use a Trello board or Excel template with status tracking.
📄 STRONGER APPLICATIONS
Invest in Powerful Case Studies
Include 2-3 short stories that demonstrate real impact with photos or quotes.
Example: A homelessness charity used "Tom’s Story" with a quote and image—resulted in funding from Garfield Weston.
Link Applications to National Policy Goals
Align outcomes with government priorities (e.g. reducing NEETs, health inequalities).
Case: A food poverty charity referenced DEFRA’s food insecurity stats in their bid to The Tudor Trust.
Involve Beneficiaries in the Application
Include direct quotes, co-design elements, or a letter of support.
Tip: Trusts increasingly value authenticity and inclusion.
Highlight Past Success with Trusts
Include a short paragraph on what you've achieved with previous funding.
Case: A youth theatre mentioned 3 past funders and leveraged credibility to win Esmée Fairbairn support.
Tailor Every Application
Avoid copy-paste submissions. Reference the trust’s criteria and interests.
Tip: Use Ctrl+F on a trust’s annual report to find the exact words they use.
🤝 RELATIONSHIPS & COMMUNICATION
Ask for Feedback on Declined Applications
Shows professionalism, and often leads to useful insights or a second chance.
Invite Trusts to Events or Project Visits
Even if they decline, it can build a long-term relationship.
Example: A London literacy charity invited funders to a “poetry slam” and got a grant after a trust officer attended.
Keep a Warm Stewardship Plan
Send short updates, photos or news to current/past funders twice a year.
Tip: Even a PDF newsletter or simple email works.
Use Trustees’ Networks
Ask board members to check LinkedIn or personal networks for connections to trust staff or trustees.
Case: One charity secured an introduction to a dormant trust through a trustee’s golf club contact!
Thank Funders Creatively
Not just a letter—use a video message, child’s drawing, or a custom infographic.
Example: A disability charity filmed a 1-minute “thank you” video from staff and users, which led to renewed support.
🧠 CAPACITY & LEARNING
Join the Association of Charitable Foundations (ACF)
Good insight into trust priorities and events where you can meet grant-makers.
Train a Volunteer Grants Researcher
Recruit a skilled volunteer to help identify new funding opportunities.
Tip: Look for retirees or postgrads in public policy or charity management.
Work in Partnerships
Co-apply with other small charities or community groups.
Case: A network of small arts charities co-applied for a regional creative programme and split a £50k grant.
Use Funder+ Support
Some trusts offer extra support like strategy help, comms advice, or loan schemes (e.g., Power to Change, Lankelly Chase).
Tip: Always ask what else they offer beyond money.
Review and Refine Every 6 Months
Track trust applications with a mini-dashboard: success rate, time spent, average grant size.
Outcome: Helps focus efforts where you're most successful.
Would you like a version of this in PDF format or a short proposal template tailored for one of your charity’s key projects? Or maybe we could build a "Trusts Tracker" sheet together?
Comparing 2024 with 2025
A couple of early and obvious differences:
Amusingly, 2025 ChatGPT has decided that I’m “an experienced trustee with marketing background looking to grow fundraising” - which I’m not. Unsure as to why they would say this (and I recommend explaining your role as part of your prompt so they don’t assume).
The format is different, the list is presented in sections with EMOJI’s aplenty.
But what about the actual content?
Only six of the tips were present in both the 2024 and 2025 top 20:
Tailor your proposals
Build relationships with trusts
Highlight successes and outcomes acheived as a result of the support of other trusts and foundations
Collaborate with other charities
Keep funders updated
Leverage the connections of your board members
The remainder of the 2025 content seems very strategy / planning focused (focus, refine, develop a pyramid, create a 12 month calendar…).
At the end of the list, it suggests that we build a ‘trusts tracker’ together - 2025 ChatGPT is keen to build tools.
Some of the suggestions and case studies lack important context:
“Ask for feedback on rejections” (yes but is that a realistic expectation in the current climate?)
“A youth theatre mentioned 3 past funders and leveraged credibility to win Esmée Fairbairn support” (easy peasy then, let’s do it)
“Some trusts offer extra support like strategy help, comms advice, or loan schemes (e.g., Power to Change, Lankelly Chase)” (except that Lankelly Chase are closing and actually, comms advice won’t keep the lights on).
Some are either irrelevant or laughable:
‘hire a volunteer to do what is essentially a paid role’
‘join the Association of Charitable Foundations’ (a membership which unsurprisingly is open only to trustees of charitable trusts and foundations)
So, do I need to retrain as a Life Coach / Michelin Starred Chef / Gladiator?
What (I think?) I learned from this experiment - and the updated 2025 version, is that we all know the basic tenets of great trust fundraising practice (and if we don’t, ChatGPT can list them for us).
What an inexperienced fundraiser won’t be able to figure out from generative AI is which of ChatGPT’s suggestions are good and which are bad.
There is no nuance here.
And this might end up being a problem, because inexperienced fundraisers might end up trying to join ACF or flexing their successful outcomes at Esmee Fairbairn in a bid to ‘win credibility’ and a large, multi-year grant.
#ThatsNotHowThatWorks
Is it possible that we’re moving to a two-tier trust fundraising approach, where experienced fundraisers are applying even more discernment to their applications and those that have less experience are taking advice from a large language model which unfortunately isn’t spewing out the best suggestions?
Whilst I hate to exclude people from the fundraising process on grounds of inexperience, I wonder if the impact of all the spamming will be that more and more trusts and foundations move towards a more pro-active grant making approach and who could blame them?
We wait and watch with interest.
Please reply to this email or leave a comment and share your own experiences of using AI for grant writing, strategic planning, prospect research and everything in between.
I am an open book.
I have “worked with” my (paid for) AI tool (on Notion) for over a year now and I find it has improved ten fold. It now understands the way I like to write and whilst it will never replace my writing, it saves me hours of time when it comes to word counts, changing layout, summarising and giving me prompts to get going.
To date it’s never given me an answer that I haven’t tweaked or changed, but as it reads more and more of my content, it really does try and use my style and language wherever it can and I have to say, I’m very impressed and use it every day.
It’s like a trainee - give it the right tools and it’ll serve you well. But always check the work first as it’s never going to be up to your standards (not yet anyway).
I don’t doubt that that time may be coming…..