Tag Archives: communication

The A.I. Tug of War in Fundraising—And How to Find Your Footing

Careers, Fundraising Analytics, Major Gift Teams, Profiles, Prospect Identification, Prospect Management, Research in Fundraising, , , , , ,

Let me ask you something: How many times has a piece of technology promised to change everything… and then promptly driven you absolutely crazy?

You know the scenarios. It can do all the things, but only after you’ve configured everything yourself. “Integration” turned out to mean something very different from what you imagined. The upgrade wiped out every custom setting you spent hours building. And whenever you try to do something just slightly outside the norm, the software fights you like a toddler at bedtime.

I could go on. We have all been there.

And yet—here’s the tension—technology genuinely has made our lives easier. Microsoft Word may not make complex formatting a walk in the park, but it has transformed how we create documents. And because it plays nicely with the rest of the MS Office suite, whole categories of headaches have simply disappeared.

Welcome to the tug of war.

The Two Ends of the Rope

When it comes to A.I. in fundraising, this same push and pull is playing out in real time. On one end of the rope are the people who believe A.I. is too messy, too risky, and too unreliable to touch. On the other end are the people who believe A.I. has ushered in such a leap in accuracy that we can use machine-generated information as-is, no human review required.

New technologies that arrive with enormous hype—and A.I. certainly arrived with enormous hype—have a way of polarizing us. But is there something useful to be found in the middle of that rope?

Spoiler alert: There is.

Yes, A.I. Has Been Around. But This Feels Different.

A.I. has been woven into our digital experience for years. Recommendation engines. Spam filters. Autocomplete. But when OpenAI released ChatGPT in 2022, it felt less like a product launch and more like a digital eruption. Things are moving fast. New and genuinely exciting capabilities are emerging. And yes, things are getting broken along the way.

For many in our field, the speed of that change feels dangerous. Whatever you do, don’t ask A.I.

But much like the anxiety that greeted Google’s debut—remember when people worried that nobody would learn anything anymore?—there is real and practical value here, if you know how to use it.

One of the most useful features of a generative A.I. chatbot is that you can ask it to show its work. Where did that information come from? What sources support that conclusion? What transactions were used to build that summary? That transparency is actually a significant feature, not a quirk.

Where A.I. Is Changing the Game for Prospect Research

At Aspire Research Group, one of the most dramatic shifts A.I. has made in our day-to-day work is in writing bios. Even setting aside the time required to gather information, writing a few well-crafted paragraphs about a prospect has always been time-intensive. Using DonorAtlas, we now have well-written bios and the underlying sources for verification—almost instantly. We can deliver a significantly stronger product at the low end, in far less time.

Until, of course, A.I. fails us. And it does fail us.

People in the arts, for example, seem to get misrepresented by A.I. with striking frequency. What is their “job,” exactly? They don’t fit the pattern that it expects. In those cases, we take over the steering wheel and drive that one ourselves.

This is not a reason to abandon A.I. It’s a reason to understand it.

Algorithms Are Only as Good as the Data Behind Them

Remember when Netflix’s recommendations felt almost eerily accurate—until they didn’t? If you shared an account with someone whose taste was wildly different from yours, the algorithm got confused. It was doing its best with messy inputs.

The same principle applies to your fundraising database. If your data is a hot mess, A.I. is going to struggle to give you reliable scores or meaningful analysis. But here’s the thing: it might still give you better results than statistical modeling did. And if better-than-before scores get gift officers out the door and into conversations with donors faster, that’s not nothing. Something is better than nothing.

But that raises the next question—and it’s an important one.

If A.I. Is Better Than What Came Before, Why Not Just Trust It?

If A.I. analysis outperforms statistical modeling, why shouldn’t we lean on it entirely? Why not let it drive portfolio assignments, staffing decisions, campaign planning?

I recently interviewed Vered Siegel on the Prospect Research #ChatBytes podcast, and she said something that I keep coming back to:

“One of the biggest shifts generative AI has introduced in our industry is that information is no longer the scarce resource. Judgment is now the scarce resource. We can generate lists and summaries and signals faster than ever, but that doesn’t automatically make our decisions better. One key aspect of being a strategic partner right now means helping the room slow down just enough to ask the right questions.”

Read that again. Judgment is now the scarce resource.

Finding the Balance

The key to leveraging A.I. well is knowing where human judgment needs to enter the picture—and deciding what level of risk is acceptable for you and your organization.

I’m not suggesting that every single name assigned to a portfolio requires a human review. Not anymore. But what if a feedback loop was built into the prospect assignment process? What if gift officers had a routine way to tell your analytics team when things are working—and when they’re not. That loop is human judgment at scale.

Here’s what breaks down when human judgment is undervalued or eliminated altogether: efficiencies go down. Not up. The risk of an error that could damage donor trust or cause your organization harm goes up. The promise of A.I. is efficiency, but that promise only delivers when the humans in the process are engaged at the right moments.

Get the balance right, and productivity goes up. New opportunities surface. Gift officers work with better information. Researchers spend their energy where it actually matters.

Get it wrong—either by refusing to use A.I. at all or by outsourcing your judgment to it entirely—and you’re just holding a rope with nobody on your end.

This Is Your Moment to Lead

Here’s what I want you to take away from all of this: the disruption that A.I. is causing in our field is real. But it’s also creating space for researchers and prospect management professionals to step into a more strategic role.

A.I. can generate the bio. It can surface the signal. It can produce the list. But it cannot decide which signals matter for your organization’s specific mission and relationships. It cannot make the judgment call about when a score doesn’t pass the smell test. It cannot be the strategic partner in the room who helps leadership slow down and ask the right questions.

Only you can do that.

The question—as always—is whether you’re ready to step up and do it.

Additional Resources

Beyond Episodic Wealth Screenings: Major Gift Prospect Identification That Hums

Prospect Identification, Prospect Research, , , , , ,

Let me ask you something: When was the last time a wealth screening rating automatically translated into an engaged prospect?

If you’re laughing right now, we’re on the same page. We all know the drill—trust but verify, capacity doesn’t equal inclination, wealth doesn’t equal relationship. But here’s what keeps me up at night: If wealth screenings have such obvious limitations, why are so many research shops still treating them as the primary engine for major gift prospect identification?

Spoiler alert: They shouldn’t be.

The Statistic That Changes Everything

 According to a CASE study of principal gifts to U.S. colleges and universities, half of these transformational gifts came from non-alumni. Read that again. Half.

We’re not talking about modest annual fund gifts here. We’re talking principal gifts—the naming opportunities, the program-changing investments, the gifts that get announced with press releases and champagne.

And half of them came from people who weren’t in the alumni database waiting to be wealth-screened.

Now, the study didn’t break down how many were parents versus community members. But that ambiguity makes the statistic even more powerful. These prospects exist in multiple spheres around your organization, and they’re making gifts that matter.

So the question isn’t whether we should be prospecting outside the database. We already know the answer is yes.

The real question is: How do we build a prospect identification process that actually works?

Let’s Start at the Very Beginning

Here’s what we know to be true: Relationships drive gifts. Not wealth. Not capacity. Not even inclination, really. Relationships.

And relationships exist in concentric circles radiating out from your organization’s core. The closer someone is to your mission, the more likely they are to give significantly. This isn’t revolutionary—it’s fundraising 101.

But here’s where it gets interesting. Once you and your development team really internalize this principle, you can start mapping out all the ways major gift prospects actually enter your pipeline. And I promise you, many of them aren’t entering via your annual wealth screening.

Think about it:

  • The grateful patient whose care team mentions a giving opportunity during recovery
  • The board member who brings a business colleague to your gala
  • The parent who gets involved with the advisory committee
  • The foundation executive who hears your CEO speak at a conference
  • The corporate partner whose VP falls in love with your program

These aren’t hypothetical scenarios. These are the everyday ways that million-dollar prospects walk through your door. And most organizations have no systematic way of capturing, vetting, and reporting on these individuals.

Your development team is probably already doing this work—identifying prospects through organic relationship-building, event attendance, and word-of-mouth referrals. The problem is, they’re doing it in isolation. Without your input. Without a process. Without documentation.

And that means opportunities are being missed, expectations aren’t managed, and you’re probably spending way too much time researching people with zero connection to your organization while high-potential prospects languish in the “someone should probably look into this person” pile.

Why Documentation Is Your Secret Weapon

I can already hear some of you groaning. Documentation? Really? You want me to document our prospect ID process when I can barely keep up with the profile requests I have now?

Yes. I do. And here’s why.

Documentation isn’t bureaucracy—it’s strategy in writing. Once you put your prospect identification framework on paper, something magical happens:

  • Leadership suddenly has opinions. And that’s exactly what you want. Because leadership has the authority to make decisions about how prospect identification actually works at your organization. Once they’re engaged, you have a powerful ally who can say “no, we’re not going to ask the researcher to find us 50 wealthy strangers with no connection to our mission” or “yes, we’re going to prioritize event attendees and board referrals over cold prospecting.”
  • You can make the case for what actually works. When you’re writing the documentation, you get to remind everyone that relationships drive fundraising. You get to frame prospect identification through that lens. And you get to set expectations—when leadership commands you to prospect outside the relationship sphere, you can point to your documented framework and say “absolutely, but our engagement ratio is going to be around 5% instead of 30%.”
  • Everyone agrees on what counts as prospect identification. This might be the biggest win of all. Once you document that event attendees require research vetting, that board referrals follow a specific qualification process, that news article mentions get the same treatment as wealth screening hits—suddenly all of these activities fall under the same umbrella. Which means they can be tracked, measured, and resourced appropriately.

But What If Your Culture Is Broken?

 I can hear you. Some of you are thinking: “This is great in theory, Jen, but you don’t understand my organization. The culture here is completely entrenched. I spend all my time researching deep profiles on people who will never be contacted. I’m not even allowed to talk directly with leadership. Documentation isn’t going to fix that.”

I’m here to tell you something that might sound harsh at first, but I promise it comes from a place of deep respect for what you do: You can do your best work anywhere.

No, really. Stay with me.

You can write your documentation and share it with team members who will talk to you. You’ll learn so much from those conversations, especially if you’re willing to listen to the frontline fundraisers who are actually in the trenches. They know which prospects have potential and which are pipe dreams. They know what information helps them and what just clutters their inbox. They’ll tell you the truth—if you ask and if you listen.

You can begin socializing your framework by giving your services marketing names that describe your actual process. This is where you get to be creative. Deliver a list of no-connection prospects under the service name “Cold Outreach Research-Wish List” and suddenly everyone understands what they’re getting.

Call your event attendee research “Hot Lead Vetting” and watch how much more enthusiastic people are about those prospects. Words are powerful. Use them strategically.

You can introduce innovations wherever you have authority to do so. For example, when you deliver a new prospect, include a brief “relationship statement” or “reasoning note” explaining why they’re a good prospect. This does two things: It educates your development team about what makes a quality prospect, and it invites feedback that helps you refine your process over time.

Here’s the bottom line: If you don’t practice your best work now—in whatever imperfect environment you’re currently in—you won’t be prepared when that golden job opportunity finally manifests itself.

The researcher who gets hired into that dream role isn’t the one who spent three years complaining about their dysfunctional shop. It’s the one who built innovative processes, documented their framework, and can articulate in an interview exactly how they would set up prospect identification at a new organization.

Practice your best work now so you’re ready for what comes next.

AI Is Here, and It’s Time to Step Up and Lead

Let’s talk about the elephant in the room: artificial intelligence.

AI has already begun disrupting our work. For some of you, that’s terrifying. For others, it’s exciting. But here’s what I know for sure—AI is poised to help you unleash your inner leader, whether you’re ready or not.

Think about everything we just discussed:

  • Writing that prospect identification framework? AI can help you draft it.
  • Coming up with creative service names that catch people’s attention? AI is brilliant at brainstorming.
  • Communicating differently with different personalities on your development team? AI can help you adapt your tone and approach.
  • Building a major gift prospect ID process that hums? AI can help you design it, refine it, and evolve it.

But here’s the thing AI can’t do: AI can’t be a leader. It can’t build relationships with your development team. It can’t advocate for resources. It can’t make the strategic decision about whether to prioritize board referrals or cold prospects. It can’t look a gift officer in the eye and say “I know you want me to research this person, but I think we’d get better results if we focused here instead.”

Only you can do that.

AI is a tool—an incredibly powerful one—but it’s still just a tool. The prospect researchers who will thrive in this new landscape aren’t the ones with the best technical skills or the fanciest databases. They’re the ones who step up and lead.

The ones who build frameworks, communicate strategy, and help their organizations make smart decisions about where to invest their prospecting energy.

This is your moment. The disruption that AI brings creates space for you to redefine your role. You can be the researcher who just finds information, or you can be the strategist who shapes how prospect identification works at your organization.

Which one do you want to be?

The Prospect ID Process That Hums

So what does a major gift prospect ID process that actually hums look like?

  • It’s documented, so everyone knows how it works and what to expect.
  • It’s relationship-focused, starting with your organization’s closest connections and working outward strategically.
  • It’s collaborative, with researchers and development officers working together to identify, vet, and qualify prospects through multiple channels.
  • It’s adaptive, using AI and other tools to increase efficiency without losing the human judgment that makes research valuable.
  • It’s communicated clearly, with service names and frameworks that help your development team understand what they’re getting and why.

And most importantly, it’s led by you—the prospect researcher who understands that wealth screenings are just one tool in a much larger toolkit, and who has the confidence to advocate for a better way forward.

The question is: Are you ready to build it?

Additional Resources

Wish you had access to more resources on prospecting? You do! The Prospect Research Institute has lots of resources to help you with prospecting:

  • Join Jen Filla for a free Backstage Tour of the Institute on 1/9/2026 at 12pm ET where you’ll learn about upcoming workshops such as: Strategic Prospect Identification – Smart Verification Framework – Solo Researcher Survival Kit
  • Connect with other prospect research professionals tackling these same challenges in the FREE Forums at the Prospect Research Institute.
  • Buy the Approach to Prospecting book or the course. This teaches you how to build a score card, which you can use for internal or external prospecting.
  • Check out our prospecting category on Prospect Research#ChatBytes the Institute’s podcast.

That Familiar Ask: ‘Can You Find Rich People?’ Here’s What to Do Instead

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You know that feeling, don’t you? The development team walks into your office (or slides into your DMs) with a sparkle in their eyes. They’ve been strategizing. They’ve been planning. And they have a shiny new idea: “Can you get a list of wealthy people in the community who might be interested in our new program?”

Your heart sinks a little because you know what comes next. Hours of research on strangers. Cold prospect lists. Fundraisers making awkward cold calls to people who’ve never heard of your organization. And then, when the gifts never materialize, they come back with new strategies for more places to look out in the community.

I’ve been there. We’ve all been there. But here’s what I’ve learned after years of watching this play out: We have more power in this conversation than we think we do.

The Uncomfortable Truth About Stranger Danger

The truth is that asking for money, especially larger investments, requires relationships. Typically, the colder the relationships the more prospects it takes over a longer period of time to get the gifts your organization needs.

The uncomfortable truth is that your frontline fundraisers know they should focus on building existing relationships before chasing down strangers, but when they’re in the moment and feeling the pressure to fund the program, your organization’s database full of donors is a software program and strangers are people.

But we researchers know that the database is full of people. People who know us and support our organization.

Becoming a Trusted Partner

You could point out to the frontline fundraiser how ridiculous it is to chase strangers instead of mining your own database of existing relationships, but how well do you think that will go down?

In most development departments, research does not hold a lot of political power. What we can have is influence over our colleagues. And influence requires trust.

Instead of making your fundraiser feel stupid, you could try an approach along the lines of the following:

“That’s a great idea, and I can definitely help you find prospects from our community. But it might take a year or even a few years for gifts to come in from people with no connection to us. What if I also do some datamining on our existing donors? I might find some good prospects who already know and trust us—those gifts could come in much faster.”

 

 

This isn’t about saying no. It’s about saying “yes and.” Yes, you can do the research they have requested AND you also have a stellar idea to bring good prospects to the table.

Sometimes You Do Need to Look Outside

There are times when it totally makes sense to search for prospects out in your community.

Consider the following scenarios:

  • Maybe you really don’t have the internal prospects to support something new.
  • It might be time for your board members to step up and start introducing your organization to their networks.
  • If it is a new initiative, you might want to tap into foundations. They often prefer new projects.
  • You may want to deliberately diversify your funding sources!
  • Engaging the community through businesses, civic groups, or government could be an important complementary strategy to individual giving.

The Power of Reframing

I used to think my job was to say yes to whatever research request came my way. But I learned that our real value as researchers isn’t in being order-takers—it’s in being strategic thinking partners.

When development teams come to us with the “research rich strangers” request, they’re not wrong to want to expand their prospect pool. But they might not be choosing the best research technique to source the prospects they need.

If you become the trusted partner that listens to the need and delivers great prospects, what do you think will happen next time they are under pressure to raise funds for a project? They will RUN to you asking you to do it again! Or even better, they will ask you for advice.

A Challenge for All of Us

Next time you get that familiar request to research wealthy community members, I challenge you to pause and ask questions such as:

  • Could you tell me more about what a BEST prospect for this project looks like?
  • If you don’t want formal institutional funding, how would you feel about a family foundation that is local and has funded similar projects?
  • Before I search externally, would you mind if I checked to see if we have any existing donors that might be a good fit and run that by you first?

You might be surprised by what you learn from the conversations. More importantly, your fundraisers might be surprised by how much faster those gifts come in when they’re using the best strategy and especially if they are building on existing relationships instead of starting from scratch.

Because you and I both know: The best prospecting doesn’t just find people with money. It finds people with money who are connected to and care about your mission.

And most of the time, those people are already in your database.

Additional Resources

Wish you had access to more resources on prospecting? You do! The Prospect Research Institute has lots of resources to help you with prospecting:

  • Connect with other prospect research professionals tackling these same challenges in the FREE Forums at the Prospect Research Institute.
  • Buy the Approach to Prospecting book or the course. This teaches you how to build a score card, which you can use for internal or external prospecting.
  • Check out our prospecting category on Prospect Research#ChatBytes the Institute’s podcast.

The Shocking Truth About Prospect Research Consultants!

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Go ahead and shock me!

Did you know that a prospect research consultant isn’t successful unless you, the front-line fundraisers, are successful? Shocking, but true! If I provide you with irrelevant data, or too much data, then you are less prepared and less strategic in your fundraising. You won’t raise as much money for your mission. I won’t get re-hired. And you won’t tell your friends good things about me.

I was reading an article in an excellent research magazine, Connections, published by the Association of Professional Researchers for Advancement. The provocative suggestion was that prospect researchers must move from “pushers to partners”. I never felt like I was an information pusher. But I have had front-line fundraisers tell me about their disappointing experiences with “pushers”.

When I founded Aspire Research Group, my goal was to bring professional prospect research to all sizes of organizations. We have been reaching that goal! And whenever I work with a client there is always some level of back and forth communication going on.

Whether it’s donor profiles, data mining, or prospect tracking, I need to understand who you are and what you want to achieve before I can provide you with information solutions that get you to your destination.

When you work with a prospect research consultant, be sure to make time for questions on both sides and for feedback after the work is delivered. If you do this, your consultant will be able to provide continually better services to you.

Consider the donor prospect profile as an example. You need more than house values and occupational titles. You need to understand what makes your prospect tick, why she has made gifts, and how her assets translate into wealth and possible gift opportunities. You need more than data – you need the information that will inform your fundraising.

Want to hear some shocking success stories? Want to find out how to improve your fundraising strategy with prospect research? Call Jen Filla at 727 231 0516 or email jen at aspireresearchgroup.com.