This is called prospect qualification. It’s the phase of the major gift cycle that many organizations either skip or collapse into the cultivation phase, spending months building a relationship with someone who was never a realistic major gift prospect.

Your fundraising time is finite. Prospect qualification is one way you protect it.

Sri Surabhi Cow Sanctuary © Tonya Hennessey

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What Wealth Screening Can and Can’t Tell You

Wealth screening is a starting point, not a conclusion. Platforms like DonorSearch and iWave aggregate public data to produce prospect wealth-capacity estimates, which are genuinely useful for prioritizing a large prospect list.

According to DonorSearch’s research, donors with a history of charitable giving to other like-minded organizations, particularly at the major gift level, are the strongest indicator of likely major gift behavior. This history is more predictive even than raw wealth.

Here are some of the key variables wealth screening can’t tell you: whether this person has any connection to your mission, whether they’re already fully committed elsewhere philanthropically, whether a life event (a business sale, an inheritance, a divorce) has changed their financial picture recently, or whether they’re simply not interested in the kind of relationship that major gift fundraising requires.

That’s why the qualification, or discovery, conversation matters so much.

The Discovery Conversation: What It Is and Isn’t

A discovery conversation is not a pitch. I want to be clear about that, because the instinct to present and persuade runs deep in fundraisers. A discovery conversation is a genuinely curious conversation designed to learn a prospect. To learn about this person’s philanthropic interests, their relationship to your cause, and whether there’s a real fit between what they care about and what you do.

You’re listening for three things: enthusiasm (do they light up when they talk about your issue area?), specificity (can they articulate what kind of impact they want to make?), and ownership (do they talk about your organization’s work as something they feel part of, or as something happening at a distance?).

A couple of questions that open qualification conversations well:

“What first drew you to [your cause area]?” — This surfaces the origin story of their affinity and often reveals a personal connection that will shape everything about how you cultivate this prospect.

“What would meaningful impact look like to you in this space?” — This question surfaces whether their vision of impact aligns with what you actually do.

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The Signals That Say ‘Yes, Keep Going’

A prospect who asks detailed questions about your programs, who references specific things they’ve read or heard about your work, who talks about the issue area with evident passion and knowledge—these are green lights.

They’re telling you they’re engaged and interested. Keep going.

A prospect who speaks in generalities, who seems unfamiliar with your work despite having been on your list for years, who is clearly in the early stages of philanthropic exploration without a strong commitment to your area—these are red lights. Make notes about your conversation and move on to the next name on your list.

When to Disqualify a Prospect — and How

Disqualification is a portfolio management decision. If after one or two discovery conversations it’s clear that a prospect has limited affinity for your specific work, or is fully committed elsewhere, or doesn’t have the capacity your program requires, move them off your major gifts prospect list.

Move them to your mid-level program. Keep them on your event invitation list. Stay in

light touch. But don’t invest major gift cultivation resources in a relationship that doesn’t have the right signals. The relationship may still be worth maintaining, just not at the intensity of a major gift portfolio.

Sometimes a prospect you’ve moved to a lighter track comes back years later with a changed life situation and a deepened connection to your work. Qualification is not a permanent verdict. It’s a read of the current moment.

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Listen to Your Intuition

After enough discovery conversations, you develop a sense that signals whether something real is present. It will be a particular quality of attention in a prospect, a warmth in how they talk about your programs, an energy in the conversation. Don’t dismiss that intuition. It’s made of pattern recognition built over hundreds of human interactions, and it’s often right.

Write it down and record it in your database notes. “This person lights up when we talk about the wetlands work. Something personal there — ask next time.” That note in your CRM is the bridge between the intuition of this conversation and the cultivation move that follows.

Coming up this Thursday in Premium: Wealth Screening Demystified—how to effectively use tools like DonorSearch and iWave, what the data does and doesn’t tell you, and how to interpret a prospect report without over- or under-reading it.

Classics at the Blackhawk Museum in Danville, California © Tonya Hennessey

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And then I got acquainted with the space, met people in the crypto-digital art sector, and started learning from good actors (I also got burned once or twice along the way). There are great people in crypto if you take the time to learn and be discerning. The underlying blockchain technology is fascinating. There’s a lot of generosity. Now, I’m paying attention to the giving numbers.

In 2025, The Giving Block—one of the leading crypto donation platforms for nonprofits—processed over $100 million in cryptocurrency donations on behalf of its nonprofit clients. The average crypto gift last year? $11,019. Compare that to the average online gift of around $128, and you start to see why this is an interesting conversation.

Crypto isn’t fringe anymore, that’s the reality. This is where a significant and growing pool of philanthropic capital lives. And if your organization isn’t set up to receive it, you’re leaving real money on the table.

Museum of Fine Art, St. Petersburg, Florida. © Tonya Hennessey

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So What Exactly Is a Crypto Donation?

When a donor gives cryptocurrency to your nonprofit, they’re transferring digital assets—most commonly Bitcoin (BTC) or Ethereum (ETH), though dozens of others are accepted—directly to your organization’s digital wallet or through a platform that handles the conversion. The IRS treats crypto as property, not currency, which has important implications for both the donor and the organization.

Here’s the part donors love: if someone bought Bitcoin years ago at a low price and it’s now worth significantly more, they can donate that appreciated crypto and avoid paying capital gains tax on the appreciation—while still claiming the full fair market value as a charitable deduction. It’s the same principle as donating appreciated stock, which many of us are already well versed in. Crypto just brings a newer, often younger donor pool into that conversation.

Who Is Giving Crypto—and Why Should You Care?

Crypto donors skew younger (but, don’t overlook the boomers and GenXers), more tech-savvy, and often hold significant assets in digital form. They may not show up in traditional wealth-screening data. They may never write a check. But they’re philanthropically motivated and looking for organizations that speak their language.

As Inside Philanthropy put it, “Crypto is often discussed as speculation or ideology. In the nonprofit world, it should be discussed as something simpler: An asset class a lot of younger people already own, and one they can donate with less friction than using a credit card.”

In 2025, stablecoin donations (cryptocurrencies pegged to the US dollar, like USDC and USDT) also surged, with donors giving over $32 million in stablecoins alone. This matters because stablecoins don’t carry the volatility risk of Bitcoin—meaning that the value doesn’t swing wildly between when a gift is made and when it’s received.

For nonprofits worried about receiving a $10,000 gift that’s worth $6,000 on a bad Friday, stablecoins offer a more predictable option.

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What Do You Need to Get Started?

You don’t need to become a crypto expert. You need a few things:

• A gift acceptance policy that includes cryptocurrency. This is your first stop. Your board needs to approve a policy that addresses how crypto gifts will be received, valued, and liquidated—or held. Most organizations liquidate immediately to avoid volatility risk.

• A platform to receive and process donations. The Giving Block, Fundraise Up, and every.org all offer nonprofit-friendly crypto donation tools. They handle the technical heavy lifting, convert to cash, and provide the documentation your organization needs for IRS compliance.

• Basic donor communication. Create a landing page or FAQ on your website explaining that you accept crypto, how the process works, and the tax benefits. Many donors who hold crypto simply don’t know their favorite nonprofits can receive it.

These are the basics to get started. Your organization doesn’t need to hold crypto on your balance sheet. You don’t need a fully-dedicated staff person. You need a policy, a platform, and a landing page on your website.

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A Note on IRS Rules: For gifts of cryptocurrency valued at more than $250, your organization must provide a contemporaneous written acknowledgment, the same as with any other gift. For gifts of $500 or more, the donor needs to file IRS Form 8283 for non-cash charitable contributions. For gifts over $5,000, a qualified appraisal is required. A valuation simply reported by a cryptocurrency exchange does not satisfy this requirement.

We’ll spend more time on crypto philanthropy over the coming months—including this Thursday’s Premium deep dive on setting up your program step by step. But this is your starting line. The donors are already there. The question is whether your organization is ready to meet them.

The proposal is well-crafted, the project is genuinely good, the organization is credible. But somewhere between the cover page and the budget justification, the writer stopped thinking about the funder and went back to thinking about themselves. The narrative slides from “here is how we will advance your mission” to “here is why our mission deserves your money.” That’s a subtle but devastating shift.

Foundation funders are not writing checks out of charity alone. They’re making strategic investments in projects they believe will deliver on their own goals. The most successful nonprofit grant writers fully internalize this: they approach each funder not as a source of revenue, but as a partner with a distinct agenda—and they map their project to that agenda with precision.

This grant proposal alignment guide gives you the framework and tools to do exactly that, from your first foundation research session through to your final narrative pass. At its center is the Funder-Project Alignment Matrix—a fillable template you can use for every serious grant prospect. I’ve included the download links for your matrix and bonus material later in this Premium piece.

“The Tweed Run” Bicycle Race, London, England © Tonya Hennessey

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That difference matters. The skills that make someone strong at written fundraising do not always translate automatically to sitting down with a donor and making a personal ask for $10,000, $25,000, or $50,000. The encouraging news is that major gift fundraising is learnable. It is not reserved for a particular personality type; it is a discipline built on process, preparation, and consistency.

This guide from The Giving Groove offers a practical introduction to major gifts fundraising, including what qualifies as a major gift, what the major gift cycle looks like, how prospect research supports success, and why fundraisers often struggle when they move too quickly to the ask.

The Cotswolds UK © Tonya Hennessey

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What Is a Major Gift?

A major gift is an individual donation large enough to deserve a personalized, relationship-based strategy rather than a broad, mass fundraising appeal.

The exact threshold depends on the organization. For a small grassroots nonprofit, a major gift may begin at $1,000. For a university, hospital system, or other large institution, it may start at $100,000 or more. For many mid-size nonprofits, a practical working definition begins around $10,000.

What matters most is not the number alone. A major gift is defined by the level of strategy, attention, and relationship-building required to secure it thoughtfully.

Major Gift Fundraising Cycle

Major gift fundraising typically follows five stages. Understanding these stages helps fundraisers know how to engage each prospect and what action makes sense next.

1. Identification

Identification asks a simple question: who has the potential capacity and interest to make a significant gift? Common signals include wealth indicators, prior giving history, board relationships, and community connections.

2. Qualification

Qualification determines whether a person has both the financial capacity and the genuine affinity for the organization’s mission. A good qualification conversation is not a sales pitch. It is a discovery process built on curiosity and listening.

3. Cultivation

Cultivation is the relationship-building stage, and it usually takes the most time. It can include donor visits, personal updates, introductions to leadership, tailored invitations, and other meaningful touchpoints that deepen a prospect’s connection before any formal ask is made.

4. Solicitation

Solicitation is the ask itself. In effective major gift fundraising, the ask is specific, personal, and ideally delivered in person when possible.

5. Stewardship

Stewardship begins after the donor says yes. Strong stewardship increases the likelihood of renewal and often leads to larger future gifts, which is why the close of one major gift is really the start of the next phase of the relationship.

According to the Association of Fundraising Professionals, donors who receive excellent stewardship after a major gift are more likely to give again and often at higher levels.

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The Most Common Major Gifts Mistake

One of the most common mistakes in major donor fundraising is rushing the ask.

Pressure is real. Budget gaps, campaign goals, and board expectations can push fundraisers toward faster solicitations. But when a donor has not been properly cultivated, the result is often a smaller gift than the relationship could have supported, or a strained connection that is hard to repair.

For significant gifts, cultivation often unfolds over 12 to 24 months, and sometimes longer. While that timeline may feel slow, it often produces a gift that reflects true alignment and a stronger long-term donor partnership.

Prospect Research for Major Gifts

Prospect research does not have to begin with expensive software. Publicly available information, such as real estate records, SEC disclosures for executives, and political giving records, can reveal useful signs of financial capacity.

Board members are also an underused source of insight. They often know who in their networks has both philanthropic interest and a connection to the organization’s cause.

A viable major gift prospect usually reflects the overlap of three elements: capacity, affinity, and linkage. In simple terms, the prospect must be able to make the gift, care about the cause, and have some meaningful connection to the organization.

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Why Major Gifts Work

At its best, major gift fundraising is not transactional. It is the work of building authentic relationships with people who want to make a difference and helping them do so at a level that is meaningful for both the donor and the mission.

That is what makes a strong major gifts program so effective. When fundraisers understand the process, respect the pace of relationship-building, and steward donors well, major gifts fundraising becomes both more natural and more successful over time.

This paid version of The Giving Groove is for readers who want to think harder and go deeper on foundation and individual fundraising. It’s shaped by more than 25 years of work in the field, and by a lot of time spent paying close attention to what actually moves donors, money, and institutions.

I work my ass off for the organizations and causes I believe in. I love the craft of fundraising: the strategy, the psychology, the language, the judgment. And I care just as much about the kind of culture it can help create—a culture of contribution, responsibility, and shared belief in something beyond ourselves.

I hope these writings offer insight, practical shortcuts, and a few genuine aha moments. And that they’re smart, lively, and worth reading even when you don’t strictly “need” the advice.

The Beautiful Pacific Coastline, Jenner, California © Tonya Hennessey

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Today, let’s slow down and take a hard look at what separates the proposals that win from the ones that don’t.

I’ve written thousands of grant applications over the years as staff in organizations large and small that work on environmental, human rights, human welfare, and corporate accountability work. I’ve also worked as a consultant helping clients submit their own proposals.

The difference between a strong proposal and a losing one isn’t always the quality of the program. It’s often the architecture: how the proposal is built, what it says and when it says it, and whether the whole thing holds together as a coherent argument.

This masterclass piece is a deep dive. We’re going to do a proposal teardown, looking at what each section must accomplish, what the most common flaws are at each stage, and which language patterns work best. I’ll share real annotated examples where I can. Pour yourself something tasty and settle in.

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Telephones Over Time Exhibit, San Francisco International Airport © Tonya Hennessey

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Start With Local Data—Not Just National Statistics

National statistics are table stakes. Every proposal on food insecurity cites USDA hunger data. Every environmental justice proposal cites EPA pollution figures. That’s not wrong—context matters—but local data is where you can differentiate yourself.

Dig into your county health department’s data. Check your city’s planning documents. Look at school district reports, local housing authority data, and census tract-level information from the American Community Survey. If you serve a specific geographic area, make the funder see that area. Numbers that are specific to your community signal that you know your community.

Bring in Community Voice—Without Tokenizing It

Quantitative data tells you the scale of a problem. Community voice tells you what it actually feels like to live inside it—and that’s often what moves a program officer.

Quotes from community members, findings from focus groups, results from community surveys—all of these can anchor your needs statement in lived experience. The key is to use this material with care and consent. Instrumentl’s research on competitive needs statements consistently finds that proposals that center community perspective—rather than describing community members as passive subjects of a problem—tend to score higher with equity-minded funders, which is most funders right now.

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Avoid Deficit Framing

This is something that has shifted significantly in the last decade. Funders, particularly those with an equity lens, are increasingly wary of needs statements that portray communities primarily through what they lack. Describing a neighborhood only through its poverty rates, crime statistics, and health disparities—without acknowledging assets, resilience, and the community’s own organizing history—can undercut your proposal.

A stronger approach: acknowledge the structural forces that created the conditions you’re addressing, name community strengths alongside challenges, and be sure to frame your organization as a community partner rather than a rescuer arriving from outside with good intentions.

Focus the Scope of the Problem

One of the most common mistakes I see is a needs statement that describes every challenge facing a community, as if sheer volume of problems demonstrates need. What it actually demonstrates is an unfocused proposal.

Your needs section should describe the specific slice of the problem that your project addresses, not the whole waterfront. If you’re running a job-training program for formerly incarcerated women in one county, your needs statement should focus on the employment barriers they face in that geography. Broad strokes might feel more compelling, but it’s the precise details that are persuasive.

Make the Case That Yours Is the Right Organization

The needs section isn’t only about the problem—it’s implicitly making the case that your organization is the right one to address it. Why you? Why now? Why here?

You can weave this in naturally by referencing your track record, your community relationships, your specific expertise, and your physical presence in the community.

Funders want to know that the dollars they invest will be well-stewarded. A well-executed needs section starts answering that question before the funder even reaches your organizational history section.

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The needs statement is an argument, not a recitation. You’re making the case—with evidence, with specificity, with honesty—that a problem exists, that it matters, and that your organization has a strong plan to address it and move the needle. When you approach it that way, it stops feeling like a box to check and becomes the foundation for your entire proposal’s argument for funding that it’s meant to be.

If yours makes them work to find what they need, they’ll move on. If your application package guides them clearly, you’ve already earned goodwill before they finish reading.

After more than 25 years in this work, I think of a well-structured grant proposal the way a good author thinks about a book: every section has a job to do, and when each one does its job well, the whole thing holds.

Here’s how to build it.

Me in Beijing, early 2012

The Cover Page: Your First Impression

Don’t overthink this, but don’t skip it either. Your cover page should clearly state your organization’s name, the project title, the funding amount you’re requesting, the project period, your primary contact information, and the date of submission. Some funders provide a required cover sheet—use it, and follow it precisely.

If they don’t, create a clean, professional one. It takes ten minutes and signals that you pay attention to details.

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The Executive Summary: 250 Words That Do the Heavy Lifting

Write this piece last, even though it appears first. Your executive summary should distill the entire proposal into a page or less—who you are, what problem you’re solving, what you’ll do about it, how much you’re asking for, and what success looks like. Program officers often read only the executive summary before deciding whether to keep going. Make it count.

The best executive summaries are specific. Not “we will serve vulnerable youth in our community” but “we will provide 180 hours of paid environmental internship experience to 10 low-income high school students in Richmond, California, over 12 months.”

The Needs Statement: Make Them Feel the Problem

This is where many proposals go soft. A strong needs statement doesn’t just assert that a problem exists—it proves it, with local data wherever possible, and connects that data to real human stakes. According to Candid, the most compelling needs statements weave together three elements: quantitative data that establishes scale, community voice that establishes impact, and a clear explanation of why this particular organization is positioned to respond.

Avoid the temptation to describe every problem facing your community. Focus on the slice of the problem your project actually addresses. Funders notice when a needs statement is wider than the proposed solution.

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Goals, Objectives & Methods: The Engine Room

Your goals are broad statements of intended change. Your objectives are specific, measurable, time-bound milestones—the SMART variety. Your methods describe exactly how you’ll achieve them and why your approach is sound.

These three sections need to align perfectly. If your goal is to reduce food insecurity in your county, your objectives should measure food insecurity, and your methods should describe activities that plausibly move that needle. Misalignment here is one of the most common reasons solid proposals don’t get funded.

Evaluation Plan: Prove You’ll Know If It Worked

Funders increasingly want to know not just what you plan to do, but how you’ll know whether it worked. Your evaluation plan should describe what data you’ll collect, how you’ll collect it, who’s responsible, and how you’ll use findings to improve the program. You don’t need a full-blown academic study for most grants—but you do need a thoughtful, credible plan.

Budget & Budget Narrative: Show Your Math

Your budget should be realistic, fully justified, and aligned with your methods. Every line item should appear because something in your methods requires it. The accompanying budget narrative or justification explains the logic behind each cost—why those personnel, why that amount, what the indirect cost rate covers. We’ll dig much deeper into budgets in an upcoming issue.

Sustainability: What Happens After the Grant

Funders don’t want to feel like the last dollar standing. Your sustainability section should honestly describe how the project or program will continue—whether through earned revenue, other funders, government contracts, or institutionalization into your core budget. Be specific and realistic. Vague assurances that “we will seek other funding sources” won’t cut it.

A well-structured proposal doesn’t guarantee a grant—little does. But it tells a funder that you’re organized, serious, and capable of managing what you’re asking for. That’s a message worth sending in every section, from the cover page right through to the last line of the budget narrative.
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In the next issue, we dig into the needs statement in much more depth—because getting that section right is one of the highest-leverage moves you can make.

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Because I know exactly how precious your time is, I’m rolling out some new resources to help you fund your missions faster and with less stress. But first…

We’ve Moved!

The Giving Groove is now hosted at groove.tonyahennessey.com. We are still fully integrated with Substack, but moving to a subdomain of my main fundraising and travel writing website allows me to maintain control of my intellectual property. (A huge thank you to Substack for generously allowing creatives to do this!)

Nosara, Costa Rica, 2010 © Tonya Hennessey

Launching Mid-April: The Giving Groove Premium

I am thrilled to announce that Premium is officially launching in mid-April!

After 30 years in the trade I love, it’s time to share the deep-dive strategies that actually move the needle. Subscriptions will start at just $8/month or $80/year (pricing will increase over time, so lock in this early rate).

Here is exactly what you will get as a Premium subscriber:

• Deep-Dive Strategy: Engaging, in-depth articles complete with sample scripts and step-by-step guides to help you navigate tricky donor conversations and overcome obstacles to breaking in with funders.

• Modern Giving Trends: The latest data and actionable thinking on Crypto giving trends, utilizing AI, and maximizing Donor-Advised Funds (DAFs).​

• Done-For-You Resources: Ready-to-use templates and specialized AI prompts. They aren’t always sexy, but they are massive time-savers.

• Expert Perspectives: Guest pieces and webinars featuring a range of incredibly talented fundraisers.

• Exclusive Access: Deep dives into complex proposal budgeting, plus access to our private Subscribers’ Chat.

Note on timing: Thursday Premium content will drop 3x a month starting in mid-April, ramping up to weekly (4x/month) in July.

The Premium archives and offerings will build over time, and I’d be honored to have you join me on this journey.

Let me know what you’d like me to cover or what you find most valuable. And if you’ve got a hot take—hit reply and tell me!

Thanks for reading, and please consider sharing The Giving Groove with your colleagues.

Best,
Tonya

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No. Absolutely not. Hard stop.

Here’s the counterintuitive truth: economic uncertainty is actually your moment. It’s when donors need to hear from you most — and when the strongest relationships get forged. Think of it like the gym in January. Everyone shows up when it’s easy. The people who show up in the cold, dark middle of February? Those are the ones who actually get results.

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Lake Geneva, Montreux, Switzerland © Tonya Hennessey

Relationship First. Ask Second. Always.

Major donor cultivation has never been about transactions — it’s about trust. And trust doesn’t pause for economic cycles.

According to the Association of Fundraising Professionals, “It is critical that the cultivation of major giving prospects continues through economic uncertainty. Major giving is all about cultivation. Even if a donor’s ability to give is limited by the economy, the relationship should continue.”

Read that again. The relationship should continue. Not the ask. Not the proposal. The relationship. This means picking up the phone not to solicit — but to check in. Sending a note about a program win. Inviting your top prospects to a site visit with zero pitch attached. These touchpoints are the infrastructure of generosity. Neglect them during down times, and you don’t just lose a gift — you lose a donor.

Personalize Like You Mean It

Major donors know when they’re getting the same email blast as your annual fund list. And nothing says “you’re not that important” like a Dear Friend letter sent to someone who just gave you $25,000.

In 2026, personalization isn’t a nice-to-have — it’s the baseline. DonorSearch notes that “major donors increasingly expect communications that reflect their unique interests and values,” and that “generic outreach is ineffective and easy to ignore.”

Build an individualized cultivation plan for each of your top 20 prospects. Map out their communication preferences, their philanthropic passions, their family milestones. Know that Margaret collects art and that her granddaughter just started college. Know that Silvio is a fly fisherman who cares about clean water. Use that. Relevance is respect.

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Talk Money Differently

When the economy wobbles, pivot the conversation — don’t avoid it. Donors with appreciated stock holdings may actually be in a better position to give charitably, even in a down market. Gifts of securities let them avoid capital gains taxes while still making impact. That’s not a consolation prize; it’s a smart play.

And if a donor simply isn’t in a position to give right now? Honor that. Acknowledge the climate. Offer a multi-year pledge option or a deferred gift conversation. What you’re really doing is planting seeds for the next cycle — and demonstrating that your organization is a partner.

Don’t Ghost Your Donors

Organizations that maintained consistent, authentic engagement during economic turbulence consistently outperformed those that went quiet.

Nonprofits that doubled down on stewardship, transparency, and relationship-building during challenging financial periods were able to sustain and even grow donor support.

Be visible. Be honest about what’s hard. Tell the story of your mission’s urgency with the same energy you’d bring to a capital campaign kickoff.

And if you’re not sure what to say, remember: donors give to people they trust. Be trustworthy first.

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The Bottom Line

The economy will always have opinions and go through changes. Your job is to make sure your donors have a positive, more in-depth opinion about your organization, your mission, and the relationship and impact you’ve built together.

[Note that a few funders hide this information even further, and it’s not in the 990. Those cases are annoying!]

I’ve been raising grant funding for more than 25 years. And that grantee list is basically a treasure map. You just have to know how to read it.

Jamaica’s Nari Ward, “Still Livin,’ Viral,” 2025, Art Basel Miami Beach © Tonya Hennessey

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Start With the 990-PF: Your Free Foundation Intelligence Report

Every private foundation in the U.S. files a Form 990-PF with the IRS. That form is public record, and it lists every grant the foundation made that year — grantee name, amount, and purpose. You can pull most of them for free through ProPublica’s Nonprofit Explorer or Candid (formerly GuideStar).

What are you looking for? Patterns. Are they consistently funding arts organizations or workforce development? Is their sweet spot a $25,000 grant or a $250,000 multi-year commitment? Have they been funding the same five organizations for a decade, or do they rotate? These answers shape your entire approach before you write a single word of your proposal.

Google Is Your Research Assistant. Use It Accordingly.

Here’s an advanced tactic I use constantly: Google the foundation’s name plus “annual report” or “grants list.” Many foundations publish detailed grant summaries that never make it into databases — and those documents often reveal exactly how they talk about the work they fund. That language is gold. When a funder says they “prioritize community-led solutions,” write your proposal with that phrase doing push-ups throughout.

You’re not mimicking them. You’re speaking their language. There’s a difference.

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Study the Grantees Like You’re Doing Competitive Intelligence. (Because You Are.)

Once you have a grantee list, look up several of those organizations. Visit their websites. Read their mission statements. Look at what they do, how they describe it, and how their work relates to yours. This tells you far more than a foundation’s guidelines ever will.

Fundraising researcher APRA (the Association of Professional Researchers for Advancement) has long noted that grantee analysis is the cornerstone of effective foundation prospect research — not because it tells you what a funder wants to fund, but because it shows you what they’ve already decided to love.

Ask yourself: Does my organization fit in this portfolio? Would a program officer see my name and think “yes, exactly” — or would they squint at the list and wonder why I’m there?

“The best foundation prospect is one that has already funded organizations just like yours.”

— A core principle from Candid’s foundation research training materials

Call a Peer. Seriously.

This is the tactic nobody talks about, and it works. If you find an organization on a grantee list that does work similar to yours, call their development director or foundation relations officer. Introduce yourself. Ask what their experience with this funder has been like.

Most development pros are genuinely happy to share insights — because they’ve been the person calling someone else for help, and they know how it feels.

You might learn that the foundation prefers LOIs over full proposals. Or that the program officer is especially passionate about a particular model you happen to use. That’s the kind of intel no database sells you.

“Prospect research is not about finding people with money. It is about finding the right people with the right connection to your mission.”

— Russ Alan Prince and Karen Maru File, The Seven Faces of Philanthropy

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Build Your Own Grantee Intelligence File

Here’s your practical takeaway: for every foundation on your prospect list, build a simple one-page summary. Who did they fund last year? How much? What kind of work? Has their portfolio shifted in the last three years? This is your grantee list analysis — and it’s worth every minute it takes.

Think of it like this: then you’re not cold-calling. You’re walking into a room where you’ve already read everyone’s book. You know what they care about. You know what makes them say yes. That’s not luck. That’s foundation 990 analysis doing its job.

The foundations worth pursuing are those that have already drawn a map to their priorities. You just have to be the fundraiser who reads it.

Now go find your people.

Have a grantee research tip that changed your prospect game? Reply and share it — the best wisdom in this work comes from the field.

• Misalignment with funder priorities is the #1 rejection trigger — and the most preventable

• Vague outcomes, shaky budgets, and organizational instability signal low readiness to reviewers

• Generic or AI-generated language is increasingly easy to spot — and quietly penalized

• Every red flag on this list is fixable before you hit send

One of my favorite street stalls on Hong Kong Island back in the day © Tonya Hennessey

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You did the research. You wrote the proposal narrative. You hit send on your submission with a flutter of hope in your chest — and then? Silence, followed by a politely worded decline. It stings. But here’s the thing: most grant proposal rejections aren’t mysteries. They’re patterns. And patterns can be broken.

Whether you’re approaching a private foundation with a formal LOI or sitting across from a major donor prospect over coffee, reviewers and donors share a surprisingly similar checklist — one that lives less on paper and more in gut instinct. Learn to see your ask through their eyes, and you’ll understand exactly what makes them pause, wince, or quietly set your proposal aside.

Here are six fundraising red flags that get proposals and LOI pitches killed before they ever have a chance.

1. You’re Pitching to the Wrong Room

The most common grant proposal mistake — and the most preventable. Sending a youth workforce development proposal to a foundation focused on environmental conservation isn’t bold outreach. It’s noise. The same is true when you present a capital campaign to a major donor whose giving history screams annual fund and intimate, personal causes.

Funder alignment isn’t just a nice-to-have. It’s the foundation of the entire relationship. Before you write a single word, do the homework. Read Form 990s. Study past grantees. Have a real conversation with the program officer before applying. Ask your major donor prospect what issues keep them up at night. When your mission sings in the same key as theirs, the rest of the conversation flows naturally.

2. Vague Outcomes That Nobody Can Measure

“We will serve hundreds of community members and make a meaningful difference.”

Lovely sentiment. Zero traction. Funders — whether institutional or individual — invest in results they can point to. When your proposal can’t answer how many, by when, measured how, reviewers start to wonder if you actually have a plan or just a hope.

The antidote is simple: specificity. Measurable outcomes tell the story of what success looks like in concrete, human terms. Numbers anchor the narrative. They say: we’ve done this before and we know what we’re doing. If your logic model is tight and your evaluation plan is clear, say so explicitly — don’t make reviewers hunt for it.

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3. A Budget That Doesn’t Add Up

Think of your budget as a second narrative — one written in numbers. When it contradicts your program description, inflates overhead without explanation, or leaves out obvious line items, it sends a quiet but unmistakable message: something here is off.

For foundation reviewers, a misaligned nonprofit budget is a capacity red flag of capacity. For major donors, it can feel like you haven’t thought this through. Both responses lead to the same place: a pass on your application.

Build your budget so that someone who hasn’t read your narrative can still understand what the money does and why every line belongs there.

4. Signs of Organizational Instability

Funders aren’t just investing in your program — they’re investing in you. High executive turnover, a board that’s functionally inactive, financials showing persistent deficits, or a Form 990 that raises more questions than it answers — these are the details that surface in a review meeting and too often aren’t addressed candidly up front.

Nonprofit financial health matters. Transparency is your best tool. If your organization has navigated challenges, say so, and tell the story of how you came through stronger. Owning your arc is far more compelling than hoping no one notices the rough patches.

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5. Generic Language That Could Belong to Anyone

In a world where AI can generate a competent-sounding grant proposal in under three minutes, the thing that it still can’t replicate is your voice, your community, your truth. When a proposal reads like it was assembled from a template — polished but hollow, technically correct but oddly soulless — experienced reviewers feel it immediately.

Foundation program officers can spot a copy-paste job in under sixty seconds. Major donors, who are often more emotionally invested in the “why” than the “what,” are equally sensitive to inauthenticity. Neither will fund what they can’t connect to.

Write like you mean it. Use real stories. Bring the community to life on the page.

6. The Desperation Signal

The last red flag is the quietest — and one of the most damaging. When a proposal or pitch radiates financial panic, it backfires. Funders want to support organizations with momentum, not rescue operations in freefall. If your entire case for support hinges on “we need this to survive,” take a breath and reframe your language. Funders want to fuel your next chapter, not your last-ditch effort.

Frame your ask around opportunity and growth. Sustainability is attractive. Urgency, without context, is alarming.

The good news? Every single one of these grant proposal red flags is fixable — before you ever hit send. None requires you to rebuild your organization from scratch. They just ask you to see your work through fresh eyes and tell your story with more precision, more heart, and more confidence.

You’ve got this. Now go make it impossible to say no.

Have a red flag story — or a comeback story? Reply and share it. The best lessons in this work come from the community.

So let’s talk budgets, because too many compelling proposals get dinged (or worse, ignored) simply because the financial picture was fuzzy, inflated, or worse—didn’t match the story being told.

I get it. Budgets feel like the unsexy part of fundraising. They’re not the soaring vision or the heart-wrenching impact story. They’re spreadsheets. Math. The stuff that made some of us choose nonprofit work specifically to avoid.

But here’s what I’ve learned in 25+ years of grant writing: your budget isn’t just a compliance document. It’s narrative too. It’s proof that you’ve thought through how you’ll actually deliver on the picture you painted in your proposal narrative.

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Highland Park Mongolian-Style Res…

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Not the “three wishes, poof, done” kind. More like the genie that escaped the bottle, whether you rubbed it or not—now running spreadsheets, drafting proposals, and building donor prospect lists for your colleagues. AI is embedded in nearly every tool we use. Pretending otherwise won’t make it go away. It’ll just leave you holding a hand-drawn map while everyone else is using GPS.

I say this as someone who has spent 25 years in the grant trenches, raising millions for environmental and conservation organizations. I’ve written thousands of proposals, cultivated hundreds of relationships, and lost sleep over more than a few funding cliffs. I also have real concerns about AI—especially the energy and water it guzzles. Fellow environmentalists, I see you.

But my pragmatic take: AI is already shaping our field. The question isn’t whether to engage—it’s how to do it responsibly.

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Quine by Larva Labs, Zero10 Digital Art Exhibit, Art Basel Miami Beach © Henne…

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The culprit? Radio silence. Think about it—you wouldn’t ghost someone after a first date and expect them to show up for an anniversary dinner. Yet nonprofits do this to donors all the time.

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Mederic Turay “Welcome Home” © Hennessey

The Black Hole Problem

When a donor clicks “submit” on that first donation, they’re making a statement: I believe in what you’re doing. But if they don’t hear from you again? They start wondering if their contribution disappeared into a black hole, or worse, if you only cared about their credit card number.

Take Coal River Mountain Watch, a scrappy West Virginia nonprofit fighting mountaintop removal mining. When someone makes their first gift—maybe after reading about how

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Think of an LOI as a really sophisticated handshake. In my 25+ years of grant work, I’ve seen some LOIs that opened doors, and others that landed in a busy program officer’s inbox and never surfaced again. The difference? Clarity, specificity, and genuine connection. That’s not luck, it’s strategy.

In this article, you’ll learn how to:

· Define what a letter of inquiry is and when to use it.

· Include the four elements funders look for in an LOI.

· Strike the right tone so your LOI feels like the start of a relationship.

· Close your LOI with a clear,…

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7-Mile Drive, Monterey, CA © Hennessey

Step 1: Prioritize like a Pro

Not all prospects are created equal, and you don’t have time to chase everything that moves. Start by ranking your list using three anchors: alignment, funding amounts, and deadlines.

Ask of each funder:

• How aligned are their stated priorities with your programs and community?

• What is the typical grant size, and does the potential return justify the staff time?

• What are the hard deadlines, LOI windows, or rolling cycles you have to hit?

Grant strategy practitioners consistently recommend building a calendar that starts with the most promising funders …

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After 25 years in the foundation trenches and millions raised, I can tell you this: strong grant narratives don’t “wow” with flowery language; they win because they make it easy for a busy program officer to say yes. Your job is to translate a complex, human, community-centered effort into a narrative that is both emotionally resonant and rigorously clear, grounded in data, evaluation, and a credible plan for impact.

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1. Name Your Unique Selling Point

If your narrative doesn’t clearly answer “Why you?” a reviewer will quietly move on. Spell out what differentiates your organization or program from others working on the same problem: a distinctive model, community-rooted leadership, a unique partnership, or specialized expertise.

2. Show Your Track Record, Not Just Your Passion

F…

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January prospecting is about sustainable pipeline building so that your funding year is calmer, more predictable, and a lot less dramatic.

Shrine to Grateful Dead Band Member Bobby Weir at San Francisco’s Civic Center © Hennessey

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Start With the Rolodex You Actually Use

Before you chase new funders, clean up what you already have. Think of your prospect spreadsheet as your grantmaking command center—if it’s a mess, the whole year gets wobbly.

• Segment your list by type: foundations, key individuals, businesses, and government.

• Add or update fields for: deadlines, typical award ranges, contact info, alignment notes, and history with your organization.

• Do a quick “triage pass” to archiv…

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I hope you found time to sit in the sunshine, go for long walks or bike rides, and otherwise unplug over the holidays and year-end break. The world feels like it’s moving so fast right now, making it even more important to take respite. Remember to laugh, sing, and feel your joy.

Taking a real pause is not a luxury; it is a survival-level strategy for people like us whose job is to think clearly, build relationships, and keep the money moving for the mission.

Since launching The Giving Groove in August, this newsletter has gone out as a free weekly issue most Tuesdays, focused on practical, real-life strategies to help you win more grants and gifts without burning out.

After 25 years of experience and many millions in grant revenue, the goal here is simple: give you the playbook of “tips and tricks” tht no one handed over at your first “Congratulations, you’re the development person now!” staff meeting.

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