Early in my career, I was the “gal Friday” of a fundraising shop at The University of Southern Mississippi. That title meant I got handed the problems nobody else had time for, and one of mine was planned giving.

My boss wanted what he called "planned giving in a can" – by which he meant a marketing firm that could build us a planned giving program without hiring a staff attorney with a JD. I found one. We worked together for years, and it worked exactly like it sounds: professional materials, steady messaging, a program running quietly in the background while the rest of us focused on annual gifts and events.

Then I moved to a small seminary. One fundraiser – me. No other staff. No budget for a can of anything, planned giving included.

I knew if I let planned giving slide, it would slide forever. So I built my own version. I made templates I could reuse. I picked logical spots on our content calendar and put planned giving education front and center in our messaging on a set schedule.

One round through that system, and a donor came forward wanting to name the school in her retirement account. Over half a million dollars, from a monthly donor nobody had flagged as a major prospect. (Over several years that gift ended up being transferred to us via an IRA rollover, so the organization got to use it right away!)

That's the whole case for what you're about to read. You don't need the can or a staff attorney. You just need the system.

Somewhere around $84 trillion is set to change hands in America over the next two decades. Roughly $12 trillion of that is expected to come to charities. Economists call it the Great Wealth Transfer. Fundraisers should call it the biggest opportunity of our careers.

And most small nonprofits are about to miss it.

Not because the money isn't there. It's already showing up in the numbers. Bequest giving rose almost 20% in 2025, the largest increase of any source of charitable giving that year, according to the newest Giving USA report. It's the third time in four years bequests have grown 20% or more.

​That's not a fluke. That's the wealth transfer arriving, one will at a time.

I hear this constantly from small nonprofit leaders, and I understand exactly where it comes from. Planned giving sounds like something for universities with prospect research teams and hospitals with named buildings. It sounds like a program you build once you already have major donors, endowments, and a gift officer whose entire job is legacy giving.

Here's what I want you to sit with instead: planned giving is not about who's wealthy today. It's about who's loyal for decades.

The donor who gives you $25 a year for fifteen years straight, never misses a renewal, opens every email, shows up to your small events? That donor is a better planned giving prospect than someone who wrote you one $10,000 check and disappeared. Planned gifts come from assets, not income. A donor doesn't need deep pockets right now to leave you something significant later. They need a relationship with your mission that's lasted long enough to matter.

That's the one resource small nonprofits actually have in abundance: donors who've stuck around.

The math that makes this worth your time

I know time is the real objection under "we're too small," so let's talk about return.

Research from AskRight puts the average return on bequest fundraising at $56.83 for every dollar spent, the highest of any fundraising activity, well above major gifts or annual giving. And the gifts themselves aren't small. Planned gifts typically run 200 to 300 times larger than a donor's average annual gift.

​Worried this will pull focus from your annual fund? The data says the opposite. Research from Dr. Russell James found that donors who name a charity in their estate plans increase their annual giving by about 77% in the years that follow. Naming your organization in a will doesn't replace the relationship. It deepens it.

National Estate Planning Awareness Week happens every October, and it exists for precisely the reason this article exists: to give ordinary people, not just estate attorneys and wealth managers, a nudge to think about what happens to what they've built.

You don't need a full-blown planned giving program or have a planned giving officer with a JD on staff to use this week well. You need five things:

1. A landing page that explains bequests and beneficiary designations in plain language
2. A way for donors to tell you, privately, that they've already included you in their plans or that they are thinking about it
3. Sample bequest language their attorney can drop straight into a will
4. A week of social and email content that keeps the conversation visible
5. A constituency that already trusts you, which, if you're reading this, you likely already have

​That's it. That's the whole on-ramp. You don't need a major gifts officer. You need one focused week, pointed at donors who already love what you do.

If you've read this far and you're thinking "I still don't have time to write all of that from scratch," I built something for exactly this moment. The National Estate Planning Awareness Week Bundle gives you all five pieces above, ready to customize: landing page copy, a letter of intent template, sample bequest language, a full week of social and email content mapped out day by day. It's built to go from blank page to ready-to-post in an afternoon, not three weeks.

And if even an afternoon feels like too much on top of everything else on your plate right now, I also offer a done-for-you version of the same package. Send me your organization's details, and I'll write the entire campaign for you, customized and ready to post, delivered within two weeks.

Both are available now, but only through 9/15. After that, I'm heads-down writing the done-for-you packages for the organizations who've already booked, so both go back in the vault until the next opening.

The wealth transfer is happening whether small nonprofits participate or not. The only question is whether the donors who've spent years loving your mission get an easy way to include you in what comes next. This week, you get to make that easy.

​Cheers,

P.S. Want more content on planned giving and sustainable revenue growth? Subscribe to the blog and get new posts delivered straight to your inbox.

P.P.S. If you're a nonprofit CEO or development lead who's tired of carrying the fundraising weight alone, a free discovery call is for you. Let’s chat.

If you liked this…

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• Planned Giving Leads Don’t Generate Themselves – But They Can Be Sparked
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• Why Nonprofits Can't Afford to Sleep on IRA Rollover Gifts

If you brought board members into fundraising hoping it would lighten your load, I want to save you some frustration right now: that's not what's going to happen. At least not at first.

This is the misconception that trips up more development directors than almost anything else. You recruit board members for fundraising. You give them a quick pep talk. You hand them a spreadsheet of names. And then you wait for your workload to shrink.

It doesn't shrink. If anything, it grows for a while.

​Here's the reframe that changes everything: your board isn't there to save you time. They're there to do something you cannot do by yourself, no matter how skilled or tireless you are. They can open doors into networks you'll never have access to on your own. Your job isn't to hand off tasks and disappear. Your job is to build the structure that makes it possible for them to succeed.

In 2015, I left a large public university to work at a small seminary. When they hired me, I was the entire fundraising staff, save for one part-time person who processed gifts.

Beyond my connection to the mission, I was drawn to the autonomy of the role. I'd get to build a fundraising program from the ground up. I knew I couldn't do that alone. But in those early days, there wasn't anyone to call on.

So I started building people, not just programs. I drew my president into the work and helped her become a genuinely wonderful fundraiser. I scouted and recommended new trustees, people I knew would be useful to the cause of revenue generation. As the board's composition shifted, our trustees started wanting to help.

That's when I built them tools: packets to help them fill tables they hosted at fundraising events, a toolkit for a thank you call campaign, specific language they could post on their own social media for Giving Tuesday. Piece by piece, I gave them what they needed to say yes and actually follow through.

Did any of this save me time? Absolutely not. I was hustling constantly to give my board what they needed to succeed. But their success was my success, and it was the organization's success too.

So many people at nonprofits believe that if the board would just "help," their workload would shrink. In the long run, it does make the job more sustainable. But at the start, the goal isn't staff relief. Your role is more of a trainer, a systems builder, and a change agent for your organization's philanthropy culture.

I built this out over years of trial and error. Now I teach it as a framework, because you shouldn't have to figure it out the hard way like I did.

The instinct at most organizations is to skip straight to the ask. Get the board a list of names, hand them a script, and hope for the best.

That's backward. Before a board member will ever raise their hand to solicit a gift, they need to believe something different about fundraising itself. This is the Reframe step in my REAL Framework: shifting how your board sees money, giving, and their own role in it.

​Most board members carry some version of the same beliefs: that asking is imposing on people, that money is a slightly uncomfortable topic separate from mission, that they personally aren't "the type" who's good at this. None of that is true, but no one ever told them so. Giving is an invitation into something the donor already cares about. Asking isn't taking. It's alignment.

Until you address that mindset directly, all the templates in the world won't get your board moving.

Once the mindset starts to shift, the next step is behavior, and this is where a lot of board fundraising plans fall apart. Organizations tend to imagine one path to engagement: the ask. But the donor cycle has room for a lot more than that, and your board is full of people who can contribute meaningfully without ever making a solicitation.

This is where I use the Fundraising Avatars with boards. Some trustees are Door Openers, wired for connections, always ready to say "you should meet this person." Some are the PR Guru, naturally talking up your mission in rooms you're not in. Some are Gratitude Champions who light up when they get to make a donor feel seen. Others are Strategic Brains who'd rather help you build the plan than pick up the phone, Loyal Givers who lead by example with their own gift, or Task Tackers who show up reliably to execute whatever needs doing.
​
​None of these are lesser roles. They're different superpowers, and a board that understands its own mix of avatars stops forcing square pegs into the "everyone must solicit" hole.

Pair that with a Board Fundraising Menu; think of it as appetizers, entrées, and desserts. Appetizers are low lift: opening a door, making an introduction. Entrées stretch a board member a little further, like joining a donor visit. Desserts are the parts people genuinely enjoy, like making a thank you call. When board members can choose from a menu that matches their avatar, engagement stops feeling like an obligation and starts feeling like a fit.

Once your board is engaged and moving, some of them will be ready for the Ask itself. This step is where coordination really matters. You need to track who is talking to who, who is asking who, what for and for how much.

And again, you need to be providing templates, resources, and structure. Give them a formula for building a compelling ask, a chance to practice it out loud, and language for handling the moment a donor says no or goes quiet. ​Give them scripts for donor conversations. ​Give them a one-page explainer on your case for support. Run a “mock meeting” practice session so the words feel natural in their mouths before they ever say them to a donor.

The last piece of REAL is the one boards skip most often: Learn. Every outcome, a yes, a no, or silence, is data. A yes tells you what worked and deserves repeating. A no is information, not failure.

​Build a culture where there's no such thing as failure in fundraising, only learning. That's what keeps board members coming back to the work instead of quietly retreating after one hard conversation.

A board member with a menu of options, a clear job description, and real training still needs you in the loop. Fundraising is relational work, and relationships wobble. Donors get quiet. Conversations stall. Board members second-guess themselves.

Check in regularly. Ask what's working and what feels hard. Celebrate the small wins out loud, in front of the full board if you can. This isn't a "set it and forget it" initiative. It's a relationship you're building with your board, the same way they're building relationships with donors.

​If you are the fundraising lead, engage your Executive Director and your Board Chairperson in the follow-up process. If you have a Fundraising Committee, the chair and members of that can also be helpful here to check in with board members to see where they are with tasks and what kind of support they might be missing in order to deliver.

None of this saves you time in month one. It might not save you time in month three.

What it does is bigger: it activates a broad, warm network of potential donors that no single development director could ever reach alone, no matter how many hours they put in. Your board members know people you will never meet. Their invitation to give carries a kind of trust that an email from the development office simply cannot replicate.

And for your donors: contact from a volunteer leader taking time out of their busy day to say thank you goes such a long way. That makes an impression.

Reframe the mindset. Engage each person where their strengths are. Ask with clarity. Learn from every outcome. Do that consistently, and you won't just add donors to your database. You'll build a culture where fundraising is shared work, not a burden one exhausted person carries alone.

That's not a shortcut. It's the long game. And it's the only version of this work that actually lasts.

Cheers,

P.S. Want more content on board fundraising, mindset, and sustainable revenue growth? Subscribe to the blog and get new posts delivered straight to your inbox.

P.P.S. If you're a nonprofit CEO or development lead who's tired of carrying the fundraising weight alone, a free discovery call is for you. Let’s chat.

If you liked this…

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• Asking Is Only 5%: Why Your Board Is Afraid of the Wrong Thing

Hi, my name is Jessica, and I'm a recovering perfectionist. In my past, I have rewritten the same subject line eleven times before letting it see daylight.

Sound familiar?

If you work in fundraising, especially if you're newer to the field, you know this trap well. You draft an appeal. You read it again. You tweak a word. You show it to a coworker. You tweak two more words. Days pass. Then a week. The appeal is still sitting in your drafts folder, waiting for a version of itself that will never exist: the perfect version.

Here's the truth nobody tells you: perfect copy stuck in revisions cannot bring in a single dollar.

I want to be clear here. Caring about quality is a good thing. Your donors deserve professional, polished communication. You should absolutely check your work against your brand guidelines. You should absolutely get the donor's name right, and the program name right, and your own organization's name right (yes, that happens more than you'd think). Those are real bars, and they matter.

But once you've cleared them, ask yourself one question: would sending this cause a scandal?

Wrong name on a major gift letter? Scandal. A sentence that could be a little tighter? Not a scandal.

Once you're past the "would cause a scandal" threshold, you're not protecting your organization anymore. You're protecting your own fear of being judged. And that fear is expensive.

Think of it like a report card. You don't need a valedictorian appeal with a perfect 100. You need a solid B+: clear ask, correct facts, on brand, nobody's name is wrong. That's launch ready. That's revenue ready.

Copy that would earn an 85% or higher is doing far more good in your donor's inbox than it will ever do sitting in an editing queue. Get it good. Proof it well. Then send it.

Because here's what actually happens when copy sits too long: the appeal deadline creeps closer, the campaign timeline gets tighter, and now you're rushing something out at the last minute anyway, except with way more stress and way less time to check it properly.

Perfectionism doesn't protect quality. It just delays it, and adds panic on top.

Or worse yet, you are launching something new and keep postponing the go-live date because the copy isn’t perfect yet. Don’t let this be you. B+ or better? Ship it!

​Nobody has ever unsubscribed because a sentence could have been tighter or could have had a smidge more hypothetical emotion. They unsubscribe because they never heard from you at all.

So, here's your assignment. Go look at your drafts folder right now. Find the appeal, the email, the letter that's been sitting there for longer than it should. Read it one more time. Check it against the real bars: is it accurate, is it on brand? Yes? Great!

Would it cause a scandal?

If not: ship it.

Your mission is waiting. Your donors are waiting. Go raise some money.

Cheers,

P.S. Want more content on fundraising and sustainable revenue growth? Subscribe to the blog and get new posts delivered straight to your inbox.

P.P.S. If you're a nonprofit CEO or development lead who's tired of carrying the fundraising weight alone, a free discovery call is for you. Let’s chat.

If you liked this…

• The REAL Framework for Board Fundraising Transformation
• Things You Might Have Missed (But Really Need to Know) From the Social Impact Staff Retention Project's Latest Report
• Diversify your Fundraising Revenue: The Six Revenue Streams Every Nonprofit Needs to Truly THRIVE
• Know. Like. Trust. Give. Advocate. The Full Journey Your Board Needs to Understand
• Now. Next. Needed: The Simple Way for Nonprofit Leaders to Tell Their Story in a Way that Attracts Funding

A few months ago, The Social Impact Staff Retention Project published their 2026 Social Impact Staff Retention Study. Access the full report here.

You may have seen the big numbers already:

• 70% of nonprofit workers are looking for or considering a new job
• 35% plan to stay in the nonprofit sector
• 22% say they are rarely or never fulfilled in their work
• 60% cite too much responsibility and not enough support as the top reason for leaving

Those numbers should make every executive director and board chair sit up straighter.

Read the full report closely, and there are deeper signals easy to miss, particularly where fundraising is concerned. Those signals carry major implications for nonprofit leaders, especially those who come from corporate environments.

Let's talk about them.

On page 5, the report compares nonprofit job-searching rates to all industries.

In 2026:

• 70.4% of nonprofit respondents are job searching
• Compared with only 43% across all industries

Corporate retention appears to be stabilizing. Nonprofit retention is not. That gap is wide and it's widening.

If you're a board member who leads in the corporate world, you may see employees settling in at your company. You may assume mobility has cooled.

That assumption doesn't hold inside nonprofits. Nonprofit professionals are still scanning the horizon at dramatically higher rates.

Shape governance decisions around corporate retention patterns instead of nonprofit data, and leaders will misread the risk entirely.

The top reason people are leaving: "too much responsibility and not enough support."

Look at the trend:

• 58% in 2024
• 59% in 2025
• 60% in 2026

It's creeping up.

Compensation complaints are steady. Unsupportive management is steady. Workload strain is rising.

That tells me something important. This isn't just about salary. It's about design.

Boards approve growth strategies. Revenue goals increase. Programs expand. Campaigns stretch. But staffing models often stay lean.

Your people feel responsibility increasing every year without structural reinforcement behind it. Retention will not stabilize on its own.

This is a governance conversation, not just a management one.

Thirty-eight percent of respondents say they are unsure whether they will stay in the nonprofit sector.

The report calls this group a canary in the coal mine. They aren't committed, but they aren't gone yet. They're watchful.

This group concerns me more than the 15% who plan to leave for other industries.

Here's why: unsure employees often stay physically. They detach psychologically. That looks like:

• Lower discretionary effort
• Less long-term planning
• Hesitation to invest in leadership development
• Quiet job searching

If you're leading a nonprofit, ask yourself: what would move someone from unsure to committed?

This one surprised me. Only 35% of those looking for new jobs cited political or funding concerns about the certainty of their role.

We often blame turnover on unstable funding. The data says internal conditions carry more weight than external volatility.

​That means the solutions sit closer to home than most boards assume: leadership support, workload distribution, role clarity, career sustainability. Internal levers, every one.

On page 6, fundraising comes in at 72% looking for new opportunities. It's not in the top three most at-risk functions.

Let's be clear: seventy-two percent is not stability.

Nearly three out of four fundraisers considering leaving means your donor relationships sit on shaky ground. Your campaign continuity does too. So does your revenue forecast.

Comparative ranking can distract from the real picture. Every functional area is under strain.

​For boards that evaluate fundraising primarily through outcomes: this is your wake-up call. You cannot separate revenue from the sustainability of the people generating it.

"Lacking growth opportunities" dropped from 58% in 2024 to 46% in 2026.

Sounds like progress on the surface. It may reflect better access to professional development. Or it may reflect a workforce too overloaded to prioritize advancement at all.

​When people are overwhelmed, survival eclipses ambition. That is not a thriving talent pipeline.

This report isn't a panic piece. It's a mirror.

Nonprofit professionals aren't disengaged from mission. They're questioning whether the sector can sustain them. That distinction matters: mission commitment is still strong. Structural confidence is weaker.

If you're a board member who doesn't live inside nonprofit operations every day, this data matters especially for you. You cannot assume corporate workforce trends apply here, that people will stay simply because the job market tightens, or that mission loyalty will override workload design.

Retention in nonprofits isn't just an HR metric. It's a revenue strategy, a governance responsibility, and a sustainability issue.

​The headlines tell you turnover is high. The deeper read tells you why.

Nonprofit boards set revenue goals. They shape expectations. They influence workload, flexibility, and support, whether they mean to or not.

Most boards are full of smart, capable people who've simply never been taught how nonprofit fundraising systems actually work.

When I work with boards and leadership teams, we don't just talk about raising more money. We build strategies that align ambition with capacity. We clarify what realistic projections look like. We create a shared understanding, so staff aren't carrying invisible pressure alone.

That kind of alignment does more than increase revenue. It reduces unnecessary strain. It builds trust between board and staff. It makes goals feel achievable instead of overwhelming.

When goals feel achievable, retention stops being an abstract HR concern. It becomes a natural byproduct of good governance.

Remember: fundraising is a relationship business. Retention matters to it directly. Donors read a lack of staff continuity as organizational instability, and it chips away at their confidence in your nonprofit. Caring about employee satisfaction and reducing turnover, for a nonprofit, is the same thing as caring about your bottom line.

​If you're reading this and thinking, "Our board needs this conversation," let's have it.

Schedule a call with me. We'll look at your goals, your staffing structure, and your board dynamics. I'll help you see where support can be strengthened and where expectations can be recalibrated.

You don't fix sector-wide retention overnight. But you can absolutely build an organization where your people feel supported, clear, and capable of staying for the long haul.

Let's start there.

Cheers,

P.S. Want more content on board fundraising, mindset, and sustainable revenue growth? Subscribe to the blog and get new posts delivered straight to your inbox.

P.P.S. If you're a nonprofit CEO or development lead who's tired of carrying the fundraising weight alone, a free discovery call is for you. Let’s chat.

If you liked this… 

• Diversify your Fundraising Revenue: The Six Revenue Streams Every Nonprofit Needs to Truly THRIVE
• The REAL Framework for Board Fundraising Transformation
• Know. Like. Trust. Give. Advocate. The Full Journey Your Board Needs to Understand
• Now. Next. Needed: The Simple Way for Nonprofit Leaders to Tell Their Story in a Way that Attracts Funding
• Asking Is Only 5%: Why Your Board Is Afraid of the Wrong Thing

If you're a nonprofit leader, there's a good chance you're holding your breath right now.

Maybe you're waiting to hear if that grant gets renewed. Maybe you're hoping your biggest donor doesn't decide to move on. Maybe you've done the math and realized that one person or one source is carrying way too much of your annual budget.

That's not a funding strategy. That's a gamble.

I've seen what happens when organizations build their entire revenue picture around a single mega donor who gives 30 or 40 percent of the annual budget. When that person walks away, whether because of a falling out, a change in priorities, or simply passing away, the organization is left with a hole that's nearly impossible to fill overnight.

The answer is revenue diversification. Not just across funding types, but within your individual giving portfolio, too.

​That's what the THRIVE model is all about.

THRIVE is a framework I developed to help small and mid-size nonprofits build a more balanced, more resilient individual giving program. Each letter stands for a different type of revenue stream:

T = Transformational Gifts (Major Donors)
H = Hope-Based Giving (Planned Legacy Gifts)
R = Retained Donors (Retention)
I = Intake of New Donors (Acquisition and Reacquisition)
V = Vested Commitments (Multi-Year Pledges)
E = Evergreen Giving (Recurring Monthly Giving Program)

You don't have to build all six at once. The goal is to understand what each piece does, where you have gaps, and how to start filling them in a way that's manageable for your team.

​Let's walk through each one.

These are your major gifts. And before you scroll past this section thinking "we're too small for major gifts," let me stop you.

Major is relative. At some institutions, a major gift starts at $100,000. At a small community nonprofit, it might be $1,000. The point isn't the dollar amount. The point is that you have donors capable of giving significantly above the average annual gift, and the goal is that you are actively cultivating relationships with them.

Major gifts don't appear out of nowhere. They grow from long-term relationship, and more often than not, the prospect is already in your database. They're giving you $25 or $50 a year. They're testing the waters. They want to see how you communicate, how you manage your programs, whether you're worth a bigger investment.

Here's a number that surprises people every time I share it: in higher education donors can give for 11-40 years before graduating to a major gift (pun intended). Eleven years. That means the transformational donor of your future is probably someone who made their first small gift to you a decade ago. (But don’t despair if you are a newer nonprofit, 21% of major gift donors had only been giving for 3 years before making their larger commitment.) (Giacomini et al. pg. 7)

The good news is that your future major donors are already in your database!

Once you've identified someone and you're in active, one-on-one relationship with them, you're looking at 18 to 24 months to close that major gift. (Giacomini et al. pg. 7)

That's what I call platonic dating. You're having coffee, hopping on Zoom, making phone calls. You're sharing where your organization is right now, where you're headed, and what it will take to get there. You're not asking at every turn. You're deepening the relationship until the ask is a natural next step, not a cold pitch.

​If you're an executive director, you should be having at least two to three of these conversations every week. Not because every person will become a major donor. Because you don't know who will become a major donors until you show up.

This is my term for legacy and planned giving, and I call it hope-based giving because that's exactly what it is. When a donor includes your organization in their estate plans, they are expressing hope in your long-term impact. They want to make sure you're still doing this work long after they're gone.

Here's what most small nonprofits get wrong about planned giving: they think it's for wealthy donors.

It's not.

Planned gifts are made from assets, not income. That loyal annual fund donor who has given you $100 every year for 15 years? She might not be able to give you much more than that right now. But she could leave you $25,000 in her will. Planned gifts are often the single largest gift a donor ever makes to an organization, and they frequently come from the most committed, longest-tenured people in your database, not necessarily the highest annual givers. In fact, the average planned gift is over 200 times larger than that same donor’s annual gift amount. (“Planned Giving Myths”)

​Now, I know that "planned giving" as a category can feel enormous and intimidating. There are trusts, charitable annuities, retirement account designations, life insurance policies, even real estate. It's a lot.
But you don't need to know everything about planned giving to get started. You just need to know two vehicles: bequests and beneficiary designations.

​Bequests: A donor works with their attorney to add language to their will directing a portion of their estate to your organization. Simple to set up. Simple to change.

Beneficiary designations: Even simpler. The donor contacts the holder of their retirement account or life insurance policy, fills out a form, and names your organization as a beneficiary for a set percentage. Then they let you know.

That's it. That's your starting point.

Start talking about these options publicly. Send a promotional email. Post about it. National Make a Will Month is in August, and National Estate Planning Awareness Week falls in October every year. Use those hooks. They give you a natural reason to start the conversation with your donor base without it feeling out of nowhere.

And here's the urgency behind all of this: we are in the early stages of the largest wealth transfer in history. Baby boomers hold the majority of private wealth in the United States. As that generation ages, that wealth will move. Nonprofits that are in that conversation now will benefit. Organizations that sit on the sidelines will not.

You can't win it if you ain't in it. 😊

Six out of ten donors will not give to your nonprofit again next year. (“Retention Time Series”)

​That's the industry average. Which means if you want to just stay even, you have to replace more than half your donor base every single year. That's exhausting, expensive, and completely avoidable with better systems.

Here's something that often gets missed in the retention conversation: retention doesn't start after the gift. It starts before it.

Where you get your donors matters enormously. If you're pulling in most of your new donors from a golf tournament or a 5K, you've already set yourself up for a low retention rate. Those folks came for the event. They may not have a deep emotional connection to your mission. They're not going to renew because they don't feel tied to the work you're doing.

Compare that to a donor who came to you through a volunteer orientation, a personal introduction, or a mission-aligned community event. That person came in connected. They're going to be far more likely to renew.

Stewardship absolutely matters, too. Does a first-time donor get a phone call from a board member? Do they receive a handwritten note? Do they hear what happened with their gift before they get the next ask? These are structures you must build intentionally, because if you leave them to chance, they don't happen.

Build the systems. Fix the leaky bucket. Getting above a 50 to 60 percent donor retention rate is one of the most powerful things you can do for your organization's long-term stability.

Even if your retention rate is excellent, you will still lose donors every year. That's just the reality. People move, circumstances change, life happens.

That means donor acquisition isn't optional. It's an annual requirement.

The goal isn't just to bring in new donors. It's to bring in the right new donors. People who are genuinely connected to your mission and who are likely to come back year after year. That's what builds a strong base.

Ask yourself: where are we finding new donors right now? And are those sources giving us people who renew?

If the honest answer is no, that's where to start. What would it look like to attract mission-connected donors instead of event-driven ones? Who are the people already orbiting your organization through volunteer work, advocacy, or community involvement who haven't made a gift yet?

​Start there.

This is multi-year pledges, and I am consistently surprised by how underutilized this is outside of higher education.

In higher education, multi-year pledges are standard practice. A donor says they'll give $5,000 a year for three years. Done. The organization projects that revenue, they plan around it, and they don't have to go re-cultivate and re-ask that same donor every year.

Smaller nonprofits rarely do this, and they're leaving a lot on the table.

Here's what a vested commitment does for you: it removes you from the cycle of making the case over and over again to the same donors. Instead of crafting a new proposal every year, you send a simple reminder. "Your pledge payment for this year is coming up. Thank you for your continued commitment." That's it.

The most common objection I hear is: “What if they don't follow through?"

The data answers this. The industry average fulfillment rate for multi-year pledges is 93%. That's not a typo. Industry averages show that between 80-90% of the dollars pledged do come in. (Ugrenovic)

The thing you do need to have in place is a follow-up system. Someone in your organization needs to be pulling upcoming pledges from the database every month and sending reminders. That's the whole system. Once you have it, you have one of the most reliable revenue streams available to you.

​And there's a bonus: many major donors actually prefer to structure their commitment over multiple years. It fits their financial planning better. Asking someone for a three-year pledge instead of a one-time gift can make the yes easier to get, not harder.

This is your monthly giving program, and "evergreen" is exactly right. Once you build it, it keeps going with minimal maintenance.

For donors, monthly giving is easy. They set it up, the gift processes automatically, and they don't have to think about it again. A donor who might give $50 once a year can give $10 a month and end up giving $120 annually. Most monthly donors give more over the course of a year than they would with a single annual gift.

For your organization, a monthly giving program is steady, predictable revenue. Once you've launched it and grown it to a meaningful size, the ongoing maintenance is relatively light:
​

• Update expired or declined credit cards when they come up
• Periodically ask long-tenured monthly donors to upgrade their amount
• Keep talking about the program in your emails and on social media so new donors know it exists
• Do a push once a year to grow the program
• Occasionally do something meaningful to recognize and celebrate your monthly giving community

That's the maintenance plan. It's manageable. And the payoff, predictable cash flow every single month, is worth the upfront work of launching.

You don't have to build all six revenue streams at once. Especially if you're a small shop with limited bandwidth.

Here's how I'd sequence it:

Start with R and I together: retention and intake. Get clear on your renewal rate and where you're sourcing donors. That foundation matters for everything else.

Add E: build or strengthen your monthly giving program. Even a small monthly giving community creates reliable, recurring revenue and raises your average annual gift per donor.

Build V and T together: as you start identifying major donor prospects, you'll find that multi-year pledges and major gifts often go hand-in-hand. Many significant donors want to spread their commitment over three to five years.

Add H as you go: don't wait too long on planned giving. Baby boomers are making these decisions right now. You want to be in the conversation.

The goal of the THRIVE model isn't complexity for its own sake. It's sustainability. It's building a revenue picture where no single source is carrying too much weight, where you know what's coming in, and where you're in genuine relationship with the people who make your mission possible.

That's what good fundraising looks like. Not frantic. Not transactional. Relational, intentional, and built to last.

If you are reading this and wishing you had a guide to help you begin to implement some of these revenue streams, let’s talk. Visit realdealfundraising.com/bookacall to find some time on my calendar.

Cheers,

P.S. Want more content on board fundraising, mindset, and sustainable revenue growth? Subscribe to the blog and get new posts delivered straight to your inbox.

P.P.S. If you're a nonprofit CEO or development lead who's tired of carrying the fundraising weight alone, a free discovery call is for you. Let’s chat.

If you liked this…

• The REAL Framework for Board Fundraising Transformation
• Know. Like. Trust. Give. Advocate. The Full Journey Your Board Needs to Understand
• Now. Next. Needed: The Simple Way for Nonprofit Leaders to Tell Their Story in a Way that Attracts Funding
• Asking Is Only 5%: Why Your Board Is Afraid of the Wrong Thing
• Listening Is a Skill: How Silence Wins Big Gifts

Giacomini, Cara, et al. CASE Study of Principal Gifts to U.S. Colleges & Universities. Council for Advancement and Support of Education, June 2022, https://www.case.org/system/files/media/file/CASEStudyofPrincipalGifts_finalrevised6.21.22_2.pdf.

“Planned Giving Myths, Facts, Stats, Ruminations.” PlannedGiving.com, 2026, https://www.plannedgiving.com/resources/planned-giving-facts/.

“Retention Time Series – Quarterly FEP Report.” FEP Reports, Generosity AI Working Group, https://publications.fepreports.org/retention-time-series/.

​Ugrenovic, Aleksandra. “What Is Pledge Fulfillment Percentage in Fundraising? How to Calculate and Use PFP?” RallyUp, 13 May 2025, https://rallyup.com/blog/pledge-fulfillment-percentage/.

If you're leading a nonprofit, you've probably felt this tension.

Your board cares about the mission. They show up for meetings. They say yes when you need volunteers. They genuinely love what your organization does.

And when it comes to fundraising?

Things stall.

I lived this from the inside early in my career.

I joined an organization that was crawling out of a major PR crisis. They were drawing far more than 5% on their endowment. The need for fundraising was urgent and obvious. Everyone knew it.

I showed up to my first board meeting ready to talk about it.

As my section of the agenda approached, the board chair noticed another member needed to leave for a flight.

So, he ended the meeting.

Just like that.

My entire section skipped.

I sat there dumbfounded. A board in a funding crisis didn't want to hear from their new VP for Advancement.

That moment taught me two things.

Board transformation is never overnight.

And as a staff member, sometimes there are hard truths you simply cannot say out loud. Not the way they need to be said. The power dynamic gets in the way. The relationships get in the way. The fear of damaging trust gets in the way.

That gap has a cost.

It slows revenue. It puts more pressure on you. It keeps your mission from growing at the pace it should.

​There is a different way. And that's exactly why I built the REAL Framework.

REAL stands for Reframe, Engage, Ask, and Learn.

It's the methodology I use with every client who comes to me struggling with board fundraising. Each step builds on the last. That sequence is not accidental. It's the whole point.
​
Let me walk you through it.

When a board isn't participating in fundraising, the instinct is to pile on more training, more asks, more accountability measures. But board members don't hold back because they don't care. They hold back because they're scared. Scared of rejection. Scared of saying the wrong thing. Scared of damaging relationships they've spent years building.

That psychological resistance is the number one blocker to board participation. And no amount of training on the mechanics of an ask will fix it if you haven't addressed the mindset first.

So that's where we start.

I use surveys and interviews to assess where board members are actually starting from. What do they believe about money? About asking? About whether your organization is worthy of a major gift? From there, we name the myths driving the resistance and replace them with something more accurate and more empowering.

This isn't soft work. It's the foundation that makes everything else possible.

​The goal: reduce the psychological friction so board members can start showing up for revenue generation.

Once mindset is addressed, we move into consistent, intentional action. And this stage is not about asking. Not yet.

Engagement is about getting board members doing something connected to the donor cycle. That might look like:

• Writing thank you notes or making thank you calls
• Identifying potential donors from their personal and professional networks
• Inviting people to events or tours
• Attending a meeting with a program staff member
• Telling their own story of why they give and what the mission means to them
• Making their own personal gift

None of these require a script. None of them require anyone to feel pushy or transactional. They're relationship-building actions that build confidence over time.

Two tools I use here are the Fundraising Avatars and the Board Fundraising Menu. The Avatars help each board member identify what kind of fundraiser they naturally are. The Menu gives them a tiered list of activities to choose from so engagement feels like a fit, not a forced assignment.
​
The goal: get board members moving. Momentum builds confidence. Confidence leads to growth.

Now we get to the part everyone assumes fundraising is all about: asking.

But asking is only about 5% of the fundraising process. It's a critical 5%, and it goes sideways when board members don't have a clear structure for doing it well.

A good ask is directed at the right person, for the right amount, at the right time, framed in a way that connects to what the donor actually cares about.

In this stage, I give board members a formula for building a compelling and effective ask. We practice. We work on body language. We talk through how to handle objections and difficult questions with confidence. (I have a free resource on responding to donor questions if you want to get a head start on that piece.)

The goal isn't perfection. It's empowerment. A board member who asks from a place of genuine belief in the mission will always outperform a board member reading from a script.

This is the stage most organizations skip entirely. It's the one that compounds all the other work.

Every outcome from an ask holds information. The question is whether you're capturing it and using it.

• A yes tells you what messaging landed, what relationship was strong, what timing was right.
• A no tells you what to adjust, what to clarify, where more cultivation is needed.
• Silence tells you something too. Maybe the timing was off. Maybe the ask wasn't specific enough. Maybe there's a conversation that needs to happen before you circle back.

The Learn stage builds an evidence-based fundraising culture inside your organization. It takes the long view of revenue growth, because sustainable fundraising is built through iteration over time, not through a single campaign push.

​The goal: create an environment where there is no failure. Only learning.

I've seen organizations jump straight to the Ask without ever addressing mindset. I've seen boards go through training and get handed a donor list with no support for what to do next. I've seen incredible board members burn out because no one ever closed the loop and helped them understand the impact of their work.

The REAL Framework works because it moves in sequence. You can't skip Reframe and expect Engagement to stick. You can't activate board members to Ask if they haven't built confidence through Engagement first. And without Learn, you're starting from scratch every single cycle.

​This framework doesn't add more work to your plate. It organizes what you're already doing so it truly produces results.

If you want a closer look at how I put the REAL Framework to work with clients, download the Real Deal Fundraising Engagement Guide. It walks through what working together actually looks like and what you can expect from the process. 

​And if you're ready to talk about what this could look like for your organization, I'd love to connect. Book a free discovery call at realdealfundraising.com/bookacall.

Your board has more capacity than you think. They just need the right system.

Cheers,

P.S. Want more content on board fundraising, mindset, and sustainable revenue growth? Subscribe to the blog and get new posts delivered straight to your inbox.

P.P.S. If you're a nonprofit CEO or development lead who's tired of carrying the fundraising weight alone, a free discovery call is for you. Let’s chat.

If you liked this… (which also doubles as the From the Archive section of the e-newsletter)

• Know. Like. Trust. Give. Advocate. The Full Journey Your Board Needs to Understand
• Now. Next. Needed: The Simple Way for Nonprofit Leaders to Tell Their Story in a Way that Attracts Funding
• Asking Is Only 5%: Why Your Board Is Afraid of the Wrong Thing
• Listening Is a Skill: How Silence Wins Big Gifts
• Authenticity and Vulnerability: Why Alignment Changes Everything

There’s a common shorthand in marketing for how individuals become familiar with brands and institutions: Know, Like, Trust.

Having worked in higher education for most of my career, I have been lucky to have a ready-made constituency that knows the institution well – our alumni. If the institution has done well, most of the alumni will also like and trust their alma mater.

But for most nonprofits wondering why they have trouble raising the funds they need, the problem usually happens upstream. In fact, I add two more crucial steps onto this funnel that make it more relevant for nonprofits, specifically.
​
Know → Like → Trust → Give → Advocate

People may know of your nonprofit from social media or word-of-mouth from a friend who benefitting from your services. They come to like you when they follow you on social media or subscribe to your email list.

Trust is harder to see in behavior, but it is a result of demonstrating good stewardship of your resource and integrity in how your organization moves. Only once they trust your nonprofit will they make a gift.

And generally speaking only those who are fully invested (in both trust and resources) will become advocates and ambassadors for your organization, thereby filling the funnel with more potential supporters!

What’s even more powerful is when you place that funnel next to the Donor Cycle:
​
Identify → Qualify → Cultivate → Ask → Steward

They are describing the same journey from two different angles.

And here’s the leadership insight:

Most boards only show up at "Give" or "Ask".
​
But fundraising strength is built long before that moment.

Before someone gives, they must know you exist.

That sounds obvious. Yet many boards underestimate how much influence they have at this stage.

Board members can:

• Open doors to new networks
• Give speeches about your nonprofit in professional and community settings
• Share organizational updates and impact stories on social media

This is not small work. This is pipeline work.

When a board member says, “I don’t fundraise,” but never introduces anyone new to the mission, what they’re actually saying is, “I don’t participate in identification.”

If you've read my post on Fundraising Avatars, Door Openers and PR Gurus belong right here.

No awareness. No prospects.

Once someone knows about your organization, the next question is alignment.

Do they resonate with the mission? Do they see their values reflected in the work?

Board members can support this stage by:

• Having coffee with a friend who shares similar values and discussing the mission
• Inviting three friends to an open house or event
• Sharing authentic stories of impact in their own voice

This is relational, not transactional.

This is where affinity is assessed. Where you begin to see who leans in naturally.

It’s also where many boards are more comfortable than they realize.

They don’t need to ask yet. They just need to connect.

Trust is where fundraising becomes serious.

This is the longest phase of the donor cycle, and it’s where credibility is built.

Board members influence trust in powerful ways:

• Leading with transparency and clarity, especially around finances
• Recruiting new board members who are respected in the community
• Helping produce an annual report or impact video that communicates results clearly

Trust is not built through charisma. It’s built through consistency and integrity.

If a board is disorganized, opaque, or unclear about financial realities, trust erodes quickly.

But when a board models steadiness and transparency, donors feel it.

This is also where listening matters most. Silence after the ask is powerful, but listening throughout cultivation is what earns the right to ask in the first place.

Only after Know, Like, and Trust have been established does the Give stage make sense.

This is the inflection point.

Board members can engage here by:

• Hosting an ask event
• Making their own meaningful gift
• Starting a monthly gift
• Considering a planned gift
• Telling their story of why they give and giving staff permission to share it

Notice something important.

Board giving is not just about dollars. It’s about credibility.

When board members invest first and speak openly about why, they reduce skepticism and increase alignment.

The ask should never feel abrupt. It should feel like the natural next step in a relationship.

If your board only engages here, you are asking them to operate at the highest-pressure point without participating in the earlier groundwork.

That’s a recipe for avoidance.

This is the stage most boards forget.

Advocates multiply impact.

Board members can:

• Encourage friends to volunteer
• Participate in thank-you notes and stewardship calls
• Emphasize outreach to first-time donors
• Continue telling stories of impact long after the gift is made

Advocacy is what transforms one-time donors into long-term partners. And stewardship is what turns satisfaction into loyalty.

If your board understands that their role extends beyond the ask, fundraising stops feeling episodic.

It becomes cultural.

As a CEO or Board Chair, ask yourself:

• Where does my board naturally engage?
• Where are we strong?
• Where is the arc breaking down?

If your board is only activated at “Give,” you are missing 80% of the journey.

But when you align board strengths to every stage of Know → Like → Trust → Give → Advocate, fundraising becomes coordinated and sustainable.

It becomes a system.

And systems outperform heroics every time.

If you’d like to assess where your board is strongest (and where you may be losing momentum in the funnel), let’s talk.

In a Discovery Call, we can map your board’s engagement across the full journey and identify practical next steps.

Fundraising is not one moment.

It is a progression.

And strong boards understand the entire arc.
​
Cheers,

P.S. If you found this helpful, there's more where that came from. Subscribe to get practical fundraising strategies delivered straight to your inbox.

P.P.S. If you're a nonprofit CEO who freezes when it's time to ask, or who knows your messaging isn't landing the way it should, let's connect. I work with leaders one-on-one to get this right.

If you liked this…

• Now. Next. Needed: The Simple Way for Nonprofit Leaders to Tell Their Story in a Way that Attracts Funding
• Asking Is Only 5%: Why Your Board Is Afraid of the Wrong Thing
• Listening Is a Skill: How Silence Wins Big Gifts
• The 3 Rs of Fundraising Mindset: What It Really Takes to Talk About Money
• Authenticity and Vulnerability: Why Alignment Changes Everything

I was teaching this framework in a workshop when I asked an executive director, “Where are you now?”

She began: “We were founded in 1984…”

I stopped her.

That’s not now. And it’s not a hook.

Her organization helps people secure stable housing. So I asked, “Tell me about someone you’re serving right now.”

She told me about a 94-year-old grandmother raising her special needs grandson. She was determined to secure a safe home for him. She was aging. He was vulnerable. And she was not quitting.

The room shifted. That’s Now.

Not a founding date. A life in motion.

If you want to sound strategic, compelling, and completely at ease in a fundraising moment, here’s the structure I teach:

Now. Next. Needed.

​It works in a ballroom, a boardroom, or one-on-one with a major donor. And it sets up the ask organically.

Start with one person: One moment. One story. One lived reality.

Then, once you have their attention, widen the lens.

After the story of that grandmother, the executive director could have added:

• “She is one of 127 seniors we served this year.”
• “Our waiting list has grown 42%.”
• “Rents in our county have increased faster than wages for five straight years.”

Now you’ve done two things:

1. You captured hearts (and your audience's attention).
2. You grounded it in scope.

You’re sequencing the data correctly for human attention. Story first. Scale second. That’s leadership. They need to care before you give them all those numbers to absorb.

Once your audience understands today’s reality, give them the vision.

​What does growth look like?

• 50 more families housed each year?
• Two additional counties served?
• A new facility that doubles your capacity?
• A staffed support model that stabilizes families long term?

Paint it clearly.

Let them see more grandmothers stable and their grandkids safe. More communities strengthened.

This is not abstract ambition. It’s concrete expansion of the good work already happening.

When you articulate vision this way, you take listeners on a journey. They move with you from where you are to where you want to be.

​And this is the key: the vision creates tension. There is always a gap between Now and Next. That gap is where fundraising lives.

If you’ve done Now and Next well, your audience is already wondering: “What will it take to get to that vision?”

That’s your cue. Name it.

• More housing units.
• Skilled staff.
• Expanded case management.
• Legal support.
• Transportation.
• Technology.
• Capital.

At the end of the day, all of it comes back to resources. And resources require funding.

When you say, “To expand into two new counties, we need $1.2 million over three years to hire staff, secure properties, and stabilize families,” you are not being awkward.

You are being clear.

This is where Now. Next. Needed becomes powerful. It sets up the fundraising ask organically, authentically, and easily. No cringe factor.

You didn’t jump from “thank you for coming” to “please give.” You walked them there.

You showed them the present, invited them into the future, and then explained what it will take.

​The ask becomes the natural next step in the story. That's the whole point

Before your next event or donor meeting, ask yourself:

• Who represents our story?
• What does that story reveal about our current reality?
• What growth or journey or story are we inviting people into?
• What will it take to get there?

Protect that arc.

​When you follow this structure, you sound:

• Grounded in reality
• Clear about direction
• Confident in the ask

And when leaders sound confident, donors feel confident.

Now.
Next.
Needed.

Start with a life. Expand to the scope. Paint the growth. Name what it will take.

Then invite people in.

That’s how fundraising stops feeling awkward and starts feeling like a natural part of the story. You do not need a longer speech. You need a cleaner journey.

​Cheers,

P.S. If you found this helpful, there's more where that came from. Subscribe to get practical fundraising strategies delivered straight to your inbox.

P.P.S. If you're a nonprofit CEO who freezes when it's time to ask, or who knows your messaging isn't landing the way it should, let's connect. I work with leaders one-on-one to get this right.

If you liked this…

• Listening Is a Skill: How Silence Wins Big Gifts
• The 3 Rs of Fundraising Mindset: What It Really Takes to Talk About Money
• Rack Up Your Nos: Why Rejection Is a Fundraiser’s Secret Weapon
• Authenticity and Vulnerability: Why Alignment Changes Everything
• Asking Is Only 5%: Why Your Board Is Afraid of the Wrong Thing

There is a moment in every donor conversation that tells you almost everything you need to know about a leader’s fundraising readiness.

It happens immediately after the ask.

You’ve prepared. You’ve built the relationship. You’ve connected the donor’s values to the work. You’ve stated the opportunity clearly and named the amount.

And then you stop talking.

That pause is not a gap.

It is the moment where partnership is either strengthened or unintentionally weakened.
​
And it is one of the hardest disciplines to master.

When I teach proposal meetings, I walk leaders carefully through the structure. Frame the impact. Name the investment. Make the invitation.

And then I say three words:

End. Pause. Listen.

That silence will feel longer than it is. It may feel like something has gone wrong. Your brain will search for ways to soften the ask, clarify the number, or add “just one more thing.”

That impulse is human. It is also the exact moment where you must manage yourself.

If you jump in and speak first, you forfeit your opportunity to hear what the donor is actually thinking. You begin responding to your own anxiety instead of their reality.
​
And anything you say in that moment is likely driven by assumption. Assumption is the enemy of clarity.

When you allow the donor to speak first, you gain something invaluable: information.

You learn whether the hesitation is about timing, amount, priorities, or something entirely different.

In major gift fundraising, it is rare to hear a definitive, final no. More often, you hear nuance. A different number, timeline, or focus. But you can only respond effectively if you actually hear it.

If you rush to fill the silence, you influence the response. You steer it. You muddy it. And then you lose the ability to diagnose what truly needs adjusting.

Fundraising, at its best, is thoughtful negotiation rooted in shared values.
​
Silence is what makes that negotiation honest.

If you are a board member sitting in the room as a peer or partner, this applies to you too.

It does not matter who delivered the ask.

Once the invitation has been made, the room belongs to the donor.

Sometimes a well-meaning board member will derail momentum by jumping in too quickly. They clarify. They soften. They add context. They attempt to “help.”

What they are often doing is relieving their own discomfort. And that discomfort can fracture the unity of the moment.

If you are present in the room, your job is to protect the pause. Let the donor speak.

Even if the silence stretches.
Even if your instinct is to rescue.
Even if you are certain you know what they are thinking.

You do not.

Only they do.

When a leadership team holds steady together, the donor experiences confidence and alignment. That steadiness builds trust. And trust deepens generosity.

Let’s name what is happening beneath the surface.

The pause feels vulnerable because you have just placed a proposal on the table. You have stated what the mission requires. You cannot control what happens next.
​
Leadership in fundraising is often about managing your internal response before managing the conversation.
​
The silence shows your composure. When you hold steady, you communicate confidence in both the mission and the donor. That confidence matters.

If you want your board to handle donor meetings well, rehearse the silence intentionally.

In practice sessions, say the ask out loud. Then count slowly to five before speaking again. Notice the urge to jump in. Let it pass.

The more you rehearse the silence, the less your body treats it like a threat. The more familiar silence becomes in rehearsal, the less intimidating it feels in real conversations.

​Listening is not passive. It is disciplined presence.

Fundraising is about alignment, not about winning.

When you ask and then truly listen, you communicate respect. You give the donor room to process and respond honestly. Respect builds trust. And trust is what sustains generosity long after a single gift is made.

​Silence, handled well, strengthens the partnership.

If you would like help scripting and rehearsing donor conversations so your board feels steady and prepared in the room, let’s talk.

Book a complimentary Board Fundraising Alignment Call and we'll work through proposal meeting strategy together.

The pause will always feel longer than it is. Hold it anyway.

​That quiet space is often where generosity begins.

Cheers!

P.S. This post is part of an ongoing series for nonprofit leaders and Board Chairs who want to build confident, fundraising-positive boards.
​
If this conversation is resonating, I invite you to subscribe so you don’t miss the next installment. My goal is to give you practical tools you can use at your next board meeting. Each piece builds on the last, and together they form a practical roadmap for strengthening fundraising culture at the leadership level.

If you liked this…

• Authenticity and Vulnerability: Why Alignment Changes Everything
• Asking Is Only 5%: Why Your Board Is Afraid of the Wrong Thing
• Fundraising is a Noble Endeavor: Why Board Beliefs Drive Revenue (Or Lack Thereof)
• The 3 Rs of Fundraising Mindset: What It Really Takes to Talk About Money
• Rack Up Your Nos: Why Rejection Is a Fundraiser’s Secret Weapon

I open my board fundraising workshops with this quote from Brené Brown:

"Vulnerability is not winning or losing; it's having the courage to show up when you can't control the outcome."

Every time I share it, I watch the room shift just slightly.

Because fundraising is exactly that.

It is showing up when you cannot control the outcome.

You cannot control whether the donor says yes or the timing of their decision or what is happening in their financial world that day.

You can only control how you show up.
​
And how you show up begins with authenticity.

When any nonprofit leader makes an ask, they are not simply delivering information. They are putting belief on display.

They are saying, in effect: I believe this work matters. I believe it deserves to grow. I believe it is worthy of investment.

There is exposure in that moment.

If you are not fully aligned with the mission, that exposure feels risky. You may hedge your language. You may soften the request. You may speak in generalities instead of conviction.

Donors can feel that.

They may not articulate it, but they sense when someone is reciting talking points versus speaking from lived belief.

Years ago, I worked for a leader who has raised billions of dollars in his career. At one point he told me he could never work for a university he did not attend.

At first, I thought that was unnecessarily restrictive. Surely skill and strategy are transferable.

It took me years to understand what he meant.

He was talking about authenticity.

Because he had personally benefited from the kind of institution he represented, he never had to manufacture enthusiasm. He never had to convince himself the mission mattered. He had lived it.

When he spoke about scholarships or research or student opportunity, he was not delivering a pitch. He was telling the truth.

That alignment reduced vulnerability. It strengthened confidence.

You do not have to draw your lines as narrowly as he did. You do not have to be an alum, a former client, or a beneficiary to serve with integrity.

But you do need to ask yourself a harder question:

Am I fully aligned with this mission?

Not casually supportive. Not intellectually persuaded.
​
Aligned.

Boards often assume confidence in fundraising comes from mastering scripts or memorizing the right phrasing. Those tools help. Preparation matters.

But true confidence comes from congruence. And for a nonprofit CEO or Board Chair, that congruence is not just a personal asset. It shapes the entire culture around you.

When your values and the organization's mission match, your voice steadies. You are not performing. You are advocating. You can speak honestly about the need, describe the vision without exaggeration, make a clear request, and then sit quietly, trusting the process.

That steadiness is contagious.

Fundraising also requires you to say, "This is what it will take," without knowing how the story ends. That is vulnerable. But it is also powerful.

When leaders are transparent about where the organization stands, clear about where it is going, and honest about what is required, donors feel respected. They feel invited into something real, not manufactured.

If leadership approaches fundraising as an uncomfortable obligation, the board will treat it that way. If leadership approaches fundraising as an expression of mission, the board will begin to see it that way too.

Tone travels.
​
You cannot control the outcome. You can control your integrity. And integrity builds trust faster than polish ever will.

If you want to strengthen authenticity in your fundraising culture, begin here:

• Why does this mission matter to me personally?
• Where have I seen its impact?
• What values does it reflect in my own life?
• Would I invest in this organization if I were not in this role?

Write the answers down. Not for publication. For your personal clarity.

When you take the time to articulate your connection to the mission, your fundraising voice becomes clearer. Your language becomes simpler. Your conviction becomes visible.

And when that conviction is visible, it gives your board permission to show up the same way. Not performatively. Sincerely.

Vulnerability, as Brené Brown reminds us, is about showing up when you cannot control the outcome. Fundraising will always require that.

​When it is rooted in alignment, it feels less like exposure and more like leadership.

Fundraising culture starts at the top. When the CEO and Board Chair are aligned, that clarity travels. When they're not, the whole team feels it.

If you want to examine how leadership alignment is shaping your board's engagement in fundraising, a complimentary Board Fundraising Alignment Call is a good place to start. We'll look honestly at where things stand and identify practical next steps to build the kind of confidence that carries through your whole organization.

Fundraising does not require perfection.

It requires alignment.
​
And when that alignment is present, generosity follows.

Cheers!

P.S. This post is part of an ongoing series for nonprofit CEOs and Board Chairs who want to build confident, fundraising-positive boards.

If this conversation is resonating, I invite you to subscribe so you don’t miss the next installment. My goal is to give you practical tools you can use at your next board meeting. Each piece builds on the last, and together they form a practical roadmap for strengthening fundraising culture at the leadership level. Next week’s piece tackles one of the most misunderstood parts of board fundraising.

If you liked this…

• Asking Is Only 5%: Why Your Board Is Afraid of the Wrong Thing
• Fundraising is a Noble Endeavor: Why Board Beliefs Drive Revenue (Or Lack Thereof)
• The 3 Rs of Fundraising Mindset: What It Really Takes to Talk About Money
• Rack Up Your Nos: Why Rejection Is a Fundraiser’s Secret Weapon
• Rethinking Board Recruitment: The 4 Ws That Really Matter