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

If you want to stall board fundraising quickly, here’s one way to do it:

Tell every board member they need to go ask wealthy people for money.

Now, let me say this clearly. Peer-to-peer asking is powerful. When a board member is willing to sit across from a donor and make a confident, values-aligned request, it can move mountains.

But that is not the only way a board fuels the mission.

And when we reduce board engagement to “who’s going to ask,” we miss the bigger picture.

Fundraising is a team sport. And every board member can play a meaningful role in generating resources.

The key is helping them understand how they are wired to contribute.

I call this finding your Fundraising Avatar.

Superpower: Connections

What you do: You introduce new people to the organization. Friends. Colleagues. Neighbors. Community contacts. You think about who should know about this mission and help make that first connection.

You are not necessarily leading the ask. You are expanding the circle.

Ask yourself: Do I know someone who needs to hear about this work?

Connects to: the Identification stage of the Donor Cycle
​
Without new relationships entering the pipeline, the donor cycle stalls. The Door Opener keeps it moving.

Superpower: Messaging

What you do: You are comfortable speaking about the mission in public or professional settings. Rotary. Chamber events. Networking spaces. You always have a solid elevator pitch ready.

You normalize talking about the organization. You raise visibility. You shape perception.

Ask yourself: Do I find myself naturally talking about this organization in my circles? 

Connects to: the Identification stage of the Donor Cycle. 

​Awareness fuels identification. Identification fuels qualification. The PR Guru strengthens the very top of the funnel.

Superpower: Appreciation

What you do: You help donors feel valued. You volunteer for thank-you calls. You write handwritten notes. You follow up after events to express genuine appreciation.

You understand that stewardship is not an afterthought. It is a growth strategy.

Ask yourself: Do I enjoy making people feel seen and appreciated?

Connects to: the Stewardship stage of the Donor Cycle

Retention is built on gratitude. Loyalty is built on recognition. This role directly impacts long-term sustainability.

​Superpower: Planning and Analysis

What you do: You think through strategy. You review donor lists. You assess return on investment. You brainstorm next steps. You ask smart, clarifying questions that make the team sharper.

In short, you enjoy connecting dots.

Ask yourself: Do I enjoy solving puzzles or making plans that lead to results?

Connects to: the Qualification, Cultivation, and Re-engagement stages of the Donor Cycle

Fundraising needs architects as much as ambassadors. The Strategic Brain strengthens systems and improves decision-making.

Superpower: Leading by Example

What you do: You invest personally. Quietly and consistently. Your giving sets the tone for the rest of the board. You demonstrate commitment without needing the spotlight.

You understand that credibility begins at the board table.

Ask yourself: Am I willing to be one of the first to give and show others this mission is worth it?

Connects to: all phases of the Donor Cycle

When board members give first, external fundraising becomes stronger and more authentic.

Superpower: Steady Execution

What you do: You say, “Just tell me what needs doing.”

You research grant leads. You gather data. You review donor lists. You help prep materials. You cross items off the list that keep campaigns moving forward.

You make progress happen, one action at a time.

Ask yourself: Do I feel most helpful when I’m chipping away at concrete tasks behind the scenes?
​
Connects to: all phases of the Donor Cycle

Momentum depends on execution. This role keeps energy from dissipating.

When board members feel boxed into a single version of fundraising, they resist.

When they see multiple meaningful pathways to contribute, they lean in.

Role clarity reduces anxiety. It replaces vague expectations with concrete action.

Over time, confidence builds.

• The Door Opener might eventually co-solicit.
• The Gratitude Leader might join a donor visit.
• The Task Tackler might take on campaign leadership.

But growth begins with alignment.

As a CEO or Board Chair, your responsibility is not to pressure uniform behavior. It is to build a coordinated system where different strengths work together toward shared goals.
​
That is how boards move from passive oversight to active partnership.

If this framework resonates with you, the next step is figuring out how to apply it to the specific personalities sitting around your board table.

Every board has a different mix of strengths. The real opportunity is aligning those strengths with the donor cycle so people know exactly how they can contribute.

That is exactly what we do in a complimentary Board Fundraising Alignment Call.

During the conversation, we will:

• Identify the fundraising avatars present on your board
• Map those strengths to real fundraising activity
• Clarify realistic expectations for board engagement
• Outline practical next steps your team can implement right away

If that sounds helpful, you can reserve a time for a Board Fundraising Alignment Call and we will talk through your situation together.

Fundraising is not powered by a few heroic asks.

It grows through consistent participation from people who understand how they contribute.

Helping boards discover that alignment is where the real momentum begins.
​
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 important parts of board fundraising.

If you liked this…

• Separate Your Emotions from Other People’s Money
• Rack Up Your Nos: Why Rejection Is a Fundraiser’s Secret Weapon
• 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

One of my recommendations for new major gift fundraisers is to go visit a college phonathon program. There you will see what it is like to build rapport fast, ask without fear, overcome objections, and get told “No” a lot.

And I mean a lot! A rock-star student caller calling future donors (alums that have as yet not made a gift to their alma mater) experience 80% refusals.

Major gift officers have a huge advantage over these incredible student fundraisers. They get the benefit of building a long-term organic relationship before asking.

But what the callers get is practice getting comfortable with rejection. That will serve every one of them well no matter what career they go into. And they get that through repetition, getting a sustained volume of asks in a short period of time.

What those callers get is PRACTICE. That’s the antidote to anxiety.

That said, if you want to reduce anxiety around fundraising, I’m going to suggest something that sounds completely counterintuitive.

Start trying to get more nos.

I’m serious.

Rack them up.
​
Because most hesitation in fundraising has very little to do with strategy. It has everything to do with the fear of rejection.

When board members say they are uncomfortable asking for money, what they usually mean is this:

“I don’t want to be told no.”

That no feels personal. It feels like failure. It feels like embarrassment. It feels like confirmation that we asked for too much.

But here’s the truth: Your job is not to secure a yes. Your job is to make the invitation. The outcome belongs to the donor. That distinction changes everything.

Years ago, when I was working directly with student fundraisers, I would sometimes flip their entire goal for the night. Perhaps we were calling a tough group and I knew they would have trouble keeping their motivation high. Instead of focusing on getting pledges, I would say:

“Rack up your nos.”

Every no meant they were actually doing the work. Every no meant they were having real conversations. Every no meant they were one step closer to a yes.

The goal wasn’t perfection.

The goal was practice.

When students focused on collecting no’s instead of avoiding them, something remarkable happened. Their anxiety dropped. Their confidence rose. Their activity increased.

And guess what followed?

More yeses.

Not because they pressured harder.
​
Because they showed up more.

Here’s something else that surprises people. In relationship-based major gift fundraising, you rarely get a full and final no. What you usually get is nuance.

• “I can’t do $50,000 this year, but I could consider $25,000.”
• “Not this quarter, but let’s revisit in six months.”
• “This project isn’t my focus, but I care deeply about scholarships.”

That is not rejection. That is conversation.

When you interpret every hesitation as a personal rejection, you shut down. When you understand it as information, you lean in.

You adjust the amount.
You adjust the timing.
You adjust the focus.
​
Fundraising is not a courtroom verdict. It is an evolving dialogue.

The truth is you cannot control the outcome of an ask.

You can control:

• Your preparation
• Your clarity
• Your alignment with the donor’s interests
• Your courage to call the question

Once you’ve done those things, you have done your job.

The donor’s response is theirs to own.

When you detach your identity from the outcome, asking becomes lighter. It becomes cleaner. It becomes far less intimidating.
​
And ironically, that calm confidence often increases your success rate.

If your board is paralyzed by the fear of rejection, they will delay. They will hedge and soften. They will avoid and procrastinate.

If you reframe the goal from “secure every yes” to “engage in real conversations,” the pressure drops.

You begin to measure success differently:

• Did we show up prepared?
• Did we make a clear, values-aligned invitation?
• Did we listen carefully to the response?
• Did we follow up thoughtfully?

That is success.

Yeses follow consistency.

Consistency requires courage.
​
Courage grows when rejection loses its sting.

At your next board meeting, try this:

Ask each board member to identify one meaningful fundraising action they can take in the next 30 days.

Not a perfect action. Not a guaranteed yes. Just an action.

Then celebrate activity, not just outcomes.
​
When you normalize nos as part of the process, you create a culture of momentum instead of a culture of avoidance.

If your board is stuck in fear of rejection, let’s work through that together.

In a complimentary Board Fundraising Alignment Call, we can examine where emotional friction slows down momentum and build a plan to create a confident, fundraising-positive culture.

Rejection is not the enemy of fundraising.

Inactivity is.

Rack up your nos.

They lead straight to your yeses.
​
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
• Separate Your Emotions from Other People’s Money
• Rethinking Board Recruitment: The 4 Ws That Really Matter

There is one mindset shift that can dramatically change how a nonprofit board approaches fundraising. (All credit for this phrasing goes to my friend, Justin Ferrell, who used it to get his student fundraisers to become more comfortable asking.)

Separate your emotions from other people’s money.

When I say that in a workshop, I can almost feel the room pause. It sounds simple. It is not.

Most anxiety around fundraising has very little to do with the mission.
​
It has everything to do with money.

Every one of us carries a money story.

Maybe you grew up in scarcity. Maybe money was tight, unpredictable, or a source of tension. Maybe you were taught that talking about money is impolite. Maybe you still live carefully, thoughtfully, responsibly.

Those experiences shape how you feel when you hear or say a large dollar amount.

But they are not universal.

For someone with significant wealth, a major gift may not represent sacrifice. It may represent alignment. It may represent legacy. It may represent an opportunity to use what they have been entrusted with to create positive change.

When a board member or nonprofit leader says, “I could never ask someone for that much,” what they are usually revealing is their own internal discomfort.
​
They are imagining how that amount would feel to them. That is projection and projection creates hesitation. Hesitation softens clarity. And soft asks rarely inspire confident gifts. Leadership requires you to notice that dynamic and step beyond it.

When you separate your emotions from other people’s money, you shift your posture.

You stop imagining that you are taking something from someone.

You begin to recognize that you are offering someone an opportunity to participate in something meaningful.
​
For many donors, giving is about:

• Expressing values
• Investing in long-term impact
• Honoring a loved one
• Creating legacy
• Strengthening community

Money is simply the tool that allows those values to take shape. Your responsibility is not to protect donors from their own generosity. Your responsibility is to articulate the mission clearly and invite them into it. The decision belongs to them.

This is where another reframing becomes powerful.

Your job is not to get the money.

Your job is to make the invitation.

That distinction reduces anxiety immediately.

When I worked with student fundraisers, I taught them to “rack up your nos.” Every no meant they were doing the work. Every no moved them closer to a yes. The goal was not perfection. The goal was forward movement, presenting the needs of the institution to interested parties.

Interestingly, in relationship-based major gift fundraising, you rarely receive a full and final no. What you receive instead is nuance.

A different amount.
A different timeline.
A different philanthropic priority.

That is not rejection. That is conversation.

When you detach your self-worth and your personal money story from the outcome, the conversation becomes lighter. More curious. More collaborative.

You are no longer carrying the emotional weight of the answer.
​
You are simply facilitating alignment.

As a nonprofit CEO or Board Chair, this mindset is not just personal. It is cultural.

If you shrink from big numbers, your board will shrink.

If you speak about fundraising with quiet apology, your board will mirror that tone.

If you model calm confidence and trust in the process, your board will follow.

I often remind leaders: if you work the process, the process will work.

The donor cycle exists to create structure. Identification. Qualification. Cultivation. Asking. Stewardship. Re-engagement. When you honor each phase, you reduce desperation and increase clarity.

Mindset is the foundation that allows the system to function.

Without it, every ask feels personal.
​
With it, fundraising feels strategic and purposeful.

If your board seems anxious around major gifts, ask:

• Are we projecting our own financial experiences onto our donors?
• Are we assuming sacrifice where there may be alignment?
• Are we carrying emotional weight that does not belong to us?

Naming this dynamic out loud can be transformative.
​
Emotional maturity in fundraising does not mean becoming detached or cold. It means becoming steady. It means trusting that donors are capable of making their own decisions. It means leading with clarity instead of projection.

If you sense that money narratives are quietly shaping your board’s engagement, let’s explore that together.

In a complimentary Board Fundraising Alignment Call, we can examine where emotional friction is slowing momentum and build a plan to create a confident, fundraising-positive culture.

Separating your emotions from other people’s money is not cold. It is respectful. It allows donors to decide. And it allows you to lead.
​
Cheers!

P.S. This post is the first 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.

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
• Your Board Wants to Help with Fundraising – They Just Don’t Know How
• Rethinking Board Recruitment: The 4 Ws That Really Matter

The Donor Cycle is one of the most grounding frameworks in fundraising. It gives structure to something that can otherwise feel mysterious or intimidating.

One graph I love shows the percentages that fundraisers stay in each stage. Notice how small the solicitation slice is (green) compared to cultivation and stewardship (pink and grey).
​
And almost without fail, when I put this chart up on the screen, I see shoulders relax.

Because most of the anxiety around fundraising comes down to one moment.

The moment when someone has to open their mouth and ask.

Of course, boards fixate on the ask. It feels exposed, vulnerable and high-stakes. I understand that fear. Asking requires courage, clarity, and the willingness to hear “no.”

And it is absolutely essential.

But here is the truth that surprises nearly everyone:

Asking is only 5% of the donor cycle.

Five percent.
​
That slice is much smaller than most board members imagine. And when leadership and boards misunderstand that, they either avoid fundraising entirely or approach it with unnecessary tension.

The donor cycle is simply a way of visualizing and systematizing how philanthropic relationships grow over time.

It begins with Identification. This is where you clarify who is most likely to care and most able to invest.

Next comes Qualification. After meeting potential supporters, you determine whether there is genuine alignment and readiness.

Then we move into Cultivation. I often call this “platonic dating.” This is relationship-building without pressure. You meet for coffee. You invite them to events. You share impact stories. You listen. You learn what matters to them. You help them understand the mission more deeply.

Cultivation is where trust is built.

After cultivation comes Solicitation, the Ask. This is where you make a direct request for a gift. The key is values alignment. The request reflects the relationship that has already been built.

Then comes Stewardship, or what I like to call “Thank and Recognize.” You celebrate shared impact. You communicate clearly about results. You express sincere gratitude.

Finally, you re-engage. You begin the cultivation process again, deepening the relationship over time.

When you look at how time is actually distributed across this cycle, about 80% of it is spent in cultivation and stewardship. Relationship-building and gratitude.

Asking? Five percent.

It is not the everyday.
​
It is an inflection point.

One of my former bosses is a minister. When I first walked her through the donor cycle and showed her that asking represented such a small portion of the overall process, she was visibly relieved.

She had a significant ask coming up with a donor we had spent considerable time cultivating. We had met with this donor multiple times. We understood her interests. She understood our vision. There was genuine trust in the relationship.

We practiced the ask beforehand. We went into the meeting prepared. That preparation eased some of her anxiety.

Afterward, she could not stop talking about how organic and authentic it felt. Of course, it felt that way. The relationship had already been built. The ask was simply the next logical step in a shared conversation. And yes, it was successful.
​
That is how fundraising should feel. Relationship first.

Board members often imagine fundraising as a constant state of asking. As if they will be pressured to request money in every conversation.

That is not how healthy fundraising works.

Healthy fundraising looks like:

• Listening carefully
• Sharing stories of impact
• Connecting mission to values
• Expressing gratitude
• Deepening trust

Then, at the right moment, calling the question.

You do have to call the question. That step is essential. You do have to follow up appropriately and secure an answer. Fundraising is not passive.

But when you understand that the ask sits within a much larger relational framework, it becomes far less intimidating.
​
It becomes purposeful. Graceful. Aligned.

If your board is anxious about fundraising, start by teaching the donor cycle.

Help them see that asking is not a daily burden. It is a small, strategic part of a much larger relationship-building process.

Invite them into cultivation. Encourage thank-you calls. Create opportunities for shared impact stories. Let them experience the joy of stewardship.

When board members realize that most of fundraising is about connection and gratitude, something shifts.

The ask stops feeling like a cliff.

It starts feeling like a bridge.
​
And bridges are meant to be crossed.

If your board feels stuck at the word “ask,” let’s unpack that together.

In 30 minutes, we’ll pinpoint where fear is creeping in and outline a clear path to board confidence. I’m opening three complimentary Board Fundraising Alignment Calls this month. You can reserve a time here.

Fundraising is consistent relationship building, not constant asking.

And when you understand that, the entire experience becomes lighter, clearer, and far more effective.

Cheers!

P.S. This post is the first 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.

If you liked this… 

• Fundraising is a Noble Endeavor: Why Board Beliefs Drive Revenue (Or Lack Thereof)
• Your Board Wants to Help with Fundraising – They Just Don’t Know How
• Rethinking Board Recruitment: The 4 Ws That Really Matter
• Culture of Philanthropy Check-Up
• The 3 Rs of Fundraising Mindset: What It Really Takes to Talk About Money