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

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

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).
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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.
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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.
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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.
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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.
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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.
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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… 

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• 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

Each year, I get a little more reflective about what actually moves the needle on Giving Tuesday. It’s one part adrenaline, one part strategy, and one part relationships – the same ingredients that fuel fundraising the rest of the year, just turned up a few notches.

This year? We hit our match. We saw strong donor response. And we learned a few things worth carrying into the next big push.

Here’s what worked:

1. The Match Game, with a Twist

Last year, we had a $20,000 match and hit it – barely. It took extending our deadline to pull it across the finish line. This year, with our donors’ permission, we split that ask into two: two $10,000 matches from two separate donors. One for Giving Tuesday. One saved for Calendar Year-End.

It created a sense of focus. One target, one day. And we met it.

Now we can head into December with some real momentum. “We hit the match on Giving Tuesday” makes a great line in every follow-up email. It tells a success story that donors helped write – and that builds confidence for the next ask.

2. Direct Contact Beat the Megaphone

Most of our gifts came through personal outreach. Not social media. Not big email blasts. Just me and my annual giving staffer reaching out by phone and plain emails from our Outlook inboxes.

That’s where the action happened. That’s where the giving happened.

I’m not knocking digital strategy – it plays its role. But, for us, Giving Tuesday was won in the inbox and on the phone. This reinforces my observations I wrote about earlier this fall about digital burnout and the reprise of analog communications.

3. Board Engagement Started Early

More than half of our board gave on Giving Tuesday. That didn’t happen by accident.

We start talking about Giving Tuesday in September. By November, they’ve heard the plan, seen the goal, and received a cheat sheet with sample language and graphics to share on social. The week before Giving Tuesday, we send that cheat sheet again.

And this year, they showed up. Not just with gifts, but with pride – and we’re closer to hitting 100% board giving for the year because of it.

4. Targeted Appeals to Past Giving Tuesday Donors and LYBUNTs

We made it easy on ourselves this year. Instead of trying to inspire everyone on our list, we reached out to the people who’ve already shown us they like giving on Giving Tuesday.

We pulled two lists:

• Calendar year LYBUNTs (gave in 2024, but not yet in 2025)
• Anyone who has ever given on Giving Tuesday before

When the subject line says, “I know you like to give on this day…” it doesn’t feel like a cold call. It’s a reminder. And it works.

5. Monthly Donors and Pledgers Want to Participate, Too

This one surprised me last year and held true again.

Donors who already give monthly or have pledge commitments still want to be part of Giving Tuesday. They like seeing the school hit a goal. They like contributing to a match. So, they give again.

That meant a few extra gifts came in from already-committed supporters. Nothing huge – but meaningful.
Here’s how we handled those emails:

"I hope you are doing well! I wanted to reach out today to let you know that it is Giving Tuesday and Starr King School for the Ministry has a goal of raising $10,000 to reach a challenge match of $10,000 (for a total of $20,000 for this beloved school).

If you would like to participate, as you have so generously done in the past, your gift would again be matched 100%. Just visit www.sksm.edu/givingtuesday TODAY and you can make your gift online.

Also, we know and appreciate ALL you have done for Starr King as sustainers this year so please don’t feel obligated to give more. I just know you have given to matches in the past and wanted to make sure you knew!"

​No pressure. Just an invitation to be part of something they’ve supported before.

Giving Tuesday doesn’t have to be a guessing game. It’s a day to do what already works in your shop – just more of it, with a little more urgency and clarity.

We focused on:

• Real relationships
• Targeted outreach
• Simple, achievable goals
• And donor behaviors we already knew from our data

It paid off. Not just in dollars, but in board engagement, team morale, and a strong hand to play as we close out the year.

And that’s the kind of success worth repeating.

Cheers!

P.S. Like this kind of insight? Subscribe to Real Deal Fundraising and get my best articles, tools, and curated resources every week – including webinars, videos, and free downloads

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When I taught my first graduate-level course this summer – Ethical and Community-Centered Fundraising – I expected good questions. What I didn’t expect was just how much anxiety would surface around one specific topic: planned giving.

These were smart, values-driven future leaders. People already thinking in terms of justice, legacy, and long-term impact. But the minute we shifted into planned giving, the energy changed.

It wasn’t the concept they struggled with. It was the conversation.

How do you bring up wills and estate plans without making it weird?
What if you say the wrong thing?
What if it feels morbid – or worse, transactional?

At their request, I created a simple guide: real phrases, grounded in real situations, to make legacy conversations feel natural, honest, and even hopeful.

Turns out, it’s not just my students who need this.
So if you’ve ever felt that same hesitation – this post is for you.

Because here’s the truth: Planned giving conversations don’t have to be awkward. They can be inspiring. They can even be joyful.

You don’t need to be a tax expert. You just need to know how to bring it up – gracefully and confidently.

Let’s start there.

Sometimes you’ll have donors reaching out first – through your website, a legacy giving survey, or in response to a donor story. Those are the easiest planned giving conversations because the interest is already there.

​But when you need to be the one to raise the topic, here are some ways to bring it up without making it feel heavy:

• “I know how deeply you care about our mission. Have you ever thought about how you’d like that impact to continue in the future?”
• “We’ve been talking a lot about your commitment to this cause. Some donors choose to include a gift that lasts beyond their lifetime – has that idea ever crossed your mind?”
• “Can I ask – have you done any estate planning? Sometimes people like to include a charitable gift, and I always make sure our most loyal supporters know that’s an option.”
• “You strike me as someone who thinks ahead. I wonder if you’ve ever explored including causes you care about in your long-term plans?”
• “You’ve done so much for this organization already. If you ever want to talk about ways to make your impact last, even after your lifetime, I’d love to be part of that conversation.”

​You’re not pushing. You’re not being morbid. You’re simply opening a door – letting them know that this kind of giving is possible, meaningful, and available to them.

You do need to have these conversations. Here’s why:

🟢 Planned gifts are huge. On average, they’re 200–300x the size of an annual gift. That’s because they’re made from lifetime assets, not income. (Source: National Estate Planning Awareness Week)

🟢 They’re already in your database. The donors who are most likely to leave you in their will? They're not wealthy strangers. They’re the consistent supporters who’ve given every year for the past decade. (Source: How to Talk About Death and Taxes)

🟢 You’ll never know unless you ask. A $25-a-month donor might be planning a six-figure bequest and never mention it unless you give them a reason to.

🟢 There’s $12 trillion on the move. The Great Wealth Transfer is projected to move $84 trillion by 2045, with $11.9 trillion going to charitable causes. That wave is already building. (Source: How to Talk About Death and Taxes)

🟢 Peer stories work. When donors hear from others like them who’ve made legacy commitments, your inbox starts filling up with questions – not awkward ones, but warm, intentional ones like: “Can I do this too?” (Source: Planned Giving Leads Don’t Generate Themselves)

🟢 You don’t need to overcomplicate it. Bequests and beneficiary designations are all most donors need to know. These are simple, flexible tools that don’t require financial wizardry or legal acrobatics. (Source: Cut Through the Clutter)

These conversations become easier when you stop thinking of them as talking about death and start thinking of them as talking about legacy.

“What if your annual support could live on forever? By including [Your Nonprofit] in your estate, you could turn your yearly gift into a lasting endowment.”

This is about continuity. It’s about making their values stretch beyond a single lifetime. It’s not about dying – it’s about staying connected to something they believe in.
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And when you position it that way, it doesn’t feel grim. It feels good.

Your donors won’t bring this up on their own unless they’ve already made a decision. Your job is to create the conditions where that decision becomes possible.

And that starts with language – gentle, honest, open-ended questions that let the donor lead, but make it clear that legacy giving is an option you believe in and value.

So don’t be afraid to ask.
​
And when they say yes? Be ready with the next step: a landing page, sample language, a checklist, or a simple conversation about how to make it happen.

📌 Want a quick win? Use these same phrases in:

• Your direct mail acknowledgments
• Thank-you calls to long-time donors
• Conversations with board members and volunteers
• Email or social media content during National Estate Planning Awareness Week

Planned giving isn’t about “the ask.” It’s about the invitation.

When you know how to extend it with confidence and care, the whole conversation shifts – from something to avoid… to one of the most meaningful parts of your work.

​Cheers!

P.S. Like this kind of insight? Subscribe to Real Deal Fundraising and get my best articles, tools, and curated resources every week – including webinars, videos, and free downloads.

If you liked this…

• National Estate Planning Awareness Week
• Cut Through the Clutter
• Planned Giving Leads Don’t Generate Themselves
• How to Talk about Death and Taxes
• Spring Cleaning for Fundraisers: Organizing Planned Giving Documentation

When I worked at the University of South Carolina from 2005 to 2010, I was proud of the cases I built. I wrote compelling scripts and talking points for our phonathon team – clear, detailed, airtight.

I led with numbers, and they were good ones. I talked about the decline in state support, the rising importance of a college degree in the job market, and the long-term economic impact of thriving public universities. I knew the statistics on student loan debt inside and out. I framed the problem clearly and gave donors a chance to be part of the solution.

And it worked. To a point.

​Looking back, those appeals were sharp – but they leaned heavily on logic and numbers. That clicked with some donors. But others? Not so much. Those appeals weren’t wrong. They were just incomplete for the wide range of minds we’re trying to reach.

Fast forward to 2012. I was at The University of Southern Mississippi, learning how to write copy for direct mail. I started ghostwriting letters for different deans, department chairs, and students. At first, I stuck to what I knew: the stats. But it didn’t feel like enough.

I needed a broader emotional range.

So I started interviewing the letter signers, weaving in their voices and their vision – what this place meant to them, not just what they wanted donors to do. That’s when I started seeing the power of storytelling.

When I came to work at Starr King School for the Ministry in 2015, I had to stretch again. The usual notes in higher ed fundraising – nostalgia, school pride, career outcomes – didn’t resonate with a justice-minded, largely layperson donor base. These were Unitarian Universalists who cared deeply about their values and how the school perpetuated those values in the world.

I needed to connect the dots with emotion, shared purpose, and a clear sense of what their giving could do.
​
That meant telling stories that didn’t just inform – they moved people.

Somewhere along the way, I realized this shift wasn’t just about moving from stats to stories. It was about recognizing how different people make decisions.

One person might want the spreadsheet. Another wants the story. A third just wants the ask – clear and bold. And someone else? They want to feel like they’re part of something bigger before they commit to anything at all.

That’s when I remembered a model I’d seen back in 2007, from Mark Murphy at Leadership IQ. It mapped out the four main persuasion styles – and it helped me understand why my old appeals worked for some and left others cold.
​
Here’s the gist:

There are two axes:
• Emotional → Unemotional
• Linear → Freeform

Put those together, and you get four types of decision-makers:

This is where I naturally live. I want the stats. I want the logic. I want the argument that makes sense.

If you're reading this post and wondering, “Where’s the ROI?” – you might be here too.
​
That’s the kind of appeal I built early in my career. And it worked with people like me. But that’s not most donors.

Think of the board member who scans your whole appeal in 14 seconds and writes the check anyway.

They don’t need the backstory. They just want the point. What do you need, what will it do, and how much are you asking?
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Closers are decisive. If you wander, they’re gone. You need to be bold, clear, and fast.

These folks are organized and thoughtful. They care about the story and the structure. Think of the alum who replies with a thoughtful email after every annual report – who joins the volunteer committee and follows up on the agenda.
​
They want a beginning, a middle, and an end. They respond when you connect emotionally but still give them a path to act.

Picture the alum who tears up thinking about the choir trip to Italy in 1983. They’re not interested in bullet points. They’re here for the moment – the meaning.
​
They want to feel something. And if your message is too structured or too clinical, they’ll check out. But if you pull them in with a meaningful quote or a powerful scene, they’ll stay – and they’ll give.

In major gifts, you can tailor every ask. You’re sitting across from one person, learning what moves them, and crafting your pitch accordingly.

But in annual giving? You’re writing to the whole list. That means your appeal has to layer styles – something for each persuasion type.

• Stats and logic for the Data Scientists
• Clear action steps for the Closers
• Warm structure for the Directors
• Emotional storytelling for the Storytellers

Don’t write the appeal that would convince you. Write the one that can meet your donors where they are – all of them.

When you're working on your next appeal, ask yourself:

• Does it have a story?
• Is there data to back it up?
• Is it structured clearly?
• Is there a moment of emotion?
• Is there a clear ask?

​
Fundraising is communication. And great communication connects.

This is one of my favorite things to teach. Reach out – I’ve got frameworks, real-world examples, and plenty of lessons learned the hard way.

Cheers!
​
Jessica

P.S. Like this kind of insight? Subscribe to Real Deal Fundraising and get my best articles, tools, and curated resources every week – including webinars, videos, and free downloads.

If you liked this…

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