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

I want to begin with a statement that may feel simple, but it carries more weight than most boards realize:
​
Fundraising is a noble endeavor.

If you are a nonprofit CEO or Board Chair, your internal reaction to that sentence matters. It shapes how you speak about fundraising. It influences how your board experiences it. It quietly determines whether your culture approaches fundraising with confidence or hesitation.

Belief comes first. Always.

This is where we must be honest with ourselves.

You either believe deeply in your mission, or you don’t.

If you believe your organization changes lives, strengthens families, advances justice, expands education, heals, protects, or restores something that matters, then you already know the work deserves resources. You know it deserves to grow. You know it deserves to be sustained for the long term.

If that belief is strong, you can work through discomfort around money. You can practice the language of invitation. You can sit in a donor meeting and speak clearly about funding needs.

If that belief is shaky, fundraising will always feel heavy. You will delay conversations. You will hedge language. You will hope someone else handles the “hard part.”

If leadership belief wavers, board engagement follows, donor conversations shrink, and revenue eventually reflects that hesitation.
​
Belief is not emotional fluff. It is operational fuel.

Early in my career, I worked in political fundraising. I was taught that fear and guilt were powerful motivators. Create urgency. Highlight threats. Push emotional buttons.

And it worked, at least in the short term.

Later, when I returned to my alma mater, I began raising money for education. Our beloved president emeritus who led the university through decades of growth, Aubrey K. Lucas, met with the new development officers. He shared something that stayed with me.

Negative fundraising is rarely truly successful.

We were raising money for education. Education is a universal good. It is something to be proud of. That effort should not be rooted in pressure or fear. It should be rooted in conviction.

That conversation reframed my entire understanding of fundraising.

If education is good, then raising resources for education is good.

If your mission serves a real human need, then securing funding for that mission is honorable work.

That realization has guided my work ever since.

When board members hesitate, the hesitation is rarely about the mission. It is about money.

Money carries history. It carries stories. It carries personal experiences that shape how we feel when we talk about it. But giving is not really about money.

Giving is about shared vision and shared values.

When a donor gives, they are not simply transferring dollars. They are aligning themselves with a cause they believe matters. They are choosing to participate in change. They are saying, “I see this work, and I want to be part of it.”

Money is simply the mechanism that allows that alignment to take tangible form.

When you internalize this truth, something shifts in your posture. You stop speaking about fundraising as if it is separate from the mission. You recognize that it is the engine that fuels the mission.

And that changes your tone.

Culture does not begin in the development office. It begins in the boardroom.

If you speak about fundraising as an obligation, your board will experience it as a burden.

If you treat fundraising as something uncomfortable that must be endured, your board will mirror that discomfort.

But if you speak about fundraising as mission work, as advocacy, as an opportunity to invite others into meaningful impact, your board will feel that shift.

You do not have to eliminate all discomfort. Most of us were not raised discussing money openly. That hesitation is normal, but how you frame the work matters.

When you believe fundraising is noble, you approach it with clarity. You talk about funding needs without apology. You connect dollars to outcomes without shrinking your language. You model confidence.
​
Boards take their cues from leadership. If you approach fundraising with pride and purpose, your board has permission to do the same.

If your board is reluctant, start here. When was the last time your board discussed fundraising as shared leadership responsibility rather than an agenda item?

Have an honest conversation about why your mission matters. Revisit the lives changed. Revisit the transformation you are pursuing. Revisit the gap between where you are and where you need to be.

Then ask this question: If this work truly matters, why would we hesitate to invite others to fund it?

When that belief becomes shared, fundraising stops feeling transactional. It begins to feel aligned.
​
And alignment is powerful.

If any of this sounds familiar:

• Your board supports the mission but avoids fundraising conversations.
• You feel like you’re carrying development alone.
• Giving is flat and no one wants to address it directly.
• Board members say yes to serving but hesitate to ask.

It’s time to take a serious look at whether your board’s leadership tone and fundraising expectations are truly aligned. If fundraising feels like a source of stress rather than shared responsibility, this is the work that shifts it.

I’m opening three complimentary Board Fundraising Alignment Calls this month. You can reserve a time here.

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. 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…

• 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 Magic Formula for Making a Confident Fundraising Ask
• The 3 Rs of Fundraising Mindset: What It Really Takes to Talk About Money

When I came back to work at my alma mater in 2011, they had just celebrated the Centennial the year before. The mailing they sent out for the 100-year mark was gorgeous – vintage photos, heavy cardstock, elegant fonts. You could see the pride in every detail.

But there was one big problem.

It cost more to send than it brought in.

When I ran the numbers, the cost to raise a dollar on that piece was $1.40. For every dollar it generated, it cost us $1.40 to get it. We weren’t raising money – we were losing it. It was like we were throwing money overboard and missing a once in a century opportunity!

The issue wasn’t just the over-the-top production. The package was confusing. Too many ask amounts, too many gift designations, and other options. Donors didn’t know where to focus. And when a donor doesn’t know what to do, they don’t give.

The next year, we simplified. One letter. Points of pride on the back. Clear ask string. That mailing had a cost to raise a dollar of 43 cents.
​
Same donor base. Better strategy.

Cost to raise a dollar is exactly what it sounds like. It’s a measure of efficiency. You take your total expenses for a campaign or fundraising channel and divide it by the amount raised.

Formula:
Cost to raise a dollar = Total Expenses ÷ Total Dollars Raised

If you spent $10,000 and brought in $25,000, your cost to raise a dollar is $0.40. That means it cost you forty cents to raise one dollar. Good.

If your cost to raise a dollar is over $1, you’ve got a problem – if you’re not executing a donor acquisition strategy where you expect to lose money upfront to gain long-term donors who’ll give again and again for less.
​
But if you’re not acquiring or upgrading donors – and your cost to raise a dollar is that high? You’re hemorrhaging money.

Recently I was teaching a webinar and got asked whether you should track staff time on any particular fundraising effort in the total expenses when calculating cost to raise a dollar. My answer is no.

I’ve never met a fundraiser who’s sitting around wondering what to do next, and I don’t think tracking every minute of your working hours is a good use of that valuable time.

Staff salaries are in your normal budget. Consider them a constant. Don’t tie yourself in knots trying to figure out if you spent 20 hours on the gala last week or 22 hours.

Examples: For a mailing, count printing, postage and processing costs (if using a mailhouse or other paying part-time folks to stuff mailers). For an event, expenses would include catering, décor, invitations (printing, postage, and processing), printings programs, etc.
​
Keep it simple and you’ll be ahead of the game.

Fundraisers talk a lot about leaky buckets – usually in terms of donor retention. But there’s another leak that’s just as costly: spending more to raise a dollar than you get back. That’s what this metric uncovers.

Most fundraisers are trained to focus on total dollars raised or number of donors who give. And yes, those are crucial. But cost to raise a dollar gives you clarity at the tactical level. It shows you where your fundraising machine is humming – and where it’s grinding your budget into dust.

Cost to raise a dollar is especially helpful when:

• You’re evaluating different channels (direct mail vs. email vs. phonathon)
• You're preparing for a budget meetings and need simple, apples-to-apples comparisons
• Leadership is asking to cut costs, and you need to defend what’s working
• You’re trying to argue against flashy design choices or work-intensive events that don’t move the needle

That Centennial piece taught me something I’ve never forgotten: Beautiful isn’t always effective. Impact matters more than gloss.

It also gave me a compelling number to take into conversations. I could walk into meetings and say, “This mailing costs us $1.40 to raise a dollar. Last year’s only cost 43 cents. Which one do you want to fund next year?”
​
I didn’t need to yell. I just needed to know my numbers.

Some channels will have higher cost to raise a dollar – and that’s okay. Phonathons, acquisition campaigns, certain events – they often cost more. But if you’re tracking those donors and seeing strong retention and future giving, that higher initial cost might be justified. But do that deliberately, for strategic reasons.

In higher ed, campaigns like student philanthropy programs or senior class gifts often have an “upside-down” cost to raise a dollar. That’s not a failure – it’s intentional. We spend more than we bring in because we’re focused on something bigger: starting the donor relationship early, before students graduate, move away, and scatter.

While they’re still on campus, their connection to the institution is at its peak. That’s the right time to invite them into giving – not just for dollars today, but for loyalty tomorrow.

Just don’t confuse “tradition” or “looking nice” with effectiveness. Know what each dollar is doing for you. Make that a habit. Teach it to your team.

And please – for the love of fundraising – don’t let your best-looking piece be your worst-performing one.

If you’ve never calculated your cost to raise a dollar, start now. Pull your last three mailings or campaigns. Be honest about all the expenses, minus staff salaries.

Run the numbers. Then start making decisions that build toward efficiency – and impact.

This metric gives you the insight you need to be smart with the resources you’ve been trusted to steward.
​​
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…

• Read Between the Dollars: 3 Gifts to Watch
• From $50 to Six Figures: How I Got Board Members to Care About Annual Giving
• Six Ways to Show Gratitude to Donors in 2026
• Scripts to Bring Up Planned Giving Without Feeling Weird About It
• 4 Power Questions to Ask Donors That Build Rapport and Lead to Major Gifts

Fundraisers love numbers – but we don’t always slow down to read them.

When I look at donor giving histories, I’m not just tallying lifetime value or calculating retention. I’m looking for inflection points. Clues. Moments that tell me a donor is thinking differently about their relationship with the organization.

You can spot those moments – if you know what to look for.

In my last blog post, I revealed my strategy for connecting annual giving to major and planned giving for board members. Through this process of telling the long version of donors’ origin stories, I saw patterns that repeated. I kept seeing similar types of gifts that signaled the donor had deepened in their connection to the organization’s mission.

Once you know them, you’ll be able to spot these in the gift histories of your current major donors. After a while, you’ll be able to see these gifts when they happen and optimize your systems to steward these donors to the next level!

Here are three gift types I always flag in donor bios:

1. The “Kick the Tires” Gift

This is the donor’s very first gift. It’s usually modest – $25, $50, maybe $100. But don’t let the size fool you.

This gift is a test. They’re watching how your organization responds. Do you acknowledge quickly? Do you give thanks personally? Do you make it easy to give again? Do they feel seen?

Most board members don’t realize that your largest donors often start right here. Not with a gala. Not with a campaign. But with a small, quiet gift and a lot of curiosity.

Track this gift like it matters – because it does.

By reframing first time gifts as “kick the tires” gifts, organizations leverage their systems to make sure every new donor has an exceptional experience and feels appreciated.

Ask yourself: Do you have any special communication or benefits that help first-time donors feel recognized? How I can I use email, phone, volunteer/board outreach, and mail to have this donor feel the love and their impact?

2. The “Hand-Raising” Gift

You’ve got a donor who’s given $100 a year for a decade. Then suddenly – boom – a $1,000 check shows up.

That’s not random. That’s intentional.

The exact numbers matter less than the jump. A $25 dollar donor jumps to $500. A $1,000 donor jumps to $5,000.

All of these are donors signaling interest. They’re re-evaluating what your work means to them. And they’re inviting you to respond.

When you see this kind of jump, drop everything and make a call. Not to ask for more – but to listen. What changed? What are they excited about? Who or what inspired the new level of giving?

This is your chance to deepen the relationship before they drift away.

Ask yourself: Do I have a notification system that will let me know when “hand-raising” gifts happens? What’s my process when I learn about them?

3. The “Breakthrough” Gift

Here’s where it gets exciting. You see a donor move into five- or six-figure territory, or they’ve set up a multi-year pledge. Maybe they’ve reached out about leaving a bequest.

This donor is no longer an annual donor – they are in the pipeline.

Yes, these bumps happen with personal visits and cultivation, but sometimes the donor decides to make the leap.

When I see this move, I bring them into a different lane. Personal stewardship. Custom impact reports. Invitations to help shape the vision, not just fund it. Because at this level, they’re not just giving – they’re investing.

This is where cultivation becomes partnership.

Ask yourself: How can I make sure I don’t miss any of these breakthrough gifts? What’s my plan to meet this donor and find out what their philanthropic goals are for the long-term?

In conclusion…

Make sure these three moments show up in your reports. More than data points, these three gift types represent real shifts in mindset. Catching them early and responding with intention is how you build a stronger, smarter pipeline.

Because fundraising isn’t just about chasing dollars. It’s about listening to the story those dollars are trying to tell you.

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…

• From $50 to Six Figures: How I Got Board Members to Care About Annual Giving
• Scripts to Bring Up Planned Giving Without Feeling Weird About It
• 4 Power Questions to Ask Donors That Build Rapport and Lead to Major Gifts
• What is Gracious Receivership and why Fundraisers Need to Practice It
• How to Ask for Donor Lists Without Delays or Drama

I was fortunate in my role at the University of Southern Mississippi. My VP made space for me – literally – on every board agenda. I had a standing spot to update the USM Foundation board on annual giving, and I could use that time however I saw fit.

Sure, I gave them numbers. But I didn’t stop there.

I used that time to give them the narratives beyond the numbers. Histories. I pulled the giving records of donors they already admired – the names they knew from building dedications and big announcements – and traced them back to their beginnings. Because almost all of them started small.

I wanted the board to see what I saw every day: Annual giving isn’t just about this year’s total. It’s about long-term trust. It’s how major donors begin. The large gifts you are getting today started with trust-building 10 or more years ago. And how you are treating your $50 donors today is how you are treating your future major and planned giving donors of tomorrow.
​
This post is about how I helped shift board thinking – from shrugging at $50 gifts to recognizing them as the first step toward six-figure support.

At every board meeting, I brought receipts. Literally.

I’d share two or three donor stories. Not headline gifts. Origin stories. I’d pull the giving history of a well-known benefactor – the kind of donor whose name was etched on a building or whose estate gift had changed our endowment – and I’d start at the very beginning.

Turns out, the beginning wasn’t glamorous. No gala. No VIP treatment. Just a reply card in the mail or a quick online donation. Often $50, sometimes $100. Inspired by a direct mail piece or a phone call from a student caller.

I told the story of how that first gift came in. How we acknowledged it. How we followed up. What kind of communication they received. How they were stewarded over time. And then I showed the leap: four-figure giving. Five. Sometimes more.

By the third or fourth board meeting, it started to click.

Annual giving isn’t just about dollars this year. It’s a pipeline. And more than that – it’s a vetting process. Donors with real capacity don’t show their full hand right away. They start small. They're testing your systems. They’re watching your stewardship. They want to know: Will my gift make an impact here? Can I trust this organization to be a good partner?

And the truth is, annual giving is the only system robust enough to keep that door open over time. It keeps your data clean. It helps you stay in touch when someone changes jobs or cities. It gives you cues about life changes that might signal major or planned giving potential.

It’s not just donor acquisition. It’s donor cultivation in slow motion.

When I layered in real data – about how much of our major gift pipeline had once started with a $25 or $50 gift – something shifted. Board members started asking about the annual giving numbers. They started taking the appeal letters home. A few even gave leadership annual gifts themselves.

The modest gifts didn’t seem so modest anymore.

And that’s the whole point.

If you want major and planned gifts tomorrow, you have to care deeply about annual giving today.
​
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…

• Your Board Wants to Help with Fundraising – They Just Don’t Know How
• Rethinking Board Recruitment: The 4 Ws That Really Matter
• Phonathons Are STILL Not Dead – Busting the Biggest Myths About Calling Donors
• How to Build a Philanthropy Calendar That Drives Digital Donations
• How to Ask for Donor Lists Without Delays or Drama