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

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

If you liked this…

• What Worked for Giving Tuesday 2024
• How to Build a Philanthropy Calendar That Drives Digital Donations
• When the Inbox Is Full, Go to the Mailbox: Why Analog Fundraising Is Making a Comeback
• All About Giving Days (Interview with Jake Strang)
• Don’t Add Another Event Until You Read This

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.
​
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?
​
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…

• Don’t Add Another Event Until You Read This
• Why Most Fundraising Plans Fail (and How to Build One That Doesn’t)
• The Problem with Totes and T-Shirts: Why Freebies Can Undermine Fundraising
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• How to Build a Philanthropy Calendar That Drives Digital Donations

Whenever my grandfather was asked what I did for a living, he’d grin and say, “Oh, she’s a professional beggar – and very good at it.”

He meant it playfully. But that joke pointed to something deeper: how fundraising is often viewed in American culture – and sometimes, how we as fundraisers view ourselves.

This work can feel loaded. Talking about money brings up all kinds of things: values, power, pride, fear of rejection. It’s personal. And when that discomfort goes unchecked, it sneaks into our conversations and undermines our confidence.

But here’s what I’ve learned: Your mindset matters more than your pitch.

How you feel about money shapes how you talk about it. And that directly affects whether you avoid the big asks – or step into them with clarity and purpose.

Over the years, I’ve noticed three mindset shifts that help fundraisers move past the awkwardness and into authentic, effective conversations. I call them the 3 Rs: Reciprocity, Receivership, and Reframing.
​
Let’s walk through them.

One of the most harmful myths in fundraising is the idea that we’re taking something from people. That donors are losing when they say yes.

That’s not what’s happening.

Giving is about alignment. When a donor gives, they’re not being depleted – they’re investing in meaning. They’re making their values visible. They’re stepping into a story that’s bigger than themselves.

That’s not taking. That’s inviting them in.

I’ve watched donors light up – not because of tote bags or nameplates – but because they felt connected. When we approach conversations with the understanding that there’s value on both sides, it changes how we show up.

Try this: When a donor shares why they give, listen closely. Then reflect it back. Say, “It means a lot to me that this work aligns with your values.” That simple moment of recognition reinforces that this is a relationship – not a transaction.

Let me ask you something: when someone picks up the lunch tab, do you fidget? When they compliment your work, do you wave it off or make a joke?

That matters more than you think.

If you struggle to receive in small, everyday moments, it’s going to be tough to stand still and grounded when it’s time to receive something much bigger – like a major gift.

Fundraising isn’t just about facilitating generosity. It’s about receiving it. That means knowing your own worth, your organization’s worth, and the worth of the mission you represent.

You’re not just asking for money. You’re offering someone the chance to invest in something meaningful.
​
Try this: The next time someone compliments you – on your work, your outfit, your presentation – just say, “Thank you.” No hedging. No “Oh, this old thing.” Practicing that kind of presence builds your capacity to receive with grace and confidence.

I’ve worked with some truly talented fundraisers – smart, strategic, big-picture thinkers – who freeze at the edge of the ask. I’ve done it myself from time to time.

The relationship is there. The timing is right. The groundwork has been laid. But when it’s time to actually say the number... they stall out.

There’s an old joke in our field about someone like that:
“How is <<that fundraiser>> like a 7/11 store?”
“They never close.”

Funny – but also kind of painful. Because many of us have been that person. I know I have.

We hesitate because we don’t want to feel pushy. We worry we’ll mess up the relationship. But here’s the truth: donors – especially high-net-worth donors – know what we do. They expect us to ask.

And when we don’t? It doesn’t protect the relationship. It creates confusion. When trust has been built, the ask isn’t a surprise. It’s the next logical step.

​Try this: Start using this phrase in conversations: “I’d love to talk with you about a way to deepen your impact.” It’s warm. It’s clear. And it helps you move into the ask without making it weird.

So, what does this mean for you?

If you want to grow as a fundraiser, start by checking your mindset.

• Do you believe there’s value on both sides of the conversation?
• Are you willing to receive, not just facilitate?
• Can you honor the relationship by being direct about the opportunity?

Fundraising isn’t begging. And it’s not manipulation.

It’s invitation. It’s partnership. It’s a shared pursuit of something that matters.

My grandfather may have called me a “professional beggar” – but he wasn’t wrong about the skill it takes to do this work well. He just didn’t know the half of it.

Get your 3 Rs in alignment, and you’ll stop feeling like you’re asking for a favor – and start showing up like the professional you already are.

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…

• 4 Power Questions to Ask Donors That Build Rapport and Lead to Major Gifts
• Why Most Fundraising Plans Fail (and How to Build One That Doesn’t)
• The Magic Formula for Making a Confident Fundraising Ask
• Microwave Fundraising vs. Crockpot Fundraising: Why the Slow Simmer Wins Every Time
• “Wait, Am I Supposed to Fundraise Now Too?” A Department Chair’s Guide to Getting Started

Let’s talk about a moment that strikes fear into the hearts of even the most seasoned fundraisers: the ask itself.

Not the stewardship. Not the cultivation. Not the coffee chat or the tour.

The moment when it’s time to name a number and ask a question.

I’ve trained hundreds of folks, from student callers to major gift officers and presidents, and this is where so many otherwise capable fundraisers freeze. They hedge. They mumble. They talk around the gift instead of actually asking for it.

That hesitation is what sinks so many proposals—because if you don’t ask clearly, the donor doesn’t know how to answer. Or worse, they walk away unclear on what you needed from them at all.

The good news? Asking well isn’t about being fearless or charismatic.

It’s about structure. It’s about using a reliable, repeatable framework that gives you confidence and helps the donor have clarity.

​Here’s what I call my Magic Formula for Making the Ask—and it works whether you’re asking for $100 or $1,000,000.

Questioning Opener + Mission Moment + Dollar Amount + Silence
​
Let’s break each part down so you can feel grounded the next time you find yourself sitting across from a donor (or dialing the phone or typing an email, for that matter).

This is one of the biggest giveaways that a fundraiser isn’t comfortable asking: they frame their “ask” as a statement instead of a question.

❌ “We’d love it if you’d help out with a gift this year.”
❌ “It would be wonderful if you supported us again.”
❌ “We’re hoping you’ll get involved this year.”

None of these are technically wrong, but they leave the donor hanging. They don’t invite a response. And they definitely don’t feel like the moment of decision that a real ask should be.

Compare that to:

✅ “Would you be willing to make a gift of $5,000 to support undergraduate research?”
✅ “Can we count on you for support at the $25,000 level this year?”
✅ “Will you help our students with a $1,000 gift to the Dean’s Fund?”

These are direct. Respectful. And clear.
​
By ending your ask with a question, you’re signaling that it’s now the donor’s turn to speak. That subtle shift sets up a healthy, balanced fundraising conversation.

This is where you tie the ask to purpose. Don’t just ask for money—anchor the ask in something that matters.

This is what moves the donor from “How much?” to “What for?”

Instead of:
❌ “Would you consider a gift this year?”
Try:
✅ “To help provide book scholarships for every student in the program, would you make a gift of $10,000?”

Instead of:
❌ “We’d love your support.”
Try:
✅ “To allow faculty to attend national research conferences this year, would you be willing to give $2,500?”

You are the bridge between the mission and the donor’s capacity to make something good happen. That’s your role. You’re not begging. You’re inviting them into something meaningful—with clarity.

And don’t shy away from being specific.

A donor can always say no to a number. That’s okay. But if you ask, “Would you consider helping us out?” and they say “No,” you’ve left yourself no room to move.
 
When you name a number, you create the chance for a real conversation. They might say, “That’s higher than I was thinking,” and now you can respond: “What would feel more comfortable for you?” or “Would you like to stretch that over a multi-year pledge?”

​Specificity unlocks possibilities. Vagueness shuts them down.

This is the part that makes or breaks it.

Once you’ve made the ask—STOP TALKING.

I know. It’s awkward. It feels like an eternity. But it’s crucial.

The silence after the ask gives your donor time to process. It allows them to think. It gives them space to share what’s really on their mind.

And what you learn in that silence? That’s gold.

Maybe the timing’s off: “I just paid my kid’s tuition bill.”

Maybe they need buy-in: “I’d have to talk it over with my spouse.”

Maybe they’re passionate—but about something else: “I’d rather support the scholarships instead of the building fund.”

If you rush in to fill the silence, you will miss all of that.

You’ll speak from your own nervousness instead of their reality—and you’ll never know what part of the ask didn’t work for them.

Practice the pause. Get comfortable sitting in it. It’s where the most honest parts of the conversation live.

Bringing It All Together:

Here’s a strong ask, built using the Magic Formula:

“To help us provide every student in our department with book scholarships, would you be willing to make a pledge of $25,000—$5,000 a year for five years?”

[PAUSE]

If they say yes—celebrate and affirm it. Then let them know next steps to document and facilitate the gift payment.

If they say no—that’s your cue to start the conversation. “Would it help to spread the gift out?” or “Is there a specific area you’d like to support instead?”

​But don’t jump ahead. Let them answer first.

I’ve got a whole system for deciding how much to ask for—based on donor history, capacity, engagement, and more.

If you'd like me to write about that next, leave a comment or shoot me a message. I'm happy to dig into that in a future post.

​Cheers!

​PS - I hope you’ll continue the conversation by subscribing to Real Deal Fundraising. When you subscribe, you’ll get my e-newsletter, which includes the best articles on fundraising, productivity, and cool stuff every week. The whole thing is curated awesomeness as well as freebies like webinars, instructional videos, and whatever else I can put together to be helpful to you!

If you liked this… 

• Why Most Fundraising Plans Fail
• 4 Powerful Discovery Questions
• Discovery Visits Demystified
• What to Say to Donors in Uncertain Times
• Questioning our Fundraising Axioms

Let’s be honest: a lot of “fundraising plans” aren’t really plans.

They’re a collection of ideas scribbled in the margins of a notebook. A to-do list that gets buried under meeting notes. Or a spreadsheet no one has opened since last fiscal year.

And when things feel uncertain or urgent, even the most well-intentioned plan gets abandoned.
​
So why do most fundraising plans fail? After 20+ years of working in and coaching nonprofit teams, here’s what I’ve seen over and over again:

Too many plans are built for imaginary versions of our organizations. You know the ones: the org with unlimited time, a full development team, and a budget for days. In real life, you’ve got a stretched-thin staff, a volunteer board, and one printer that jams every third sheet.

The best fundraising plans start where you are. They work with your current capacity – not against it. They help you make choices, not just lists.

Staff turnover is one of the biggest challenges that can set you back in fundraising and burnout is often the cause. If you build your plan around the staff you have and use technology to leverage that plan, you can mitigate burnout and turnover.

If your plan doesn’t tell you how much money you can expect to raise – and from which methods – it’s not a plan. It’s a wish list.

A strong fundraising plan includes projections based on past data, average gift sizes, and realistic conversion rates. This lets you set expectations, allocate resources wisely, and make the case for investments when needed. I did an entire blog post showing you how to build those projections so you know what you are able to raise, not just what you wish you would raise.

No more spaghetti-on-the-wall fundraising. Just clear goals with measurable outcomes.

​Even when a plan exists, it often fails at the handoff: no one knows who’s doing what – or worse, everyone thinks someone else is handling it.

That’s why the final step of a good plan is assigning each task to a specific person. And then assigning a backup person to be cross-trained. This keeps your plan running when life happens – vacations, sick days, job changes – and builds resilience into your team. That’s why I wrote about building a responsibility calendar to protect your plan and ensure it becomes real.

No more scrambling. Everyone knows their role, and the show goes on.

It’s clear. It’s doable. And it starts with what I call the MVPPP Framework, which is part of my Smart Start Fundraising System course:

• Message – Your compelling case for support
• Vehicles – The channels you’ll use to reach donors
• Prospects – Who you’re asking
• Partners – Who’s helping you ask
• Plan – Bringing it all together with structure and accountability

This framework works whether you’re a one-person shop or leading a full advancement team. It’s not about doing everything. It’s about doing the right things on purpose.

My new course, The Smart Start Fundraising System, is officially here! It’s designed for nonprofit leaders who are tired of spinning their wheels and ready to raise more  –  strategically, confidently, and without burnout.

🎯 Inside, you'll learn how to craft a compelling message, choose the right methods, identify and engage donors, mobilize your board, and build a plan you can actually execute  –  all using my proven MVPPP framework.

✅ 5 Pre-approved CFRE credit hours available
✅ Four high-impact bonus trainings included
✅ A 21 page workbook plus tools, templates, and spreadsheets you can plug and play
💻 Enrollment is open now! Price is $549

Take a look, see what’s inside, and get started at your own pace:
👉 Take a closer look here.
Because passion doesn’t build a fundraising plan. But clarity? That’ll take you the distance.
​
Cheers!

​PS - I hope you’ll continue the conversation by subscribing to Real Deal Fundraising. When you subscribe, you’ll get my e-newsletter, which includes the best articles on fundraising, productivity, and cool stuff every week. The whole thing is curated awesomeness as well as freebies like webinars, instructional videos, and whatever else I can put together to be helpful to you!

I learned the power of recurring gifts when I ran a faculty/staff giving campaign. I saw how quickly even $5 payroll deductions added up across the year when dozens upon dozens of donor participated. When I arrived at a much smaller institution that really needed unrestricted gifts, I knew they needed a strong monthly giving program that would help us reach our annual goals.
​
Recurring giving is a powerful strategy that can transform your nonprofit’s fundraising model. A successful recurring gift program provides steady, unrestricted income and builds a loyal donor base that supports your mission long-term. Here’s how to build a thriving recurring gift program from scratch.

A recurring gift program allows donors to give smaller, automated contributions on a monthly basis, typically via credit/debit card or bank draft. These "set it and forget it" donations make giving simple and budget-friendly for donors, while providing nonprofits with reliable revenue.

Why You Should Launch a Recurring Gift Program:

• Cost-Effective: Solicited only once, recurring gifts reduce acquisition costs.
• Predictable Revenue: Monthly gifts offer a consistent income stream.
• Higher Lifetime Value: Studies show that recurring donors give more over time compared to one-time or annual donors.
• Increased Donor Loyalty: The regular engagement helps deepen the relationship with your organization.

​
Why Donors Love Monthly Giving
Monthly giving resonates with donors for several key reasons:

• Convenience: Automated payments make it easy to maintain their support without additional steps.
• Budget-Friendly: Smaller, regular donations are easier to fit into monthly budgets.
• Eco-Friendly: Recurring gifts reduce paper usage and reliance on direct mail, aligning with donor values around sustainability.
• Impactful: Donors feel a deeper connection, knowing their consistent support enables ongoing projects and growth.

Here’s a step-by-step approach to creating a sustainable recurring gift program that will drive long-term success.

Choose a donation platform that securely stores donor payment information and processes automated monthly contributions. Key features to consider include:

• Mobile Optimization: Ensure the sign-up process is seamless on all devices.
• Security: Look for Payment Card Industry (PCI) compliance and encrypted data storage.
• User-Friendly Maintenance System: Make sure the system is easy for staff to manage, update, and integrate with your CRM.

Pro Tip: The ability to automate receipts and acknowledgments in your software will save staff time and maintain a consistent donor experience.

Engage your team and leadership early. Present a clear case for why a recurring gift program is a strategic priority using data and examples:

• Highlight the benefits of consistent revenue and lower acquisition costs.
• Address any concerns about additional workload or technology investment.

Share a short executive summary and draft donation page copy with key stakeholders to secure buy-in and streamline implementation.

Develop a unique brand identity for your recurring giving group to create a sense of community. Consider naming the group and designing a logo (e.g., "The [Organization] Sustainers"). This branding helps build a strong identity and a feeling of belonging among donors.
Examples:

• Charity: Water’s "The Spring" 
• The Adventure Project’s "The Collective" 
• Starr King School for the Ministry’s "The Starr King Sustainers"

Begin by reaching out personally to a select group of 25-50 loyal donors, volunteers, or board members. These individuals are likely to be early adopters and provide valuable feedback for refining your program.
Action Steps:

• Make personalized calls or set up Zoom meetings to introduce the program.
• Explain the benefits of becoming a founding member and gather testimonials from these early donors.

Once you’ve piloted your program, it’s time for a full launch. Use a multi-channel approach to reach your audience:

• Email: Highlight the ease and impact of monthly giving.
• Social Media: Share testimonials and visual stories of impact.
• Direct Mail: Include a simple option to sign up for monthly giving on reply cards.
• Phone Campaigns: Engage donors directly and answer any questions they have.

Keep the momentum going by regularly reporting progress. Consider using a thermometer graphic to illustrate growth in monthly donors and total contributions.

While your main goal is sustainable support, offering small perks can enhance donor loyalty without significantly increasing costs:

• Access to an exclusive Facebook group or early event registration.
• An annual Zoom Q&A with your CEO or program director.
• Personalized thank-you notes or recognition on your website.

These gestures help make donors feel special and connected to your mission.

Ongoing maintenance is key to the success of your program. Be proactive about updating expired credit cards and follow up with donors whose payments fail. In January, send timely letters for tax purposes covering all of the gifts the donor made in the previous tax year. I’ve always liked to send monthly donors a sticker and/or car decal for every year they are in the program. 
Upgrade Strategy:

• Every 12-24 months, ask existing donors if they’d consider increasing their monthly gift. Even a small increase can have a big impact over time.

Persistence is crucial when building a recurring gift program. Plan an annual campaign to recruit new donors and replace any who have lapsed.
​
Case Study: When we started "The Starr King Sustainers" program in 2016, we had just 11 donors giving under $1,000 monthly. By 2024, we grew to over 110 monthly donors contributing nearly $6,000 each month, providing a stable base of support for our mission.

​Building a successful recurring gift program takes time and effort, but the payoff is substantial. With a thoughtful approach and consistent stewardship, you’ll create a loyal base of donors who are passionate about supporting your mission month after month.