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

3/1/2026

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

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

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

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

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

And it is absolutely essential.

But here is the truth that surprises nearly everyone:

Asking is only 5% of the donor cycle.

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

The Donor Cycle, in Plain Terms

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

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

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

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

Cultivation is where trust is built.

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

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

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

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

Asking? Five percent.

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

Relationship First. Always.

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

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

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

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

Reframing the Fear

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

That is not how healthy fundraising works.

Healthy fundraising looks like:
  • Listening carefully
  • Sharing stories of impact
  • Connecting mission to values
  • Expressing gratitude
  • Deepening trust

Then, at the right moment, calling the question.

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

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

What This Means for Nonprofit CEOs and Board Chairs

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

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

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

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

The ask stops feeling like a cliff.

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

Ready to Reduce Board Anxiety Around Asking?

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!
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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.
SUBSCRIBE
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
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Fundraising Is a Noble Endeavor

2/15/2026

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Fundraising Is a Noble Endeavor

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

You Either Believe in the Mission or You Don’t

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.
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Belief is not emotional fluff. It is operational fuel.

What Shifted My Thinking

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.

Giving Is Not About Money

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.

Leadership Tone Shapes Board Culture

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.
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Boards take their cues from leadership. If you approach fundraising with pride and purpose, your board has permission to do the same.

The Cultural Reset

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.
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And alignment is powerful.

Ready to Strengthen Your Board’s Fundraising Culture?

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.
Reserve Your Board Fundraising Alignment Call
Fundraising is not separate from your mission. Fundraising fuels your mission.

And when you truly believe that, you become a stronger advocate, a clearer leader, and a far more confident fundraiser.

Cheers!
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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.
SUBSCRIBE
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
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Wear the Suit: Presence starts in your mind, not your closet.

8/22/2025

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Wear the Suit: Presence starts in your mind, not your closet.

 Back in 2007, I was prepping for a presentation to my peers – young professionals like me, running fundraising call centers across the country. We were mostly in our 20s, ambitious, a little scrappy, and working in a company culture that leaned casual.

I was thinking about wearing a skirt suit. It felt like the right thing for the moment. But I was second-guessing it hard.

What if they thought I was stuck up? Or trying too hard? Or trying to be something I wasn’t?

I asked my husband what he thought.

He said, “Wear the suit.”

I explained the whole situation again, sure he didn’t get it.

He said again, “Wear. The. Suit.”

By the third time, I was exasperated.

That’s when he clarified: “If you’re going to wear the suit, wear the suit... Stand in it. Own it. Don’t apologize for it. You’re stepping into the authority you already have – but you’ve got to embody it. If you do that, what anyone else thinks won’t matter.”

That moment stuck.

​Because it was never about the suit. It was about how I carried myself in the suit.

You can’t control how other people read you. But you can decide how you show up.

You can choose to walk into the room with the posture, presence, and clarity of someone who belongs there. You can lead – even when you're still growing.

So whatever your “suit” is – your outfit, your opening line, your tone – don’t just put it on.

Wear it.

Let’s bring it into your world:
What’s your version of “the suit”? That thing that helps you stand taller and lead stronger when it counts?

Drop it in the comments – I’d love to hear what helps you show up with presence.

Cheers!

​Jessica
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P.S. Like this kind of insight? Subscribe to Real Deal Fundraising and get my best articles, tools, and curated resources every week – including webinars, videos, and free downloads.
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Why Commission-Based Fundraising Is a Red Flag (and What New Nonprofits Should Do Instead)

8/10/2025

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Why Commission-Based Fundraising Is a Red Flag (and What New Nonprofits Should Do Instead)

Starting a nonprofit can feel like launching a rocket with duct tape and a dream. You’ve got passion, vision, and maybe a few donors – but not nearly enough resources. So when someone offers to help with fundraising in exchange for a cut of the money raised, it might feel like a godsend.

It’s not.

(Sorry, I didn’t do that justice. Let me try again.)

IT’S NOTTTTTT!!!!

Commission-based fundraising is one of the first ethical missteps many new nonprofits make – and not because they’re careless. It’s because they don’t know any better. Meanwhile, there are companies that do know better – and they prey on organizations still trying to find their footing.
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Let’s talk about why commission-based fundraising is a problem, the myths that keep it going, and what to do instead.

What’s the Big Deal About Commission-Based Pay?

Commission-based pay structures – where fundraisers receive a percentage of what they raise – are widely considered unethical in the nonprofit sector.

Not because it’s illegal. It’s not. The IRS doesn’t prohibit it. But that’s not the bar you want to be setting for your organization.

Professional groups like the Association of Fundraising Professionals (AFP) have long held that this practice crosses ethical lines. Here’s why:
  • It creates a conflict of interest. Tying compensation to gift size can push fundraisers to pressure donors or overpromise – damaging trust along the way.
  • It hurts donor relationships. If a donor thinks your gift officer’s paycheck depends on their generosity, that can leave a bad taste and end future giving.
  • It turns fundraising into a transaction. This work is about partnership, not procurement. Your mission isn’t for sale.

This Is Happening More Than You Think

I see this come up all the time in social media groups for nonprofit founders. At least once a month, someone will ask, “Is commission-based fundraising okay?” They’re just trying to figure out how to move forward with no staff and limited funds.

And every time, like clockwork, commission-based fundraising companies show up in the comments to say, “It’s totally fine!” and there I am, in the replies, trying to explain why it’s not fine.
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I’m not trying to be the fun police. I’ve just seen how this plays out – and it’s never pretty. New nonprofits deserve better than shortcuts that backfire.

Myths That Keep Commission Models Alive

Let’s tackle some of the most common counterpoints I hear – because these arguments pop up over and over again:

💬 “Isn’t salary technically paid from money raised? So what’s the difference?”
Yes, most nonprofit salaries come from donated funds. The difference is in structure. A salary pays for a fundraiser’s time, experience, and judgment. It’s not tied to the outcome of a specific gift. That distinction matters – because it keeps the motivation focused on relationships, not revenue.

💬 “There’s no law against it, so it must be fine.”
Ethics and legality aren’t the same thing. Just because something’s allowed doesn’t make it wise – or aligned with best practices. Commission-based fundraising can hurt your credibility with savvy donors who know the difference.
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💬 “We can’t afford a salary. Commission is all we can offer.”
This is the one that really pulls at the heart. I get it. But commission isn’t your only option. If you don’t have funds to hire someone, try this instead:
  • Lean on your board. A strong fundraising board isn’t just for show. These folks should give and help you find new supporters.
  • Recruit mission-aligned volunteers. People who believe in your work and have strong networks can be powerful early advocates.
  • Learn the craft yourself. Fundraising is about building trust. You don’t need to know everything today – you just need to start showing up.

The Trouble with Outsourcing Fundraising Entirely

Outsourcing might sound like a great fix, especially when you’re wearing every hat. And there are reputable consultants who can teach and guide. But outsourcing your entire fundraising operation – especially donor relationships – is risky business.

Here’s what you give up when you hand it all off:
  • Authentic connection. Donors give to people, not platforms. If someone else is forming the relationship, they’re the one who earns the trust.
  • Control of your message. You need to know what your donors are hearing and how they’re being treated.
  • Your own learning curve. Early fundraising is messy. But that mess teaches you what works – and what doesn’t. You don’t want to miss those lessons.
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Fundraising isn’t something to delegate away. It’s a core part of your leadership role.

So What Should You Do Instead?

If you’re building a nonprofit from scratch, start here:

✅ Build a fundraising board.
Don’t settle for warm bodies. Find people who will give, ask, and connect you with others who care.

✅ Invest your time in relationships.
Whether someone gives $10 or $10,000, treat them like a partner in your mission. Show up. Say thank you. Follow up. Every relationship counts.

✅ Start small and grow with purpose.
You don’t need a six-figure campaign to begin. Start where you are, stay consistent, and build momentum step by step.
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✅ Find a mentor – not a miracle.
Look for people who will teach you, not sell you. A good advisor will build your capacity – not just close deals.

Final Thoughts

Commission-based fundraising isn’t just an ethics issue – it’s a growth issue. It can derail donor trust, distract you from mission work, and create headaches you don’t need.

Starting a nonprofit is brave work. And it takes guts to say no to the fast and easy path when you’re feeling the pressure to raise money quickly.

But there is a way to fundraise with integrity. It starts with doing the work yourself, building trust one conversation at a time, and keeping your eyes on the long game.

You don’t have to build your mission alone.

But you do have to build it right.

And you will.
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Cheers!
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P.S. Like this kind of insight?
Subscribe to Real Deal Fundraising and get my best articles, tools, and curated resources every week – including webinars, videos, and free downloads.
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Rethinking Board Recruitment: The 4 Ws That Really Matter

7/20/2025

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Rethinking Board Recruitment: The 4 Ws That Really Matter

When I ask a nonprofit leader what they’re looking for in a new board member, I often hear one of three things:
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“We need someone with deep pockets.”
“We need someone who knows people.”
“We just need someone who will actually show up and help.”

That’s where the old 3 Ws model comes from: Wealth, Window Dressing, and Worker Bee.

(Quick note: I didn’t come up with those labels – and they’re not meant to be demeaning. These short-hand categories have been floating around the nonprofit world for decades because they’re easy to remember and speak to the roles board members often play.)

But that “Worker Bee” bucket? It was doing too much. There’s a big difference between someone who’s eager to help and someone who brings a specific, strategic skill set that your organization really needs.
So I’ve updated the model. Here’s what I use now:

The 4 Ws of Board Value

1. Wealth
Financial capacity and willingness to give meaningfully. These board members lead with their giving and help bring others to the table.

2. Window Dressing
These members come with name recognition, public credibility, or powerful networks. And let’s be clear: this isn’t fluff. Think of actual window dressing – it draws people in. Visibility, reputation, and access to new audiences can absolutely drive momentum, when paired with authentic engagement.

3. Willing Hands
These are the doers. They show up, roll up their sleeves, make thank-you calls, stuff envelopes, and volunteer at events. Their time and energy are often the engine behind day-to-day progress.

4. Wisdom
These folks bring specific expertise – finance, legal, marketing, investments, HR, governance, DEI. They help your organization make informed, strategic decisions.

A Visual Way to Think About It

​You can picture this concept as a four-part Venn diagram – each W intersecting with the others. The center is where your dream board prospects live: those rare folks who bring all four.
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Note: This image is a helpful visual, but not mathematically perfect. Some combinations (like Wealth + Wisdom) don’t appear distinctly due to the limitations of 4-part diagrams.

A Practical Way to Use It

In real-world board recruitment, it can help to ditch the diagram and move to a simple grid.

A spreadsheet like the one below makes it easier to evaluate prospective members based on the categories they fulfill – and shows where you’re strong or where you need to recruit intentionally.
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Each person is evaluated on whether they bring one, two, three, or all four of the Ws. Then you can sort, filter, and prioritize your outreach.
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The Real Goal

Build a board full of people who bring at least two of these categories – and who align with your mission and values. Look for overlaps. The magic is in the mix.

And don’t leave this work to the board alone.

Your fundraising staff and executive leadership need to be working hand-in-hand with the nominating committee – from the very beginning. They know the needs, they understand the gaps, and they’ll be the ones partnering with these new board members down the road.

When you use the 4 Ws to guide your recruitment, you’re not just filling seats. You’re building something durable, strategic, and deeply aligned with your mission.

P.S. Want to take the first step?
Grab my free Board Fundraising Menu –  a customizable and printable tool that helps your board members choose where and how they can plug into fundraising. It’s clear, easy, and surprisingly motivating.
DOWNLOAD THE FREE MENU
Cheers!
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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!
SUBSCRIBE
If you liked this…
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Microwave Fundraising vs. Crockpot Fundraising: Why the Slow Simmer Wins Every Time

7/13/2025

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Microwave Fundraising vs. Crockpot Fundraising: Why the Slow Simmer Wins Every Time

A few years back, I worked with a team that was stuck in microwave fundraising mode. If there was a quick-cash tactic out there, they were doing it: golf tournaments, raffles, sponsorship deals heavy on the benefits, you name it. It kept the lights on, but it wasn’t building anything lasting. I gave a presentation about crockpot fundraising – relationship-building, long-term strategy, donor engagement – and it started to click. I wanted to challenge them to try something new and to move out of their "microwave" comfort zone. I promised them that if they could do that, it would pay dividends down the line and make fundraising easier and more enjoyable.

I've been in rooms full of nonprofit leaders who are scrambling to make payroll, stressed over budget gaps, or just plain overwhelmed by the pressure to "do more with less." And in those moments, it's tempting to reach for the quick fix – a car wash, a 5K, a golf tournament, a donut sale, a last-minute sponsorship deal. These microwave fundraising tactics can bring in a little fast cash, and I won't pretend they never have a place. But let's be honest: they're not going to carry your mission for the long haul.

Microwave fundraising is all about urgency. It's transactional. It gets warm fast, but it cools off just as quickly. These events are often labor-intensive, draining your staff and volunteers. The ROI is usually modest. They’re familiar, easy to organize, and feel reliable. But they’re not always the healthiest choice for your organization. They only feed a few folks, and they don’t build connection to your mission or long-term sustainability.
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Here's a side-by-side breakdown that captures the heart of the metaphor:
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Caption: Microwave vs. Crockpot Fundraising: A visual comparison of quick, transactional tactics vs. slow, relationship-centered strategies.

Then there's crockpot fundraising. It takes longer to get cooking, no doubt. And yes, there’s a learning curve. But it’s healthier for your mission in the long run. These strategies usually involve more “vegetables” – meaning thoughtful, nourishing activities like donor conversations, stewardship touches, and consistent storytelling. It takes time. You can’t flip a switch and expect results tomorrow. But when you commit to it – when you really let it simmer – the flavor builds. The connections deepen. The nourishment multiplies.

Crockpot fundraising feeds a crowd. You’re not just generating one-time gifts – you’re building community. It’s transformational. It deepens loyalty. It keeps donors connected to the mission. It gives your work staying power.

It means investing in consistent donor communications, one-on-one conversations, thank-you calls, stewardship, and strategic asks. First-time donors become recurring givers. Recurring givers become advocates. Advocates become legacy donors.

Is it slower? Yes. But it is sustainable. It doesn’t burn you out or box your organization into lopsided agreements just to chase a check. It feeds your mission in a way that microwave tactics never will. It keeps your team grounded and your donors inspired.

So when you're weighing your next move, ask yourself: Are we microwaving or crockpotting this? One will keep you hustling for scraps. The other will feed your mission for years to come.

Let it simmer. You'll be glad you did.
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Cheers!
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​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!
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Take Your PTO: Why I’m Logging Off – and Why You Might Need To, Too

7/6/2025

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Take Your PTO: Why I’m Logging Off – and Why You Might Need To, Too

In a few days, I’m heading out of the country with my family. No laptop. No inbox. No quick peeks at work in the evenings. Just real, present time with the people I love most. (Peep the picture above of my kids in their first Uber ride last week.) 😊

We recently had one of those “now or never” conversations. Our kids are growing up fast, and we realized that if we didn’t start making international travel part of our family story, we might miss the chance. I want them to see the world – to experience other ways of being, other values, other rhythms of life. I want them to be citizens of the world, not just the United States.

So we’re going. And I’m letting myself go all in.

Here’s the truth: I’m not stepping away from work despite being a fundraiser. I’m doing it because I am.
Fundraising is heart work. It’s personal, demanding, often overwhelming. That passion can make rest feel like a luxury – something we have to earn or squeeze in around the edges. That shows up across the sector: data from January 2025 show that nonprofit workers leave more unused PTO than all industries except government.

But rest isn’t a luxury. It’s part of the job.

I’ve shared before why self-care for nonprofit fundraisers matters – and not just for bubble baths, but for building real boundaries and intention. I’ve also explored burnout in our profession and how it quietly silences the best of us.

Taking breaks gives us perspective. It reconnects us with our “why.” It lets us return creative, grounded, and ready. When leaders model this, they build a culture that values people – not just productivity.

If you’ve delayed that vacation or pushed through burnout thinking your mission can’t wait: the work will be here when you get back. And you’ll be better for having stepped away.

I’ll be off until mid-July. I hope you find your own window to rest, recharge, and remember who you are outside the job.

You deserve it. And the people you serve deserve the best version of you – not someone running on fumes.

Cheers!
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P.S. Don’t worry – while I’m away, I’ve scheduled fresh content to post on my TikTok, LinkedIn, Instagram, YouTube, and Bluesky. So if you need encouragement or inspiration, it’ll be waiting for you.

PPS - 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!
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If you liked this…
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Your Board Wants to Help with Fundraising – They Just Don’t Know How

6/22/2025

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Your Board Wants to Help with Fundraising – They Just Don’t Know How

Let’s bust a myth right now: “Our board won’t help with fundraising.”
That’s almost never the full truth.
Most board members want to help. They believe in your mission. They want your organization to succeed. What they don’t have is clarity or support.
They don’t know what to do, where to start, or how to help in a way that feels comfortable and meaningful.
​In other words: this is usually a training problem, not a motivation problem.

If you want board members to engage with fundraising, you have to give them a roadmap.

That’s why I created a “Board Fundraising Menu” – an easy, low-pressure way to show board members that fundraising is more than just asking for money. (Full transparency: this is an idea inspired by Andy Robinson, who has great books about how to train your board to raise money.) It’s about helping create the conditions where giving is more likely.

I used this with a higher education Board of Trustees and told them it was an “All You Can Eat” menu but they had to pick at least one from each category: Appetizers, Entrees, and Desserts. I walked them through filling it out in the meeting and left with a list of folks who could write notes, open doors, make calls, and host events!

​Here are 3 specific actions your board members could take today:

Appetizer: Sign and personalize donor letterS

If picking up the phone makes them queasy, that’s fine. Start here.

A short handwritten note or a personally signed appeal letter makes a huge difference – and helps board members feel included without the pressure of a direct ask.

Entrée: Host a house party or donor touR

This one’s for your connectors.
​
Board members don’t have to ask for money – they just need to open the door. Hosting a gathering where staff shares impact stories or tours a program site is a powerful way to build trust and widen your prospect funnel.

Dessert: Make thank-you calls to donorS

No one is ever mad about a thank-you call.
​
And hearing directly from a board member? That’s memorable. It boosts donor retention (especially for first time donors) and builds board confidence in your development process.

But here’s the truth: board members need support.

Okay, okay – you’re busy. I know. You’re running events, managing emails, answering the auditor’s questions, and cleaning up after the copier jammed again.

But they’re busy too. They’re volunteers. They have full-time jobs, families, responsibilities – and most of them have never done this before. Anyone would feel unsure operating outside their expertise.

So when a board member says, “I’ll introduce you to my friend,” the best thing you can do is write a draft email for them to send.

Not because they can’t write one, but because it saves them time and anxiety. It gives them something to react to. They can edit it to sound like themselves – but only they can send it.

If they offer to make calls, set them up for success with a guide that explains the data set, answers frequently asked questions, and provides scripts and samples. And don’t forget to give them a seamless way to get all that feedback to you so it can be recorded in your database too!

Your role? Be their concierge. Their guide. Their teacher.
​

When you hold their hand through these steps, you're not just getting results today – you’re building better, more confident board members for the future.

The secret? Board members are your partners.

If this kind of clarity and confidence sounds like something your board needs, I’ve built something for you. Tired of chasing your board or getting ghosted after a meeting? Inside the Smart Start Fundraising System, you’ll get a plug-and-play plan to turn passive board members into proactive partners.
​
Because fundraising isn’t a solo sport. It’s a team effort. And your board? They're not just fiduciaries – they’re your fundraising partners. But they need the tools, training, and support to step into that role effectively.

Want the full board engagement menu?

It’s included in the Smart Start Fundraising System – along with a plan to actually activate it.

💡 You’ll learn how to:
  • Train your board without making them panic
  • Assign roles that align with their personalities and strengths
  • Make board fundraising support sustainable, not sporadic

🎯 Enrollment is open now.
Click below to get started and download the full board fundraising menu inside:

👉 [Click here to enroll now]

Because “they won’t help” can become “they’re amazing ambassadors” – with the right structure in place.

Cheers!
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Why Most Fundraising Plans Fail (and How to Build One That Doesn’t)

6/1/2025

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Why Most Fundraising Plans Fail (and How to Build One That Doesn’t)

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:

1. The plan is not aligned with real capacity.

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.

2. The plan is disconnected from results.

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.

3. The plan doesn’t assign real accountability (Or backup).

​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.

So what does a successful fundraising plan look like?

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.

Want to build your best fundraising plan yet?

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!
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​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!
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Nonprofit Branding: How to Make Your Mission Memorable

3/9/2025

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Nonprofit Branding: How to Make Your Mission Memorable​

When it comes to nonprofit fundraising, one thing is clear: Your mission is the heart of your organization. But while your cause drives everything you do, a strong, memorable brand is what helps you stand out and attract the major gifts that will take your work to the next level.

Whether you’re at a large, established institution or running a smaller startup nonprofit, your brand should reflect who you are, what you stand for, and how people can get involved. A polished brand boosts credibility and builds trust, but a memorable one moves people to action.

​Your Mission Is the Core of Your Brand

Before thinking about logos, colors, or marketing campaigns, start with the foundation of your nonprofit brand: your mission. What drives your organization? What problem(s) are you solving? What’s your CEO’s vision for the future? These aren’t just feel-good statements – they should be at the core of every message you share.

Example: The Monson Free Library

This small library in Maine has embraced its fun and quirky side by creating TikTok videos that showcase the staff’s personality while highlighting their programs. By tapping into the creativity and passion of their team, they’ve built a brand that’s as unique and welcoming as their services. The community now sees the Monson Free Library as more than a place for books – it’s a place to have fun, get involved, and support something bigger than themselves. Learn more.

Actionable Tip: Start by asking yourself these questions:
  • What do we stand for?
  • How do we create positive change in people’s lives?
  • What kind of emotional connection do we want to build with our audience?​
Answer these clearly, and you’ve got the heart of your brand. Everything else builds from there.

​Visual Identity: Be Consistent, But Stay Flexible

When you think of branding, visual elements like logos, color palettes, and fonts come to mind. These are crucial for creating a consistent, professional presence. But let’s be real – sometimes, nonprofits get so caught up in the “rules” of branding that they lose the ability to stay nimble. There’s a balance between maintaining brand integrity and being flexible enough to seize opportunities in the moment.

Many nonprofits create brand guides with rigid rules for logos, colors, and language. And while I love a good style guide, if these guidelines slow you down or make it harder to engage donors, it’s time to rethink them. A major gift might hinge on a timely, heartfelt social media post or a quick thank-you email. If your guidelines require three layers of approval for every little thing, you could miss your moment.

Example: The Trevor Project

The Trevor Project underwent a major rebrand in 2019, replacing a formal font and muted colors with a bolder typeface and a vibrant, colorful design. The updated branding, along with fresh messaging and visuals, emphasized inclusivity, hope, and support for LGBTQ+ youth. The change strengthened their identity as a safe, approachable, and supportive organization while making them more visually appealing to young people. See their rebrand.

Actionable Tip: If your branding guidelines feel like red tape, ask yourself:
  • Does this branding choice serve our mission, or is it just a formality?
  • Can we be more flexible in how we communicate without losing integrity?

​Messaging That Moves People to Action

​Now, let’s talk about the most important aspect of branding – your story. Whether you’re crafting an email appeal, a social media post, or a campaign landing page, your messaging should inspire action. Major donors don’t just give to organizations; they give to stories they believe in. That’s why it’s essential to center your messaging around the people you serve and the change you’re driving in the world.

Storytelling Tip: Showcase Personal Stories

People want to feel emotionally connected to your cause. Show them the impact they can have through the eyes of those you help.

Example: St. Jude Children's Research Hospital

St. Jude’s branding and messaging revolve around powerful, emotional stories of families whose lives have been transformed by their medical care. These stories create a deep personal connection, inspiring donors to give and stay engaged. Explore their storytelling approach.

Actionable Tip: Incorporate donor-centered language into your messaging:
  • Focus on what the donor’s gift makes possible.
  • Share authentic stories of people whose lives have been impacted by your work.
  • Use visuals (photos, videos) to bring your cause to life.

Building a Memorable Brand: Flexibility, Authenticity, and Consistency

A memorable nonprofit brand is more than a logo or a catchy slogan – it’s a vehicle for connection. It drives donor engagement, cultivates long-term support, and inspires major gifts. To build a brand that resonates, focus on three key principles:
  1. Be flexible enough to adjust messaging and tactics based on current events, donor feedback, or unexpected opportunities. Don’t let rigid branding guidelines hinder meaningful engagement.
  2. Be authentic in your communications. People give to organizations that feel genuine and trustworthy, so let your mission shine through every touchpoint.
  3. Be consistent in your message and visual identity across all channels – your website, social media, and email appeals. Consistency builds recognition and trust over time.

Make Your Brand Matter

Branding isn’t about flashy logos or catchy taglines – it’s about making an emotional connection with your supporters. When your brand reflects your mission, values, and unique story, it becomes a powerful tool for attracting major gifts and building lasting relationships.

Your nonprofit’s story is powerful. Make it memorable. Make it matter. And don’t be afraid to let your passion shine through.

Now – it’s your turn. Have you been through a rebrand? Was the process the transformation you hoped for? Do you feel your branding guidelines and processes support your fundraising work or hold you back? Let me know in the comments!

​Cheers!
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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!
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    Jessica Cloud, CFRE

    I've been called the Tasmanian Devil of fundraising and I'm here to talk shop with you. 

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