Dear Charity Clairity,

We’re planning a fundraising event and want to make sure it actually raises money — not just attendance or awareness. We keep seeing so many different “fundraising event ideas,” but we’re not sure how to choose the right one or what really matters most in making an event successful.

What actually makes the difference between an event that raises meaningful money and one that doesn’t?

— Trying to Do This Right

Dear Trying,

Kudos to you for asking the right question, and doing so before it’s too late in the process!

You’re already ahead of too many organizations who begin with the format — gala, walk, auction, dinner, online campaign — and then move quickly into logistics — venue, catering, ticket price, program flow — before stepping back to ask what you’ve just asked.

And you’re also right to be cautious.

Because here’s something not talked about nearly enough:

Fundraising events are one of the most expensive and labor-intensive strategies nonprofits undertake.

They require significant investments of:

• Staff time
• Volunteer energy
• Upfront cash
• Opportunity cost (what else you could be doing instead)

Which means the real question isn’t just “How do we plan a successful event?”

It’s: “Is this event likely to produce a return — financial and relational — that justifies the investment?”

Start with a clear-eyed cost/benefit analysis

Before you go too far down the planning path, be sure the bang is worth your buck.

Take a step back and ask: What will this really cost us, and what is the realistic return?

Not just in dollars, but in:

• Staff bandwidth, and potential burnout
• Volunteer effort, and how it may dilute their attention
• Donor attention, and whether you’re trading ticket purchases for pure donations
• Other opportunities you may be foregoing

Events can absolutely be worthwhile. But compared to other fundraising strategies, they are rarely the most efficient way to raise money — unless they are designed with intention and the understanding they are part of a continuum of layered, complementary strategies.

If the primary outcome is simply getting people in a room, you may find you’ve invested heavily for a modest return.

Cover your costs before you count your revenue

One of the most important ways to improve your odds of success is to separate cost recovery from fundraising.

In other words: aim to cover your expenses before the event takes place.

This is where sponsorships and underwriting come in.

Think about:

• Sponsors to underwrite the overall event
• Underwriters for specific elements (e.g., reception, dinner, program, video, print materials)
• Leadership or challenge gifts that help offset costs

I’ve seen events transform financially with this one shift. Several organizations I’ve worked with secured a handful of sponsors to cover nearly all their fixed expenses. That meant every ticket sold, every auction bid, and every gift made that night went directly to the mission — not to paying off the party expenses.

That’s a very different outcome than ending the evening hoping you at least broke even.

Be intentional about who you’re bringing into the room

Not all audiences carry the same long-term fundraising potential.

So before finalizing your guest list — or your strategy for filling the room — ask:

Who are we trying to engage, and what might they do after this event?

Strong events are built around audiences with potential to:

• Increase their giving
• Become recurring donors
• Introduce others to your organization
• Deepen their involvement over time

If your room is filled primarily with people who already give at their maximum level, attend out of obligation, or have little connection to your mission — your ability to grow revenue will be limited.

On the other hand, when you intentionally cultivate a mix of loyal supporters, new promising prospects, and engaged connectors (table hosts, ambassadors), you create the conditions for both immediate and future giving.

Create mission moments that truly move people

People don’t give because they attended an event.

They give because something they experienced there made them want to help.

At some point during your event, you need to bring everything back to:

• Why your work matters (vision, mission, and values)
• Who it impacts (population and/or problem to be addressed)
• What is possible with support (specific impacts)
• When this support is needed (urgency)

This is not the time or place for broad overviews or long speeches.

It’s the time for something real, specific, and emotional:

• A story
• A voice
• A moment people can connect with emotionally

This could take many forms. For example:

• A short video featuring a beneficiary or volunteer
• A live story shared by someone directly impacted by your work
• Storyboards or photo displays placed thoughtfully throughout the venue
• Opportunities for guests to meet and interact with beneficiaries or program leaders during the reception or at their tables

What matters most is authenticity. People should feel like they’re encountering something genuine — not a performance, but a window into your mission.

And just as importantly, these moments need the right conditions: no distractions, no competing activity, and a clear signal that this moment matters.

When people feel something real — hope, empathy, inspiration, even urgency — they become far more open to giving.

Give people ways to act while they’re feeling inspired

In fundraising, timing matters.

If someone feels moved but has no immediate way to act, that energy dissipates quickly.

That’s why strong events don’t rely on a single way to give. They offer multiple, intentional pathways for people to respond in the moment:

• A fund-a-need paddle raise tied directly to your mission (e.g., “Let’s raise money tonight for a new food pantry!”)
• A thoughtfully curated silent auction, including several fund-a-need items (e.g., $25 buys dinner for a family of four; $50 buys a bag of groceries for a week; $100 delivers nutritious meals to seniors)
• A simple raffle
• Interactive elements like a wine wall or similar fun activity
• A “spontaneous offer” to buy a lunch or dinner with someone who just spoke or was featured in your video

These aren’t just add-ons. They’re extensions of the emotional experience.

The key is alignment and restraint. Choose the elements that fit your audience and reinforce your message. Too many activities can feel scattered. A few well-executed opportunities will almost always outperform a crowded agenda.

Plan your follow-up before the event even happens

Finally, remember this: the event is not the end of your fundraising. In many ways, it’s the beginning.

What you do in the hours, days, and weeks after your event will determine whether the value of everything you invested — time, talent, and treasure — continues to grow or quickly fades.

Plan in advance for:

• Prompt, personal thank-you outreach
• Clear communication of results and impact
• Invitations to stay engaged (give, volunteer, learn more, attend again)

The goal is to carry forward the feelings people experienced, and give them a way to act again.

Because events that truly raise money don’t do so only in the moment. The memories and emotions they create continue to motivate generosity long afterward.

So, what makes the difference?

It’s not choosing the “right” fundraising event idea.

It’s building the conditions where people naturally want to give — not just today, but tomorrow and beyond.

When you:

• Go in with a clear understanding of cost vs. return
• Cover your expenses up front
• Bring the right people into the room
• Move them with a meaningful mission moment
• Give them ways to act while they’re inspired
• And follow up in a way that deepens the relationship

…you dramatically increase the likelihood your event will be worth the investment.

That’s how events move from being costly obligations to becoming powerful engines for both immediate and lasting support.

Events that raise money don’t do so only in the moment. The memories and feelings they engendered continue to motivate generosity long afterwards.

So, keep trying. In fundraising, nothing is ever “a wrap!”

— Charity Clairity

The post How to Plan a Fundraising Event That Actually Raises Money appeared first on Bloomerang.

If you’re searching for fundraising event ideas this spring, you’ll find no shortage of lists.

Walks. Galas. Auctions. Picnics. Workshops. Online challenges.

The problem isn’t the lack of ideas.

It’s that most of these lists assume the idea itself is what makes an event successful.

After 40+ years working with nonprofits, I can tell you with confidence:

The format of your event matters far less than the experience you create — and what you invite people to do as a result.

I’ve seen small, simple gatherings generate extraordinary generosity. I’ve also seen large, beautifully produced events raise very little net revenue, and even less long-term commitment.

So, while spring is certainly a popular season for events, this isn’t really about spring fundraising ideas. It’s about how to use any event — this spring, later this year, or next — to:

• Inspire people with your mission
• Help them feel connected and useful
• Turn that inspiration into meaningful, lasting support

Because at its core, philanthropy isn’t about transactions. It’s about connection, meaning, and the moment someone realizes they can make a real difference. And when that happens — when people feel inspired and useful — the money follows.

Why Most Fundraising Events Underperform (Regardless of the Idea)

Many organizations start in the same place: “What kind of event should we do?”

It’s a reasonable question, but it’s putting the cart before the horse. The most important question is this: Why hold a fundraising event?

It’s essential to get clear on your objectives — what you truly want to achieve today and in the future — before you start thinking about logistics.

First, ask yourself: What are our priorities right now? Creating awareness? Building community? Raising project-specific money? Retaining or upgrading major donors? Given limited resources, you may want to consider whether other strategies fulfill those priorities more effectively and yield a bigger bang for your buck. At the very least, you’ll want to make sure your priority objectives are integrally woven into your event strategy.

[Find a framework for evaluating different strategies against each other here.]

Once you settle on an event, instead of asking:

• What’s easy to organize?
• What’s been done before?
• What seems popular or “fun?”

Ask:

• What experience will truly move people?
• How will we connect folks to our mission?
• Where will generosity naturally emerge?

Event Blueprints: Winning vs. Losing

The best events are designed around creating a meaningful, memorable experience for the people involved.

Yet too often, events are designed around what’s easiest to produce or what’s been done before. Even though they take up a ton of time, talent, and treasure, they’re essentially running on auto-pilot.

The result is usually predictable — and not in a good way.

Auto-pilot event designs lead to a few predictable outcomes:

• Decent attendance; low engagement. Active listening, learning, participating, and viscerally experiencing doesn’t happen.
• Pleasant; not memorable. The program feels routine or disconnected from the mission — people feel vaguely “noble” for attending, but they do so out of obligation rather than anticipatory or reflective joy.
• Modest giving; no growth. Money is left on the table as guests polish their halos a bit, but then tuck them away in a closet until the following year.

If you’re stuck in the past — or stuck on what board members tell you works for other organizations — you won’t notice new or uniquely “you” opportunities as they present themselves.

This is why so many “easy fundraising event ideas” don’t actually produce strong results. Not because the ideas are wrong, but because the design is incomplete.

You can’t simply copy what other people do. Rather, you must:

• Connect people to shared purpose,
• Show them impact, and
• Move them emotionally.

When you design your event with your particular vision and constituents in mind, you don’t have to push nearly as hard for the gift. People want to give.

5 Strategies Behind Fundraising Event Ideas That Actually Work (and Raise More Money)

These are the patterns I’ve seen consistently in events that not only raise money, but build lasting donor relationships. If you want your creative fundraising event to succeed, focus less on the format and more on these five strategies.

1. Start with the Experience, Not the Logistics

Before you decide whether you’re hosting a gala, a walk, or a garden party, ask:

What do we want people to feel when they leave?

Inspired? Hopeful? Energized? Connected? Proud to be part of something meaningful?

Your event should be designed backward from that desired emotional outcome.

This is where many organizations unintentionally go off track. They spend the majority of their time on venue, food, schedule, and decorations. All important — but none of these, on their own, create a meaningful experience.

A small, mission-centered dinner where guests hear directly from someone impacted by your work can be far more powerful than a large, formal event with little connection to purpose.

The goal isn’t just to host an event to check it off your to-do list. It’s to create “WOW” experiences — moments people will remember, and want to be part of again.

Remember, there’s no one reason people attend events. It’s certainly not just to give you money. If that’s all it was, they’d have simply made a contribution and stayed home. Your job is to anticipate all the reasons they may be attending, and try to ensure your guests’ needs are met.

When you get people fired up, that’s how you’ll raise more money — beyond just ticket sales — because you’ve tapped into donor passions and made them feel they matter.

2. Build in a Compelling Reason, and Opportunity, to Give

If people leave your event inspired, but unsure how to help, you’ve missed an opportunity.

Every effective fundraising event needs a clear and intentional pathway from inspiration to action.

This isn’t just about making an ask. It’s about designing a transformative experience that:

• Builds emotional connection,
• Shows people the impact they can have, and
• Gives them meaningful ways to respond — both during and after the event

At the Event: Design the Giving Moment

A strong giving moment doesn’t happen by accident. It’s built, step-by-step.

Start with a story that feels real. This might be a client or beneficiary (live or on video), an admired staff member sharing a specific moment, or an inspired donor explaining why they got involved. What matters is authenticity and specificity. One real story will do more than a broad overview ever could.

Create a focused moment of attention. If people are distracted, the message won’t land. Pause service, bring the room to attention, and signal that this moment matters. You’re not competing with the event — you’re creating its centerpiece.

Connect the story to impact. Help people understand what their gift will do. What will change? Who will it help? Why does it matter now?

Make a clear, confident ask. Someone needs to say, plainly: here’s the need, and here’s what we’re asking you to do.

Once your core giving moment is established, you can layer in giving opportunities:

• Fund-a-need (paddle raise): Often the most powerful extension of your story
• Auctions: Keep them curated and relevant
• Raffles: Simple and accessible
• Interactive elements (wine wall, etc.): These add energy and fun, if they fit your tone

The key is restraint. Too many elements can dilute focus. A few well-chosen options will outperform a crowded agenda every time.

3. Raise Money Before the Event Even Begins

One of the biggest misconceptions about fundraising events is that the primary revenue happens during the event itself.

In reality, some of the most successful events generate a significant portion of their support before anyone walks in the room.

Sponsorships are a top winning strategy — often the difference between an event that loses money or breaks even, and one that generates real net revenue.

• Seek sponsors to cover your costs, so all ticket sales are profit
• Offer underwriting opportunities for various event elements (reception, dinner, auction, video, print materials)

Table hosts, who commit to filling and supporting a table, are a way to both fill the room and your coffers. Ask key donors to buy tables and challenge their friends and colleagues to match their giving. This plays on the psychological principle of influence known as “social proof.”

Peer-to-peer fundraising events, like walks or runs, are a great example of raising money before the event starts. Participants reach out to their networks in advance, expanding your reach and building momentum before the event even takes place.

When people arrive already invested, something important shifts: they’re not just attendees. They’re participants in the mission.

4. Make It Easy, and Meaningful, for People to Participate at Different Levels

Not everyone will engage with your organization in the same way. Some will be new. Some will be longtime supporters. Some may be ready to do more, but haven’t yet been asked.

Strong fundraising events create multiple entry points:

• A first-time guest who makes a modest gift
• A returning donor who increases their support
• A highly engaged supporter who steps into a leadership role

This is especially important for small nonprofits, where every relationship matters.

The goal isn’t just to maximize one-time giving. The goal is to create pathways for people to deepen their involvement over time.

5. Follow Up in a Way That Builds Relationships (and Future Giving)

The event is not the end of the fundraising process. In many ways, it’s the beginning.

After the event is when relationships — and trust — are truly built and cemented. And trust is the foundation of all sustainable fundraising.

What you do in the days immediately following your event will determine whether attendees remain one-time participants, or become ongoing supporters. So be sure to plan this in advance — so you can strike while the iron is hot!

The period immediately after your event is when emotions are still fresh, connections are strongest, and people are most open to continuing their involvement.

Follow up quickly and personally, ideally within 24–48 hours. Whenever possible, make this feel specific to the guest, showing you know them and they’re important to you.

• Thank people for participating
• Acknowledge what they did (attended, gave, hosted, volunteered)
• Reinforce how their involvement mattered
• Include a photo or video snippet to remind them of the experience

Close the loop on results. Let people know what was raised, what it will support, and why it matters.

Invite the next step. Not everyone will give at the event — and not everyone who gave is done giving. Offer clear pathways to continue the relationship:

• A follow-up opportunity to contribute
• A visit or conversation
• A way to learn more about your work
• Opportunities to stay engaged (volunteer, advocate, social media, upcoming events)

Events should never stand alone.

How to Choose the Right Fundraising Event Idea

Once you understand these strategies, choosing the right format becomes much easier.

Instead of asking, “What are some creative fundraising ideas?” try asking:

• Which format will best support the experience we want to create?
• Where can we most naturally tell our story?
• How can we engage people before, during, and after the event?

A few formats that often work well include:

• Small, mission-focused gatherings that prioritize connection
• Peer-to-peer events that expand your reach through relationships
• Thoughtfully designed galas or dinners that center on storytelling and purpose
• Simple outdoor or community events that create shared experiences

None of these are inherently better than the others. What matters is how you use them.

If You’re Planning Something This Spring…

If your event is already on the calendar and coming up soon, you may not have time to rethink the entire format. But you do have time to strengthen it.

Focus on:

• Clarifying your message and story
• Strengthening your mission-focused giving moment
• Reaching out to key supporters in advance
• Planning thoughtful, timely follow-up

Small shifts in these areas can make a significant difference in both the immediate results and the long-term impact of your event.

A Final Thought

There will always be new lists of fundraising event ideas. Some will be labeled “easy.” Others “creative.” Others “low-cost” or “high-revenue.”

But the organizations that consistently succeed with events aren’t chasing new ideas. They’re focusing on what makes any idea work:

• Creating meaningful experiences
• Connecting people to purpose
• Inviting them to belong to something larger than themselves

When you do that well, your event becomes more than a date on the calendar. It becomes the beginning — or deepening — of a transformative relationship.

And that’s where true, lasting generosity begins.

If you’re looking for tools to help you plan, promote, and follow up on your fundraising events more effectively, Bloomerang offers solutions designed to support the entire donor journey — so you can focus on creating experiences that truly inspire giving.

The post Fundraising Event Strategies That Actually Work: How to Raise More Money This Spring (and Beyond) appeared first on Bloomerang.

Yet isolation and emptiness are not, naturally, very human things. So, what may seem useful in the short-term is no good at all in the long-term.

Humans tend to want (and need) to fill their cup, not drain it.

Which is why a new book by philosopher Rebecca Newberger Goldstein is worth a look. For everyone, but particularly for philanthropy facilitators. Because it helps, among other things, to explain what your donors are looking for in their relationship with your cause. Drawing on biology, psychology and philosophy, Goldstein looks beyond happiness as the goal of a well-lived life, asserting we are “creatures of matter who long to matter.” Or as John Kaag, philosophy professor, notes in a recent Atlantic review of Goldstein’s The Mattering Instinct: “we are consumed by an obsession with our own significance.”

Human Beings, and Donors, Are:

1. Meaning Seeking

So much of life and human history is driven by our elemental, instinctual need to matter. Fortunately, as the brilliant innovator of Culture Club, Hugh MacLeod, writes: “The market for something to believe in is infinite.” And the search for significance influences identity, relationships, culture, politics and, yes, philanthropy.

Your job, as a philanthropy facilitator, is to offer donors something fulfilling in which they can believe.

Towards this end, try framing your work with donors as a process of meeting their very human unmet need to matter and belong. For, clearly, this is at the heart of some of the most pressing problems afflicting society today — loneliness, extremism, and polarization. All these things are values-related – and tied to how we value ourselves.

People want to like what they see when they look in the mirror.

Much of our perception of our own value is tied to how others see us. But, as social ties fray and technology drives people more into isolation, people will seek alternative paths to feeling valued. One such path is through philanthropy – voluntary action for the public good. This can be a beautiful win/win/win – for the donor, your organization, and society writ large.

This gives nonprofits, and fundraisers, an enormously important role in shaping a world where goodness and light prevail.

2. Wired to Care

Goldstein draws on biology to show how our brains and bodies are wired for empathy, cooperation, generosity, and connection. When we can’t connect, we despair. This is one of the reasons why, despite living in a country that’s one of the wealthiest ever on the planet, so many Americans describe feelings of burn-out, malaise and depression.

The loneliness epidemic is something your nonprofit can help to address by creating a community to which prospective supporters will want to belong.

Sadly, too few nonprofits look at creating a sense of belonging as a priority fundraising strategy. But, in fact, it may be everything if your organization is to thrive as a vibrant philanthropic project.

Because people are driven by the need to care and be cared for.

You see, survival doesn’t necessarily mean the strongest or most aggressive. It depends, as much if not more, on cooperation and empathy. It’s what Darwin meant by positing “survival of the kindest,” not the “fittest,” which was actually a Spencerian notion. David Brooks summed this up in his last opinion column for the New York Times: “Despite what the cynics say, I still believe we’re driven not only by the selfish motivations but also by the moral ones — the desire to pursue some good, the desire to cooperate, to care for one another and to belong.”

How to Help People Matter

The more you get to know your supporters, and understand their particular mattering instinct, the better you can help them achieve a sense of purpose that fulfils them – while helping your cause fulfil its mission.

How humans express mattering differs.

Goldstein describes four “mattering projects” by which people seek significance:

1. “Socializers” Want to Matter to Others.

They may respond to volunteering, invitations to meet you and/or other like-minded supporters, and to be specifically helpful with assigned projects.

2. “Competitors” Want to Matter More Than Others.

They may respond well to a leadership opportunity or naming recognition.

3. “Transcenders” Want to Matter to God (or the Universe).

They may respond well to values-driven stories drawing on spirituality, communal traditions and legacy.

4. “Heroic Strivers” Want to Do Something (Whether Artistic, Athletic or Intellectual) That Matters to Them.

They may respond well to an opportunity to make a transformational difference – perhaps by helping you build a new or expanded program.

To Meaningfully Contribute, Donors Need Your Help

A conclusion of Goldstein’s book is humans are all fighting entropy — the natural tendency of any closed system to slide from order into chaos. She completes the book by asserting that winning this fight, and living a good life, means finding a way to contribute by assisting in, in her words, “the spread of flourishing, knowledge, love, joyfulness, peace, kindness, comity, beauty.”

Framing your work as a philanthropy facilitator also as a facilitation of personal meaning, offers a uniquely human lens through which to view your vitally important work.

It transcends simply raising money. It surpasses simply manifesting your organization’s mission and vision. It finds its center through engaging folks in a philanthropic – ‘love of humankind’ – journey.

You Matter Too

You matter, and show you care, when you:

• Help others matter. In fact, you might say purpose evolved to help humans accomplish big things together.
• Shape a values-based, love-centered culture people want to embrace. As one of my favorite culture barometers, Hugh MacLeod, reminds us: “Deliberately designed culture creates invisible systems that drive coherence and performance.”
• Help people live their best, most meaningful lives. People are starved for meaning, hope and love. Again, the words of Hugh MacLeod address this directly: “The point is giving people a legitimate excuse to do what they already want to do: connect.”
• Help the world bend toward peace, love, justice and balance. Person by person. Organization by organization. Community by community.

Remember, just as your social benefit organization seeks long-lasting donor relationships that drive sustainable philanthropy, so do donors seek lasting personal fulfillment.

This lasting transformation is what your work facilitates.

A world of shared values where all co-exist in harmony.

And everyone knows they both matter, and belong.

Everything else follows from there.

The post Why Donors Give: The Deep Human Need to Matter appeared first on Bloomerang.

The beating heart of leadership, especially in fundraising, is not strategy. It’s connection. And connection begins with a real, human conversation.

Not a pitch. Not a performance.

A conversation: where thoughts, emotions, and truth are shared—and trust is built.

Where Conversations Go Awry

Here’s the hard truth: sometimes, without realizing it, we present ourselves in ways that quietly shut the door.

We default to habits that shrink our voice instead of amplifying it.

We make ourselves small.

We undermine our own influence before we’ve even begun.

If you want to be the kind of leader others lean in to—whose words invite trust and energy instead of uncertainty and dismissiveness—you need a better path forward.

That path starts with two essential steps: (1) reframing how you approach communication as a leader, and (2) using a clear, powerful checklist to guide every conversation. Let’s proceed!

1. Approach: Reframing Your Communications

We all want to come across as thoughtful, respectful, and open. But too often, in the name of humility or caution, we unintentionally shrink our voice. You can have the best message in the world, but if your delivery is uncertain, people will hear the uncertainty, not the message.

Here are three common traps that quietly undermine your presence—and how to begin shifting away from them.

1. Take care not to diminish yourself by hedging.

Hedging happens when you add unnecessary qualifiers or soften your statements to avoid seeming too direct. It’s meant to keep you safe, but it often has the opposite effect—signaling uncertainty or a lack of confidence.

Examples of hedging to avoid:

• “I’m not an expert, but…”
• “I may have this wrong, but here’s a thought…”
• “This probably isn’t the best idea, but maybe we could…”
• “I know you’re busier than I am.”

These phrases create distance between you and your message. Instead, say what you believe with clarity and intention. You can remain collaborative without compromising your presence.

Try instead:

• “Here’s what I’m seeing.”
• “I recommend we consider…”
• “From my experience, this approach tends to work well.”

When your language apologizes for your presence, people assume you don’t believe in what you’re saying. By shrinking to avoid discomfort, you give away the influence you came to build.

2. Recognize when you’re channeling your inner critic.

Sometimes the person most undercutting your leadership isn’t across the table—it’s in your own head. We all have an inner critic who gets in our ear when we’re feeling unsure of ourselves, or simply guarding against appearing ego-centric or know-it-all.

Common ways this shows up:

• “Sorry if this is off-base…”
• “This may sound dumb, but…”
• “You’ve probably already thought of this, but…”

The inner critic tries to protect you from judgment by judging you first. But in doing so, it keeps you small. Learning to notice and interrupt that voice is a leadership skill in itself.

Try instead:

Take a pause. Name the inner critic privately. Then speak from your wiser, more grounded voice—the one that says “You’ve got this!”

• “Here’s an idea I’d like to explore.”
• “I’ve been thinking about something that may be useful here.”

You have a valuable voice. Use it.

3. Don’t let “being nice” dilute your message.

There’s a difference between being kind and being conflict-avoidant. Many leaders, especially women and people from historically underrepresented groups, are taught, explicitly or not, that being “nice” means being soft, agreeable, and self-effacing.

But when you overcorrect for likability, you risk losing clarity. And people-pleasing mode can result in others trusting your reliability less.

Examples of over-niceness in communication:

• “I totally understand if this isn’t what you were thinking…”
• “I’m happy to go with whatever works best for everyone else…”
• “I hope this isn’t asking too much…”

Being nice isn’t the problem. Leading with care, empathy, and respect is a gift. But when “nice” means burying your needs, ideas, or boundaries, it becomes a liability.

Try instead:

• “Here’s what I need from this conversation.”
• “I want to make sure we’re aligning before we move forward.”
• “This may be a stretch ask, and it’s important.”

If you’re a fundraiser, what good is likability if it doesn’t translate into desired action responses?

Do you want folks thinking “Claire is so nice, so polite and so gracious.” Or would you prefer “Claire really knows her stuff. I always know she’ll support me and steer me in the right direction.” Or even “Sometimes Claire and I disagree, but she always gives me food for thought.”

Break Habits to Reclaim Your Leadership Voice

These patterns—hedging, self-critique, and performative niceness—aren’t signs of weakness. They’re signs of habit. And they’re habits you can unlearn.

By noticing them in the moment, and shifting toward clear, grounded language, you step more fully into your leadership. You speak not to impress or protect—but to connect.

Next: Let’s make this practical.

The Leadership Conversation Checklist will help you bring presence, clarity, and impact into every conversation—from one-on-ones to high-stakes meetings.

2. Checklist: Communicate More Powerfully

Whether you’re stepping into a donor meeting, leading a team check-in, or navigating a tough decision, your presence sets the tone. Use this checklist to help you “check in” with yourself, so you avoid undermining habits and lead with clarity, confidence, and connection.

Before the Conversation: Anchor Yourself

• What’s the purpose of this conversation?
  Define your goal. What outcome matters most?
• What do I know to be true or valuable here?
  Start from a place of grounded belief, not self-doubt.
• Am I anticipating rejection, or preparing for connection?
  Notice your mindset. One invites openness, the other defensiveness.
• Have I identified my inner critic’s voice?
  Name it so it doesn’t hijack the moment.
• Do I trust the value I bring to this space?
  Say this out loud if needed: “I have earned my seat at this table.”

During the Conversation: Beware of “Shoot Yourself in the Foot” Language

Be aware of your words, tone, and energy.

• Am I hedging or over-qualifying?
  Watch for shrinker phrases like “just,” “actually,” “almost,” and “maybe.” As in “I just think,” “Actually, I disagree,” “I almost want to suggest,” “Maybe we should.” Speak with intention.
• Am I apologizing unnecessarily?
  Women, especially, have a tendency to say “sorry” for no good reason or for simply taking up space on the planet. Catch yourself whenever you say “Sorry to bother you but …” “Sorry if this is a silly question . . .”
• Am I suggesting I’m incoherent?
  Questions like “Does that make sense?” “Am I being clear?” or “Do you know what I mean?” imply you’re difficult to understand. Replace them with “I look forward to hearing your thoughts,” or “Let me know if you have questions about this.”
• Am I using undermining disclaimers?
  Simply say what you have to say. Eliminate qualifiers like “I’m just thinking off the top of my head…,” “I’m no expert in this, but,” or “You know more about this than I do, but . . .”
• Am I hiding my point of view behind a question?
  Declarative statements are what cause people to trust you as an authority. And it’s not the same thing as being an authoritarian, which is a misuse of authority. Avoid sharing your opinion in the form of an interrogatory, for example, “Does everyone feel sure about this direction?” This conveys uncertainty. Rather, try “My experience tells me this is the wrong direction for us to take.” This offers a level of expertise on which others can rely.
• Am I using undermining uptalk?
  This is when you raise your tone at the end of what you’re saying so it sounds tentative. There’s a huge difference between an authoritative “Let’s do this!” and a questioning “Let’s do this?” Whenever you raise your pitch, it comes across with less gravity.
• Am I sounding uncertain?
  Let’s say you’re recommending new software or a technology tool. Would you lead with “I’m not certain this will work” or “I don’t have personal experience with this” or “This may not be for us, but…”?
• Am I apologizing for taking up someone’s time?
  What you have to offer is valuable, or you wouldn’t say it. Beware of add-ins like “a little bit” or “just a minute” or “just a sec”—anything implicitly suggesting what you have to say isn’t worth much time or space.

Remember to Weave in Warmth

Warmth opens doors facts alone cannot. It reminds people you’re not just a leader; you’re a person they can relate to. Strong communication isn’t just about clarity. It’s also about connection.

Don’t forget to bring a little humanity into the room.

Include a warm, genuine opening or closing when it fits the moment. A personal anecdote, a touch of humor, or a quick glimpse into your life can shift the energy and make space for trust.

One peer shared how everything changed in her team meetings when she started with a small story—something simple, like a funny moment with her child that morning. Then she’d dive into her report, filled with data and strategy. For the first time, her colleagues leaned in. They listened. They even praised her contributions.

Why? Because she’d humanized herself. In just a few words, she invited connection—and quietly challenged whatever assumptions they might have held about her.

Try this:

• Begin with a light, real-life moment to set an inviting tone.
• Close by expressing genuine interest: “I’d love to hear your thoughts on this.”
• Let your tone express awareness and concern. It should say: I’m here. I care. This matters.

After the Conversation: Reflect and Refine

Grow your awareness, not your self-doubt.

• Did I communicate what truly mattered?
  Not just what was safe or expected.
• Where did I feel strong? Where did I hold back?
  Notice, without judgment.
• What energy did I leave behind?
  Did I leave people with clarity? Trust? Momentum?
• What one thing will I try differently next time?
  Tiny shifts, repeated often, lead to powerful change.

Final Thought: Leadership Is a Conversation

It’s a relationship—built one interaction at a time.

And in fundraising, especially, that relationship begins and deepens through meaningful, human conversation. The most powerful leadership conversations aren’t one-way monologues. They’re two-way doorways to something greater than either of you can build alone.

Every conversation is an act of co-creation.

• You’re not just presenting your experience—you’re making space for someone else’s.
• You’re not just pitching your vision—you’re inviting someone else to help shape it.
• You’re not performing—you’re partnering.

The way you show up—especially in the quiet, human moments—is your leadership.

So, before you diminish yourself, pause. Reframe. Choose to reveal yourself as the kind of leader people want to follow—and join with.

Don’t shrink. Every voice is needed. Yours. Your conversation partner’s.

Start with presence. Lead with clarity. Speak as someone who belongs. Because, you do.

The post Before You Diminish Yourself: Leadership Conversation Checklist appeared first on Bloomerang.

With an expensive Live Auction item, how do you get multiple people to bid together on one item they will enjoy together? For example, the item may be an Aruba trip in a 3-bedroom condo.

– Don’t Want to Waste Best Items

Dear Don’t Want to Waste,

Kudos for planning ahead to maximize the revenue you receive from the auction items you worked so hard to secure. It can be frustrating and demoralizing (both for the folks who solicited the items and the folks who donated them) when items don’t fetch top value.

But, many charities may not have constituents capable of making the types of bids that would cover the full value of, say, a $7,500 vacation. Or, perhaps they are capable, but haven’t been paying attention or are not particularly interested. Part of your job is to capture bidder attention.

Pique bidders’ interest early and often

Underlying your question is this truth: Most people don’t make spur of the moment “big purchase” decisions. If the night of the auction is the first time they’re presented with an opportunity to buy a big trip (or any other big-ticket item), they just won’t be ready to come to this decision. Here’s how to help bidders get over the decision-making hump – before and during the auction.

Make bidding easily approachable

Selling a trip can be tricky. Aside from the price, most Americans don’t have a lot of vacation time. They may be skeptical the opportunity you’re offering is worth their investment. They think about not just the immediate cost, but also the lost opportunity cost (in other words, other possible places to which they could have traveled).

Make the opportunity sound “one-of-a-kind” wonderful

Spend some time crafting an enticing description of the item. Use strong verbs and adjectives (e.g., indulge, discover, explore, savor, escape, luxurious, exclusive, handcrafted, limited-edition, award-winning). If it’s been donated by one of your donors, learn what’s unique about the property and destination so you can promote it on your website, social media and pre-event emails. Perhaps it’s only available once annually. Or it comes with housekeeping, an add-on chef and use of a car. Or it’s the only property in the area with a private plunge pool, hot tub and direct beach access.

Explain a bit about the location and sights

Emphasize moments, not just logistics. You might talk about what the donors have suggested the winner will want to do there. “Rent a car so you can go explore these amazing locations.” “It’s 10 minutes from the airport. You’ll be on the beach, in the sand, in just a flash.” “The famed Sunday market in town is a stroll away – a great place for fresh produce and local art.”

Make it sound easy as pie to get there

Use a map in your pre-event messaging, and on poster boards and slide shows at the event. “This is where Aruba is located. There are direct flights from several local airports, including X, Y and Z. You can easily take a day trip to…”

Prepare your auctioneer with some extra content tidbits

For example, you can check YouTube videos and online travel platforms to offer up some facts about native flora and fauna, traditional food, local shopping and other alluring details that paint a picture bidders will want to enter into. “And, they also have the most amazing scuba diving where you can go to see fish you won’t see anyplace else!” “They have a 3-star Michelin restaurant that’s a destination on its own!”

Use your auction committee to plant the seeds – for donations and purchases

The best auctions have the advantage of a great volunteer committee behind them. Make your committee large enough you have plenty of folks who can both offer and solicit items. Be sure to hold several brainstorming sessions in advance of the event so members can piggyback ideas off of one another.

Brainstorm items

A successful auction is all about having items that will (1) fetch a good price, and (2) resonate with your particular audience. For silent auctions, restaurants, wine, theater and sports events tend to do well. But for live auctions, your items should be something it would be hard to purchase anyplace else. Experiences do the best: a spectacular vacation property; dinner for 8 cooked by a celebrity chef; box seats for the World Series; the opportunity to conduct the local symphony, and so forth.

I can recall a meeting where one committee member suggested she could donate a meal cooked in-home by her private chef. Then two other members said they could offer the same thing! This was followed by another member offering up a flight on their private jet! Who knew?

Brainstorm selling ideas

Spend some time spit-balling how you’ll entice bidders. This is where you might bring up the notion of several bidders joining together on an item. It’s possible several committee members who are friends may jump on this idea. Or they may have friends or family members to pitch it to. The key is to get potential bidders thinking about this in advance, so they have a plan for the night of the auction.

Marketing strategies to prepare your guests for bidding

1. Email marketing

Rather than linking to all items simultaneously, big ticket marketing works best when you highlight live auction items individually. Use an enticing subject line to inspire opens (e.g., “Enjoy a once-in-a-lifetime getaway.”). Link to your amazing description with pictures, testimonials, and even a video. You can even suggest: “This would be perfect for a family or friends getaway!”

2. Social media works

Storytelling is the best approach. For example, you can tell how excited you are to have just secured the exclusive summer home of Mr. and Mrs. Generous, who are offering up their amazing (“and this is what you have to look forward to”) Aruba condo. The more you do in advance, the more time interested folks have to talk their friends and family into joining them!

3. Event displays and descriptions

Use poster boards, or an interactive video screen, with a sensuous description and images. This also serves as entertainment for guests. Make sure you also have a printed program or handout. Different sources suggest items sell for 30% to 50% more when there are written descriptions at your tables. When people can see, hear, feel, taste and touch the item, it helps them trust they are making a good decision to bid on it.

4. Video on stage

During the selling process, it helps when folks can visually imagine themselves on the beach, at the pool, or sitting around the firepit. It gets them to care, so they’ll want to bid more – and continue bidding until they win!

Hopefully this will help you not waste all the benefits your item has to offer!

P.S. See more about What Elevates A Live Auction From Good To Great?

– Charity Clairity

The post How to Encourage Group Bidding on Expensive Nonprofit Auction Items? appeared first on Bloomerang.

I’ve been working in annual giving and have recently been asked to help us diversify our funding by applying for grants. We have a handful of foundation funders currently. I need to reach out to them for renewed or increased support, and also find us at least as many new supporters. I’m starting to research funders, but am really not sure what a realistic ask amount might be for any of them. I could use a few pointers!

— Feeling at Sea

Dear Feeling at Sea,

It’s definitely scary when you’re dumped in the deep end without having first been given swim lessons! So, let’s go back to the shallow end for a minute and start at the beginning.

What to consider when asking for a nonprofit grant

The realistic ask amount depends on a number of factors, including the prospective funder’s mission, giving history, current giving focus and capacity, and your own organization’s relationships and past history with grant seeking and reporting.

Your organization’s grant history

If you have a history of receiving grants, and a reputation for excellent reporting and follow-through, you’ll be in a position to ask for more than if you’re a newbie.

Why? Because the foundation of grantmaking, and all philanthropic relationships, is trust. Foundations talk to one another. If you submit a proposal to Foundation C, and they see you’ve been funded in the past by Foundations A and B, they’re likely to contact A and B to find out a bit about their experience with you.

Your current funders can serve as “social proof” that you’re a good investment.

But what if you have little grant history?

Your organization’s community relationships

Your lay leaders can also offer social proof and put in a good word for you.

That’s why it’s useful to send a list of funders to whom you’d like to apply, complete with names of foundation staff leadership and trustees, to all your board members. Ask them to indicate if they know anyone on the list–and whether they’d be willing to reach out on your behalf.

Fruitful fundraising relies heavily on relationships and, when you have one, you’ve got a stronger likelihood of success.

But you can’t capitalize on relationships unless you know they exist! So, make it your business to find out.

The cost of the project for which you’re applying

Begin with clarity on your needs.

Sit down with program staff and interview them about everything that will be required–direct and indirect costs. Management, line staff, administrative support, supplies, travel expenses, and marketing, rent, utilities, insurance–you name it. Always include a percentage for overhead. It makes no sense to ask for less than you realistically need.

Sit down with finance staff for help crafting a budget. The budget is a microcosm of the entire proposal. In fact, often, the budget is the first thing a funder will look at in evaluating your proposal.

Generally, budget line items should include:

• Your project’s direct and indirect expenses
• How much you’re asking from this funder
• How much you’re asking from other funders
• Where the balance, if any, will come from (e.g., fundraising from individuals; earned income)

NOTE: After you get the hang of this, you can develop a template budget (including all the usual categories that constitute line items for you)–obviating the need to sit down with finance staff every time.

A budget narrative can be helpful in explaining each line item.

It also helps you to make sure your numbers add up (nothing will destroy credibility faster than a sloppy budget). For example, for travel expenses, add a note describing specific travel needs and costs; for staff, show the FTE multiplied by the hourly wage and hours worked. Besides checking and double-checking your math, you’ll also want to include a paragraph explaining how you’ll sustain this project once you no longer have foundation funding.

Your alignment with the funder’s mission and priorities

Most funders are quite explicit in their guidelines about what they’ll fund and won’t fund. You can also take a look at funders’ Form 990-PFs which give complete lists of grants awarded, including recipient names and amounts. Don’t rely completely on the past however, as priorities change.

When you send a misaligned proposal (either purpose or size), you undermine your credibility – both now and for the future.

So, be careful. If you have any doubts, place a phone call to the funder so you can talk out whether or not there is a good match. Funders are, after all, just people. Many will appreciate the fact you’re doing your homework. [Just don’t call them if they plainly state “no phone calls.”]

Hopefully these tips will help get a handle on next steps, so you find your land legs!

–Charity Clairity

The post How To Make a Realistic, Successful Nonprofit Grant Request? appeared first on Bloomerang.

Dear Charity Clairity,

For sustaining donors (monthly), I send a quarterly thank you. Is that sufficient? Do you have a better idea?

— Balancing Priorities

Dear Balancing Priorities,

Let us begin with something I truly believe: You can never thank donors too much.

Yes, it’s work. But the effort is well worth the investment. Because donors who feel appreciated give more and more often.

But, wait. You say these folks are already giving more often? True. But… they’re free to stop at any time. They’re also free to make a larger commitment at any time. That’s what you really hope for. Because a $50/month donor ($600/year) can easily become a $60 donor ($720) without batting an eye. If you have 100 donors doing this, you’ll generate an additional $7200. 1,000 donors? $72,000. That’s so much easier than trying to get one or two major donors to give you this sum.

So, yes, it’s work to thank a little bit more often. Yet it’s one of the most surefire ways I know to increase donor lifetime value.

A thank you is an opportunity to connect meaningfully

Why not reframe your approach from “chore” to “opportunity?” Researcher Penelope Burk has worked over two decades in assessing what donors want, and a prompt, personal, outcome-focused thank you is at the top of the list. In a Burk Donor Survey, 40% of respondents said they had received at least one thank-you letter in recent memory they would describe as exceptional. Its “warm, personal tone making the letter feel like it was written just for me” was cited most often.

• 45% of donors said it was an outstanding thank-you letter that inspired them to give again.
• 23% said they gave more generously because of the quality of the acknowledgement they received.

If your modus operandi is calculating how little you can get away with when it comes to donor acknowledgements, you’re missing the boat.  You’ll still have the original pledge, but you’re unlikely to get an upgrade or legacy commitment.

On top of that, your donors just won’t feel as good as they could. And isn’t part of the social benefit sector’s mission to spread joy – thereby making our world, and the people in it, just a little bit happier?  As the “Father” of modern fundraising, Hank Rosso, is famous for saying:

“Fundraising is the gentle art of teaching the joy of giving.”

Let’s talk a bit about simple ways to leverage the thank-you process to inspire greater happiness and loyalty.

6 keys to effectively thank monthly donors

There is a HUGE difference between thank you’s that fulfill the requirement of acknowledging gifts and thank you’s that inspire donor love and devotion. Don’t forget: monthly donors are some of your best bets for legacy gifts. So, keeping them committed and identified with your cause is tremendously important.

1. Flatter your donor.

People respond to compliments; in fact, they crave them. “You are amazing.” “You made this happen.” Flattery is a gift. When you help people feel appreciated and loved, you help them attain the highest goal to which most people aspire in their search for meaning.

2. Lean on impactful visuals.

A picture, indeed, is worth 1,000 words. Close-ups with captions work wonders. Here are two examples from Vida Joven, which sends something brief (it doesn’t need to take even an hour of your time) every month:

3. Focus on the outcome.

Put this together with the wonderful qualities the donor possesses (e.g., vision, insight, caring, understanding, generosity, compassion, remembrance). “Jimmy will go to bed with a full tummy tonight – because you cared.” “You remembered – because Gloria couldn’t.”

4. Stand out!

It’s critical your donor perceives they are being thanked. Don’t add in an ask. Don’t go on and on with your organization’s case for support – which can make your communication sound like another pitch. Keep it simple. Heartfelt. Pure gratitude.

5. Close warmly.

“Sincerely” is a bit formal and does nothing to build a relationship. A thank you letter is a place to gush a little. Instead, try something heartfelt or mission related: “In gratitude,;” “Warmly,;” “With appreciation and admiration,;” “For the love of theater,;” “In celebration of you,;” “From the bottom of my heart,” etc. Here’s another Vida Joven example:

6. Add a targeted, personal touch.

For those who give a gift that’s above your average, it’s worth acknowledging this special commitment with an “above average” thank you. After all, you probably thank donors of $1,000 differently than donors who give $100 or less, right? A $100/month ($1,200/year) donor should be treated similarly. Pick up the phone! [ Grab my free “Donor Thank You Calls E-Book + Script.”] Leave a pure gratitude voicemail if you don’t reach them. Send a personalized thank-you text or video. And make sure, when sending a newsletter or connecting in person, you offer opportunities for donors to get involved in other ways than just giving. Make them feel valued as people, not just wallets, and they’ll value you as well.

Bottom line: you’ve already done the hard part

One of the least acknowledged benefits of monthly giving programs, from the donor perspective, is that giving more frequently in smaller amounts can give your donor a recurring pleasure high.

This is a great argument for a monthly giving program as a way to offer donors greater rewards. Lean into it!  Think of “recurring gifts” as a two-way street. They keep giving AND you keep giving.

They’re doing it monthly. Maybe you should too?

Hope this seems like a balanced approach,

— Charity Clairity (Please use a pseudonym if you prefer to be anonymous when you submit your own question, like “Balancing Priorities” did.)

How often does your organization thank monthly donors? Let us know in the comments.

The post What’s the Best Way to Thank Monthly Donors? appeared first on Bloomerang.

We’re revamping our giving levels and rethinking the “perks” donors receive at different tiers—beyond a name on the website or in the program guide.

Here’s where I’m getting stuck (at least in my head): how do we handle tax deductibility when benefits get more experiential?

For example, we’re considering things like a 15% discount on festival and year-round ticketing (with an obviously unknown value), or a set number of free tickets (when ticket prices vary). I know the old rule of thumb used to be that benefits under $75 could be ignored—but it looks like the rules have changed.

Most of our giving levels would start at $1,000. Could offering a 15% discount on tickets throughout the year fall under the “insubstantial benefit” rule?

— Tax Deduction Confused

Dear Tax Deduction Confused,

You’re asking exactly the right questions. As nonprofits get more thoughtful (and creative!) about donor experiences, tax deductibility can feel like a maze.

Let’s break it down—starting with the basics, then getting into how tickets and discounts fit into the picture.

Quid pro quo rules: the basics

If a donor receives anything of value in return for their contribution—event tickets, discounts, gifts—the fair market value (FMV) of those benefits must be subtracted from the donation to determine the tax-deductible portion.

• The donor must be told the FMV of the benefits they receive.
• The nonprofit must disclose this information in the solicitation or acknowledgment.

Typically, this looks like: “Your donation of $X is tax-deductible to the extent it exceeds the fair market value of the benefits received, which we estimate at $Y.”

Where the $75 rule really fits

This is one of the most misunderstood parts of the tax code.

The $75 rule doesn’t mean benefits under $75 can be ignored. Instead, it means that if a donor gives more than $75 and receives something in return, the nonprofit is required to provide a disclosure statement showing:

• The value of the benefit
• The deductible portion of the gift

In other words, it triggers a disclosure requirement—it doesn’t eliminate the need to value benefits.

The de minimis (token exception) rule

There is a separate token exception for benefits of insubstantial value (IRS Rev. Proc. 90-12).

Under current IRS guidance, a benefit may be considered insubstantial—and the full gift deductible—if:

• The value of the benefit is the lesser of 2% of the donation or $125, and
• The cost of the benefit to the organization is less than $12.50

This typically applies to logo items (mugs, totes, calendars) or front-end premiums like address labels—not tickets or discounts, which usually have a measurable market value.

Special cases: tickets, discounts, and variable value

This is where things get more nuanced.

1. Free Tickets (with varying prices)

You’ll need to assign a reasonable FMV, even if prices fluctuate. Many organizations use the average ticket price or the highest general admission price.

If a giving level includes “two free tickets,” that value must be subtracted from the donation total—unless the donor waives the benefit in writing.

2. Percentage Discounts (like 15% off tickets)

Discounts are tricky because the value isn’t fixed. You’ll need to estimate the maximum reasonable benefit a donor could receive.

For example:

• Four $25 tickets = $100
• 15% discount = $15 benefit
• Multiply by how often the discount could reasonably be used in a year

You can be conservative—but you must be reasonable.

How to stay donor-friendly (and IRS-friendly)

1. Keep benefits within “insubstantial” limits

For a $1,000 gift, 2% equals $20. If the estimated FMV of a discount exceeds that amount, the gift is not fully deductible.

Discounts also scale quickly. For example, if tickets are $25 and a donor buys six tickets in a year, a 15% discount equals $22.50—already over the 2% threshold.

And remember: discounts are not token gifts. They represent real, recurring financial value.

2. Limit the scope of discounts

A year-round 15% discount will almost always exceed de minimis limits unless tightly restricted.

Instead, consider options like:

• “Up to four discounted tickets annually”
• “Valid for one festival event”
• “One-time 15% discount code”

This preserves the feeling of a perk while keeping the FMV manageable.

3. Allow donors to waive benefits

If donors can waive benefits in writing, their gift may remain fully deductible. Be sure this option is clearly communicated—otherwise, the IRS assumes the donor received value simply by having access to the benefit.

4. Separate perks from donations through membership

Many museums and zoos use a membership model. Under IRS rules, certain recurring benefits may be considered insubstantial if:

• The annual payment is $75 or less, and
• The benefits include things like discounted admission, gift shop discounts, or member-only events, with per-person costs within token limits

This approach can offer flexibility while keeping compliance clear.

And if this still feels confusing (you’re not alone), it’s always wise to consult a nonprofit-savvy attorney or CPA.

— Charity Clairity

The post Are Fundraising Ticket Perks Tax Deductible? appeared first on Bloomerang.

Dear Charity Clairity,
Our board doesn’t want to “fundraise” because they think asking is icky. What are some ways to get them involved that don’t (yet) involve asking, but that warm them up to the idea donors actually LIKE our organization and APPRECIATE the opportunity to get more engaged. I’ve been telling them this, but they don’t seem to believe me. Do you have any actionable tips for board members – like assignments I might make — that wouldn’t make them run for the hills?

— They Just Won’t Fundraise

Dear “They Just Won’t Fundraise,”

You’re not alone. “Our board won’t help” is easily one of the top three frustrations we hear from fundraisers and executive directors.

Here’s the plot twist: the number one complaint we hear from board members is, “Staff never give us anything to do.”

That’s a pretty big disconnect—especially when it comes to one of the most essential responsibilities of a board: making sure the organization has the resources it needs to fulfill its mission.

Like you, we talk about this all the time. (And yes, we’ve written about it here, here, and here.) Yet somehow, the gap between staff and boards persists.

So where does the disconnect begin?

We’ll be honest—it usually starts with staff.

In our very human attempt to be “nice” during board recruitment, we often skip the hard but necessary conversations. The result? Board members who care deeply about the mission, but aren’t prepared for their fiduciary role—especially when it comes to fundraising.

So let’s pause and ask:

1. Do you talk openly about fundraising responsibilities during the recruitment process?
2. Is fundraising included in your board member job descriptions?
3. Does your board orientation session clearly cover their role in fund development?
4. Do you offer ongoing board development to help members serve as ambassadors, advocates, and—eventually—askers?
5. Are you providing the encouragement, clarity, and cheerleading they need along the way?

Why are board members so afraid of fundraising?

Most people are afraid of asking.

To many board members, it feels like begging—and that’s uncomfortable. Add to that our cultural reluctance to talk about money at all, and suddenly “fundraising” becomes the thing they’ll avoid at all costs.

They’ll gladly help in a hundred other ways—just not with that “yucky” word that starts with fund.

What’s often missing is this simple truth: fundraising isn’t just asking. It’s a relationship-driven process that includes identifying supporters, nurturing connections, stewarding generosity, and yes—sometimes inviting someone to give.

The key is to start with what feels natural and build confidence from there.

How to take the “yuck” out of fundraising

First: Try reframing it.

What if, instead of “fundraising,” we talked about philanthropy facilitation? Same goal. Very different feeling. It replaces the dreaded four-letter word with something far more meaningful: philos + anthropy—love of humanity.

Next: Give board members options.

Create a menu of specific ambassador and advocate roles they can choose from. Ask them to indicate what they’re comfortable doing, then meet one-on-one to assign roles, answer questions, and set them up for success.

Here are a few easy, confidence-building ways board members can get involved:

1. Say thank you.
   Writing notes, sending emails, signing letters, or making gratitude calls (even leaving a warm voicemail) helps board members connect with supporters—and experience the joy of appreciation firsthand.
2. Open doors.
   Board members can introduce people from their networks who might be a good fit, often by helping schedule a friendly visit with the executive director or another leader.
3. Add personal notes.
   One of the simplest, most meaningful tasks: reviewing a donor list, flagging familiar names, and adding a handwritten note to an appeal, invitation, or thank-you.
4. Guide a tour.
   If you have a space people love to see—backstage, a campus, a pantry, a preserve—this is a no-pressure way to welcome supporters and share impact.
5. Bring a guest.
   Inviting friends to an event or tour is a powerful act of advocacy. It feels good, personal, and generous—because it is.
6. Host a house party.
   These gatherings harness the power of social proof. The board member becomes a trusted advocate, and guests get an up-close look at the mission—through stories, experiences, and human connection.

Finally: Check in.

This isn’t their day job. Don’t assume tasks will magically happen without a nudge or two. Ongoing encouragement and clarity go a long way.

Here’s the good news: board members will fundraise when they understand their options, feel supported, and aren’t forced into roles that don’t fit.

Your job isn’t to strong-arm them—it’s to help them feel good about helping.

When board members facilitate generosity, they’re not asking for money. They’re offering people the chance to do something meaningful, aligned with their values, and deeply human.

That’s not yucky. That’s joyful.

— Charity Clairity

The post How Do You Get Board Members to “Fundraise”? appeared first on Bloomerang.

When a donor sees a cause as part of their identity, giving becomes transformational. It’s no longer just about solving a problem—it’s about expressing who they are and what they stand for.

This idea is central to Meaningful Philanthropy by Jen Shang and Adrian Sargeant, whose research shows deeper gifts are rooted not in data, but in identity, ownership, and belonging. Shang, a philanthropic psychologist, and Sargeant, one of the world’s leading experts on donor behavior, argue that when giving is tied to a donor’s identity — who they believe themselves to be — it becomes far more powerful and long-lasting.

Let’s explore how to tap into this psychology and reframe fundraising around what truly drives lasting generosity.

Rethinking why major donors give

Ask most fundraisers why major donors give, and you’ll likely hear a confident answer: “They want to see impact.” It’s a tidy, logical explanation. Yet it assumes these donors are primarily numbers-driven. Show them the cost per meal, the ROI of your programs, the percentage increase in lives changed, and the money will follow. Right?

Not always.

In truth, many major donors are driven more by meaning than metrics. Their giving isn’t just about fixing a problem; it’s about expressing who they are. Giving is a reflection of identity, values, and purpose. In fact, research shows high-net-worth donors often pursue philanthropy as a path to greater personal fulfillment. A way to feel their lives matter in ways beyond business success or wealth accumulation.

If you’re leading with data and outcomes alone, you may be missing the deeper motivator. It’s not just about solving presented problems, but about reinforcing the kind of person they believe they are or aspire to become. And they believe, because of their connections and resources, they’re able to achieve goals for the community the community can’t achieve on their own.

Heady, potent stuff.

Identity and ownership in giving

So, what does it mean for a donor to own a problem? It’s not about financial control or decision-making power. It’s about emotional investment. Ownership happens when a donor feels a deep, personal connection to the cause. When they stop seeing the mission as your work and start seeing it as their work too. It’s no longer just a problem to be solved—it becomes their problem to solve.

This shift is fundamentally about identity and, per Shang and Sargeant, many high-net-worth donors see themselves as entrepreneurial spirits.

When they enter into the domain of complex social problems, they’re eager to apply their curiosity, intelligence, and skills in ways that affirm their self-image. As they do this, they begin to internalize the mission. They start to see themselves not just as helpers or contributors, but as embodiments of the values your organization represents.

A donor who supports environmental conservation doesn’t just want cleaner rivers; they see themselves as a protector of the planet. A donor funding education for girls doesn’t just want higher graduation rates; they identify as someone who believes in equality, self-esteem, and opportunity.

When a donor sees their gift as an extension of who they are, giving becomes self-expression.

The limits of impact

For years, fundraisers have been coached to lean hard on outcomes: show donors exactly what their gift will accomplish, quantify the results, and prove effectiveness. And yes, that’s important. But focusing solely on impact metrics can flatten the donor experience. It risks turning giving into a transactional financial exchange for a measurable result.

What gets lost in the metrics-forward approach is meaning.

Research in philanthropic psychology shows meaning drives behavior more deeply and durably than data. And this is particularly true when meaning is tied to a donor’s identity. Jen Shang and her colleagues found that when donors were addressed using identity-affirming language (e.g., “you are generous”  vs. “please donate”), they gave significantly more.

The power of meaning

The key insight from Shang and Seargent’s research is that donors are motivated not just by what their gift accomplishes, but by what their giving says about who they are. Consider these two messages:

• “Your $10,000 gift helped build 5 wells, serving 2,500 people.”

• “Your gift shows you are the kind of person who brings life and dignity to communities others have forgotten.”

Both are true. But only one speaks to who the donor is. 

It’s not just what the donor’s gift does; it’s what their gift says about them. And when donors feel that emotional and identity-level resonance, they give more, and they stay longer.

Your job is to help donors feel their importance. Transformational fundraisers say: “Your gift is a reflection of who you are. Together, we’re shaping the world — and your legacy.”

The philanthropy facilitator’s role

I often exhort fundraisers to remember they’re in the happiness delivery business, citing MRI studies showing people get a “warm glow” jolt of dopamine when they even contemplate giving, but the dopamine rush fades quickly.

Philanthropy facilitators who want deeper gifts, and deeper loyalty, must make a shift. They must engage with donors in a manner that centers on purpose, identity, and belonging.

Shang and Sargeant emphasize transformational giving is not driven by the size of the donation, but by the meaning behind it. When a donor feels seen, known, and affirmed through their giving, they move from participant to partner.

From giving to feel good to giving because it’s part of who they are.

Infuse meaning into your fundraising

The good news is, you don’t need a psychology degree to infuse meaning into your fundraising. But you do need to shift from one-way “asking for money” monologues to two-way dialogues inviting donors to share their deepest worries, hopes, and dreams — all so you can create a meaningful match between their values and the values your organization enacts.

Giving becomes most transformational when donors feel a shared identity—not just with the cause, but with a community of like-minded people who are working together to make a difference. This sense of communal belonging is immensely powerful. It says: You’re one of us. This is what we stand for. This is what we do together.

A major source of meaning for donors comes from feeling they belong to something larger than themselves. 

Top 5 ways to build meaning

1. Ask identity-based questions

Instead of simply asking for support, ask donors:

• “What part of our mission speaks to you most deeply?”

• “What values guide your giving?”

These questions don’t just gather intel; they invite the donor to reflect on who they are, and how their identity connects to your work.

2. Use language that affirms who they are

Identity-affirming language can significantly increase giving. Try using phrasing like:

• “You are the kind of person who…”

• “As someone who believes in justice…”

Rather than describing what their gift does, describe what their giving says about them.

3. Tell stories they can see themselves in

Don’t just tell stories of impact; tell stories of identity. Highlight individuals (donors, volunteers, beneficiaries) whose values reflect those of your audience. The goal is for donors to say, “That’s me. That’s what I believe in too!”

4. Create a sense of belonging

Invite donors into a community, not just a campaign. This can take many forms:

• Name giving circles that reflect shared values (e.g., “The Welcome the Stranger Circle,” “The Justice Society,” “The No Child Left Behind Society”).
• Share stories from other donors—not just their gifts, but their why (e.g., I used to run a regular newsletter feature highlighting one donor per issue: “Why I Care, Why I Give.”)
• Use newsletters or events to showcase collective impact and language like “together,” “our shared mission,” “as a community.”

When donors feel they’re part of a values-driven movement they stay engaged longer and give more.

5. Frame results through purpose, not just performance

Yes, share metrics, but tie them back to meaning. Instead of:

• “We reached 1,000 students this year.”
  Try:
• “Together, we stood up for the belief that every child deserves the chance to learn.”

Numbers are important, but they’re most powerful when they reflect shared ideals.

A call to meaningful fundraising

Donors, especially major donors, aren’t just investing in what you do. They’re investing in who they are through you. When donors feel that their giving reflects their core beliefs, when they see themselves as part of a community with shared purpose, their support deepens.

So, here’s your challenge: Shift the conversation. Move beyond metrics alone. Ask questions that invite reflection. Use language that affirms identity. Create spaces, real or digital, where donors feel they belong. Not as outsiders funding your mission, but as insiders shaping it.

Deeper meaning really does lead to deeper pockets. More importantly, it leads to deeper relationships, deeper trust, deeper connections, and deeper change. And isn’t that what philanthropy facilitation is really about?

The post Deeper Meaning Equals Deeper Pockets: When People Own Problems, They Want To Solve Them appeared first on Bloomerang.

Dear Charity Clairity,

What separates the “okay” live auction fundraisers from the great? Is it the auction items themselves? Or something like the food, speakers, or something else?

— Seeking the Secret Sauce

Dear Seeking,

Many people assume a standout live auction is all about landing the right big-ticket items. But in reality, the difference between an “okay” auction and a great one rarely comes down to any single component. The real secret is planning, planning, planning — thoughtfully designing every element well in advance so they reinforce one another and build toward a cohesive, high-energy experience. When an event is carefully orchestrated from start to finish, the whole becomes far greater than the sum of its parts. Items matter, yes. But their impact depends on the emotional arc, pacing, mission moments, and energy you’ve set up long before the auctioneer takes the stage.

The real driver: energy and engagement

The biggest difference between a mediocre auction and a great one is something you can’t put on a spreadsheet: the energy in the room. Great planning creates the conditions for that energy to build and stay high. This will dictate the final numbers far more than the specific prizes up for bid. A moderately appealing package can spark spirited competition when the room is buzzing; conversely, even a dazzling trip or once-in-a-lifetime experience can fall flat if the energy is low.

This emotional temperature is shaped long before the auctioneer hits the stage. Guests are forming expectations and readiness to participate. Strong events start priming attendees early — with engaging preview materials, fun teases of the top items, a warm welcome at check-in, mingling at the reception, and well-placed “teaser” moments that plants anticipation. “Okay” auctions just hope guests arrive in a giving mood. Great ones nurture and shape that mood in advance.

The auction as theater: flow, pacing, and production

A live auction is fundamentally a theatrical performance. The auctioneer is the narrator, but the nonprofit is the producer. And great producers understand pacing, tension, and release. Three ingredients matter most:

1. Curate a tight list of items

The first auction I ever held as a fundraiser had so many items, the guests were either asleep by the end or were completely tuned out and talking to each other. Nothing saps energy faster than offering too many items. Once you pass about seven or eight, the room’s energy dips and bidders fatigue. Great live auctions are intentionally brief and punchy. Keep them to no more than one hour to keep people’s attention and energy high. If you’re adding the auction to an already existing event, keep the live auction component between 10 and 30 minutes. Choose every item to appeal to your specific audience, not to reflect what donors happen to give you. So, think about what might do well with your audience. A flight on a private jet might appeal to only one or two in your crowd, whereas a private meeting, consultation or behind-the-scenes visit with a VIP (e.g., a teacher, doctor, actor, sports figure, politician or financial wizard) might engender lively bidding and big bucks.

2. Sequence for momentum

Order matters. The opener sets the tone—something light and fun is ideal. Middle items should be your strongest, because that’s when attention peaks. And closing items should either be communal and joyful (like a dessert dash or group experience) or serve as a bridge to a Fund-a-Need. Great auctions feel like a rising arc, not a series of disconnected moments.

3. Treat production like an investment

Lighting, sound, and staging play an important role. Don’t wait until the last minute to think about them! Guests must be able to clearly hear the auctioneer, see the screens, and understand the bidding increments. A strong professional auctioneer who knows how to read the room is worth their fee ten times over. Don’t skimp here. I once ran an auction using a lovely volunteer who was great in rehearsal, then had too much to drink during the event. It was a disaster, with the crowds’ energy shifting to simply be embarrassed for her. A volunteer auctioneer almost never has the professionalism, rhythm, timing, or room-reading skill required. Just make sure to prepare them so they can simultaneously elevate competition while staying aligned with mission messaging.

Mission moments: the heartbeat of the event

One of your most powerful planning decisions is where, and how, to place your mission in the program flow. People bid more generously when they feel emotionally connected to the cause. A well-crafted mission moment (e.g., a short video, personal story, or brief speech from someone impacted) can transform bidding from a “fun purchase” into an opportunity to make a difference. And when timed correctly, it sets up a successful Fund-a-Need conclusion to your event. When the mission is centered, bidders feel proud of their generosity. And proud generosity fuels bidding wars.

Food, speakers, and ambience: the amplifiers

These supporting elements matter, as they either support or sabotage your carefully planned energy arc.

Food

You don’t need a Michelin-star menu, but you do need efficient service. Long gaps between courses, slow wine pours, or awkward table logistics can deaden energy and cool the temperature in the room. Your seating chart matters too. Put people together who will enjoy each other’s company.

Speakers

Short is powerful. Long, wandering remarks drain energy. Great events coach speakers to be concise, heartfelt, and mission-focused. Give speakers a time limit, and rehearse them beforehand.

Venue and layout

Too much distance from the stage, too many obstructed views, or a long, cavernous room dilutes engagement. Lighting that feels too bright or too dim shifts the emotional tone. Small details accumulate into big effects.

The whole is greater than the sum of its parts

When a live auction underperforms, the reasons are usually predictable:

• Too many items
• Weak program flow or poor timing
• Lack of emotional buildup
• Volunteer auctioneers instead of professionals
• Mission moments that fail to connect
• Technical or production issues
• Guests who aren’t primed for generosity

The most successful auctions work because someone took the time to intentionally choreograph the entire experience. The thoughtful integration of all these elements is the real secret sauce.

— Charity Clairity (Please use a pseudonym if you prefer to be anonymous when you submit your own question, like “Seeking the Secret Sauce” did.)

How does your organization elevate a live auction? Let us know in the comments.

The post What Elevates A Live Auction From Good To Great? appeared first on Bloomerang.

Dear Charity Clairity,

My son and I want to start a fundraiser for two cancer-related charities. We tried to have an actual fundraiser event but sadly it did not work out. I’d like to now just do an online donation drive. Ideally I’d like to use an app or service to hold the money until we’re ready to donate it directly to the organizations. How can we best achieve this?

— In the Dark

Dear In the Dark

There are several ways to go about this. Your choice somewhat depends upon (1) whether your donors want tax deductions and individual tax receipts, or (2) whether they’re content to simply give regardless of tax deductibility. Let’s look at the pros, cons, compliance considerations, and practical steps for setting up your fundraiser under both scenarios.

1. If your donors care about tax deductions

When donors want or expect tax-deductible receipts, you must route their contributions through a bona fide 501(c)(3) organization, and not through your personal bank account, PayPal, Venmo, or any pooled holding account — unless that account is legally owned by a charity. U.S. law is very specific:

• Only the organization that legally receives the donation can issue the receipt.
• Donations made to individuals are not tax-deductible, even if you later give the money to charity.

You have two strong options here: fiscal sponsorship or charity-hosted fundraising pages.

(1) Fiscal sponsorship: The easiest way to pool tax-deductible donations

If you want to collect donations in one place, tally a total, hold the funds temporarily, and then distribute them to two cancer nonprofits, fiscal sponsorship is the cleanest and most professional approach.

What is fiscal sponsorship?

A fiscal sponsor is an established 501(c)(3) that agrees to accept donations on behalf of a project (in this case, yours). They legally own the funds until they grant them to your chosen nonprofits. Many people think of fiscal sponsors as “nonprofit umbrellas” that extend their tax-exempt status to projects aligned with their mission.

How it works in practice

1. You apply to a sponsor or set up a simple agreement (Memorandum of Understanding).

2. The sponsor creates either:

• A dedicated project account, or
• A simple donation page for your fundraiser.

3. Donors give directly to the sponsor.

4. The sponsor handles receipts, accounting, and holding the funds.

5. When you’re ready, the sponsor grants the pooled funds to the two cancer organizations you’ve selected.

Why fiscal sponsorship works so well for multi-charity fundraisers

• Donors receive tax-deductible receipts right away, with no ambiguity.
• No funds pass through you personally, which avoids tax complications and builds trust.
• You can pool everything and present a unified fundraising total, something donors may appreciate.
• Sponsors are experienced at managing donor-designated gifts, reporting, and compliance.
• Your fundraiser appears more official, which can increase giving.

What it costs

Most fiscal sponsors charge a 5–10% administrative fee. This covers accounting, monitoring, and processing donations. The fee should be part of your written agreement.

Who offers fiscal sponsorship?

• Community foundations
• Nonprofits focused on health or social impact
• Organizations listed in the National Network of Fiscal Sponsors or the Fiscal Sponsor Directory

If you have a nonprofit you already support who you think may fit the bill, it’s a good idea to approach them first and see if they’d be amenable to serving as your sponsor. If you’re already a donor or volunteer there, they may agree to a minimum fee.

(2) Charity-hosted fundraising pages: A simple, direct, low-effort option

If your two chosen cancer-related nonprofits already use modern fundraising platforms, they may create peer-to-peer or team pages for you.

How this works

• Each nonprofit creates a special fundraising page for your campaign.
• You share the links with your community.
• Donors click the page corresponding to the charity they wish to support.
• The charity receives donations directly.
• The charity issues receipts automatically.

Pros

• No admin work for you beyond promotion.
• Donors get automatic receipts.
• You’re not handling money at all, eliminating compliance risks.
• Easy to set up if the nonprofit supports peer-to-peer campaigns.
• Automatic tracking of total raised per page — the platform shows the running total and progress toward goals.

Cons

• You cannot combine totals across two separate fundraising pages automatically; this must be done manually.
• The nonprofits must agree to create the pages—and not all will.

2. If your donors don’t care about tax deductions

If your donor base is small, personal, informal, or simply unconcerned about deductibility, you can gather contributions into a single shared account and later donate the total to the charities of your choice. Transparency is essential to protect trust. Donors must understand their gift is not tax-deductible because they are giving to you, not a charity. You, in turn, pledge to donate the pooled funds to charity.

Saving the pooled funds in a segregated account

Alas, there are no good apps of which I’m aware that will accomplish this for you. A start-up called Braid looked promising, but dissolved in 2023. GoFundMe is an option if you’re raising for a single charity, but will not work if you have multiple beneficiaries.

The only truly compliant option is a segregated personal bank account (or sub-account) dedicated to this purpose. This works for bookkeeping, but the responsibility and risk fall on you. This approach works when:

• Donors personally know and trust you.
• The campaign is small and informal.
• No one expects a tax receipt.
• You are transparent that the money flows through you.

Directly encourage donors to give to the charities on their own

Another low-complexity path is simply to encourage donors to give directly to each charity via each of their official websites.

• You provide donors with the two official donation links.
• Donors receive receipts directly from each organization.
• There are no administrative fees

The only downside is you cannot pool the donations into one gift. And if you care about reporting back to donors regarding how much you collectively raised, the only way to accomplish this is to ask donors to self-report the size of their donation so you can track total giving. Realistically, a lot of your donors will want to keep the size of their donations anonymous.

Which path should you take? A simple guide

If donors want tax deductions:

Best choice: Fiscal sponsorship

• Pools funds
• Keeps everything compliant
• Sponsor issues receipts
• Most professional-looking
• Slight administrative fee

Good Alternative: Charity-hosted fundraising pages

If a charity uses a P2P platform, and you create a personal fundraising page under their umbrella:

• All donations are made directly to the charity
• Donors receive their own tax receipts from the charity
• You get a visible tally of total money raised
• You never touch the funds
• You can easily show your progress toward a goal

If donors don’t need or care about tax deductions:

Best choice: Set up your own segregated bank account.

• Easy to set up
• Lets you pool collected funds so you can report back on the total to your donors
• No tax deduction (true either for donors or you personally, as money collected from others, ethically, is not your charitable gift

Final thoughts

Whether your donors prioritize tax deductions or simply want to support a meaningful cause with no fuss, you can choose a structure that fits the scale, tone, and goals of your fundraiser.

• If your priority is pooling the money and presenting a unified gift, fiscal sponsorship is the most flexible, credible, and compliant option.
• If your priority is simplicity, charity-hosted pages or a segregated bank account may work best.

Hopefully I’ve been able to shine a bit of a light so you’re no longer in the dark.

— Charity Clairity (Please use a pseudonym if you prefer to be anonymous when you submit your own question, like “In the Dark” did.)

Have you run an online fundraiser for multiple charities? Let us know in the comments.

The post What’s The Best Way To Run An Online Fundraiser For Multiple Charities? appeared first on Bloomerang.