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Don’t Add Another Event Until You Read This

6/15/2025

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Don’t Add Another Event Until You Read This

I get it – events feel like momentum. They’re visible. They’re exciting. And if your board or staff is worried about revenue, the first suggestion is often:

 “What if we did another fundraiser?”

But here’s the thing I wish more nonprofits understood:

​More events aren’t always the solution. Sometimes, they’re the problem.


Events are expensive – even when they "make money"

Sure, your spring gala might net $12,000 after expenses. But how many staff hours did it take to plan? How many other fundraising activities were delayed or abandoned in the lead-up?

Did it bring in new major donors or long-term monthly supporters? Or was it mostly your usual crowd eating chicken and bidding on a silent auction basket?
​
I’m not saying you should never do events. But I am saying you need to know what each one is actually doing for your mission – and at what cost.

I have strong feelings about 5Ks and golf tournaments – and here’s whY

Because they trick you into thinking you’re fundraising, when what you’re really doing is facilitating a transaction.

Participants are there to run, or to play golf. They’re not connecting to your mission. They're not hearing stories of impact or seeing their role in your work. They’re getting a t-shirt and a swag bag – and then they’re gone.
​
You might as well be selling donuts on the street corner.

So how do you know if an event is actually worth it?

Ask yourself:
  1. What’s the ROI?
    What are you really raising after you subtract hard costs and staff time? If it’s costing $0.85 to raise a dollar, that’s not a fundraiser – it’s a stress-inducer. And occasionally events can flip and end up being over a dollar to raise a dollar – in other words, losing money.
  2. What’s the point?
    Are you trying to raise money? Attract new donors? Steward existing ones? Events with no strategic purpose are a time-sink. Be honest about your goals.
  3. Who is coming – and are they giving again?
    If most attendees are one-time supporters who disappear after dessert, the event might be more flash than follow-through.

What if we have an event and I can’t cancel it?

​Now, if you’ve got an event that’s locked in – maybe it’s tradition, or there’s a sponsor you don’t want to lose – make it count. Infuse as much mission into that event as you possibly can. Don’t just entertain – connect. I once went to a Broadway revue fundraiser for a group supporting teens in foster care, and in between each number, they played short audio clips of the teens sharing their stories. It was powerful. I still remember those voices. That’s what sticks. And that kind of emotional resonance is what opens the door for deeper engagement. Pair that with a strong follow-up plan – something that nurtures those attendees beyond their ticket or entry fee – and you can turn one-time guests into long-term donors who truly understand and care about your work.

The Hidden Cost No One Talks AbouT

​Every event on your calendar takes time – time your team could be spending building real relationships with major donors, deepening stewardship, or crafting a compelling campaign that brings in five- or six-figure gifts. That’s the real opportunity cost. It’s not just the hours spent on centerpieces or silent auction items – it’s the connections you didn’t make, the asks you didn’t have time to prep, the impact that got delayed because your best energy was tied up elsewhere. If you want transformational gifts, you need the bandwidth to pursue them. Events rarely give you that. A smart plan does.

How to Stop Letting Events Run Your StrategY

In my Smart Start Fundraising System, we assess your fundraising “vehicles” – the methods you use to reach donors. Events are just one of many vehicles. And often, there are smarter, leaner options with better ROI.

But the real magic happens when you zoom out and create a Plan – one that aligns your fundraising activities with your goals, capacity, and budget. Not every organization needs a gala. Some need a good direct mail strategy. Others need better donor journeys or stronger partner engagement.

When your events support your overall plan instead of driving it, everything clicks.

Before you plan another event…

Ask yourself: Is this the best use of our time, energy, and budget?

And if you’re not sure?

💡 That’s exactly what my course, The Smart Start Fundraising System, helps you figure out.

We walk through your fundraising menu, evaluate the ROI of each activity, and build a plan that plays to your strengths – without burning your team out.

🎯 Enrollment is open now!
You’ll get instant access to the training, tools, templates, and bonuses – plus 5 CFRE credits.

👉 [Click here to enroll today] and start building a smarter, more sustainable fundraising plan.

Because you deserve a fundraising strategy that works as hard as you do.

Cheers!
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​PS - I hope you’ll continue the conversation by subscribing to Real Deal Fundraising. When you subscribe, you’ll get my e-newsletter, which includes the best articles on fundraising, productivity, and cool stuff every week. The whole thing is curated awesomeness as well as freebies like webinars, instructional videos, and whatever else I can put together to be helpful to you!
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If you liked this… 
  • Beautiful on a Budget: How to Design Stunning Fundraising Event Decor for $250 or Less
  • Why Most Fundraising Plans Fail (and How to Build One That Doesn’t)
  • The Problem with Totes and T-Shirts: Why Freebies Can Undermine Fundraising
  • My Exhaustive Event Planning Checklist
  • Phonathons Are STILL Not Dead – Busting the Biggest Myths About Calling Donors
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Why Most Fundraising Plans Fail (and How to Build One That Doesn’t)

6/1/2025

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

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

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

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

1. The plan is not aligned with real capacity.

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

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

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

2. The plan is disconnected from results.

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

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

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

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

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

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

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

So what does a successful fundraising plan look like?

It’s clear. It’s doable. And it starts with what I call the MVPPP Framework, which is part of my Smart Start Fundraising System course:
  • Message – Your compelling case for support
  • Vehicles – The channels you’ll use to reach donors
  • Prospects – Who you’re asking
  • Partners – Who’s helping you ask
  • Plan – Bringing it all together with structure and accountability
This framework works whether you’re a one-person shop or leading a full advancement team. It’s not about doing everything. It’s about doing the right things on purpose.

Want to build your best fundraising plan yet?

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

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

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

Take a look, see what’s inside, and get started at your own pace:
👉 Take a closer look here.
Because passion doesn’t build a fundraising plan. But clarity? That’ll take you the distance.
​
Cheers!
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​PS - I hope you’ll continue the conversation by subscribing to Real Deal Fundraising. When you subscribe, you’ll get my e-newsletter, which includes the best articles on fundraising, productivity, and cool stuff every week. The whole thing is curated awesomeness as well as freebies like webinars, instructional videos, and whatever else I can put together to be helpful to you!
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​If you liked this…

  • Nonprofit Productivity and Time Management
  • Goals versus Projections: What’s the Difference?
  • Building Fundraising Projections for your New Fiscal Year
  • The Responsibility Calendar: The Key to Making Your Fundraising Plans a Success
  • Who’s Afraid of Burnout and Turnover? You Should Be.
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The Problem with Totes and T-Shirts: Why Freebies Can Undermine Fundraising

5/18/2025

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The Problem with Totes and T-Shirts: Why Freebies Can Undermine Fundraising

My grandfather wasn’t a big donor. He only gave to a handful of causes in his lifetime. But there was one organization that always stood out: St. Jude Children’s Research Hospital. He gave faithfully – moved by the emotional weight of their television commercials. The stories got him every time.

But even though he was already giving, they kept sending him address labels. Over and over again.

At the time, I didn’t get it. Why send him stuff he didn’t ask for when he was already clearly connected?

Years later, working in fundraising myself, I learned what was going on. Those labels weren’t a thank-you. They were part of the ask. A fundraising tactic. A subtle nudge rooted in the psychology of reciprocity: we gave you something, now give something back.

And while it might work once, that kind of giving rarely sticks.

The truth is, these built-in freebies – address labels, calendars, stickers – don’t deepen connection. They dilute it. They train donors to expect something with every letter, and more importantly, they shift the focus away from the mission.
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I still wonder: would my grandfather have kept giving without the commercials? Maybe not. But I know this for sure – it wasn’t the address labels that made him care.

When Fundraising Starts to Feel Like a Loyalty Program

We’ve all seen it – and some of us have inherited files full of it:
  • Calendars that take all year to design
  • Sheets upon sheets of address labels
  • Stickers that end up in the recycling bin
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These “free” items are anything but free. They come at a cost – not just to your budget and your time, but to your donor relationships.

Why These Kinds of Premiums Can BackfirE

Let’s get practical. Including giveaways in your appeals may seem harmless, but it creates three major problems:

1. It sets the wrong tone.
You’re not building connection – you’re mimicking a subscription box. That’s not what we’re here to do.

2. It costs more than you think.
Printing, shipping, design, fulfillment – it adds up fast. Those funds could go straight to your mission.

3. It attracts short-term, low-retention donors.
This is the biggest problem. Donors who give because of a trinket are less likely to renew, upgrade, or become champions for your cause. You want committed supporters, not one-time transactions.

And There’s a Legal Catch, Too
​

Let’s talk taxes. When you include a premium with your appeal, you risk turning that gift into a quid pro quo contribution – where only part of the donor’s gift is tax-deductible because they received something in return. To avoid that, the item has to be of “insubstantial value” – meaning so cheap it’s practically worthless. And if the gift is that insignificant, why bother sending it at all? You’re adding printing, packaging, and postage costs for something that can’t carry real meaning or message weight. It’s a logistical headache with no lasting return.

What Donors Actually WanT

Here’s what’s wild: Most donors don’t even want the stuff. They want to be moved. They want to know their gift means something.

That’s where Near, Dear, and Clear comes in:
  • Near: They feel close to the cause.
  • Dear: The mission matches their values.
  • Clear: They understand what their gift will do.
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No label sheet in the world can deliver that. But a compelling story can.

When Thoughtful Tokens Do Make Sense

This isn’t a full-on war against every branded item. There’s a time and place – but intention matters.
  • Give tokens in stewardship, not acquisition.
  • Let them be surprises, not bait.
  • Make sure they reflect your mission, not just your logo.

A bookmark made by a student in your afterschool program? That’s beautiful.
A bulk-ordered mug with your fiscal year slogan? Probably unnecessary.
​
Would you give your best friend a water bottle to say thank you?
Or would you write them a heartfelt note of thanks?

So What Should You Do?

If you’re stuck in a cycle of sending “stuff” or trying to break the premium habit, here’s where to begin:

1. Lead with stories.
Make your appeal emotionally rich and mission-focused. Don’t let a keychain carry the message.

2. Map the full donor journey.
Gifts shouldn't unlock access to your best content. Welcome everyone into the story, not just your VIPs.
​
3. Test it.
Try a premium-free version of your next appeal and track the results. You might find your message carries more weight on its own. And don’t forget to track retention of those new donors acquired (with premiums and without) in the next year of giving.

Fundraising That Feels Better (and Works Better)

The truth is, you don’t need gimmicks to raise money. When you lead with purpose, your donors feel it. And they’ll stick around.
​
Mission-centered messaging doesn’t just build trust – it builds staying power.

Ready to ditch the swag and write stronger appeals that actually retain donors?

The Smart Start Fundraising System will show you how. I break down what motivates giving without resorting to trinkets and help you build a complete plan grounded in what matters.

[→ Get on the waitlist now or check out the course here.]
​
Cheers!
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​PS - I hope you’ll continue the conversation by subscribing to Real Deal Fundraising. When you subscribe, you’ll get my e-newsletter, which includes the best articles on fundraising, productivity, and cool stuff every week. The whole thing is curated awesomeness as well as freebies like webinars, instructional videos, and whatever else I can put together to be helpful to you!
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If you liked this…
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  • Beautiful on a Budget: How to Design Stunning Fundraising Event Decor for $250 or Less
  • 4 Power Questions to Ask Donors That Build Rapport and Lead to Major Gifts
  • What With Love, Meghan Can Teach You About Donor Relations
  • Culture of Philanthropy Check-Up
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Phonathons Are STILL Not Dead – Busting the Biggest Myths About Calling Donors

4/27/2025

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Phonathons Are STILL Not Dead – Busting the Biggest Myths About Calling Donors

Every few months, another university quietly kills its phonathon. And just like that, inboxes everywhere light up:
  • Do we even need calling anymore?
  • Isn’t this outdated?
  • Should we just move everything online?

​Let’s set the record straight.

Phonathons are not dead. And many of the arguments used to declare their demise are based on myths – not real data, not field experience, and definitely not what’s actually happening on the ground at most institutions.
So let’s bust some of the biggest myths I hear over and over again:

​Myth #1: “Nobody picks up the phone anymore.”

Reality: Pick-up rates (contact rates) are absolutely impacted by things like caller ID, time of day, area code, and list segmentation. But even in the post-pandemic world, institutions are still having real, quality conversations with alumni, parents, and friends. When done right, phone outreach still delivers contact, conversation, and conversion.

In fact, one partner institution recently doubled their call completion rate within a single year, simply by improving their strategy – things like making more attempts per record, using smart list management, and building trust through clearer caller ID.

The problem isn’t that people don’t pick up. The problem is we’ve stopped giving them a good reason to.

Myth #2: “We don’t need phonathon anymore.”​

Reality: This one usually comes from someone who hasn’t worked a call shift or analyzed the pipeline lately.
If you’re serious about long-term fundraising success, you need phone outreach. Here’s why:
  • Data Integrity: The call center is often the only channel regularly updating email addresses, employment info, and demographic data straight from the source.
  • Lead Generation: Trained callers can surface major and planned gift prospects who would never flag on your radar otherwise.
  • Pipeline Health: If you’re not engaging younger donors now, good luck finding them when they turn 50 and have capacity.
  • Scalability: Personal donor contact at scale is rare. The phone still offers that sweet spot between high-touch and high-volume.

​One institution I advised recently saw a huge bump in average gift size – up over 50% – and their calling center is now on track to exceed their full fiscal year results any day now. You can get great ROI from calling… if you treat it like the professional fundraising channel it is.

​Myth #3: “The phonathon loses money (or only breaks even).”

Reality: It’s supposed to break even – or come close. Phonathon isn’t just about the immediate dollars in the door. It’s about the long game: donor reactivation, new donor acquisition, pipeline building, and massive volumes of updated data. That work fuels years of future fundraising success.

If your phonathon is consistently losing money, the issue usually isn’t the channel – it’s the execution. Maybe your manager is under-supported. Maybe you’ve got outdated or clunky software that makes it impossible to track results or process credit cards smoothly. Maybe you aren’t calling enough to make your fixed costs worthwhile.
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But let’s be clear: the blame doesn’t lie with the callers – or with the channel itself.

​​Myth #4: “Call center manager is just an entry-level gig.”

Reality: Running a call center is one of the hardest jobs in advancement. It demands a unique skill set: donor communication, hiring and training, shift logistics, data reporting, budget management, and tech troubleshooting – just to name a few.

And yet, too often this role is underpaid, undervalued, and handed off to someone with no real support or path for growth.
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Here’s the truth: If you want your phonathon to succeed, you need a strategic leader managing it. When that happens, everything gets better – culture, results, retention, and ROI.

​Myth #5: “We’ll just go multichannel instead.”

​Reality: I support multichannel fundraising 100%. Donors need options. But cutting your call center with no plan to replace what it actually does isn’t innovation – it’s just short-sighted.

If you eliminate phone outreach, here’s what you’re walking away from:
  • High-quality data updates
  • Scalable relationship-building
  • Lead generation for your major and planned gift teams
  • A training ground for your future advancement professionals

​Ask yourself: What’s the plan to make up for all of that?

If your phonathon isn’t performing, it’s not because the channel is dead. It’s probably due to low volume of work, poor strategy, clunky systems, undertrained callers, or a lack of clear goals. All of those are fixable.

That’s what I help institutions do every day – reset, retool, and rebuild programs that actually work.

If you’re ready to stop chasing trends and start making smart decisions about your donor outreach, let’s talk. Whether you need a strategic audit, caller training, or a full-scale turnaround, I’ve got your back.

Bottom line: Phonathon isn’t broken. The way it’s managed might be.


And with the right approach, calling still works – and it works beautifully.

Cheers!
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PS - I hope you’ll continue the conversation by subscribing to Real Deal Fundraising. When you subscribe, you’ll get my e-newsletter, which includes the best articles on fundraising, productivity, and cool stuff every week. The whole thing is curated awesomeness as well as freebies like webinars, instructional videos, and whatever else I can put together to be helpful to you!
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PPS – If you need to freshen up your phonathon, be sure to check out my book Successful Fundraising Calls: A Phonathon Scripting Workshop available through Academic Impressions and my e-book How to Staff Your Phonathon Super-Fast available to download instantly here in the Real Deal Fundraising Store.
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If you liked this… 
  • In Depth: Is Phonathon Really Dead?
  • In Depth: The Five Pillars of Annual Giving
  • In Depth: Rethinking How we Train Phonathon Callers
  • 10 Traits All Former Phonathon Callers Share
  • Phonathon During a Pandemic: Case Study from Western Carolina University
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New Fiscal Year Approaching – Are You Ready for the ride?

4/16/2025

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New Fiscal Year Approaching – Are You Ready for the Ride?

Jessica here! Today, I’m thrilled to welcome a guest post from my friend and colleague, Melissa Derrick Adair, who brings a wealth of experience and insight. I like to introduce Melissa as the most competent person I’ve ever met, especially since she changed my life by teaching me about the “filter by color” function in MS Excel. 😊 Her post below is packed with practical wisdom and actionable tips – I know you’re going to love it.

Have you ever thought that annual giving is just a classic roller coaster? You might think I’m referring to thrill you get from the ride – but I’m thinking deeper about the science behind the ride.
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Roller coasters use a combination of gravity, inertia and momentum to propel riders through the track. If you look closely, the biggest hill is first. This is called the lift hill. The lift hill uses a chain or other mechanism to pull the cars to the top. Take yourself back to your last roller coaster ride. Do you remember the excitement and anticipation you felt slowly creeping towards the top? When you reach the top of the lift hill, the train is filled with potential energy – in fact the height of that hill has a direct impact on the rest of the ride. As the train tips over the top of the lift hill, gravity, momentum and inertia take over.

IS YOUR LIFT HILL TALL ENOUGH?

For a rollercoaster, the kinetic energy gained from the initial descent dictates how the rest of the ride will go. If the lift hill is too short, there will not be enough energy built up for the cars to make it through the entire ride.

In annual giving, the three months before the fiscal year start is our lift hill. This is the time where you should be looking ahead towards the next fiscal year and setting your plan. Setting the plan now allows time to ensure that your strategy can make an impact starting on day 1. Ask yourself:
  • What key initiatives do I want to anchor my fundraising calendar? A good strategy typically includes a key initiative for each quarter (i.e. initial donor renewal, calendar year end, giving day, fiscal year end, etc…)
  • Do I have the tools necessary to implement my strategy? The pre-fiscal year period is a great time to ensure that you will have the platforms and vendors needed to implement your vision.
  • Do I have the staff needed to execute my vision? If you are adding new initiatives or expanding initiatives, you may need additional personnel or expertise to successfully implement.

DO YOU HAVE A GOOD DESIGN?

Have you ever noticed how a roller coaster doesn’t just have a series of loops? It has turns, slopes and other elements to ensure that as the train moves through the track it can build up more energy. In annual giving, your plan should be like the rollercoaster and include more than just solicitation.
  • Be Prompt with Stewardship. Thank your donors quickly to reassure the donor that their gift was received and appreciated. Always include a quick thank you (like an immediate email). You may also want to have larger “thank a donor” campaign included as part of a key initiative.
  • Always be Cultivating. In annual giving, it is all about cultivation. Our goal is to influence donor behavior, encouraging them to climb the donor pyramid with increasing and repeating support. A key component of this is cultivation. Your donors should receive outreach intended to engage and keep them connected with your mission. You should ensure your magazine, website and social media also include strategically timed gifts-at-work examples.
  • Space It Out. To avoid donor fatigue, be mindful of the donor view and ensure your plan includes adequate spacing between solicitation appeals to the same audience. When planning your 1st quarter initiatives, think about the timing and how closely that may match up with any fiscal year end audiences.

ARE YOUR PROSPECTS READY TO RIDE?

Another key part of any roller coaster ride is ensuring that all the passengers are ready for the ride. Amusement park attendants do final checks to ensure passengers are secure. As you look ahead to the next fiscal year, be sure that your prospects are ready for your outreach. Studies continue to show that fundraising campaigns utilizing multiple channels of outreach create more opportunities for potential donors to connect with your organization and have higher rates of conversion. Now is a great time to ensure that your prospects will be able to receive your omnichannel outreach.
  • Enrich The Data. Send key prospects to data enrichment services to capture and verify demographic information like address, email and cell phone.
  • Collect Donor Preferences. Ensure online donor forms and event registration forms include areas to provide preferred contact information as well as opt-in by communication channel.
  • Update your CRM. Ensure demographic updates received through returned mail, email correspondence or phone outreach are updated in your CRM. Ensure your outreach CRM is compliance ready with spaces to store opt-in preferences by channel.

When I started out in annual giving, the running joke was that once the fiscal year flips, you wipe the slate clean and start all over again. But after two decades of leading annual giving fundraising strategy, I’ve learned that it is far from the truth. What you do in the final quarter of your fiscal year has a direct impact on the next year’s results. So, as you are looking ahead to next year, remember the importance of a good design. Have a strong initial climb with a mixture of loops, turns and slopes throughout the path.  And always ensure your passengers are ready for the ride!

​Melissa Derrick Adair

Melissa is an innovative fundraising leader with 25 years of proven success driving fundraising strategy through omnichannel direct marketing approaches. She has collaborated with hundreds of non-profits, primarily in Higher Education, Greek Life and healthcare. Her specialty is developing comprehensive, data-driven strategies for prospect identification, cultivation, solicitation and stewardship. Melissa served as the chief fundraising strategist for Ruffalo Noel Levitz for more than a decade. She is known across the industry for her expertise, particularly in data-driven strategy, using language to optimize fundraising results and texting compliance. Melissa earned a B.A. from the University of Georgia and an M.B.A from Mississippi State University.
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P.S. If you found this post helpful, be sure to subscribe to my blog so you don’t miss more content like this. And while you’re at it, check out Melissa’s work and sign up for her newsletter too – you’ll want her voice in your inbox.
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If you liked this… 
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  • Culture of Philanthropy Check Up
  • Planning for the Unexpected
  • The Missing Piece of Your Strategic Planning: A Benchmarking Study
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4 Power Questions to Ask Donors That Build Rapport and Lead to Major Gifts

4/12/2025

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4 Power Questions to Ask Donors That Build Rapport and Lead to Major Gifts

As a college freshman, I responded to an announcement on the Honors College listserv (that may give you a clue how long ago this was) for a job talking on the phone to alumni. I thought this was a dream job. All I needed to do was talk to people and make money. As an extrovert who had been trained by her manners-minded Southern mother to “make good conversation” my whole life, I had no qualms about keeping the conversation going and making folks like me on the phone.

After becoming a student supervisor in the call center, I quickly realized that most folks needed more structure and examples of what to say to have success at building rapport in conversation. It was indeed an art. I’ve now spent a couple of decades helping to systematize and teach the process of successfully talking to someone new. Over the years, I’ve learned that the secret to great conversations is the same whether you're a college student, a seasoned fundraiser, or even a 7-year-old girl chatting with her great aunt. It all comes down to asking the right questions.

Questions help us connect and connecting with a donor is essential before you ever ask for a gift. The right questions remove roadblocks and pave the way for a strong, lasting relationship between the donor and your organization. People give to people they like. As a fundraiser, you’re the bridge connecting the donor to your institution. Your goal in a discovery visit is to listen, learn, and understand what truly motivates them.
​
Bad rapport-building does more harm than good. Questions should always stimulate a lively back and forth. Think dialog, not monologue. The best questions also extract valuable information, make the donor feel appreciated, and naturally lead to the next step in cultivation.
​
Here are my favorite questions to ask during a discovery visit:

1. How did you become involved with our organization (or mission)?

This simple yet powerful question invites the donor to share their personal story. Did they have a life-changing experience? Was a loved one impacted? Did they connect with your work through a friend or colleague? Understanding their “why” gives you insight into what matters most to them and helps tailor your approach moving forward.

2. What are your philanthropic priorities, and where does our organization fit in?

This question helps you understand where you stand among the causes they support. Are you a top priority, or do they view your organization as one of many they give to? It also gives you a glimpse into their overall generosity and what drives their giving decisions.

3. Who else should I be talking to?

Your donors often have strong networks of like-minded individuals. Asking this question uncovers potential new prospects and champions for your cause. It also signals that you respect their influence and see them as more than just a financial contributor.

4. How do you prefer to communicate and stay involved?

Some donors want regular updates, while others prefer to give quietly without much engagement. Some enjoy receiving physical mail, while others prefer a quick email or social media updates. Understanding their preferences ensures you’re communicating in a way that resonates with them, making cultivation and stewardship more effective.

The key to a successful discovery visit isn’t just asking great questions – it’s truly listening to the answers. Take notes, follow up thoughtfully, and use what you learn to deepen the relationship. Building real rapport makes every future conversation easier and more meaningful. When the time comes to ask for a gift, you’ll know exactly how to approach it in a way that aligns with their motivations and values.

What’s your favorite discovery question to ask donors? Drop it in the comments—I’d love to hear what works for you!
​
Cheers!
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​PS - I hope you’ll continue the conversation by subscribing to Real Deal Fundraising. When you subscribe, you’ll get my e-newsletter, which includes the best articles on fundraising, productivity, and cool stuff every week. The whole thing is curated awesomeness as well as freebies like webinars, instructional videos, and whatever else I can put together to be helpful to you!
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How to Build a Philanthropy Calendar That Drives Digital Donations

4/6/2025

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How to Build a Philanthropy Calendar That Drives Digital Donations

Every year in November, National Philanthropy Day would roll around and I’d sigh and say to myself: “Next year, I’m going to be ready.” I’d swear that I would plan ahead, write the emails, prep the social media graphics, and really celebrate the day with our donors.

Then February would roll around and I’d see adorable Valentine’s Day posts from other schools – “We ❤️ our donors!” – and then again on St. Patrick’s Day – “We’re lucky to have you!” And I’d think: Next year. Definitely next year.

Finally, last summer, I had had enough.

We blocked time, pulled out the project management software, and started building a full philanthropy calendar – complete with stewardship moments, giving day content, and awareness-based messaging. And now? We don’t miss those chances to talk about philanthropy. We show up with intention. And the best part? Once this year is done, we’ll already have an entire year’s worth of content ready to refresh and reuse next time around.

Honestly – it’s one of the best things we’ve done.

Why every nonprofit needs a philanthropy calendar

If you’re in higher ed advancement (and especially if your fiscal year starts July 1), now is the time to build your calendar for the next year – before you're juggling events, campaigns, and year-end appeals.

When you plan your giving-focused content in advance, you give your team the time and space to tie fundraising to moments that matter – national observances, cause-based awareness days, and your own institutional milestones. You stop scrambling. You start seeing results.
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Digital fundraising isn’t just about being visible. It’s about being intentional.

What kinds of dates belong on your calendar?

Start with the obvious ones: your founding date, commencement, homecoming, or the birthday of a beloved former president with a named scholarship fund. Then build out from there.

Here are a few ideas to get you thinking:
  • World Gratitude Day (Sept 21) – a lovely touchpoint to show donor appreciation
  • National Philanthropy Day (Nov 15) – a perfect moment to thank donors and highlight giving’s impact
  • National Estate Planning Awareness Week (3rd week of October) – opens the door for gentle legacy giving education
  • National Scholarship Month (November) – great for student stories, recruitment, and stewardship
​
The more your calendar reflects your organization’s story, the more it will resonate with your community. These aren't throwaway posts – they’re meaningful messages that reinforce your mission and make giving feel timely and personal.

Tools to make it happen

Use scheduling tools like Buffer, Later, or Hootsuite to plan ahead. Build Canva templates you can reuse year after year. And make sure someone on your team is tracking which content types drive engagement – not just likes, but actual clicks, gifts, or email signups.

Once you get into the rhythm of planning ahead, the content starts to build on itself – and pretty soon, you're not starting from scratch every year. You’re refining, reusing, and getting stronger with every cycle.
​
You don’t need a massive team or a fancy agency. Just a plan, a few tools, and a commitment to showing up for your donors in meaningful ways.

Need a head start?

I’ve done the heavy lifting for you  –  get your free Year-Round Philanthropy Calendar with dates organized by theme and by month and ideas for implementation.
​

This curated list of dozens of dates is tailor-made for fundraising, stewardship, and storytelling – including giving days, mission-aligned observances, and the quirky holidays that make for surprisingly great donor content.
Get Your Free Year Round
​Philanthropy Calendar here
Just drop your email, and you’ll be able to download it instantly. Easy.
​
One calendar. A year’s worth of opportunities to show up, connect with your donors, and tell the story of your mission.
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What dates are important for your messaging and content throughout the year? Let me know in the comments.
​
Cheers,
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​PS - I hope you’ll continue the conversation by subscribing to Real Deal Fundraising. When you subscribe, you’ll get my e-newsletter, which includes the best articles on fundraising, productivity, and cool stuff every week. The whole thing is curated awesomeness as well as freebies like webinars, instructional videos, and whatever else I can put together to be helpful to you!
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Cut Through the Clutter: Focus on the Two Planned Giving Options That Really Work

3/29/2025

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Cut Through the Clutter: Focus on the Two Planned Giving Options That Really Work

Most fundraisers hesitate to talk about planned giving because they feel like they need to be experts in trusts, annuities, and tax law. The good news? You don’t. You just need to focus on two simple, flexible options that work for nearly everyone.

Planned giving is a powerful way for donors to leave a lasting legacy, but the sheer number of options can create confusion and hesitation. Each option comes with its own set of benefits and complexities. While these options certainly have their place, trying to promote all of them can dilute your message and overwhelm your supporters.
​
In today’s post, I’m making a case for simplicity. Instead of trying to master every planned giving option, focus on the two that are most common, simplest, and most flexible for donors: bequests and beneficiary designations.

The Two Simple, Flexible Options

After years of experience, it’s clear that the majority of nonprofit organizations would benefit most from sticking with two straightforward approaches: bequests and beneficiary designations.

1. Bequests
Bequests are perhaps the simplest form of planned giving. They allow donors to include a gift to your nonprofit in their will. Not only are bequests easy for donors to understand, but they also require minimal ongoing effort on your part once the gift is in place.

Why Bequests?
  • Simplicity: Most donors already have a will in place or plan on making one at some point, so adding your organization as a beneficiary is a small change with a big impact. Bequests are also revocable, meaning they can be changed or removed at any time (which gives many donors peace of mind).
  • Flexibility: Donors can decide how much to give and even set up multiple bequests for various causes. If a donor already has a will in place, they can simply file a codicil to their will (kind of like an amendment) to add a bequest.
  • Long-Term Impact: Bequests help ensure that your mission continues well into the future. Most donors can afford to give more out of their lifetime assets than is possible for them out of their income, meaning bequests are often much larger than annual gifts.
To make it even easier, consider offering sample bequest language. I’ve developed a straightforward template that organizations can use to guide donors in drafting their wills. This sample language takes the guesswork out of the process – helping donors feel confident in leaving a legacy gift.

2. Beneficiary Designations
The second option, beneficiary designations, is equally compelling. This approach is often used for individual retirement accounts, pensions, 401(k)s, and life insurance policies. By naming your nonprofit as a beneficiary, donors can provide significant support without having to alter their wills.

Why Beneficiary Designations?
  • Flexibility: Once the donor decides which account they want to make your nonprofit the beneficiary of, they can choose to give you all the proceeds or a percentage. This means they can easily support multiple charities and their surviving spouse and heirs. Beneficiary designations are also fully revocable, which as I mentioned, appeals to most donors.
  • Ease of Set Up: Beneficiary designations are usually set up with a simple form. No need for the donor to visit their attorney. All they need to do is ask the company that holds the account for their beneficiary form, fill it out, and submit it.
  • Widespread Appeal: This method appeals to a broad range of donors, from younger supporters who are just beginning to plan their futures, to older donors looking to maximize their tax benefits.
To support your efforts in this area, you might post a Beneficiary Designation Checklist which lists all the kinds of accounts that can have beneficiaries. Simple, clear instructions can demystify the process and boost participation.
​
In my store you’ll find social media templates for planned giving, which include a template Beneficiary Designation Checklist and pre-written Web Copy to create a planned giving focused landing page on your website.

Keep It Simple, Keep It Effective

By narrowing your planned giving strategy to these two options – bequests and beneficiary designations – you create a clear, focused message that resonates with donors. Not only do these methods simplify your messaging, but they also provide the flexibility that many donors are looking for when planning their legacies.
​
Instead of overwhelming your supporters with a menu of complex options, concentrate on making it as easy as possible for them to learn about and pursue these two powerful tools. Whether it’s through offering a handy sample bequest language template or leveraging engaging digital content to promote beneficiary designations, a focused approach is key.

final thoughts

When it comes to planned giving, less is often more. Focusing on just these two options will make your planned giving efforts clearer, easier to promote, and ultimately more successful. Keep it simple, and you’ll see results.

What planned giving opportunities does your organization focus on? Where will you focus your efforts for the rest of 2025? Let me know in the comments!
​
Cheers!
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PS - I hope you’ll continue the conversation by subscribing to Real Deal Fundraising. When you subscribe, you’ll get my e-newsletter, which includes the best articles on fundraising, productivity, and cool stuff every week. The whole thing is curated awesomeness as well as freebies like webinars, instructional videos, and whatever else I can put together to be helpful to you!
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If you liked this…
  • Spring Cleaning for Fundraisers: Organizing Planned Giving Documentation
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Spring Cleaning for Fundraisers: Organizing Planned Giving Documentation

3/15/2025

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Spring Cleaning for Fundraisers: Organizing Planned Giving Documentation

​It’s that time of year again – when we roll up our sleeves, open our closets, and get everything in order. Why should fundraisers be any different? Just as a good spring cleaning refreshes your home, organizing your planned giving documentation can breathe new life into your fundraising strategy. A well-structured planned giving system not only keeps you compliant and prepared for future revenue but also sets the stage for stronger donor relationships. Here’s a step-by-step approach to auditing your data, collecting key donor details, promoting planned gift opportunities, and streamlining your documentation process.

​I. Audit Your Planned Giving Data

Before you can plan your next move, you need to take stock of what you have. Start by auditing your current planned giving records:
  • Review Your Existing Records:
    Go through your files and CRM to identify which donors have planned gifts on file. Determine the estimated value of these future gifts. This isn’t just about tallying numbers – it’s about understanding the potential impact on your organization.
  • Check for Essential Data:
    One crucial piece of information is the donor’s birthday. Why? Knowing when your donors were born not only helps you project future revenue (especially when combined with other data points) but also gives you a chance to personalize your stewardship efforts and promote opportunities (like IRA rollovers) that are right for their age bracket.
I once had to project future revenue from our planned gifts for an accrediting agency. Sounds straightforward, right? Not so much – because I was missing a key piece of data: donor birthdays. Turns out, knowing a donor’s age helps with more than just sending a thoughtful birthday card. While it’s not the most cheerful topic, actuarial data can help organizations estimate when planned gifts might be realized. If you don’t have birthdays in your CRM yet, now’s a great time to start collecting them, it’ll help with stewardship today and strategic planning down the road!
  • Double Check Documentation:
    It’s considered best practice to log even verbal commitments for planned gifts so that you can steward those donors. However, closing the loop and getting a planned gift letter of intent and supporting documentation is the gold standard. Understand which donors’ gift intentions are verbal only, written intent, and written intent with documentation. This will help you prioritize folks for follow-up.

​II. Collect Key Donor Data

Once you’ve audited your existing records, the next step is to fill in any gaps, especially with critical data like birthdays. Capturing birthdays is a good idea for everyone in your database not only legacy donors!
  • Why Birthdays Matter:
    Birthdays aren’t just dates on a calendar – they’re opportunities. They allow you to send a personalized birthday card or a thoughtful email, reinforcing your relationship with the donor. Such touches can make all the difference in donor retention and long-term engagement.
  • How to Collect Data:
    • Update Your CRM: Make sure every donor profile includes a birthday field.
    • Use Surveys and Forms: Include a simple question about birthdays in your regular donor surveys or update forms.
    • Stewardship Touchpoints: Every time you have an interaction with a donor, verify that you have their current information.

III. Promote Planned Gift Opportunities and Track Leads

Now that your data is in shape, it’s time to get the word out about your planned giving opportunities – and track every inquiry that comes your way.
  • Outreach Strategies:
    Develop an integrated promotional plan that spans multiple channels:
    • Email Campaigns: Send targeted emails that explain the benefits of planned giving and include a clear call-to-action.
    • Social Media Posts: Leverage your platforms to educate and engage. Quick tips or success stories about planned gifts can capture attention.
    • Donor Events: Host webinars or in-person events to discuss planned giving, answering questions in real time.
  • Tracking Leads:
    Implement a system to track all inquiries related to planned gifts:
    • Database or it didn’t happen: Make sure every inquiry is logged in your CRM.
    • Lead Capture Forms: Create a dedicated form on your website for planned giving inquiries.
    • Follow-Up Reminders: Set up automation or calendar reminders to follow up with interested donors promptly.

IV. Documenting Planned Gifts: A Step-by-Step Process

Once a donor decides to move forward with a planned gift, it’s critical to have a clear, standardized process for documentation. This ensures nothing slips through the cracks and that every commitment is properly recorded.

1. Guide Donors Through the Initial Steps
  • For Bequests:
    Encourage your donors to consult with their attorney to update their wills. Provide clear, simple instructions on how to include your organization as a beneficiary. Offering sample bequest language can make this step much less daunting.
  • For Beneficiary Designations:
    Direct donors to fill out the appropriate beneficiary forms for their life insurance policies or individual retirement accounts. This step is often straightforward and can be promoted via social media and email. My social media templates to promote planned giving opportunities includes a Beneficiary Designations Checklist to promote the kinds of accounts that qualify.

2. Collect and Secure Documentation
After the donor has taken the initial steps, ensure that you collect the necessary documentation:
  • Planned Gift Letter of Intent:
    Have the donor complete a formal letter of intent. This document should outline their planned gift and serve as an initial record of their commitment.
  • Supporting Documents:
    Request copies of any official documentation:
    • For bequests, a copy of the relevant page from their will or codicil of their will.
    • For beneficiary designations, a copy of the completed form or a confirmation from their financial institution.
​
3. Organize and Track the Documentation
  • Hard Copy Files:
    Maintain a secure physical file for each planned gift, containing all original documentation and correspondence.
  • Digitized Cloud Files:
    Scan documents and store them in a secure, organized cloud storage system. Use clear naming conventions and folder structures for easy retrieval.
  • CRM Integration:
    Upload digital copies of the key documents into your CRM. Record essential details in donor profiles to ensure you have a centralized record of every planned gift.
  • Action Step:
    Create a standardized checklist that outlines each step of the documentation process – from guiding the donor to collecting and storing the necessary documents. This checklist will serve as a training tool for your team and help maintain consistency across the board.

V. Final Thoughts: A Clean Slate for Future Success

A well-organized planned giving system is like a well-tended garden – regular maintenance pays off in beautiful blooms year after year. By auditing your data, collecting key donor information, promoting planned gift opportunities, and establishing a clear documentation process, you’re setting the stage for both immediate and long-term success.

Implement these spring cleaning steps today, and watch as your planned giving program becomes more efficient, donor-friendly, and robust. Not only will you be better prepared to project future revenue, but you’ll also be fostering stronger, more meaningful relationships with your donors.

Remember, every great legacy starts with a single, well-documented planned gift. Get organized, streamline your process, and make it easier than ever for donors to leave a lasting impact on your mission.
What’s on your list for fundraiser spring cleaning? Let me know in the comments!
​
Cheers!
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PS - I hope you’ll continue the conversation by subscribing to Real Deal Fundraising. When you subscribe, you’ll get my e-newsletter, which includes the best articles on fundraising, productivity, and cool stuff every week. The whole thing is curated awesomeness as well as freebies like webinars, instructional videos, and whatever else I can put together to be helpful to you!
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If you liked this… 
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New year, New donors: Building a Monthly Giving Program

1/7/2025

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How To Build a Recurring Gift Program from Scratch: A Step-by-Step Guide for Nonprofit Fundraisers

I learned the power of recurring gifts when I ran a faculty/staff giving campaign. I saw how quickly even $5 payroll deductions added up across the year when dozens upon dozens of donor participated. When I arrived at a much smaller institution that really needed unrestricted gifts, I knew they needed a strong monthly giving program that would help us reach our annual goals.
​

Recurring giving is a powerful strategy that can transform your nonprofit’s fundraising model. A successful recurring gift program provides steady, unrestricted income and builds a loyal donor base that supports your mission long-term. Here’s how to build a thriving recurring gift program from scratch.

What is a Recurring Gift Program and Why Start One?

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

Why You Should Launch a Recurring Gift Program:
  • Cost-Effective: Solicited only once, recurring gifts reduce acquisition costs.
  • Predictable Revenue: Monthly gifts offer a consistent income stream.
  • Higher Lifetime Value: Studies show that recurring donors give more over time compared to one-time or annual donors.
  • Increased Donor Loyalty: The regular engagement helps deepen the relationship with your organization.
​
Why Donors Love Monthly Giving
Monthly giving resonates with donors for several key reasons:
  • Convenience: Automated payments make it easy to maintain their support without additional steps.
  • Budget-Friendly: Smaller, regular donations are easier to fit into monthly budgets.
  • Eco-Friendly: Recurring gifts reduce paper usage and reliance on direct mail, aligning with donor values around sustainability.
  • Impactful: Donors feel a deeper connection, knowing their consistent support enables ongoing projects and growth.

8 Steps to Launch Your Recurring Gift PrograM

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

Step 1: Explore Technical OptionS

Choose a donation platform that securely stores donor payment information and processes automated monthly contributions. Key features to consider include:
  • Mobile Optimization: Ensure the sign-up process is seamless on all devices.
  • Security: Look for Payment Card Industry (PCI) compliance and encrypted data storage.
  • User-Friendly Maintenance System: Make sure the system is easy for staff to manage, update, and integrate with your CRM.
Pro Tip: The ability to automate receipts and acknowledgments in your software will save staff time and maintain a consistent donor experience.

Step 2: Build Internal SupporT

Engage your team and leadership early. Present a clear case for why a recurring gift program is a strategic priority using data and examples:
  • Highlight the benefits of consistent revenue and lower acquisition costs.
  • Address any concerns about additional workload or technology investment.
Share a short executive summary and draft donation page copy with key stakeholders to secure buy-in and streamline implementation.

Step 3: Create an Identity for Your PrograM

Develop a unique brand identity for your recurring giving group to create a sense of community. Consider naming the group and designing a logo (e.g., "The [Organization] Sustainers"). This branding helps build a strong identity and a feeling of belonging among donors.
Examples:
  • Charity: Water’s "The Spring" 
  • The Adventure Project’s "The Collective" 
  • Starr King School for the Ministry’s "The Starr King Sustainers"

Step 4: Start Small with Personal OutreacH

Begin by reaching out personally to a select group of 25-50 loyal donors, volunteers, or board members. These individuals are likely to be early adopters and provide valuable feedback for refining your program.
Action Steps:
  • Make personalized calls or set up Zoom meetings to introduce the program.
  • Explain the benefits of becoming a founding member and gather testimonials from these early donors.

Step 5: Launch a Broader CampaigN

Once you’ve piloted your program, it’s time for a full launch. Use a multi-channel approach to reach your audience:
  • Email: Highlight the ease and impact of monthly giving.
  • Social Media: Share testimonials and visual stories of impact.
  • Direct Mail: Include a simple option to sign up for monthly giving on reply cards.
  • Phone Campaigns: Engage donors directly and answer any questions they have.
Keep the momentum going by regularly reporting progress. Consider using a thermometer graphic to illustrate growth in monthly donors and total contributions.

Step 6: Offer Meaningful PerkS

While your main goal is sustainable support, offering small perks can enhance donor loyalty without significantly increasing costs:
  • Access to an exclusive Facebook group or early event registration.
  • An annual Zoom Q&A with your CEO or program director.
  • Personalized thank-you notes or recognition on your website.
These gestures help make donors feel special and connected to your mission.

Step 7: Steward, Maintain, and Upgrade DonorS

Ongoing maintenance is key to the success of your program. Be proactive about updating expired credit cards and follow up with donors whose payments fail. In January, send timely letters for tax purposes covering all of the gifts the donor made in the previous tax year. I’ve always liked to send monthly donors a sticker and/or car decal for every year they are in the program. 
Upgrade Strategy:
  • Every 12-24 months, ask existing donors if they’d consider increasing their monthly gift. Even a small increase can have a big impact over time.

Step 8: Conduct an Annual Recurring Gift PusH

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

Conclusion: Start Your Recurring Gift Program TodaY

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

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

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

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 Jessica has been a wonderful colleague and mentor over the years.  In the beginning of my annual giving career, I found her expertise, experience and willingness to help, invaluable.  Her advice and custom phonathon spreadsheets had a direct impact on our phonathon’s success and my ultimate promotion.  As I progress in my career, I continue to value her insight and professionalism." 

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