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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.
​
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
​
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.
​
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.
​
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.
​
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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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!
SUBSCRIBE
If you liked this… 
  • What With Love, Meghan Can Teach You About Donor Relations
  • 8 Essential Skills for Success in Fundraising
  • Discovery Visits Demystified: Tips for Effective Donor Meetings
  • What Makes for Great Rapport Building
  • Culture of Philanthropy Check-Up
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What With Love, Meghan Can Teach You About Donor Relations

3/23/2025

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​What With Love, Meghan Can Teach You About Donor Relations

If you're new to nonprofit fundraising, navigating interactions with high-net-worth individuals can feel intimidating. You might wonder if you have the right background, experience, or social skills to connect with major donors. But here’s the truth: building relationships in philanthropy isn’t about wealth or privilege – it’s about cultural capital, etiquette, and most importantly, emotional intelligence.

​Meghan Sussex’s new Netflix series, With Love, Meghan, offers a fresh take on hospitality, cultural awareness, and the art of connection – skills that can elevate your fundraising career and help your nonprofit thrive. Let’s explore how these soft skills can help you build confidence, engage donors authentically, and create lasting relationships.

1. Hospitality and Thoughtful Details Matter

In With Love, Meghan, she emphasizes the importance of creating welcoming experiences, from personalized touches to beautifully curated environments. In Episode 1 “Hello Honey”, Meghan shares, “The joy of hostessing for me is surprising people with moments that let them know I was really thinking of their whole experience.” She even takes care to tie the knots on gifts with a bow so they are easy to open. Fundraisers can apply this same mindset by:
  • Personalizing interactions – A handwritten note, remembering a donor’s favorite coffee order, or following up on a personal detail they mentioned builds trust and connection.
  • Making events feel special – Thoughtful planning, from seating arrangements to cultural considerations and dietary requirements, ensures donors feel valued and included.
  • Being present and engaged – As Meghan says in Episode 6 “Juice is Worth the Squeeze”, “Take time to be present, to sink into the good stuff.” A warm smile, a firm handshake, and active listening go a long way in making people feel seen and appreciated.

2. Cultural Competence Builds Stronger Connections

One of the standout elements of Meghan’s approach is her ability to navigate different cultures with grace. In Episode 3 “Two Kids from LA,” she connects with chef Roy Choi over their shared Los Angeles roots and love of food. Later, in Episode 4 “Love is in the Details,” she and her Argentinian friend Delfina Figueras bond over Meghan’s experience studying in Argentina and speaking an Argentinian dialect of Spanish. As a fundraiser, your ability to understand and respect the cultural backgrounds of your donors can set you apart.
  • Educate yourself – Learn about your donors’ traditions, values, and interests so you can connect on a deeper level. Be curious and ask questions to learn more.
  • Adapt to different settings – Whether attending a gala, a business lunch, or a casual coffee meeting, knowing the unspoken rules of engagement helps you feel more comfortable and confident. In some episodes, we see Meghan barefoot in the kitchen or in a casual Northwestern University sweatshirt, but in others we see her dressed more like the Duchess of Sussex. That kind of adaptability will serve you well in fundraising.
  • Show genuine respect – Small, but important gestures, like pronouncing someone’s name correctly, using their preferred pronouns, or acknowledging significant holidays, demonstrate respect, care, and consideration.

3. Storytelling is Your Superpower

Throughout With Love, Meghan, she uses personal anecdotes to create intimacy and connection. In Episode 7, “Elevate the Everyday”, Meghan talks about the importance of celebrating the meaning behind everyday things, and we watch a moment when she learns about potstickers from her friend Vicky Tsai, who explains they are folded to resemble ancient Chinese money. Meghan’s enthusiasm is unmistakable as she responds, “I love hearing the meaningful stories behind things!” Fundraising is no different – stories drive impact.
  • Make it personal – Share stories that showcase the real impact of your nonprofit’s work, and tailor them to what matters most to your donor.
  • Listen first, then share – Major donors appreciate fundraisers who ask thoughtful questions and listen more than they talk. Meghan shows consistent and genuine curiosity in all the episodes, learning from her guests because of her enthusiasm to know more.
  • Find common ground – A shared experience, passion, or value can turn a transactional conversation into a meaningful relationship.

4. Presentation and Etiquette Set the Tone

Meghan’s show highlights the power of presentation – not just in her fashion but in communication, demeanor, and environment. Her friends mention in “Juice is Worth the Squeeze” how careful she is to accommodate everyone’s dietary needs and preferences, no matter how busy she is. In Episode 5 “Surprise and Delight”, she shares, “You take something really pretty ordinary and make it extraordinary. It’s really easy to do, but the tiniest attention to detail makes it feel special.

First impressions matter in fundraising, and attention to etiquette can help you feel more at ease in professional settings.
  • Dress appropriately for the occasion – You don’t need designer labels, but polished and professional attire shows respect.
  • Master introductions – Knowing how to confidently introduce yourself, shake hands, and engage in small talk makes social situations smoother. It’s also important to know how to introduce two other parties to each other with thoughtful details.
  • Be gracious and adaptable – In Episode 8 “Feels Like Home”, Meghan takes great care in wrapping a gift for Alice Waters, incorporating natural elements into the presentation. This level of thoughtfulness can be applied to donor stewardship as well.
  • Consideration in event planning – Meghan also demonstrates consideration by ensuring menus are printed and table tents are placed in front of each dish, ensuring guests feel comfortable and informed.

Bonus Tip: Treat Everyone with Respect and Care

​I was taught early in my career to treat everyone with the same level of engagement and care, from the janitor to the CEO. Watch how Meghan treats her crew - feeding them, including them, and making sure they feel valued. That level of care and consideration can set you apart in fundraising and beyond.

Why This Matters for Your Career

​Developing cultural capital and etiquette isn’t just about impressing donors – it’s about equipping yourself with the skills to excel in your career. Fundraisers who can build authentic relationships, adapt to different social settings, and communicate with confidence are in high demand. These skills open doors to new opportunities, leadership roles, and professional growth.

You don’t have to be born into wealth or attend elite schools to succeed in major gift fundraising. I certainly didn’t. You might not end up marrying a prince, but by cultivating cultural awareness, practicing thoughtful hospitality, and honing your storytelling and etiquette skills, you’ll become a stronger fundraiser – and help your nonprofit build the relationships it needs to thrive.

Like Meghan, you don’t need to be a full-time royal to lead with grace. By embracing hospitality, cultural awareness, and attention to detail, you can make every donor feel valued – and that’s what truly elevates fundraising to an art form.

Have you watched With Love, Meghan? What did you notice? Any takeaways that I might have missed? 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!
SUBSCRIBE
If you liked this…
  • Spring Cleaning for Fundraisers: Organizing Planned Giving Documentation
  • How to Talk About Death and Taxes: Getting Comfortable Having Planned Giving Conversations
  • How to Keep Donors Connected in a Crisis: Near, Dear, and Clear
  • 6 Ways to Show Donors Gratitude in the New Year
  • Valentine’s Day for Donors: The Art of Stewardship
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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.
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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!
SUBSCRIBE
If you liked this… 
  • How to Talk About Death and Taxes: Getting Comfortable Having Planned Giving Conversations
  • Leveraging National Estate Planning Awareness Week for Planned Giving Success
  • Why Nonprofits Can't Afford to Sleep on IRA Rollover Gifts
  • 6 Ways to Show Donors Gratitude in the New Year
  • Discovery Visits Demystified: Tips for Effective Donor Meetings
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Trends & Predictions: Nonprofit Fundraising in 2025

12/17/2024

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Trends & Predictions: Nonprofit Fundraising in 2025

I remember the feeling of confidence I had going into 2020. I had been in the fundraising field for over 15 years (full-time), and at the time, I thought I had most things figured out. I would have confidently made broad, sweeping predictions about the future. And, as we all know, I would have made a complete fool of myself. Because everything we thought we knew was turned upside down by the global pandemic just a few weeks later.
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That humbling experience taught me a critical lesson: predicting the future isn’t about certainty; it’s about curiosity. It’s about studying trends, tracking the breadcrumbs, and embracing flexibility. As we look toward 2025, the nonprofit fundraising landscape continues to evolve, shaped by technology, shifting donor expectations, and global economic conditions. Here are a few trends to watch and how they might reshape the way we fundraise:

1. Highly Personalized Donor EngagemenT

Gone are the days when a generic email blast could sustain your donor base. Modern donors expect nonprofits to know their preferences, interests, and giving history. This shift demands a deeper investment in donor data and segmentation strategies.
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What this looks like in practice:
  • Personalized video messages from organizational leaders thanking donors for specific gifts.
  • Tailored campaigns that reflect the donor’s passions – think targeted appeals for programs they’ve supported in the past or issues that align with their values.
  • Leveraging AI to analyze donor behavior and suggest optimal engagement strategies (more on AI below).

2. AI and Predictive AnalyticS

AI has moved beyond being a buzzword – it’s now a practical tool reshaping nonprofit fundraising. From automating administrative tasks to analyzing donor data, AI is helping fundraisers work smarter, not harder.

Emerging applications in fundraising:
  • Predictive analytics: By analyzing historical data, AI can identify which donors are likely to upgrade their gifts, lapse, or respond to specific campaigns. This enables fundraisers to act strategically and proactively.
  • Content generation: Tools like ChatGPT can help draft compelling appeals, social media posts, or event invitations, giving fundraisers a head start while maintaining their voice.
  • AI-powered donor stewardship: AI tools can automate personalized thank-you emails, gift anniversary reminders, and touchpoints, ensuring donors feel appreciated without overwhelming staff time.
However, as AI becomes more prevalent, ethical considerations must remain at the forefront. Donor confidentiality is non-negotiable – organizations must carefully vet AI platforms to ensure donor data remains secure and private. Similarly, while AI can streamline processes, it’s no substitute for genuine, human connection. The most successful fundraisers will treat AI as a powerful enhancement to relationship-building, not a replacement for the trust and care that donors deserve.
​
By prioritizing ethics, privacy, and authenticity, nonprofits can leverage AI responsibly while maintaining the integrity of their donor relationships.

3. Automation for EfficiencY

With limited staff and growing expectations, nonprofits are turning to automation to streamline repetitive tasks. Automation allows teams to focus on what truly matters: building relationships and driving impact.
​
What’s being automated:
  • Email workflows for donor journeys, from onboarding new donors to lapsed donor reactivation.
  • Social media posting schedules, freeing up time for engagement and content creation.
  • Grant tracking and reporting processes, ensuring deadlines are met with minimal stress.
By automating these tasks, organizations can improve efficiency without sacrificing quality.

4. Emphasis on Mission TransparencY

Donors today demand clarity on how their contributions are being used. Organizations that can clearly articulate their impact and demonstrate accountability will stand out in an increasingly competitive philanthropic landscape.
​
How to show transparency:
  • Detailed impact reports shared via email or social media.
  • Real-time project updates through live streams or donor-exclusive newsletters.
  • Open discussions about challenges, successes, and lessons learned.
Transparency isn’t just a nice-to-have; it’s becoming a baseline expectation for earning donor trust.

5. New Channels for Donor EngagemenT

The way people consume information and interact with brands (including nonprofits) is constantly evolving. In 2025, expect to see growth in emerging channels like:
  • Short-form video content offers bite-sized storytelling opportunities.
  • Text-to-donate campaigns capitalize on the growing use of mobile devices for philanthropy.
  • Virtual and hybrid events create global accessibility without sacrificing the intimacy of in-person connection.
Experimentation will be key here, and nonprofits that adopt a “test and learn” mindset will stay ahead of the curve.

FINAL THOUGHTS

The future of nonprofit fundraising is both exciting and daunting. The tools and strategies available today offer incredible potential to engage donors in meaningful ways – but only if we approach them thoughtfully. As we navigate these trends, let’s remember the lessons of the past: stay adaptable, keep learning, and never forget that at the heart of every fundraising effort is a desire to connect people with purpose.

What trends are you seeing in your work? Let’s keep the conversation going 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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6 Ways to Show DONORS Gratitude in the New Year

12/7/2024

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6 Ways to Show Donors Gratitude in the New Year

As we turn the page to a new year, it’s the perfect time to reflect on the incredible impact your donors have made on your organization. Donor appreciation isn't just about wrapping up last year's success - it’s about laying the groundwork for lasting relationships that will sustain your mission well into 2025 and beyond.
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In nonprofit fundraising, donor retention is key. It’s much easier (and more cost-effective) to retain a donor than to acquire a new one, which is why a thoughtful approach to showing gratitude can be a game-changer. Starting the new year on a note of appreciation can make all the difference in keeping those relationships strong. Here are six creative and practical ways to show your gratitude this New Year:

1. New Year’s Cards

Instead of sending out traditional holiday cards, why not opt for a New Year’s card? It’s a great way to stand out, especially since January mail isn’t competing with the December rush. At my current institution, where we serve a multi-religious community, we steer clear of specific religious holiday cards, but New Year’s cards offer a respectful and inclusive option.

This isn’t just about sending a card; it’s about showing donors they’re valued as you enter a fresh chapter. By sending a message of gratitude and well wishes for the year ahead, you remind them that their support is crucial to your mission’s success.

Why It Works: A New Year’s card avoids the crowded December mailbox, acknowledges diverse traditions, and sets a positive tone for the year ahead.

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What to Say to Donors in Uncertain Times: The Near, Dear, Clear Fundraising Framework

3/26/2020

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What to Say to Donors in Uncertain Times: The Near, Dear, Clear Fundraising Framework (updated May 2025)


We are all scrambling. ​

If you’ve found yourself rewriting the same appeal three times -- or wondering if it’s even okay to make an ask right now -- you’re not alone. In a year marked by economic uncertainty, political tension, and donor hesitation, fundraisers are feeling the weight of every word.

The solution isn’t silence. It’s clarity. And that’s where Near, Dear, and Clear comes in.

How can we keep our donors connected to our organizations in this unstable environment?

Back in 2020, when it became clear that I would not be allowed to travel anymore for work, I fell back on a maxim I heard somewhere early in my fundraising career. It rhymes so that’s convenient and an aid to memory.

Near
Dear
Clear


In any circumstances where rapid change is taking place, we must take great pains to keep our donors near, dear, and clear. What does that mean as a guide to practical action?

Let’s take each part of the maxim in turn:

Near: Be in Contact & Stay Close

You will need to leverage all forms of media at various levels to keep in touch with your donors.

First, for your major donors, set up as many one-on-one Zoom meetings as you can reasonably handle each week to check in with them. Take it week-by-week so it will not be overwhelming but striving for 6-8 substantial phone calls or Zoom meetings with major donors per fundraiser seems appropriate.

Secondly, utilize digital means of connection as much as possible. Send email or text updates to your constituents. Don’t bombard them with info but if you have meaningful information to report, do so on all available channels. If you have Facebook groups, use those to communicate too. Encourage your supporters to share info so it gets in more newsfeeds and inboxes.

Third, for your mid-level donors or major donors that you cannot check in with immediately, don’t forget about good old mail and phone. You can do a quick check-in calling campaign one day per week and write some hand-written notes.

What to say: 
  • "You're part of this work, and we’re grateful you’ve stayed with us.”
  • “We thought of you when we saw this update: because your gift made it possible.”

Dear: Express Gratitude & Lead with Values

Your messaging needs to let donors know that you care about them as people. It’s not just about expressing our usual level of stewardship and gratitude. This is thanking them for believing enough in your organization’s mission to hang in there in this time of great change and uncertainty.

​Express gratitude not only as a staff member but express gratitude on behalf of those your organization serves. Let them know that because of them, your mission continues and will continue after this crisis.

What to say:
  • “This mission isn’t just close to our hearts; it’s at the center of our community’s future.”
  • “We believe generosity is a force for good, especially when things feel uncertain.”

Clear: Make the Ask Simple

Make sure your organization is crystal clear on its priorities. The first of which should be the health, safety, and welfare of those they serve. Repeat this often to your constituents.

However, do not shy away from honestly telling donors how this crisis is affecting your organizational needs and its finances. Your major donors and board members especially deserve the candid talk about what is needed, what might be needed, and why.

What to say:
  • “A gift of $50 helps cover a week of meals for a student in crisis.”
  • “Will you make a gift today to help us stay steady and serve boldly in 2025?”

Did you find the framework of near, dear and clear helpful in thinking about how you are keeping donors connected these days? What other strategies have you tried in the last couple of weeks that keep donors near, dear, and clear? Tell me below in the comments!

Again, I hope this was helpful to you. If it was, please leave me a comment below.

Take care and be well,

Jessica ​
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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 - Want more messaging tools that build trust and drive giving - without gimmicks? Inside my Smart Start Fundraising System course, we unpack the words, frameworks, and mindset shifts that actually move donors to action. [→ Get on the list here.] Course launches 06.03.25!
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​Culture of Philanthropy Check-Up

4/18/2017

 
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Building and maintaining a culture of philanthropy is hard work. It is deep work that takes years to build and moments to destroy. But having a healthy culture of philanthropy makes work more fun and makes fundraising easier. It’s worth having a periodic check-up to assess how your institution is doing.

Answer these questions for your institution:

Board Support
  • Does your board of directors (or board of trustees) support the organization as current year donors at 100% participation?
  • Board support is a sign of stakeholder investment. It also shows that your closest advocates are current with their support. The level of the support doesn't matter so much as the consistency and recency of that support. PS - It's easier to ask for others to give if you are a current donor.

Staff Support
  • Does your fundraising staff support the organization as current year donors at 100% participation?
  • Does at least 50% of your organization’s overall staff (and faculty) support the organization as current year donors?
  • Again, staff support is a measurement of stakeholder investment. Does your staff (especially your fundraising staff, believe in the mission enough to back it with their personal funds? The level doesn't mean as much as the participation.

Alumni support (or Grateful Patient support)
  • This category assesses whether those served by your organization’s mission give back to the organization later. This is a sign of institutional effectiveness.
  • What is your alumni (or similar) participation rate? You’ll know whether this is good for your organization or not. The level at which this metric is outstanding varies widely from institution to institution.

Fun Factor
  • Does your organization frequently have concrete signs that fundraising is seen as an enjoyable community endeavor? (For example, an annual gala, a stewardship picnic, a “Dancing with the Deans” competition, etc.)
  • List what you currently do to put the “fun” in fundraising.
  • Write down three new ideas to improve your fun factor.

Communications
  • How often do your constituents hear from the organization without a fundraising pitch?
  • Do these communications include stories of impact?
  • Are you communicating in different media? Email, print, video, etc?

Stewardship and Donor Relations
  • Do you have meaningful giving societies?
  • Do you have a person designated to assist donors with any “customer service” type issues? 
  • How is your data management and data integrity? Nothing kills a philanthropic feeling like your name being wrong on an invitation.
  • Stewardship is not just the purview of the staff member with "donor relations" in his or her title. It is an office-wide perspective of service and connection. From your front desk associates to student workers/interns to your accountants on staff to gift officers and especially advancement services and gift processing staff, improving donor relations should be everyone's primary objective.

Other questions to think about:
  • Does your organization show the impact of giving clearly and broadly?
  • For major donors, do you create unique reports and experiences that connect for them their gift to the impact in the world?
  • Do you see expressions of gratitude at all levels of the organization? Where could your organization do better?
  • Are the needs of the institution are clearly expressed for donors of all levels using different media?
  • Does the institution set expectations for giving through specific asks, giving society thresholds and endowment minimums?
  • Are fundraising goals embraced by both fundraising staff and program staff/faculty?

How did you feel about the assessment? Where are you doing well? Where should you improve? 

As always, comments and questions are welcome and encouraged!

Cheers,

Jessica

PS - If you liked this post, you might also like these: 
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PPS - If you found this article helpful, please comment and let me know. Also subscribe to Real Deal Fundraising so you don't miss a post! You'll get my  guide to Call Center Games for Free!​​
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What makes for great rapport building? Plus, a list of rapport building questions

3/14/2017

 
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Connecting with a donor or potential donor is so vital before you ask for a gift. It's like removing many of the roadblocks between you and that "YES!" response you want.

People want to give to people they like. It's not much of a secret. Ultimately, as a fundraiser you are a conduit for the relationship between that donor and the institution (not with you personally) but they must enjoy speaking with you to want to continue a relationship with the institution.

This is an important skill for any fundraiser to develop, from phonathon callers on up to executive directors, deans and development officers.

I have been to MANY call centers where they use the same tired rapport-building questions year after year after year. We cannot let this happen. No one wants to spend their precious time telling a new person why they haven't been back to campus lately just like they did last year.

Bad rapport-building has the opposite effect on the donor than that which we wish to cultivate.

The first rule of building rapport is it must be DIALOG not MONOLOGUE. You must ask questions that will solicit meaningful conversation and back and forth. You (no matter if you are a student caller or the Vice President of Advancement) must not deliver a litany of great-stuff-happening-at-our-institution without stopping for breath.

So, following this rule, we must construct meaningful rapport building questions.

The second rule about rapport building is that these questions get stale. Every year (at least) new rapport builders should be generated and put into rotation.

Here is some guiding criteria for generating these questions. Rapport building questions should:
  • Extract meaningful information (like employment and campus affinities).
  • Make the prospect like the caller/staffer as quickly as possible.
  • Be delivered in a genuine way.
  • Not be able to be answered with “Yes” or “No”.
  • Not merely deliver talking points about the college or university.
  • Provide opportunities for smooth transitions to the first ask.
  • Collect new demographic information about prospects and verify current info (but not in a “canned” or perfunctory way).

What are some examples of strong rapport-building questions?
  • Were you close to any faculty members while you earned your degree?
  • Are working in the same field in which you earned your degree?
  • Did you know that the <> recently <>? Isn't that great?
  • I thought you might like to know that we've had a lot of success in <>. What do think about that?
  • I see that you attended our recent <>. Do you have any feedback for <> about that event that I could pass along?
  • You know, I am not sure about the answer to that question. But I can get back to you if I could get your cell phone number or email. I'll research that and contact you.
  • Why did you make your first gift to <>? What keeps you giving?
  • What are you most passionate about here at <>?
  • I see you are <> as I was/am. That's wonderful to know. Do you know <>?

Does your rapport building need a refresh? Do you have some favorite rapport-building questions that I forgot to mention on my list? Comments and questions are, as always, welcomed and encouraged!

Cheers,
​
Jessica Cloud

PS - If you liked this post, you might also like these:
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PPS - If you found this article helpful, please comment and let me know. Also subscribe to Real Deal Fundraising so you don't miss a post! You'll get my guide to Call Center Games for Free!​​
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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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What Folks Are Saying

 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." 

​- Ross Imbler, Director of Annual Giving, Lewis and Clark Law School
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