 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. 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:
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.
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.
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
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 4 Power Questions to Ask Donors That Build Rapport and Lead to Major GiftsAs 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!  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!
 How to Build a Philanthropy Calendar That Drives Digital DonationsEvery 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. 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:
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. 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.  What dates are important for your messaging and content throughout the year? Let me know in the comments. Cheers,  PS - I hope you’ll continue the conversation by subscribing to Real Deal Fundraising. When you subscribe, you’ll get my e-newsletter, which includes the best articles on fundraising, productivity, and cool stuff every week. The whole thing is curated awesomeness as well as freebies like webinars, instructional videos, and whatever else I can put together to be helpful to you! If you liked this…
 Cut Through the Clutter: Focus on the Two Planned Giving Options That Really WorkMost 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?
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?
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 thoughtsWhen 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!  PS - I hope you’ll continue the conversation by subscribing to Real Deal Fundraising. When you subscribe, you’ll get my e-newsletter, which includes the best articles on fundraising, productivity, and cool stuff every week. The whole thing is curated awesomeness as well as freebies like webinars, instructional videos, and whatever else I can put together to be helpful to you! If you liked this…
 What With Love, Meghan Can Teach You About Donor RelationsIf 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:
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.
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.
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.
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,  PS - I hope you’ll continue the conversation by subscribing to Real Deal Fundraising. When you subscribe, you’ll get my e-newsletter, which includes the best articles on fundraising, productivity, and cool stuff every week. The whole thing is curated awesomeness as well as freebies like webinars, instructional videos, and whatever else I can put together to be helpful to you! If you liked this…
 Spring Cleaning for Fundraisers: Organizing Planned Giving DocumentationIt’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 DataBefore you can plan your next move, you need to take stock of what you have. Start by auditing your current planned giving records:
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!
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.
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
2. Collect and Secure Documentation After the donor has taken the initial steps, ensure that you collect the necessary documentation:
3. Organize and Track the Documentation
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!  PS - I hope you’ll continue the conversation by subscribing to Real Deal Fundraising. When you subscribe, you’ll get my e-newsletter, which includes the best articles on fundraising, productivity, and cool stuff every week. The whole thing is curated awesomeness as well as freebies like webinars, instructional videos, and whatever else I can put together to be helpful to you! If you liked this…
 Nonprofit Branding: How to Make Your Mission MemorableWhen it comes to nonprofit fundraising, one thing is clear: Your mission is the heart of your organization. But while your cause drives everything you do, a strong, memorable brand is what helps you stand out and attract the major gifts that will take your work to the next level. Whether you’re at a large, established institution or running a smaller startup nonprofit, your brand should reflect who you are, what you stand for, and how people can get involved. A polished brand boosts credibility and builds trust, but a memorable one moves people to action. Your Mission Is the Core of Your Brand Before thinking about logos, colors, or marketing campaigns, start with the foundation of your nonprofit brand: your mission. What drives your organization? What problem(s) are you solving? What’s your CEO’s vision for the future? These aren’t just feel-good statements – they should be at the core of every message you share. Example: The Monson Free Library This small library in Maine has embraced its fun and quirky side by creating TikTok videos that showcase the staff’s personality while highlighting their programs. By tapping into the creativity and passion of their team, they’ve built a brand that’s as unique and welcoming as their services. The community now sees the Monson Free Library as more than a place for books – it’s a place to have fun, get involved, and support something bigger than themselves. Learn more. Actionable Tip: Start by asking yourself these questions:
Visual Identity: Be Consistent, But Stay FlexibleWhen you think of branding, visual elements like logos, color palettes, and fonts come to mind. These are crucial for creating a consistent, professional presence. But let’s be real – sometimes, nonprofits get so caught up in the “rules” of branding that they lose the ability to stay nimble. There’s a balance between maintaining brand integrity and being flexible enough to seize opportunities in the moment. Many nonprofits create brand guides with rigid rules for logos, colors, and language. And while I love a good style guide, if these guidelines slow you down or make it harder to engage donors, it’s time to rethink them. A major gift might hinge on a timely, heartfelt social media post or a quick thank-you email. If your guidelines require three layers of approval for every little thing, you could miss your moment. Example: The Trevor Project The Trevor Project underwent a major rebrand in 2019, replacing a formal font and muted colors with a bolder typeface and a vibrant, colorful design. The updated branding, along with fresh messaging and visuals, emphasized inclusivity, hope, and support for LGBTQ+ youth. The change strengthened their identity as a safe, approachable, and supportive organization while making them more visually appealing to young people. See their rebrand. Actionable Tip: If your branding guidelines feel like red tape, ask yourself:
Messaging That Moves People to Action Now, let’s talk about the most important aspect of branding – your story. Whether you’re crafting an email appeal, a social media post, or a campaign landing page, your messaging should inspire action. Major donors don’t just give to organizations; they give to stories they believe in. That’s why it’s essential to center your messaging around the people you serve and the change you’re driving in the world. Storytelling Tip: Showcase Personal StoriesPeople want to feel emotionally connected to your cause. Show them the impact they can have through the eyes of those you help. Example: St. Jude Children's Research Hospital St. Jude’s branding and messaging revolve around powerful, emotional stories of families whose lives have been transformed by their medical care. These stories create a deep personal connection, inspiring donors to give and stay engaged. Explore their storytelling approach. Actionable Tip: Incorporate donor-centered language into your messaging:
Building a Memorable Brand: Flexibility, Authenticity, and Consistency A memorable nonprofit brand is more than a logo or a catchy slogan – it’s a vehicle for connection. It drives donor engagement, cultivates long-term support, and inspires major gifts. To build a brand that resonates, focus on three key principles:
Make Your Brand Matter Branding isn’t about flashy logos or catchy taglines – it’s about making an emotional connection with your supporters. When your brand reflects your mission, values, and unique story, it becomes a powerful tool for attracting major gifts and building lasting relationships. Your nonprofit’s story is powerful. Make it memorable. Make it matter. And don’t be afraid to let your passion shine through. Now – it’s your turn. Have you been through a rebrand? Was the process the transformation you hoped for? Do you feel your branding guidelines and processes support your fundraising work or hold you back? Let me know in the comments! Cheers!  PS - I hope you’ll continue the conversation by subscribing to Real Deal Fundraising. When you subscribe, you’ll get my e-newsletter, which includes the best articles on fundraising, productivity, and cool stuff every week. The whole thing is curated awesomeness as well as freebies like webinars, instructional videos, and whatever else I can put together to be helpful to you! If you liked this...
How to Talk About Death and Taxes: Getting Comfortable Having Planned Giving Conversations2/28/2025  How to Talk About Death and Taxes: Getting Comfortable Having Planned Giving ConversationsA couple of weeks ago, I was hosting an in-depth workshop about getting comfortable asking for money. The attendees were engaged and enthusiastic until the topic shifted to planned giving. “How do you even touch on that topic? What a downer, talking about death!” That’s when I realized that planned giving is all about death and taxes – two topics almost guaranteed to make Americans squirm in their seats. Yet if you’re looking to secure a sustainable future for your nonprofit, these conversations are essential. By addressing them with grace, you can help donors plan for their future, maximize tax benefits, and leave an enduring impact. Let’s explore strategies to make these conversations feel natural – and even inspiring – by knowing who your planned giving prospects are, leveraging real-life testimonials, and using content to pull donors in who are already interested in these giving options. The Great Wealth TransfeR The "Great Wealth Transfer" refers to the projected shift of substantial assets from the baby boomer generation to younger generations over the coming decades. Estimates suggest that approximately $84 trillion will be transferred in the United States by 2045, with $72.6 trillion going directly to heirs and $11.9 trillion allocated to charitable causes. Planned giving isn’t just another giving option – it’s a missed opportunity if left unaddressed. Who are Your Planned Giving Prospects? When it comes to planned giving, the biggest mistake nonprofits make is assuming that only the wealthy are viable prospects. The truth is, the best predictor of a planned gift isn’t the size of someone’s bank account – it’s their loyalty. Research consistently shows that donors who make bequests aren’t necessarily the ones writing big checks during their lifetime. Instead, they’re the steady, long-term supporters who have been giving consistently for years (James, 2013). If someone has been giving $25 or $50 every year for the last 20 years, they might not look like a major donor, but they could be one of your most important legacy prospects. Age and Timing MatteR People tend to create or update their wills during significant life transitions – getting married, having children, retiring, or facing a health scare. While the median age for making a first will hovers around the 50s or 60s, that doesn’t mean you should wait to talk to your donors about legacy giving (Caring.com, 2023). If you’re only marketing planned giving to seniors, you’re missing the opportunity to reach people when they’re making their very first estate plans. A donor might include your organization in their will at 35 and revise it multiple times over the years – but once a nonprofit is in, it’s much more likely to stay. Engagement, Not Wealth, Drives Legacy GivinG The best planned giving prospects are those who feel deeply connected to your organization – volunteers, board members, monthly donors, and those who show up at events year after year. They may not see themselves as philanthropists, but they already view your nonprofit as part of their story. Engagement builds the kind of emotional investment that leads to legacy gifts. Fundraisers who focus only on wealth indicators will miss some of the most committed, mission-driven donors out there. Shift the Focus: It’s All About LegacY Instead of letting the conversation dwell on death, reframe it around the idea of legacy. (Cue that clip from Hamilton “A legacy is planting seeds in a garden you never get to see.”) Planned giving is less about what happens when we’re gone and more about how we can continue to support the causes we care about in perpetuity: a planned gift is a way to ensure that one’s values and passions live on. The Annual Donor Endowment ConcepT What if your most loyal donors could turn their yearly gifts into a source of funding that lasts for generations? Explain it like this for donors who give year after year,: "Imagine converting your annual support into a lasting endowment. By designating [your nonprofit] as a beneficiary in your estate plan or including a bequest in your will, your commitment can live on, providing stability and growth for our mission indefinitely." Attracting Leads Through Content CreatioN Rather than waiting for donors to approach you about planned giving, take a proactive role by creating engaging, informative content.
Practical Tips for Successful ConversationS
Cheers!  PS - I hope you’ll continue the conversation by subscribing to Real Deal Fundraising. When you subscribe, you’ll get my e-newsletter, which includes the best articles on fundraising, productivity, and cool stuff every week. The whole thing is curated awesomeness as well as freebies like webinars, instructional videos, and whatever else I can put together to be helpful to you! If you liked this:
 Portfolio Power: How to Prioritize Your Prospects for High-Impact Fundraising When it comes to fundraising, managing a donor portfolio effectively is crucial for success. Your portfolio is more than just a list of names – it's a dynamic strategy for building relationships and maximizing your organization’s impact. Whether you’re new to major gift fundraising or a seasoned pro, understanding how to prioritize and manage your prospects is the key to hitting your fundraising goals. Does size matter? A major gift portfolio is not just about quantity; it’s about quality. As a relationship manager, you may wonder how many prospects one person can effectively handle. The truth is you need to strike the right balance. A full-time relationship manager can usually handle 100 to 120 prospects in their portfolio. But here’s the thing – if they’re also tasked with direct mail, event planning, and other duties, you’ll need to adjust that number to ensure they can focus on nurturing relationships. Setting Realistic ExpectationS It all starts with setting realistic expectations. If your team is stretched thin, don't overload them with too many prospects. You want them to have enough time and energy to engage meaningfully with everyone on their list. If managing a portfolio is their sole focus, 120 prospects may be doable, but if they’re juggling multiple roles, scale it back. This is where your strategic thinking comes into play: make sure you're staffing in a way that allows for the high-touch, personalized engagement that major gifts demand. Cleaning Your Portfolio RegularlY Here’s where the magic happens: regular portfolio clean-ups. It’s easy to get stuck in the “someday” mindset when it comes to following up with non-responsive prospects, but a cluttered portfolio can become a barrier to success. Clean up your portfolio at least twice a year. Document all attempts to reach out (emails, calls, social media), and if someone has been non-responsive for six months or more, it’s time to consider moving them off the list. Now, I know it might seem daunting to remove prospects from your portfolio but think about it like pruning a plant. It’s not about giving up on those individuals; it’s about focusing your energy on prospects who are truly ready to engage with your mission and make a meaningful gift. It’s better to have a smaller, more engaged list than to hold on to names that aren’t moving the needle. How to Execute a Clean-UP When you're cleaning up your portfolio, you don’t have to do it all at once. Instead, approach it in batches. Identify those who are no longer responsive or have indicated that they’re not interested in making a major gift. And here's a key tip: don’t just remove them without bringing in new prospects to replace them. As you remove, you should be adding fresh prospects who have the potential to move through your donor pipeline. This ensures your portfolio remains a living document – always in motion, always focused on those who can have the greatest impact. Stabilizing Your Portfolio Over TimE If you’re just starting in your role or working with an inherited list, the early stages of portfolio management can feel overwhelming. You might find yourself making frequent changes, moving prospects on and off your list several times per year. But don’t worry! That’s a normal part of the process. Give it time, and soon you’ll begin to see a stabilizing effect. Within 18 months to two years, your portfolio will likely stabilize, with only a handful of prospects moving in and out twice a year during your clean-ups. In the beginning, expect to move about 15-20 people out and bring in a similar number, every six months. But after some time, the changes become more manageable. This is the point where your portfolio is functioning like a well-oiled machine, allowing you to focus more on nurturing relationships and less on managing logistics. Focus on Multi-Channel EngagemenT Effective portfolio management doesn’t happen in a vacuum. To be truly successful, your outreach should be multi-channel – phone calls, emails, events, meetings, and even social media. This variety not only keeps your communication dynamic but also ensures that you're meeting your prospects where they are. Don’t just rely on one method of outreach. Embrace the full toolkit to keep your prospects engaged and ensure that no one falls through the cracks. By working smarter, not harder, you can maintain a portfolio that remains focused on those prospects who have the potential to make a significant impact on your organization’s mission. The more you engage across multiple channels, the more likely you are to move prospects along in the pipeline. And whatever you do, don’t automatically remove “your” prospects from other communication channels in the name of maintaining control. This is often a tactic of new major gift officers trying to be the sole contact for the prospect but what this does is practice is isolate those individuals from the organization. Your donors want and need to hear updates about the organization from multiple sources. You just need to be aware of the other info they are getting and how you can be a resource for them if they have questions or concerns. Your outreach should complement the other institutional communication channels, not replace them. The Power of Focused AttentioN At the end of the day, it’s all about focusing your energy where it matters most. When your portfolio is clean, well-maintained, and actively engaged, you're setting yourself and your organization up for success. It’s about prioritizing your time, energy, and resources to ensure that your major gift efforts are as impactful as possible. Remember, managing a portfolio is not a one-and-done task. It requires regular attention, strategic thinking, and a clear understanding of your goals. The beauty of an effective donor portfolio is that it’s not just a list – it’s an evolving tool that reflects the growing relationships you’re cultivating with your donors. Take Action: Build and Maintain a Portfolio That Works for YoU If you’re new to portfolio management or simply looking to improve your system, don’t hesitate to reach out for advice or share your own experiences. I’d love to hear what’s working for you and what challenges you’re facing. Don’t forget to leave a comment or send a message – I’m always here to support you on this fundraising journey! Remember: Your portfolio is powerful, and with the right approach, it can be your secret weapon for achieving fundraising success. So, go ahead – prioritize those prospects and watch your impact grow. Cheers!  PS - I hope you’ll continue the conversation by subscribing to Real Deal Fundraising. When you subscribe, you’ll get my e-newsletter, which includes the best articles on fundraising, productivity, and cool stuff every week. The whole thing is curated awesomeness as well as freebies like webinars, instructional videos, and whatever else I can put together to be helpful to you!
 Discovery Visits Demystified: Tips for Effective Donor MeetingS Whether you're just starting out in fundraising or you've been in the game for years, discovery visits are a vital part of cultivating major donors. But let's be honest—these meetings can sometimes feel a little intimidating. I get it! You may be unsure what to say, how to prep, or how to break the ice and build rapport. But here’s the thing—I absolutely love discovery visits. Seriously. There’s something thrilling about meeting new people and hearing their stories. For me, the research and discovery process is one of the most exciting parts of the job! I love asking questions, learning about the donor’s passions, and seeing if there’s a spark that could lead to a meaningful connection. I know a lot of fundraisers aren’t as excited about this step as I am, but that’s okay! I’m here to walk you through it and help make these visits less daunting and more enjoyable. By the end of this post, you'll have practical tips that will make you feel confident walking into your next meeting, knowing exactly how to steer the conversation and build those meaningful relationships. Let's dive in! How to Get the VisiT Getting a discovery visit on the calendar can be the hardest part, but it’s totally doable with the right approach. Here are a few ways to get your foot in the door:
I would characterize what I’ve outlined above as the “standard process” for getting a visit. I would use this process with VIP level donors or those I know somewhat but want to get to know better. For a big list of donors that you need to meet and qualify, let me offer an alternate option that leverages technology to make it easier for you and the donor.
The Basics of Donor ResearcH Now that you’ve got the visit, it’s time to do your research. You don’t want to go into a meeting blind – knowing your donor is a key part of the process. Start by digging through your database. Look through all previous gifts and interactions with your organization. If you don’t find much there, don’t worry -- take your research to Google. A quick search of their name can reveal news articles, social media profiles, and any philanthropic work they may have been involved in. Pay attention to family, work, and causes. For example, if a potential donor recently made a sizable gift to a local education initiative, they may be open to supporting your nonprofit’s education program as well. Knowing this ahead of time will help you frame your conversation. Inside a Discovery VisiT First thing’s first – gratitude. If the person you’re meeting with has made a gift before, start by thanking them for their past generosity. If they haven’t, thank them for taking the time to meet with you. Regardless of their past giving history, expressing sincere appreciation sets the tone for a positive conversation. Once you’ve shown your appreciation, it's time to move into an update on your organization or to introduce them to your mission. Share the exciting things happening at your nonprofit, but also highlight how they can help. Keep it brief, but impactful. Your goal here is to engage them with your cause and get them excited about what you're doing. Now, here's the magic part--getting to know them. This isn't the time to launch into your fundraising pitch. Instead, ask questions and, most importantly, listen. What do they care about? What drives them? What challenges have they overcome in their personal or professional life? These conversations are where you’ll uncover vital clues about their affinity, propensity, and capacity to give.
Listen for subtle hints about what might inspire them to contribute. Maybe they have a connection to a specific program, or perhaps they’re passionate about supporting young people, the arts, or healthcare. Your job is to be present, attentive, and note those little clues that will help you figure out what type of donor they could be and how they might prefer to give. And remember, the environment matters too. Are you meeting at their home, office, or a coffee shop? Wherever you are, take note of the surroundings – they can tell you something about the donor’s lifestyle, interests, and values. If you are new to this, it’s okay. You’ll start to notice things over time and soon it will be second nature. For instance, if a donor mentions hosting events in their home, that generally indicates both generosity and means. If the prospect casual references international travel, that is also a marker of them being potentially a high net worth individual. You can ask them what their philanthropic priorities are. This is a revealing question that can give you insight into their values and what motivates them. What to Do With All This InformatioN Once you’ve done your research and mapped out a strategy, it's time to hit the ground running. The first task you have is to put all that juicy, golden information into your database. Make extensive notes soon after the meeting and get it in the database. Later on, someone else is going to need that important context. Next, use everything you’ve learned about the donor’s affinity, propensity, and capacity to tailor your approach. If they’re passionate about your mission and seem generous, but haven’t given much yet, don’t push them for a large gift immediately – focus on building the relationship and uncovering opportunities for them to engage more deeply. And most importantly, listen. Donor visits are about building rapport, not making a quick ask. You’re planting seeds for future giving, and you want to nurture that relationship, not rush it. The general benchmark is that from the discovery visit to a new major gift is usually 18 to 24 months. You can ask a new prospect for a modest ($500 - $1,000) annual fund ask but hold on the larger ask until you know more and they are more invested in your mission. In many ways, major donor cultivation is like platonic dating. You want to meet, make a great connection, have a plan for your next interaction, and over time understand each other more deeply. Wrapping UP Discovery visits are one of the most exciting and rewarding parts of fundraising. When done right, they help you connect with your potential major donors on a personal level, setting the stage for long-term partnerships. With a little preparation, a lot of listening, and an understanding of how to gauge a donor’s affinity, propensity, and capacity, you’ll walk away from each visit feeling confident and inspired. So, whether you’re in the early stages of your donor journey or you’ve been at it for years, always remember that real deal fundraising is about building relationships that matter. Take the time to get to know your donors, show appreciation, and listen closely—and you’ll be well on your way to a successful, sustainable fundraising strategy. Let me know in the comments your favorite techniques for discovery visits! Cheers!  PS - I hope you’ll continue the conversation by subscribing to Real Deal Fundraising. When you subscribe, you’ll get my e-newsletter, which includes the best articles on fundraising, productivity, and cool stuff every week. The whole thing is curated awesomeness as well as freebies like webinars, instructional videos, and whatever else I can put together to be helpful to you! If you liked this post, you may also like these:
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Jessica Cloud, CFREI've been called the Tasmanian Devil of fundraising and I'm here to talk shop with you. Archives
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