A 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.
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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" 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. 
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Planned giving isn’t just another giving option – it’s a missed opportunity if left unaddressed. 

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.

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.

​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.

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.

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."

​Rather than waiting for donors to approach you about planned giving, take a proactive role by creating engaging, informative content.

• Write Educational Blog Posts: Cover topics like the benefits of planned giving, how to set up a bequest, and donor success stories.
• Host Engaging Webinars: Invite estate planning experts to break down the process in easy-to-understand language and answer common questions.
• Offer Downloadable Resources: Provide guides, checklists, and templates that donors can reference when planning their gifts.
• Celebrate National Estate Planning Awareness Week: See this blog post about the power of rolling out concentrated planned giving content via email, social media, and video once or twice a year. ​Utilize testimonials: Nothing is quite as powerful as a peer recommendation, and that’s true even in planned giving. Highlighting donors who have already set up planned gifts for your cause is a winning strategy.

These content pieces not only educate your audience but also position your nonprofit as a trusted resource in an often-complex area of giving. All of this content should drive interested prospects to a web form where they can contact you if they want more information or guidance or if they have already set up a planned gift to benefit your nonprofit but haven’t let you know yet. Conversations are a lot less awkward when the prospect has already expressed interest in discussing planned giving opportunities.

1. Keep It Simple: Use plain language and avoid jargon. Explain terms like “bequest” and “beneficiary designation” in everyday language.
   • Example: "A bequest is simply a gift you include in your will. It’s a way to ensure that even after you’re gone, your values and support for our cause continue to make an impact."
2. Use Consistent Messaging: Develop conversation scripts or guidelines that incorporate testimonials and the endowment concept. Having a consistent approach helps build confidence – for you and your donors.
3. Create a Resource Hub: Dedicate a section of your website to planned giving. Include FAQs, step-by-step guides, and downloadable resources.
4. Follow Up Thoughtfully: After your initial conversation, send a personalized thank-you note or follow-up email summarizing key points and offering additional resources. This reinforces that you’re there to support them throughout the process.

Planned giving isn’t about difficult conversations – it’s about meaningful ones. When you shift the focus from death and taxes to legacy and impact, you create opportunities for donors to shape the future of the causes they care about. By fostering engagement, sharing inspiring stories, and providing clear, accessible resources, you make it easy for supporters to take the next step. Start normalizing these discussions today, and you’ll find that donors are not only willing to talk about planned giving – they’ll be grateful you opened the door.
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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: 

• Leveraging National Estate Planning Awareness Week for Planned Giving Success
• Why Nonprofits Can't Afford to Sleep on IRA Rollover Gifts
• Discovery Visits Demystified: Tips for Effective Donor Meetings
• Portfolio Power: How to Prioritize Your Prospects for High-Impact Fundraising
• Nonprofit Productivity: Time Management Tips for Fundraisers

​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. 

​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.

​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.

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.
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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.

​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.

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.
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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.

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.
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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.

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.
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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.

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!​

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!

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:

• Leverage your network. Use board members, volunteers, or other contacts who have a relationship with the potential donor. A personal introduction is one of the most effective ways to get a meeting.
• Introductory letter. If you have some lead time, sending a well-crafted introductory letter can help. It’s a formal way to make your first impression.
• Email follow-up. If you’ve sent the letter and haven’t heard back, try sending a couple of follow-up emails. Keep them polite, concise, and reiterate why you'd love to meet.
• Phone call. Sometimes an old-fashioned phone call is the best way to cut through the noise. When leaving a voicemail, keep it brief but enthusiastic about the opportunity to connect.
• Do your homework. If you’re hitting a wall, research the potential donor online. You might uncover a shared connection or mutual interest that can serve as an opening for a conversation.

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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.

• Begin with email. Many seasoned fundraising pros will tell you that you MUST send a letter first. Others will say that a phone call is essential. I have pioneered my own system of securing an “anchor” visit (important, urgent, or with a VIP) and then filling in the schedule with emails.
• Use bulk emails that look more personal. I like to design HTML emails that look simple like a direct email from Outlook or Gmail. If you have a large prospect list to work through, this can save you a ton of time that might be spent copying, pasting, and customizing emails to prospect who may never respond. I wrote more about how to implement this in my time management post recently.
• Supercharge the Process with Calendly and Zoom. Sending emails will save you time. Sending bulk emails that look personal will save you tons of time. Adding a Calendly link for the donor to go ahead and pick out their meeting date and time in two more clicks can rev up your meetings! Adding a Zoom option can reduce your need to travel, saving budgetary dollars and time. If they merit another visit after the Zoom introduction, you can go see them in person.
• Phone a Select Group. Once I’ve sent a couple of bulk emails to get a visit, I will look at the tracking metrics in our email software and identify who actually opened the email and maybe clicked the Calendly link. That list is usually manageably short. I remove any who already signed up for a meeting and call the rest of those on the phone. I also call any very promising prospects who don’t have an email on file.

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.
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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.

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.

• Affinity — Do they like your organization? Do they have a passion for your cause?
• Propensity — Are they a generous person in general? What other nonprofits do they support?
• Capacity — How much could they give? Would the gift likely come from assets or income?

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.
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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. 

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.
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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. 

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!