702. Working Session: Planned Giving Without the Overwhelm - Pedro J. Rivera

Summary

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We Are For Good Podcast – Episode 702

Working Session: Planned Giving Without the Overwhelm
Guest: Pedro J. Rivera (Principal and Founder, PJR Consulting)
Date: April 22, 2026

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Episode Overview

This working session tackles the often daunting topic of planned giving for nonprofits. Hosts Jon McCoy and Becky Endicott welcome veteran fundraiser and consultant Pedro J. Rivera, who distills planned giving into actionable steps, dispels common misconceptions, and shares how to confidently engage donors in legacy conversations without discomfort or overwhelm. By the end, listeners leave with a practical 30-day starter plan and a reframed mindset about the transformative power of planned gifts.

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Key Discussion Points & Insights

Demystifying Planned Giving

• Planned giving, simplified: It’s a future gift—often bequests, retirement accounts, or life insurance—from a donor’s assets, generally via their will or estate plan.
• Why now? The generational wealth transfer (estimated at $72–84 trillion by 2045 in the US) means nonprofits that don’t proactively engage in planned giving risk missing out on transformative resources.

  "If you aren't asking, you're essentially leaving your organization's future to chance."
  — Pedro J. Rivera [04:16]

Navigating the "Elephant in the Room"

• Acknowledges the discomfort around discussing death.
• Suggests reframing as a conversation about legacy, values, and generational impact.

  “You’re not necessarily talking about death, you’re talking about the legacy and the impact that they're continuing past their lifetime.”
  — Pedro J. Rivera [05:46]

Finding Your Best Planned Giving Prospects

• Forget wealth, focus on loyalty: Consistent donors (e.g., giving 7 of the last 10 years) are top prospects.
• “No kids” factor: Donors without immediate heirs are statistically more likely to leave a gift.
• Target life stages: Ages 60–75 often prompt estate planning and updates.
• Volunteers and former board members: Have deep ties and understand long-term organizational needs.

  “The lapse donor, which I call the super donor. Sometimes they give $25 every year for 20 years and then... their biggest gift is going to be the gift at the time of their passing.”
  — Pedro J. Rivera [06:47]

Seamlessly Weaving Planned Giving into Communications

• Annual giving & planned giving are cousins: Loyal annual donors are prime candidates.
• Simple PS strategy: Add a postscript about legacy giving to every appeal letter.
• Newsletter “legacy spots”: Share brief donor stories about why they left a legacy gift.
• Website basics: Prominently display your tax ID, sample bequest language, and “ways to give” options.
• Subtle reminders: Include legacy giving prompts in email signatures and stewardship materials.

  "Just making sure you put language of bequests in your website... you don’t have to pay a fancy website, just putting language sample wording..."
  — Pedro J. Rivera [11:55]

The 30-Day Starter Plan

Pedro’s actionable steps for jumpstarting a planned giving program in a month:

1. Days 1–10:
   • Draft or review your gift acceptance policy to include planned gifts (real estate, crypto, etc.).
2. Days 11–20:
   • Run a “loyalty report” to identify 20–30 longtime donors.
   • Found a “legacy society” to recognize known/planned gift donors.
3. Days 21–30:
   • Personally call loyal donors to say thank you and listen for “legacy cues”—don’t ask for money.
   • Send a brief donor insight survey asking about legacy intentions or interest.

   “Pick up the phone, meet those 20, 30 people, say thank you, ask them why they stay. Don’t ask them for money yet. Just listen for legacy cues.”
   — Pedro J. Rivera [13:03]
   “We did a donor insight survey... and we went from 0 to 13 plan identified gifts.”
   — Pedro J. Rivera [13:57]

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Notable Quotes & Memorable Moments

• On reframing planned giving:

  “Stop assuming your donors don’t want to talk about leaving a legacy. We often project our own money baggage or death anxiety onto our donors. If you don’t ask, you don’t get the answer. The truth is giving a legacy gift is one of the most joyful, meaningful things a person will ever do.”
  — Pedro J. Rivera [01:01], [15:03]

• On loyalty and impact:

  “It’s often not talked about in just day to day materials... it’s like putting it out there and sharing that story is planting seeds. And you never know who is going to include that in a very personal capacity...”
  — Host [11:55]

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Timestamps for Key Segments

• [01:01] – The joy and meaning of legacy giving
• [03:04] – Pedro’s background and experience
• [04:16] – Why planned giving matters now
• [05:46] – Reframing the legacy conversation
• [06:47] – How to identify loyal planned giving prospects
• [09:18] – Messaging strategies for planned giving
• [11:55] – Integrating legacy language into your materials
• [13:03] – Pedro’s 30-day starter plan
• [15:03] – “One good thing” — Invite the conversation; it's an act of love

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Additional Resources & Where to Find Pedro

• Pedro J. Rivera: pjrconsultingllc.com and on LinkedIn (Pedro Jose Rivera, Esq.) [15:57]
• Join the We Are For Good Community at weareforgoodcommunity.com

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Tone & Takeaways

This episode uses clear, approachable language to strip away the mystique and nerves around planned giving. The tone is supportive, encouraging, and action-oriented. Pedro’s message, echoed by the hosts, is that legacy conversations are invitations to joy and meaning, not awkward asks—and that every nonprofit can and should embrace them now.

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Transcript

[Host (possibly John or Becky)]

Hey, friend. Before we get started, we wanted to invite you into our global gathering. Four times a year, we bring the We Are for Good community together for one day, one focus. And this Impact up it's all about storytelling. Impact up story is happening on Thursday, May 14, and we'd love to have

[Co-host or Announcer]

you there because the stories you choose to tell have the power to change everything. And we want to help you tell them better. So join us online from noon to 1:30 Central Standard Time for a free virtual session including a keynote with storytelling phenom Afdel Aziz and a roundtable conversation with four amazing nonprofit leaders. Then that evening, in nearly 50 cities around the world, we're gathering with local meetups to keep the conversation going in person.

[Host (possibly John or Becky)]

You can find a meetup near you or join us [e-mail] ImpactUp what starts here? Ripples.

[Pedro J. Rivera]

Stop assuming your donors don't want to talk about leaving a legacy. We often project our own money baggage or death anxiety onto our donors. If you don't ask, you don't get the answer. The truth is giving a legacy gift is one of the most joyful, meaningful things a person will ever do.

[Host (possibly John or Becky)]

Welcome to Working sessions on the We Are For Good podcast. In every session, we're tackling one essential topic and give you practical steps to take meaningful action within your mission. Today we're bringing you the experts and playbooks to help you move forward with clarity and confidence. Let's get to work. Hey friends, welcome back to Working Sessions. And we are taking a topic that has honestly, can I be ridiculously honest right now? It's always overwhelmed me, you know, for years in nonprofit work and fundraising, I always felt like not ready, not prepared to talk about planned giving. And I don't know if you listening today may feel that, but we wanted to have a working session designed to talk specifically about the overwhelm that that a lot of us feel because there's a way to do plan giving without that. And we have brought an incredible guest to the podcast, Pedro J. Rivera. He is the principal and founder of PJR Consulting and he's here to take our hand and kind of walk us through plan giving. He has bring in more than 30 years of experience at the intersection of law, philanthropy and fundraising, raising just a casual 150 million for nonprofits and universities. And through his work at PJR Consulting, he works specifically with Latinx nonprofits to build sustainable fundraising strategies. And of course, planned giving is one of his superpowers. So today he is breaking it all the way down bite sized pieces for us of what it actually is, where to start, and just how to have that conversation without it feeling weird. So we're going to leave today with a 30 day starter plan by the time we're done. Pedro, to have you in the house means the world. Thanks for coming to working Sessions today.

[Pedro J. Rivera]

Thank you, John. A pleasure to be here today.

[Host (possibly John or Becky)]

Well, I mean as a first time guest on the podcast, but you're not new to the We Are for Good community. I would love to give you a chance just to tell us a little bit about your background and the work that you're doing today before we hop into the working session.

[Pedro J. Rivera]

Sure. So I have 30 years between legal wealth management and fundraising experience and I've been doing fundraising and plan giving for the last 16 years. I've worked with NGOs, large nonprofits, small nonprofits. Before I went into consulting practice, I worked at a higher ed institution and I've also launched three plan giving programs. Because I did wealth management and I did trust work. I feel plan giving was always been like my juice or my favorite subject. You know, it's a relatively simple subject matter that gets overcomplicated by a lot of people in the fundraising world.

[Host (possibly John or Becky)]

Thank you for breaking it down. First of all, you're like connecting it back to trust, which is such a cornerstone theme of this year on the podcast, but it's also like the evergreen bedrock of what fundraising is built upon. So I love that you're bringing it back to that. It is trust building work and if that's there conversation, everything that follows is so much easier. So I love the way you've table set this conversation. Let's dive into like really demystifying plan giving. I mean, where does it get overcomplicated for folks? And in plain language, could you talk about why does it matter and why should an organization listening today really prioritize thinking about this right now? Sure.

[Pedro J. Rivera]

So plain giving a simple term for a future gift. It's a donor's expressing. I believe in this mission so much that I want to be part of it. And even, even after I'm gone. It's mostly a simple terms a typical gift from a donor's asset such as a will, a retirement account or a life insurance rather than their monthly paycheck. So most planned gifts are really bequest by gift or a gift left by will. So it's, it's really simple gift that's left by an instrument as will for the organization of their choice. Why does it matter now we are expecting the biggest wealth transfer in the history. It's called the great wealth transfer. It refers to the massive shift of assets currently taking place as the baby boomer generation, which is our grandparents or some of us, our parents generation, passes their wealth down to the younger generation and charitable causes. It's estimated that between 72 trillion to 84 trillion will change hands in the United States over the next two decades through roughly 2045. So if you aren't asking, you're essentially leaving your organization's future to chance.

[Host (possibly John or Becky)]

The business case is absolutely there. The moment in time feels there. I wonder if you would just kind of name the elephant in the room. I mean, these are conversations of gifts that go into effect after someone passes away. You know, what's an entry point for that conversation? Because I think in our culture across the US a lot death is not the most, I don't know, comfortable of subjects for people. And it feels like it's intermingled. When you're talking about a legacy gift like this, how do you think about it or reframe that for me?

[Pedro J. Rivera]

You know, I, I think in many ways the best way to talk to, to donors about planned gifts and particularly loyal loyalist donors that have been giving to you, you know, for a long time. You've like, you know, you've been such a stead our family for the last 10, 20 years. I'm curious, what is it about the work that you want to see continue for the next generation? You know, you can also sometimes talk to many of our supporters, find that naming us as 1% of beneficiary of their IRA or their estate is the easiest way to make a big impact without touching their current bank account. And have you ever considered this? So you're not necessarily talking about death, you're talking about the legacy and the impact that they're continuing past their lifetime.

[Host (possibly John or Becky)]

Let's talk for a minute about finding your best prospects. So like, who should organizations be looking for? Maybe what are some ways you could look at your data that you already have, maybe in your CRM, and identify who would be a really strong legacy prospect? Even if you don't have a giant research budget or a dedicated prospect researcher on your team? What does that look like?

[Pedro J. Rivera]

Yeah, well, I always tell people, stop looking for the wealthiest people. Start looking for the most loyal, the people who are kind of giving you on a monthly basis, there's a couple of identifiers that identify people as a plan giving prospect. And you don't need to have an expensive wealth engine. You know, we have a 710 rule which is people who have given seven out of the last 10 years. Consistency is much of a high predictor of a legacy gift than a high ultra high net worth donor. The lapse donor, which I call the super donor. Sometimes they give $25 every year for 20 years and then all of a sudden you see that they stopped. They might have stopped because they're living on a fixed income, but their biggest gift is going to be the gift at the time of their passing. Then the other other things that you should look no, no kids factor. Donors who don't have any immediate heirs are statistically the most likely to leave a transformational gift to a nonprofit. And then strategic demographics. While you shouldn't ignore younger donors, certain life stages naturally prompt estate planning, ages like 60 to 75. This is a sweet spot and I can identify with this because I am 60 and I'm in the midst of revising our estate plan with my husband. These are individuals like me that retired or nearing retirement and have finished paying for their children education and are actively revising their wills. The other people that you should consider are volunteer and committee members. They have seen the work firsthand and if someone has volunteered for five or plus year, they're your top tier prospect and the elephant in the room. The former board members. They already understand the organization's long term financial needs. You should be talking to them about leaving a legacy gift.

[Host (possibly John or Becky)]

Pedro, just underscoring all of this that you said. First of all, thanks for normalizing this and saying that you're personally working on it in your life. I think that is a beautiful testament to like this is what people that want to do good in the world, this is the kind of conversation they want to have because they do see the pain points and especially for missions that we've been closely tied into through volunteer or service in different capacities. It's like of course we want to continue that legacy. Like that tracks so much. I'm wondering, you know, I was in the seat of annual giving for the majority of my career or in marketing and I just think there is. It's often not talked about in just like day to day materials or communications. So I'm curious from your perspective what you've seen of how can you really weave planned giving into your messaging without necessarily launching some giant program. But is it something you can fold into existing appeals or newsletters or just a donor visit? What does that look like to start placing these seeds into different conversations and communications?

[Pedro J. Rivera]

Yeah, I love annual giving. I feel like annual giving and plan giving are cousins or Siblings, the younger and the older, you know, second cousins twice removed. No. Yeah, exactly. Because I think, you know, annual giving kind of not only identifies donors that are loyal to the organization. So I think in everyday appeal I call it the PS strategy. And every appeal letter you can have, you can put a P.S. and say, hey, have you ever considered leaving a legacy to X and Y organization or to organization? Check the box in the back for more info. So then they identify themselves as people who want to do a plan gift. And in annual giving, when you're sending to a huge amount of people, the, the annual appeal at the end of the year, the other other ways that the newsletter, I call it like the legacy spot or whatever you'd like to call it, you can kind of, you know, the futures, the, you know, the, our, our crusaders, our pioneers, our heroes spot. And instead of having text heavy articles that you probably had some organization right for, you share a three sentence story of a donor who left a gift in their will and why it had made it possible. I'll give you an example of something that I did with one of our one, a legacy spot. When I worked at a nonprofit organization, we actually ended up getting a gift, a $25,000 bequest gift this donor had never given to the organization. So as I did my research, what I found out was that this person had never gotten married, had never had kids and in early in her career she had gotten a fellowship through the nonprofit organization that I was working. And this was her thank you gift for her the kind of career that she had. And I was able to find that out through the executor of the state who was our niece. And we were able to, to kind of not only launch our plan giving program, but create a legacy spot to talk about the impact that it did and the importance of that. So I think, you know, those are very easy, relatively inexpensive things to do. And then the other most obvious is kind of like on your website making sure that you put your tax ID number that you put words like leave a legacy in your email in your website. Also on my email signature. When I worked at a nonprofit I would always put things, consider leaving a legacy on my signature. So would people would, you know, talk to me about it. And just making sure that you put language of bequests in your website. You don't have to pay a fancy website, just putting language sample wording and you can get these simple wordings in many places online.

[Host (possibly John or Becky)]

A simple bequest language.

[Pedro J. Rivera]

Yeah, yeah, bequest language. And make sure that you put it on your ways to give page, which you can also, with that also add the ira, the requirement minimum distribution, the gifts of stocks, the donor advice funds are all good technical ways that people can also leave a gift to the organization.

[Host (possibly John or Becky)]

Yeah, I think that story you share is really poignant because one of our core values is play the long game. And we believe that in relationships, certainly. But Becky and I both have several examples of our careers of looking back to planned gifts that arrived of no one in the office had an actual relationship, but it was the foresight, the connection of many years before us of maybe a previous staff member, a relationship or a service opportunity. And it's just like putting it out there and sharing that story is planting seeds. And you never know who is going to include that in a very personal capacity that maybe they don't even want to feel comfortable sharing with their family until later in life. So at the top of the podcast, I promise that we're going to leave our listeners today with a 30 day starter plan. So I'd love for you to kind of break down for someone listening today, or maybe they're on their commute, maybe they're at your desk ready to act. What are the next two or three steps that you would advise someone to take over the next 30 days? If this is a conversation that's piquing your interest and you're like, oh my gosh, we got to, we gotta pour into this at our organization, where would you start?

[Pedro J. Rivera]

Great. So if you're at your test right now, here's your homework for the next month. Days 1 through 10, Draft and Pass a simple gift acceptance policy. Review your gift acceptance policy. Make sure that you include planned gifts like real estate, crypto, any other kind of possibility of leaving a gift. Between days 11 to 20, run the what I call the loyalty report. Find 20 to 30 people who've been giving to you for a decade or more and call them, talk to them. The other thing is between days 11 and 20, create a legacy society. You know, people would like to be part of groups and memberships and the legacy society are the people who have left you a gift by will in in their planned giving. And day 21 to 30 is action time. Pick up the phone, meet those 20, 30 people, say thank you, ask them why they stay. Don't ask them for money yet. Just listen for legacy cues. Also consider sending a donor insight survey and asking questions about legacy gifts. I did a donor insight survey at one of the first places that I relaunched a plan giving program. And we went from 0 to 13 plan identified gifts. People who had named us in the will that we weren't even aware of. These donor insight surveys can be 1012 questions nowadays. They can be done electronically. We did it by mail. But this is a great way to self identify people and also identify people who are curious and want to have a conversation.

[Host (possibly John or Becky)]

What a great place to start. Bookmark this, friends. I mean, this is literally a 30 day action plan that you're going to feel so much momentum if you just kind of get some of these pieces in place. And I think people do want to be part of something, especially our giving. It's so tied to our identity, how we want to show up in the world who we want to be associated with. So I love the call out of just creating a simple way to do that and include people in a really special capacity for such a amazing thing that they're doing. Can we just like talk about how incredible it is that people are making that kind of a commitment? Friend, this has been so helpful. I gotta kick it to you for a one good thing. What's a secret to your success? Or maybe a good habit? It doesn't have to be related to planned giving, but you know, that's bonus points if you can tie it into planned giving.

[Pedro J. Rivera]

My one good thing is stop assuming your donors don't want to talk about leaving a legacy. We often project our own money baggage or death anxiety onto our donors. If you don't ask, you don't get the answer. The truth is giving a legacy gift is one of the most joyful, meaningful things a person will ever do. By not bringing it up, you're depriving them of the chance to make their life's work permanent. And invitation is an act of love.

[Host (possibly John or Becky)]

Pedro, I feel like you're taking me by the shoulders because I said that I was intimidated to have this conversation. And you're like, you're refusing people of joy and like connection and all of this stuff.

[Pedro J. Rivera]

Absolutely.

[Host (possibly John or Becky)]

So thank you for the reframe. I think it's a powerful unlock. It's something that absolutely every organization should be talking about. I mean, my friend, we gotta give you a second to just kind of connect the dots for us. If people listening are like, I need more Pedro in my life, I totally get it. Tell us a little bit about where people can find you, how they can connect with your work at PJR Consulting.

[Pedro J. Rivera]

Yes, you can find me on my website at www.pjrconsultingllc.com or connect with me on LinkedIn and I'm under Pedro Jose Rivera, Esq. I'm always eager to discuss how we can build a more equitable and sustainable future for nonprofits in the sector as a whole. So thank you for having me.

[Host (possibly John or Becky)]

Awesome my friend. Thanks for the way you pour into the community. Appreciate all the insights you brought today. Really grateful for you.

[Pedro J. Rivera]

Thank you. Have a good day.

[Host (possibly John or Becky)]

Hey friend, thank you so much for joining us today. If you find yourself looking for a place to stay connected and keep learning between episodes, I hope you'll come and join us inside the we are for Good community. Yeah, it is free, it's full of incredible non profit leaders like yourself, and it's now an app in the Apple App Store and Google Play Store. So you can take this community with you wherever you go. Head over to weareforgoodcommunity.com to find us. We cannot wait to see you inside.