Turning sector benchmarks into messages that connect

Dani Cluff: Here we go. We’ll give it just a second as everyone starts to join. As we do, I’ll introduce myself. My name is Dani Cluff, and I’m over here with the team at Bloomerang. I’m happy to have you all with us today, along with Tim Sarrantonio, and I really hope I said your name correctly.

Tim Sarrantonio: You did.

Dani Cluff: Perfect. While people are getting logged in, I’d love for people to drop in the chat where they’re joining from. I’m always curious to see where people are. I’m located in Minneapolis, Minnesota, so I’m basking in the wonderful fall weather. Tim, remind me, where are you located?

Tim Sarrantonio: I’m in Niskayuna, New York, which is in the upstate region of New York above the Hudson Valley, specifically the Capital Region by Albany.

Dani Cluff: Oh, nice. So you’re getting into that fall weather too.

Tim Sarrantonio: We are. It’s spooky season, folks. If you don’t know me, my father was a pretty prolific horror author. So Halloween...Patton Oswald called him the king of Halloween. So this is my favorite time of the year.

Dani Cluff: Oh, I love it. As we get started today, a couple of housekeeping notes. We’ll have the chat running throughout today’s webinar. I know Tim wants to hear from you, and you can chat with everyone else on the webinar today. We’ll also have the Q&A area open, so if you have any questions as we go, drop those there so we can keep track of them and they don’t get lost in the chat. Tim will have a resource that we’ll send out in our follow-up email today, as well as a link to the recording of the webinar so you can watch it again and share it with any friends who weren’t able to join today.

If you’re not familiar with Bloomerang, we are a giving platform built for purpose. We’re created to help nonprofits build stronger relationships and grow your impact. If you want to learn more, we’ll launch a poll at the end of today’s webinar that lets you opt in to hear more communication from Tim himself. I know he’ll have a lot to share today, so you’re going to want to hear more. You can also use the poll to learn more about Bloomerang if you would like. Tim, we’re so excited to have you joining us today. I’m gonna hand things over to you so you can get to the information people really want to hear.

Tim Sarrantonio: Awesome. Thanks, Dani. I want to thank the Bloomerang team, who have been fantastic supporters of the Generosity Roundtable and the peer learning network that you’re going to hear a little bit about today. Some of the insights we have on addressing retention come from there. Today I’m going to share how to turn sector benchmarks into messages that connect, and we’re going to hear from your peers.

I’m paying attention to the chat. I saw some Bills chat, for instance. Hopefully I don’t lose you already. I’m a sad-sack Jets fan, so it’s never a good day here. My backup team is definitely the Bills, who are doing well up here. We’ve got people from Florida, Maryland, Ontario, Minnesota, and that’s what I love about all the ways we can learn together.

If you don’t know who I am, I’d love to hear in the chat if you’ve ever seen me speak before, because this is going to be completely different from anything you may have seen me do. I was just telling Dani in the green room how excited I am to be presenting this with the folks at Bloomerang. I’ve worn a lot of different hats in the sector, and I’m excited to be wearing this Bloomerang partner hat today. We’ve got a lot of folks connecting with each other in the chat, so let’s get into it.

Before we start, I’d love for you to dive into the chat and think about the last training or conference session you sat through, something similar to this. I know Bloomerang puts on a lot of great webinars, and we’ll continue to do that through the end of the year and Giving Tuesday. Did that speaker work at a place like yours? What was the experience? Was the person on the stage someone you would consider a peer of yours? That’s a critical question for how we learn. It’s not enough to tell you benchmarks. We need to think about the different ways we take the context of the content we’re given and act on it.

I’ve started to do some research on this after fifteen years in the sector working for a nonprofit technology company, and as we’ll hear more about my history working directly in nonprofits, most of what we learn is from somebody else’s stage. Ninety-seven percent of nonprofits are running under $5 million a year. That’s some of the most recent data from the National Council of Nonprofits, and the number has held strong for a while now. Ninety-two percent are under $1 million a year. The vast majority of you are doing this with maybe one other person helping you. I had a session earlier today where someone talked about the importance of getting the marketing team on the same page as the fundraising team, which is something I experienced in my career, as we’ll see.

This influences how you think about problem solving in your own work. Who you digest information from, and how you contextualize it, is critical to your success. There’s some data that shows this. I did some analysis of some of the biggest conferences out there. You have big national ones that draw a lot of fundraisers or marketers, small regional events, and chapter associations. Typically, the more localized and geographically focused an event is, the more likely you are to see somebody like you on the stage doing a panel, a presentation, or a workshop. You might have a few consultants. But especially when you get to larger events, and to professional and peer association groups, you’re going to see a lot of consultants. That increases as you move up to the national stage.

This isn’t automatically a bad thing. There are great insights that people from a company like Bloomerang can bring to the table. That’s why we’re excited to have them presenting at the Nonprofit Social Media Summit next month, as my collaborator Julia Campbell and I are so excited about those insights. But when you’re attending a free event, there’s always a question of what they’re trying to sell me or tell me to do. No matter what, everybody has some sort of intention. We’re not walking into these things hoping something good will happen. You walked into this webinar hoping to learn something.

What excites me is a growing focus on ensuring that peers and experts can talk to each other and share these insights, either in large aggregate pooled ways, like what we’re seeing with the Fundraising Effectiveness Project, as you’ll hear, or in a more intimate way, like what the Weavers are doing as part of the Aspen Institute.

Here’s why this matters. Right before this talk, I saw a comment on LinkedIn that asked: would you rather have A, a $5,000 gift, or B, a $5,000 professional investment in your career? Somebody posted that question just before I joined. I’m looking at the chat, and I love that you’re all saying B. You’re taking your professional development seriously.

But my argument is that the answer depends on where somebody is in this maturity model, which is a pretty standardized one. One of my favorite books on nonprofit capacity, from the TCC Group, focuses on this, and it’s a very elegant explanation of where your organization might be in the life cycle. I’m going to ask you to take a poll shortly, but first I want to explain the life cycle. And I love that we’re the B crowd. You are my people, because it’s about the long-term sustainability of not only your organization but your own mental health. There’s a direct correlation between the happiness you have in your work and the excitement you bring, and that translates into how you write appeals and talk to donors. If you’re sad about work, you’re not going to be excited to talk to folks about it. We don’t want to enter into toxic positivity. It’s not only about mindset. It’s also about the resources that align with it.

If you’re not aware of the maturity model, it’s just a way to understand where your organization may be. When it comes to resources, this has nothing to do with how old the nonprofit is. Let’s start with startups. This is baby Tim, probably 2007 or 2008, almost twenty years ago. This was my first nonprofit job, at a day labor agency. Somebody caught me on camera like they were watching TV in Chicago and snapped a photo of me, which is why it looks like that. The vast majority of nonprofits in our sector are in this stage. Most nonprofits are actually $50,000 and under. They might be all volunteer or have a small skeleton staff. People in this stage don’t have a lot of time, talent, or treasure. What they need to lean into is building trust. That’s the main currency that runs through all of this. In the research we’ve been doing at the Aspen Institute, trust is critical, and it’s something you can control. You can’t always control the money. You sometimes can control your time and a little of the talent you can bring to the table. But you can work on a conversation that makes somebody trust you, because you can fill them with confidence, and we’ll talk about that. A lot of it comes down to understanding their motivation and matching it with yours.

A first step for somebody in this stage is, realistically, if somebody offered a nonprofit in this stage $5,000, they’re going to take it. That’s kind of the problem with the advice we receive: by the end of this you’ll see that the vast majority of advice comes from mature nonprofits who can give it or take it, while the vast majority of people are here. So, Elka, this is for you. We just got our EIN and we don’t even have a nickel in the bank account. I feel your pain. I remember downloading my first CRM. It was an open source thing, with a 300-page PDF manual. It’s wild.

Then I moved on. You work through things. This is the larger understanding I’ve come to after twenty years in the nonprofit sector: we don’t have a practice field. The decisions that Elka is making at the startup stage could be life and death for the organization. It’s the thing that kept me up wondering how I was going to pay my student loans. As you can see in my little independent bookstore photo, we’re not rolling in dough, folks. This was around the housing crisis, when I started to enter the nonprofit sector, and you haven’t been a nonprofit professional until you’ve lived through some sort of crisis. So congratulations, everybody. We’re putting you through the wringer right now.

How do you navigate that? First and foremost, you need a little bit of a practice field to understand what’s going to work and what’s not. You’ve got to be able to experiment a bit. You say, let me try this out. I’m not always going to swing for the moon or the fences. Sometimes priorities feel like a shot in the dark. I did a Generosity Roundtable session earlier today. It’s a conversational role-playing game that I designed. Two folks joined a virtual table earlier today, and one of them was clearly articulating, look, I’m a team of one. Where do I focus? What we ultimately come down to is: why do people care about you? Seth Godin says, people like us do things like this. At this stage, a critical thing to figure out is who is showing up for you, who is already sitting at your table, so to speak.

Someone said they’re still working on their model. Very good. Keep giving me those stories, because I love them.

This is where it starts to get interesting. In the world of nonprofit technology market analysis, they might say SMB, and this is the M, the mid-market nonprofits. These are folks that might have $500,000 in revenue. They have some decent infrastructure, and it isn’t always about money. It’s also whether they have systems in place. This is where implementing a tool like Bloomerang is critical. I implemented a CRM with Reading with Pictures, a comic books and literacy nonprofit that I founded. I started testing things like peer-to-peer fundraising and different community events. What was powerful was then understanding, okay, this is what we need to make sure we maintain. Then you look behind you and ask, what can we do next? How can we improve? The blood pressure starts to lower a bit at this stage when things seem fine.

Then you get into maturity. This is when I shifted from organizations that were trying things, especially the second nonprofit I worked for, an art studio for adults with developmental disabilities. We were very events-focused for our fundraising, so building an individual giving program from scratch was a lot of work. The job I had right after that was at a Catholic school, where I just wandered in and they had a massive machine already running. It was an old database and everything was set. They wanted to improve some things, which is why I was there, but generally it was a good rocket. My first week there, I was handed a $10,000 check. I didn’t do anything. This is also where, when you see consultants saying, I raised $9 million, it’s like, no, you didn’t. Systems did that. You helped. We have a lot of folks who feel content to sit on their islands in the sun and tell us what to do when they haven’t been in the muck for a long time. What I loved about this part of my journey was that professional development felt fun. It felt like I was exploring a new way of thinking about the world and seeing technology pair with the community the Catholic school had deeply built over decades. It’s a hundred years old, and that history was simply connected by the technology.

Absolutely. Joy.

Then you get to the top, and you’re sitting there hoping things continue to be great. This is where leadership especially can sit on their laurels and say, we’re good. We don’t need to experiment anymore. Last year’s plan becomes this year’s plan, and that’s just not realistic. At my last organization, I helped over 800 nonprofits join a technology company. The practical reality is that it didn’t matter where they were. From startups through mature organizations, there’s always room for improvement.

That comes down to listening. How do we do that regardless of where you are? First and foremost, Dani, I’d love to launch the poll. Now that I’ve walked through my own journey, I’d love to hear where you might be in your own maturity life cycle stage. We’ll leave this open for a moment. I’m also checking the chat to make sure I didn’t miss anything. I’m so happy that all of you went all in on professional development, because I think that type of long game is really good.

Alright, Dani, let me see if I can see any results. Nice. Most folks are in the infrastructure stage, about 25 percent of you. Some of you are in the renewal stage. Thank you for feeling comfortable to say that. I love that.

Someone said, I just started last week, so it’s hard to tell. Exactly, Lindsay. I think we sometimes punish folks for saying, you know what, I’m just starting out, and I’m trying to figure out what’s right for me. A lot of this comes down to listening to your community and your peers, and you can do this in ways that go beyond yelling into a Facebook group, asking what technology you should use. I’m rolling out a few pieces this month. One of the things Dani mentioned is a resource. I write articles pretty consistently for free on my blog. There’s no Substack you have to apply to or anything like that. I have a whole series coming on Facebook groups and online reviews for technology, and overall how you can trust your vendors, including case studies. Organizations like Bloomerang listen to two critical things, and that’s where you can start to listen to your peers and the experts.

I love that, Joy, in terms of how it doesn’t matter the age for your maturity. My grandma is 98, and she’s the youngest person I know. Think about that in your own life and apply that practical reality to how people move about the world.

Let’s get into it. I’ve got about twenty-five minutes before I open it up for questions. That’s my goal. We have a lot to go through when it comes to understanding how to listen. First, we’re going to do a deep dive on data from the Fundraising Effectiveness Project, at fepreports.org. We’ll have a new set of research released later this month, and this is the largest analysis of individual giving in the world. Bloomerang is a member. My former company is a member. We have several other data providers who believe in the power of insight and in aggregated, anonymous, ethically sourced data to understand what is happening with our donors. Things like the Giving Signals report get built on top of that too, because we have a lot of great foundations for asking, where are we? That’s one thing we’re going to drill into today, and it’s what you signed up for: turning those benchmarks into messages. We’re going to talk about the benchmarks.

For the past year I’ve also had the pleasure of being part of the Aspen Institute’s Alliance for Social Trust, in a work group specifically focused on bottom-up trust. I’m going to bring a little of that insight into our conversation today. That’s the cool part about building a peer learning network with partners like Bloomerang who can put my learnings in front of a bunch of people, because it amplifies. You could take this into your board meetings and your conversations. Ultimately, we’re trying to help you stay out of stagnation. I especially want to help the 7 percent looking for renewal. I want to help everybody.

This is 2025 data. The data from 2026 is still being compiled, so for simplicity I’m asking what happened last year, because that helps inform what could happen going into the end of this year. We’ll have a better idea at the end of this month. Generally, the narrative is that dollars are up, and donors are down or at least stagnant. Retention is rebounding a little, but some of the discussions we’ve had are about whether it’s only the larger donors who are sticking around. Have we basically burned through the people who could potentially give to us? My argument is no. Generosity is boundless. It is abundant. It is within every single person you talk to. It’s a matter of mapping that motivation into a system that activates that engagement, and that’s what we’ll talk about at the very end of this talk. At the very least, I want you to look at these numbers and not despair, but to see an opportunity. Instead of looking at an empty chair as somebody who has left your organization, look at it as an opportunity for somebody to sit down and join the others who are already at the table.

If we have a table of ten people, imagine that eight of them leave and don’t come back to continue the conversation with your organization. First and foremost, we have to focus on the two people who are staying. New donor retention is about 18 percent in the sector. That’s two out of ten people. But what we’ve also found is that if you can help people feel that the table is for them to sit down at, they will come. They will come.

Most folks who look at the data I just showed, or at the fepreports.org website, which is completely free thanks to GivingTuesday’s Data Commons and the Association of Fundraising Professionals Foundation for Philanthropy, with support from all of our data providers as well as a broader committee of really amazing folks like Alice Ferris, who I know has been part of the Bloomerang ecosystem for a bit too, fantastic stuff that she does, use it to educate their leadership. Eighty-six percent of people use FEP data to educate their leadership. They may say, look, we have a retention problem. They might even take what is called the Fundraising Fitness Test, a free tool for looking deeply at your own retention. There are also a lot of great things inside Bloomerang that can do this. But most folks are not using it to adjust their day-to-day campaign planning.

What the data generally tells us at the top level is to double down on stewardship. I think stewardship is important, but it’s not the only thing. You can’t focus solely on stewardship, because some folks don’t respond to getting thank-you notes and things like that. It’s more about the impact they hope to have. But it’s always a good bet. Trust is consistency. It’s also the last time somebody heard from your organization when you weren’t asking for money.

Then there are mid-level donors. What we define as mid-level is something you can discuss. FEP reports has preset buckets for this type of analysis, and your database may also have this. Generally, we’re talking about people giving above $500. My initiative, the Generosity Roundtable, has a fiscal sponsorship relationship. We’ve taken on grants and individual gifts to help expand the network, and the average gift is $500. For me, I have to think about what mid-level is for that type of organization. Then, how do you make your relevancy clear? There are 1.9 million nonprofits in the United States alone. That’s beyond the GoFundMes, the mutual aids, the giving circles, the “buy this app” type of thing, and whatever AI thing is getting pitched. Our donors have a lot of things fracturing their attention. Why are people at your table? Showing up consistently has gotten me some backing from a coalition I’m associated with, so this does matter. See? Peer learning.

What the reports can’t see is that a lot of data is not being tracked. The phrase I love, from a Chronicle of Philanthropy article I read earlier this year, is that we’re measuring vinyl in a Spotify world. I’d argue that for the high-fidelity fans out there, vinyl still matters to some people. They want that enriched sound, and your major donors and legacy donors might prefer vinyl. But these analyses are great, and I was a board member of the Giving Institute for several years, there’s still a lot they miss. There are a lot of things you don’t see when you read these big national reports. I don’t think we all know where good stewardship actions land after a gift.

Can we talk more about stewardship? We’ll get into that, Culver, because stewardship is one element that can help motivate somebody. Philanthropic psychology ultimately drills into the fact that people are motivated by community building and by the impact it shows, and they weren’t guilted into it. We’ll get into that in the next section. But there’s a lot we’re missing. That doesn’t mean it’s not happening, and that’s an important distinction. The absence of data does not mean the absence of things occurring. You might be missing things. You’re never going to be able to quantify a hug. What’s the financial ROI of a high five at an event? You don’t know. You’re not supposed to know. Part of it is the art and science here.

The story behind the numbers ultimately gets to the question of what good stewardship looks like, because good stewardship is going to look like something that matters to the motivations of the individual receiving it. The more connected donors feel, the more they give. Recent research from Charity Navigator and Mutiny Company found that donors who feel connected to a cause gave about 7.6 times more than donors who indicated they weren’t connected at all. People do give in disaster relief situations, for instance, but ultimately, connection is critical.

What builds connection? Well, the psychology. The Institute for Sustainable Philanthropy has an eight-week course on this. Everything you’re going to see in the Generosity Roundtable is derived from research into philanthropic psychology, which is ultimately about what makes somebody a generous person. Not why they give, but what is going to activate them for their time, talent, treasure, and ultimately trust. Good stewardship is rooted in understanding this.

All stewardship comes down to this. First, understanding their identity. Do you know who they are? Not demographics, but the underlying why. Second, did they make this gift because they wanted to, or did you use some sort of pressure tactic? This is where we need to be very careful about things like, it’s Giving Tuesday, nobody gives a [expletive]. Hopefully I’m allowed to slightly curse on a Bloomerang webinar, but I have to really stress that. Don’t write that in your email. I wrote one of the most definitive reports on this. Don’t put that in your email. It’s GivingTuesday, nobody cares. The practical reality is that they will care if there is real urgency that pays off. One thing Ephraim Gopin has pointed out for years is the false match. If we won’t hit our goal unless you give to us, and then the goal gets extended, people pick up on this. That leads to competency, meaning do people believe what you’re saying, and are you building a community around it? As Seth Godin says, people like us do things like this. What is your version? Joy, Claire, Elka, what’s your version of “people like us do things like this”?

The way I’ve organized this is that I basically got sick of having these conversations over and over. You’re in a meeting for two or three hours. It doesn’t matter if you’re at a tech company or a small community-driven nonprofit. Bad meetings are terrible. The Generosity Roundtable is, at least for individual teams, a way to navigate that and cut your time by about 50 percent. Hundreds of people have played this, and it’s awesome for groups too: event planners, workshops, things like that. What we’re seeing here is the Connect Center, a small nonprofit, I would argue in that adolescent stage of the maturity life cycle. They are my fiscal sponsor. They have about $500,000 in revenue and they are rocking it in their own way. They were the first people we played this with.

The Generosity Roundtable is a role-playing educational gaming system that I designed to get teams on the same page, and there’s a peer learning network around it. Anybody who opts in, I’m not going to start hitting you up to buy the thing. If you think it’s cool, I’d love for you to check it out. You get free conversations on a monthly basis with your peers, lessons from webinars and insights from this session, and reports back on things happening at tables across the sector, brought into your living room so you can understand and even replicate them, with experts like Rachel Muir, Julia Campbell, and Chiri and Koshy, all people you can see at the Nonprofit Social Media Summit, for which Bloomerang is our giving platform partner. We’re not playing the game today, but I wanted to introduce the way I took years of conversations and thousands of problems brought to me and designed something that says, let’s look first at the motivation for why somebody is in the room, why they’re at the table. All the philanthropic psychology I just mentioned helps organize this into a little way to think about the world. I’m going to go through each of them.

We’re good on time. If you’re wondering how to start to steward people, it’s understanding their motivation. Let’s go through each of the ten archetypes and why they might activate in your own community. As you’re watching, do you see yourself in this? I have a little quiz that’s free and doesn’t ask for an email. Do you know somebody who’s an evaluator? Do you have questions about how to interact with a connector? Throw them in the chat.

Evaluators are very business-driven. This is probably a board member who works at a bank, something like that. They just want to see the numbers. It’s not that they don’t care. They make their decisions based on hard facts. Everybody knows somebody like this. I was putting together my end-of-year appeal for the community foundation I’m part of, and I adopted the evaluator as the lapsed donor tone, kind of putting myself in their shoes. That’s honestly one of the ways I use this. If I’m going to design segments, I ask who is in a segment. Somebody who’s lapsed, who hasn’t given to your nonprofit in two or three years, probably isn’t going to be brought back by a good story. I love the cheering on, too.

Very similar, in terms of being a little more numbers-driven, is the builder. It’s almost like introverts and extroverts. An evaluator says, I’m going to sit at my computer, give me some spreadsheets, I want to figure it out. A builder might be in the field, in food pantry work, for example. These are capital campaign folks. They’re not necessarily dreamers per se, but they look at something and ask, what could fill this? What could replace this? What could strengthen this? Capital campaigns, endowments, and clear governance activate these folks. Depending on your cause and the community you’re trying to appeal to, this is a slightly different way you talk to somebody.

Trust keepers are rooted in reputation. Not the Taylor Swift version, but the one that ultimately comes down to: do I trust you? Am I in the circle of trust? You know these people. They say, I’m going to go talk to Barbara and get her opinion. These are people who may be important behind the scenes if you’re doing a capital campaign. Maybe it’s a silent phase where you get these folks involved and start to build consensus around an initiative before bringing it to a larger group. They’re awesome to gut check against. This also applies if you’re doing donor surveys, or if you’re just starting out. Don’t spend money on a survey. Don’t run around. Just go talk to somebody and ask, why did you give? Why do you trust us? Pull that out.

The ambassador is connected to this, especially for people doing peer-to-peer fundraising. This activates them. They want to be out there bringing the excitement to the community. October is officially Ambassador Month here at the Generosity Roundtable, so there’s even a digest I sent out to all the hosts working in the community. Again, it’s a physical game people can have, and we have dozens and dozens of people who have it. Ambassadors are the types of folks people look at and say, I like that they’re out in front. They like public recognition, so you always have to balance this. You don’t want to overcorrect and say, whatever you want, Mr. and Mrs. Ambassador. It’s about the larger community, because you might make a big announcement with one donor, but the way you go about it could turn off all these other potential people because they feel, but where was my place in this? An ambassador can help navigate that.

We’re almost halfway through these, and then we’ll land the plane. Story keepers are great. A lot of times we hear, especially from consultants, about the power of storytelling, and that is true. There’s a lot of research showing how intensely activated humans are by stories. If you’re looking for a default to fall back on, story keepers are a great one. Focus on the best possible individual story. You don’t want to throw everything against the wall. You want a tight, focused narrative. For me, nonprofit leaders like you are overwhelmed. You’re trying to figure out what to do next. You feel lonely, and you feel scared that you’re going to make the wrong decision. You need a practice field. You need something that cuts down on time and gives you a little safety walking into the next conversation. That’s what we do at the Generosity Roundtable. What’s your version of that?

Symbolists are very focused on not just the story. It’s not the individual story, it’s the brand. A brand is the feeling people have when they interact with all your stuff. It’s not a product. It’s not your mission statement. It’s not what you put on your website. It’s not the look or the logo. A brand is the feeling. This is what Marty Neumeier has been teaching for decades.

Connectors are people who zero in on putting the dots between things. Matching gift challenges, peer-to-peer campaigns, and volunteer activation work well here. I think we sleep on our volunteers a lot when it comes to this type of thing. Psychology drives us toward what makes us feel connected to somebody else. To Joyce’s point, there’s even been some interesting research showing that if you introduce unnecessary numbers into your narrative, it might throw people off. So ask what the number is going to bring up. That’s something we learned in Pennsylvania too, which I’ll share.

Stewards are people who are very locally rooted. It’s that kind of gentleness. They want to know that things are being cared for. This is an important one. Sometimes I feel we reduce the strategy down to just thank-you notes, and that’s what these people are. But it’s one of ten reasons people show up.

Finally, advocates, especially for people working in areas that interact with the government a lot more, health and human services, for instance. You want to draw these people in and get them activated. There’s a lot of great research from GivingTuesday showing that people who do “yes, and” behavior, for example, I am a volunteer and I signed a policy update, are more likely to give. Then you have your disruptors, which could be a lot of different things. These could be systems people. They could be in tech. They can be focused on social justice. There’s a really great book that Jen Shang wrote with Adrian Sargeant called Meaningful Philanthropy, with entire chapters and breakdowns of these types of people. I’d also argue that a lot of the ultra-high-net-worth individuals out there probably think of themselves as disruptors with their philanthropy. Especially when you’re thinking about innovations or different ways to work with folks, don’t forget these folks. They can just be a little exhausting, obviously.

Ultimately, how do you read motivation in your own numbers? All engagement is simply taking motivation and turning it into a system. For retention, the focus is on what reinforces that motivation: good stories for the people who resonate with that, and numbers for the people who resonate with that. Retention is reinforced motivation, because donors also tell their friends.

Channels are going to be different. Certain people might respond to certain things, especially if you have an older crowd looking for more trustworthy information, in a world driven by social media that shows Dungeons and Dragons characters dancing alongside Mayor Mamdani in New York City for whatever reason. It’s wild out there when it comes to what people can look at. Some folks say, if you send me something on the internet, I’m not going to trust it. You have to take that into account. But small gifts, especially recurring gifts, are definitely digital-forward, so you have to find that balance, and a lot of it can be focused by understanding why people are at the table.

One note on motivations is that people’s identity is fluid. Even while you were reading this, while I was presenting, you likely started to think, well, I’m kind of like that, but also I’m a little like this sometimes. That’s the reality. It’s not that somebody is just one thing. It’s that the psychology does indicate humans are a little predictable. When they do things, that first reinforced behavior is important, because then you have an idea of what type of thing works.

If you want to find your own archetype, you can go to generosityspectrum.org, where I have the link to the quiz, or you can scan this QR code. I might try to find it during Q&A and drop it there. This is just one way to get a little more comfortable with the world of the Generosity Roundtable. We’re coming up to our time for Q&A, so I want to draw out one example of what we saw at the table last week at the Pennsylvania Association of Nonprofit Organizations. Someone asked about archetypes and generations. I’m going to bookmark that question for Q&A.

At the Pennsylvania Association of Nonprofit Organizations conference last week, we introduced a fictional scenario of a human services organization. About 35 people in the room worked through different scenarios relating to retention, and what ultimately gets an organization that feels a little stagnant to get its groove back. They all landed on the same idea. This is a room of your peers, and donor trust gets rebuilt in between the asks. The FEP data also reinforces this: retention goes up significantly when you close the window between the first and the second gift. I know Bloomerang has done a bunch of research on this too. It’s what’s happening in that space. As people worked through these problems, they focused on making sure different departments and roles are talking to each other, not focusing on flash, not focusing on highly polished narratives, but on honesty and involving clients in the storytelling.

This is a little checklist they came up with in the game, which was awesome to watch live. It’s going to be on the website too, at generosityspectrum.org, but Dani and the Bloomerang team will include it in a follow-up email. Again, it’s just a blog. I’m not asking for your email or anything like that. If you do opt into the email, we have a really amazing set of conversations coming up starting October 6 where you get to talk with your peers for free on a monthly basis. It’s not a sales pipeline or anything like that.

Where this leaves us is that the places we learn should be shaped by the people doing the work. A lot of what I’ve learned and presented here comes from lived experience. What the Aspen Institute has started to reinforce is that we want to focus on practice-based evidence, meaning you should focus on what you’re doing in the smallest, most replicable way and build on that. That works for any size of organization. I hope you can continue to learn with us on the different stages we have. Something is happening every single month. We have a big virtual event and in-person gameplay happening across the Nonprofit Social Media Summit thanks to the support of folks like Bloomerang. I want to thank the team at Bloomerang. I’m happy you’re on this stage with me today and that you’re learning alongside me. Dani, that gives us about fifteen minutes for Q&A.

Dani Cluff: Absolutely. We have a few questions going, but if anything pops up as we go through this, add it in the Q&A area. I know sometimes people have to hop off a little early, so I’m going to launch that poll really quickly so people can fill it out while we go through some of these questions. Did we want to start with the question that popped up in the chat: is there a correlation you’ve noticed between archetypes and generations?

Tim Sarrantonio: I love this question because I get to get a little philosophical. The idea of an archetype is rooted in Carl Jung and the idea of the collective unconscious. What this means is that it transcends age. It’s like an essence of who we are in our being. You may go so far as to call it a soul. In fact, today is the start of the Big Read. If I were going to make a book recommendation, it would be David Brooks’s How to Know a Person, which talks about this type of underlying essence in a person.

I think part of the joy, Dani, is wondering whether this correlates to different generations. I don’t know yet. I just made the archetypes up a few months ago. All it was was organizing what I know to be universal truths. Generally, I think there are people with whimsy and symbolic joy who are old, and I’ve talked to the most focused seven-year-olds about why to buy a hedgehog, with all the math and evaluation behind it. So I think it depends on the context. I don’t think it’s a generational thing. That’s a beautiful question, though.

Dani Cluff: If you’re interested in more of the generational pieces, Bloomerang’s Giving Signals report that came out this year breaks down some of the generational differences you’ll see in giving. We also have a generational giving report that might not be quite as up to date, but I think it’s still live.

Tim Sarrantonio: That came from the peer-to-peer side. If it’s on what used to be known as Qgiv, that was a pretty fantastic report. If you’ve improved on that, even better. I love those reports. I’ve always been a massive fan of the research Bloomerang does.

Dani Cluff: Well, good. I know we have a couple more questions. What is the best way, in your opinion, to engage with ambassador types who consider themselves investor angels and are very much about their ROI?

Tim Sarrantonio: What I heard was three different types of archetypal motivations: an ambassador who also has a very evaluation-minded focus, and who wants to disrupt things. What you need to understand is the core thing driving them. Sometimes math is a cover for “make me feel comfortable.” It’s a wall people put up versus the key itself that needs to be unlocked. It’s a matter of asking yourself whether this person is full of it. I’ve talked to a bunch of funders around here, a lot of guys going blah blah blah, change the world, and it’s like, but are you going to write the check? And then they don’t write the check. You don’t want your time wasted by people who talk the talk. See who’s walking the walk, and look at their actions. That’s the best thing, especially if you’re talking to folks who have a little more money they can throw around for a pilot. Look at what they funded beforehand to get a better understanding of what the future could be. It’s not always the same, but previous behavior is a very good indicator of future behavior.

Dani Cluff: Absolutely. Then we have one more question. This is just a general reminder: we are going to share the video later, so you can go back and watch anything if you had to hop off early or came late. I’m double-checking the chat.

Tim Sarrantonio: I’m responding to the person. The deep dive on the different archetypes is forthcoming, because I invented those. I do a deeper dive on the archetypes on my website at thetools.generosityspectrum.com. The deeper book on how to talk to people and be compassionate is David Brooks’s. For reference, the Weavers, an initiative underneath the Aspen Institute that I’m part of, are having a Big Read, and we’re all reading this book together until November. It’s like a big book club, and it’s a beautiful book. They’re even ending it with a conversation with David Brooks in November. Just look up the Big Read with the Weavers.

Dani Cluff: I love that. There was another question in the chat. Oftentimes it seems like there’s a big thing with funders, which is, are you like me? Are you the same gender, same race? How do you get past the “are we the same kind of background” question? Any tips?

Tim Sarrantonio: That’s a tough one without knowing the context. Especially, we have to acknowledge the funding inadequacies and disparities that exist. One of the people in the Generosity Roundtable network is Floyd Jones, for instance, who focuses on Black-led nonprofits and how funders only route about 1 percent of funding to those types of organizations. But I’ve also talked to tons of nonprofits in rural West Virginia or Montana that have difficulty accessing money, and that’s not a race thing whatsoever. A lot of this comes down not to identity on the demographic side, but to access, resources, and money. Ninety-seven percent of nonprofits make under $5 million, and 92 percent are under $1 million. That type of issue is emblematic from a class standpoint, but then you do have these deeper issues.

It’s hard to answer because I don’t know what your goal is. Do you care about those people, or should we try to find people who look like you who are funding those initiatives? That’s one approach. Number two is that there’s more intersectionality, to use a fancy term, with a bunch of different people talking together and trying to fund things in collaborative ways. That is a trend. I focus on where we’re going. There are a lot more conversations on that because of the very thing that person flagged in the chat. It’s very frustrating, but I think some changes are happening. Several members of the network are part of the community-centric fundraising movement, Rachel D’Souza, for instance, who is at GiveCon as well. Dani, what else do we have? I know we have time. This is great. Keep them coming.

Dani Cluff: Absolutely. Someone asked, do you have advice for nonprofits that traditionally ask for one gift per year from their donors? Do you recommend mailed appeals, or more asks throughout the year?

Tim Sarrantonio: Talk to them more. You might do the appeal once. That’s what my local community foundation does. So here’s what I’m doing as a peer in that exact same situation. Before I move on from the last one, if that individual wants to reach out and talk a little more, find me on LinkedIn, please. Happy to talk so I can better understand how to help. I’m going to hold on to the slides for this one. It’s a brand-new presentation, so let me work through that. But I’m very free to share things, so if you need something in particular, let me know.

Back to the main question. I’m taking that one mailing and segmenting it into three different groups. The only data we get is from the community foundation, which exports it from their founding system and gives it to us to match against the mailing list. We don’t have Bloomerang, by the way. Because we have limits, I had to focus on just money to start, which is not where you want to do a lot of your baseline segmentation. I know that sounds counterintuitive, but retention is not about the money. It’s about the feeling that somebody feels welcome to come back. Because I only have money, I’m starting with that and saying: people who gave last year for the first time, people who’ve given consistently over five years, and another group who may give sporadically but haven’t given in a while. Those are the three main ones.

Then I’m outlining the baseline motivation for the tone. For the people who have lapsed, it’s an evaluator. For the people who have been coming back pretty consistently, I’m taking more of a story keeper tone, and I’m zeroing in on one story across all of them. Rachel Muir taught me this type of thing. You have that one story that draws from things you’ve ideally told them at least once earlier in the year. Say this nonprofit has only put out one Facebook post. Talk about that if it was a good thing. Talk about the one good thing you can pull from earlier in the year and reinforce it in your appeal. Moving forward, you have to start communicating with them on a monthly basis in some baseline way. It could be a social post at the very least. Do something, so you’re top of mind, because most of the rest of the year you’re competing against 10,000 other things being yelled at them. That’s how I would go about it to start, and that’s how I am going about it.

Dani Cluff: We’re getting more activity. We have another question in the chat. This organization is pre-launch with no donor numbers yet. Do you have any recommendations for identifying donor motivations from the start, before they have any data or retention to read?

Tim Sarrantonio: Talk to people. Set up a call. The first person I showed my game to, besides my kids and my wife, was my mother-in-law, who runs a food pantry in New Bedford, Massachusetts. She’s an older conservative lady from New Bedford and she was the perfect person to talk to. I said, tell me the truth. What’s dumb? What don’t you like? That type of market research is free because they care about you. Go call the friend on the board that you dragged into the meetings. Start there. The moment you have somebody new, talk to them. Set aside time, buy them lunch or coffee, get a little information, and ask a few things, like why did you give, and why would you keep giving? And that’s it. Don’t ask them for money at the end of the talk. Ideally, take a picture with them and say, wasn’t it great that we had this conversation? You could turn it into content if you get comfortable doing that too. But you just talk to them. For some reason this is the one where I’m a little baffled why people don’t just start there. I know we’re scared to talk to people, but it can be that simple. You don’t have to run a survey or anything like that.

Dani Cluff: I love it. Do you have any recommendations for smaller teams lacking resources that want to mirror back that intention to their donors? Different tactics that don’t require a lot of time and effort they may not have the capacity for?

Tim Sarrantonio: I want to find the wording of that again. The chat keeps moving on me as I’m trying to read it.

Dani Cluff: I know. We have a highly engaged chat, which is what we wanted.

Tim Sarrantonio: Folks, please reach out to me if I don’t get to your questions. I love this stuff. I’m a teacher, as somebody said. That’s all I want to do. Mirror back. Use their words. I think I got the crux of the question. One of the things we found in the research was a pretty detailed analysis of recurring giving. When we looked at the data on why people gave, they were talking about things that had to do with their identity, and people were using the words back to them. If somebody says, I gave because I wish I had this resource when I was going through what I’m going through, as we saw with an LGBTQ center where the donor said, I wish you were around when I was coming out, those are the words you should be using. You have to get their opt-in. You have to build that story collaboratively with the person. But use their words. The way you mirror it back is you literally mirror it back. That’s why the donor conversation is important, and why things like surveys work. This is also where you could start to do large-scale analysis. Maybe a follow-up, Dani, is all the love I have for looking at unstructured data and AI. It’s the only time I’ll use the word AI in this entire presentation, because it’s a great sense-making tool for understanding how to mirror something back. What is the most common word or sentiment? You could even load the motivations in. Maybe I’d need to build a little skill or markdown file for people to use in their own appeals for this, Dani. But I’d rather work with Bloomerang on that.

Dani Cluff: Fantastic. I know we’re at the top of the hour, so I want to be respectful of everyone’s time. I know Tim has said many times that if you didn’t opt in, or you think of a question later, he would love to work with you and help answer your questions. As a reminder, we are sharing the recording, and a link will go out later this afternoon so you can go back. You won’t get the actual slide deck itself, but you will see the slides in the recording.

Tim Sarrantonio: If you want to look at the archetypes, I’ll get there, folks. It’s so new. I want to pressure test it before sending it out there. A lot of what we’re doing in the peer network is people dropping resources like M+R and Giving USA, because I served on those and I know these resources. The vision of the peer network is to bring all of this together so you can help navigate it yourself too. So check out the game. It’s pretty cool. Otherwise, Dani, this was such a pleasure. This is what I expected of my first, and hopefully not last, Bloomerang webinar.

Dani Cluff: I love it. Thank you so much, everyone, for taking time out of your busy schedules. I know time is a valuable resource, so we appreciate you sharing yours with us. And Tim, thank you again. I know it’s been said many times in the chat, but this was an incredible session. Thank you for lending us your time and your expertise today.

Tim Sarrantonio: Thank you. Absolutely.

Dani Cluff: Fantastic. Have a wonderful rest of your day, everyone.