Why Your Fundraising Outreach Isn’t Working Like It Used To

There’s a moment in fundraising where you start to feel it.

You’re doing the work.
You’re following up.
You’re being thoughtful in your outreach.

And still… things just aren’t moving the way they used to.

Response rates are slower.
Conversations take longer to start.
What used to feel straightforward now feels heavier.

It’s easy to assume the problem is in the execution.

Maybe the message needs to be stronger.
Maybe the research needs to go deeper.
Maybe you just need to try harder.

But what if that’s not actually what’s happening?

In this episode, we break down what’s really changed in fundraising, why the same level of effort isn’t creating the same level of movement, and what that means for how you approach your work moving forward.

Because this isn’t just about improving your outreach.

It’s about understanding the environment your outreach is landing in.

And once you see that shift, it changes everything.

If this is something you’ve been feeling in your work, I’ve opened up early access to a new program designed to help you adapt to this shift:

👉 https://www.letstalkfundraising.com/majorgifts

This is The AI Advantage for Major Gifts, a 6-week live cohort where you’ll learn how to apply AI directly to your day-to-day fundraising work so you can:

• Know exactly who to prioritize
• Walk into meetings prepared
• Capture and use donor information more effectively
• And stop starting from scratch

Not in theory. In your actual work.

Because at this point, the question isn’t whether fundraising is changing.

It already has.

The question is what you’re going to do in response to it.

💡 Want to take the next small step?

→ Free Download: 12 Fundraising Prompts You'll Actually Use

→ Course:  The Fundraiser's AI Starter Suite

Transcript

Moving Fast Creates Momentum

Keith Greer 0:01

There was a stretch in my last role as a major gift fundraiser where I started getting pulled into a lot of conversations with other fundraisers in my organization. Not because I had some official leadership role, and honestly, not because I had all the answers, but because when I stepped into that position, I was starting from scratch. And if you looked at the analytics from the role before me, the portfolio had been pretty quiet. So in those first few months, I made a decision. I wasn't going to sit back and try to figure everything out before I started. I was going to move. And I moved fast. In my first three months, I did more outreach than had been done in that role over the previous three years. More emails, more calls, more attempts to start the conversation. And over the course of that first year, it wasn't even close. More visits, more conversations, more solicitations. And what started to happen was momentum. Things started moving. People started responding. Opportunities started to open up. And when that happened, something interesting followed. Other fundraisers started coming to me. Sometimes because their supervisors didn't really have a clear answer for them. And sometimes it's because I think our analytics team would point them in my direction and say, hey, go talk to Keith. Something is working there. And almost every time the question sounded the same, they'd come to me and say, I've been looking at your contact reports and I don't get it. And I'd go, like, what do you mean? And they'd say, I copied your outreach emails, I adjusted them for my donor, I sent them out, I followed up five or six times, just like you did, and I'm just not getting the same response rates. Like, what am I missing? And it's a fair question because on the surface, it does look like the same work, the same email, the same number of follow-ups, the same intention behind it. But the results were completely different. And for a long time, I think people assumed that meant one of two things. Either there was something special about the way the message was written, or there was something about me that was different. And I like to think it's about me, but honestly, neither of those were actually true because what they were copying was the email, but what was actually working was everything that was around that email. So let's talk fundraising. So here's what I started to notice in those conversations because it wasn't a lack of effort, and it wasn't that people weren't following up, and it definitely wasn't that they didn't care about getting it right. In most cases, they were doing exactly what they had been taught to do. They were writing thoughtful outreach, they were being intentional with their language, they were spacing out their follow-ups so they didn't come across as, you know, pushy. They were trying to be good fundraisers. And if you zoom out for a minute, that approach makes a lot of sense. For a long time, that's how this work was done. You reach out, you give someone space to respond, you follow up a few times. And over time, those touches turn into a conversation. And that approach didn't come out of nowhere, it was built on real results. But as I kept working my own portfolio and watching what was happening around me, something started to feel off. The same level of effort wasn't creating the same level of movement that it had years before. Things weren't breaking, but they weren't moving the way that you would expect either. A message would go out and it would just sit there a little longer than it used to. A follow-up would need one more touch point than you had planned for. A conversation that felt like it should start quickly would take a few extra weeks to actually get going. And none of that feels dramatic when you're kind of in the moment. It just feels like the work is heavier. And I think we've all felt the work being heavier lately. Like it takes more to get to the same place. And when that happens, it's really easy to turn inward and you know, assume that the problem is in our execution. Maybe the message needs to be stronger, maybe the research needs to go deeper, maybe the timing needs to be better. So you adjust and you were fine and you try again. But what I started to realize is that the friction I was feeling wasn't coming from the quality of the outreach. It was coming from the environment that the outreach was trying to land in. And that's a very different problem that we have to solve because when the environment changes, the way people pay attention changes with it. And when attention shifts, everything about how we show up in this work has to shift with it. And as I started to sit with that, I began looking a little bit more broadly at what was happening across the sector. Because when something feels off in our own work, there's always that question in the back of our minds, is it just me or is something bigger going on? And over the last few years, we've actually had some really clear signals that help answer that question. So if you've looked at the fundraising effectiveness project's most recent reports, including their 2025 data, there are a few trends that continue to show up over and over again. Donor retention is declining, fewer people are giving, and the overall number of donors is shrinking. At the same time, total dollars raised have held steady or even increased in some cases, which creates this really interesting dynamic because on the surface it can look like everything is fine, revenue is coming in, campaigns are still being completed, organizations are still growing. But underneath that, the base is shifting. You have fewer people participating in philanthropy, and a larger portion of giving is coming from a smaller group of donors. And according to the Fundraising Effectiveness Project's 2025 report, donor retention rates are still hovering around that 40% mark and they've been trending downward over time. So if you talk to people who have been in this field for a few decades, they remember when retention rates were closer to 50 or even 60% back in the 90s. And that difference matters because retention is one of the clearest indicators we have of how connected people feel to the organizations that they support. At the same time, the number of donors is continuing to decline, which means that even though dollars may be stable, participation is narrowing. And when participation narrows, competition naturally increases. Because now, instead of engaging a broad base of donors, organizations are often reaching toward the same smaller group of individuals. And all of this is happening in a world where attention itself is becoming more fragmented. So if you go back a few decades, the number of things competing for someone's attention on any given day was relatively limited. There were fewer channels, fewer messages, fewer organizations that were asking for their financial support. Today that's completely different. According to the IRS data, the number of registered 501c3 nonprofits in the United States has grown from under 600,000 in the late 1990s to nearly 1.6 million today. That's not a small increase. That's a massive expansion in the number of organizations all trying to tell their story, build relationships, and invite people into their mission. And that doesn't even begin to account for everything else that's competing for their attention. Things like media and entertainment and social platforms and professional obligations, personal responsibilities. Every one of those things is asking for a share of someone's focus. So when you think about what it takes for your outreach to land, it's not just about whether the message is well written. It's about whether it can even be seen and whether it can be recognized, and whether it can hold attention long enough to create a response. And when you put all of that together, the pattern starts to really come into focus. And it's not just that response rates feel lower, and it's not just that things take longer to move, it's that the environment surrounding this work has completely shifted. The number of donors is smaller, the competition for those donors is higher, and the amount of attention available to engage them is more limited than it has ever been. And when all of those things move at the same time, it changes what it takes for this work to move forward. And when you step back and look at all of that together, it starts to point to something bigger than just changing tactics. It starts to point to a shift in the environment that the entire profession is operating in. Because this isn't unique to fundraising. Every industry that relies on attention and engagement and human behavior has had to wrestle with this. And the ones that are growing today, they didn't just keep doing what used to work and hoped it would hold. They either grew up inside of this new environment or they've adopted themselves to meet it where it is. They've learned how people move through information now, how they decide what gets their attention, how they engage, and how quickly they move on. And they've adjusted accordingly. And not perfectly by any stretch of the imagination, and they haven't done it all at once, but they have done it intentionally. And when you look at fundraising, there's a part of this that's a little uncomfortable to sit with because we haven't really done that. We've made improvements, we've added tools, we've layered in new technology, but underneath it, a lot of the core thinking hasn't shifted. We're still organizing our work around models that were built decades ago. We're still relying on metrics that assume a level of attention and engagement that just doesn't exist in the same way anymore. We're still structuring outreach in ways that depend on people noticing us instead of designing our work around how people actually engage now. And again, that's not a failure of attention. It's not because people aren't trying. It's because those systems worked for a very long time. They were effective, they were reliable, they helped build the profession into what it is today. But the environment they were built for is not the one we're working in anymore. And if we're honest about that for a minute, there's a real big tension there because it raises a question that's not always comfortable to ask. What happens when the tools, the models, and the instincts that built your success are no longer fully aligned with the way that the world works now? Not completely broken, I mean they're not useless, but just slightly out of sync. And when something is slightly out of sync, you can still get results, but it takes more effort, takes more time, it takes more energy to get to the same place. And that's the part that I think a lot of us are feeling right now. Not that the work doesn't matter, not that donors don't care, but that it's getting harder to create movement using the same approaches we've always relied on. And when you sit with that for a moment, it can feel a little uncomfortable because it's not just a question of what tactic do I change. It's a question of how do I need to think about this work differently. And I think one of the easiest ways to understand what's happening here is to actually step outside of fundraising for just a minute. Think about how we consume content. Like back in the late 1990s, if you're old enough to remember those days, when the Seinfeld finale aired, over 76 million people tuned in to watch that single episode live. That's roughly a third of the entire population of the United States watching the same thing at the same time. There weren't that many options for them to choose from. There were a handful of channels, a shared cultural moment, and a pretty limited set of choices for where your attention could go. But now, fast forward to today. In 2025, the most watched broadcast television episode was the season three premiere of a show called Tracker. And actually never even heard of this show until doing research for this episode, and specifically for this talking point. But as the most watched broadcast episode of 2025, it had just under 13 million viewers, which is still a big number, but it's not even close to what we used to see. And it's not because people stopped watching TV, it's because they're watching everything. Streaming platforms, YouTube, podcasts, thank you for being here, social media, news, work, family, everything is competing for a slice of the same finite attention. And on top of that, those platforms have gotten really good at understanding how people engage. They're not just putting content out into the world and hoping it lands. They're learning from behavior. They're adjusting what they show you based on what you've clicked, what you've watched, what you've ignored as well. So they're meeting you where your attention already is and they're guiding it from there. So instead of everyone gathering around the same few things, attention is spread out across thousands of different directions. And you can see a similar pattern inside of our sector. Back in the late 90s, there were fewer than 600,000 registered 501c3 nonprofits in the US. Today that number is approaching 1.6 million if it hasn't already surpassed it since the IRS's 2024 data. So that's not just growth, that's a complete expansion of how many organizations are trying to build relationships, tell their story, and invite people into their work. So when we think about what it takes to reach someone now, we're not just competing with other nonprofits, we're sharing space with everything else in their life. Every email, every notification, every piece of content that's trying to earn even a few seconds of their attention. And what that means in a really practical sense is that attention isn't centralized anymore. It's fragmented, it's moving, it's constantly shifting based on what matters in that moment. And when attention starts to behave that way, the way we show up in this work has to account for it. Because it's not just about being clear and it's not enough to just be compelling. It's about being present in a way that actually aligns with how people are engaging with the world right now. And when I look back at that outreach strategy now, the part that stands out to me isn't how much I was doing. It's how closely it lined up with how people were already moving through their days. Because at the time, I didn't really have language for it. I wasn't thinking about attention models or engagement patterns. I was just trying to get in front of people in a way that felt natural and consistent. But what that ended up creating was actually presence and not in a single moment, but across multiple moments. A name they saw more than once, a message that showed up in more than one place. It's a pattern that started to feel familiar, even if they couldn't quite place why. And when I think about the questions those other fundraisers were asking me, they were focused on the email, you know, how it was written, how it was structured, what words did I use. But the email wasn't doing the heavy lifting. It was just one piece of a much larger system because what was actually happening was that I was meeting people in the same fragmented way that they were already engaging with everything else in their lives. Quick glance here, a brief moment there, a small touch point that didn't require a big commitment of attention. And those moments started to stack. Not all at once. I mean, we're not going for an avalanche that comes crashing down on you. We're thinking more like a light snow. It starts just as a dusting, something easy to ignore, barely even noticeable. And then a little more falls, and a little more after that, until at some point you look up and realize if you want to get out of your house, you're gonna have to do something about it. And that's what those touch points were doing. They were building quietly, layer by layer, until responding didn't feel like starting something new. It felt like stepping into something that had already been forming. And that's the part I think it's easy to miss. Because when we look at outreach, we tend to evaluate it one message at a time. Was this email good enough? Was this call the right approach? Did this follow-up with them land? But the experience on the other side isn't happening one message at a time. It's happening as a sequence. It's happening as a series of small interactions that build on each other. And when that sequence lines up with how someone actually moves through their day, it works. Not because any single touch point is perfect, but because the overall experience feels natural. And when you step back and connect that to everything that we've been talking about, that's where this really starts to click. The reason that approach worked is because it matched how people actually engage with the world now. And there's a moment from earlier in my career that I try not to think about. It's one of those that when it comes back up, I still kind of kick myself over and over again. I was I was working with a donor who was interested in naming a room in a building that had just been completed. It hadn't been unveiled to the public yet. So there was this really unique window where we could bring someone in, show them the space, help them see what it could become with their name attached to it. And this donor, they were engaged. Every conversation felt like it was moving things forward. They were asking good questions. I was following up with photos and mock-ups and details about the space. We were building towards something, and it felt steady. It was moving in the right direction. So we kept going, week by week, month by month. And after about six months, I got to a point where I thought, we're getting close. This feels like it's heading somewhere. So I reached out and I asked them directly, are you ready to move forward with this gift? And the response that came back, oh, it stopped me. They told me they had just made a six-figure commitment to their alma mater. They'd endowed a scholarship. Ugh, and I remember sitting there reading that message and trying to make sense of it because everything, everything I thought I understood about where we were, it didn't match what had just happened. And I went through all of the questions. Did I misread this? Was I off? Was this never actually going to happen? Were they playing me? And after sitting with all of that for a bit, I reached back out and I asked them if they would be open to sharing what led to that decision. And they were. And what they said is what stuck with me. They told me they would have made that gift to name the room two months ago if I had asked. Two months. And as we talked through it, they shared that this wasn't new for them. This was how they approached giving. They waited to be asked. They had been ready, they had been paying attention, they had been trying to give signals along the way, and I didn't pick up on them. I thought we were still building towards something, and they were already there. And when another organization stepped in and made the ask, that's where the gift went. And just like that, the moment was gone. And I've replayed that in my head more times than I can count because I didn't recognize where they were in the process when they were there. I missed the timing. I missed the moment. And here's the part that's even harder for me to sit with. That's the one where I got an answer. That's the one where I asked the question and they told me what happened. Most of the time, we don't get that. Most of the time it just looks like a donor who didn't move forward, or a conversation that didn't go anywhere, or something that felt like it had potential and then just faded. And we move on. But how many times is something like that happening and we never know? How many times is someone ready and we're still preparing? How many times are we right there and we just don't see it clearly enough to act? And when you put those two pieces together, the way people are engaging with the world now and the reality of how easily we can miss the moment, it starts to shift how you think about the work because this isn't just about doing more. Lord knows we don't need any of that in our lives. It's not about adding more touches or writing better emails or trying to push harder to get a response. It's about working in sync with how attention actually works today. It's about recognizing that the way people move through their day, the way they notice things, the way that they decide to engage, that has changed. And when that changes, our role has to change with it. And not in the sense that the fundamentals of fundraising go away because the fundamentals are still great. Relationships still matter. Trust still matters. Understanding your donor still matters. That part hasn't changed. But how we support that work, how we create momentum, how we recognize where someone actually is in the process, that's where things start to look different. Because if I go back to that moment with that donor, the challenge wasn't in the effort. The challenge wasn't even strategy, it was clarity. And at the time, I didn't have a good way to do. That. I was still early in my career and I hadn't refined that skill yet. But today there's so much more data that goes into that decision. So I defaulted to what felt responsible: keep building, keep preparing, keep moving things forward carefully. And in doing that, I missed the moment. And that experience, that's what really started to change how I approached my work. Because I realized I didn't just need to work harder, I needed better visibility. I needed a way to quickly understand who I should be focusing on, see patterns in my portfolio that I wasn't catching on my own, track conversations in a way that actually reflected where the relationship was, and recognize when someone was ready to move before that moment passed. And for a long time, that was just difficult to do. Not impossible, but it was slow. It was manual. It was dependent on how much I could hold in my head at any given time. And that's really where all of this started to shift for me because as AI tools started to become more accessible, I began building things for my own work. Not to replace the relationship side of the fundraising and not to automate the human side of it, but to support my thinking, to support my strategy, to support my work, to give me a starting point so much faster, to help me see what I might be missing, to surface patterns that would have taken me hours or days, sometimes even months, to piece together on my own. Things like tools to help identify which prospects were most likely to be a good fit for my portfolio. Ways to standardize my contact reports so they were actually useful in tracking movement. Systems that could look at the work I had already done and highlight people who might be ready for an ask. Or people who needed a different kind of attention. Or people who probably shouldn't be in my portfolio anymore at all. And what I found was when I had that kind of visibility, everything started to move differently. It wasn't faster in a rushed way, but it was faster with more clarity, more confidence, more alignment with what was actually happening in front of me. And that's really what I've been building toward with this program, the AI Advantage for Major Gift Fraising. And it's not about replacing what you do, it's about supporting how you work. So you can spend less time trying to figure out what to do next, and more time moving relationships forward. So if what we've been talking about today, if that feeling of things just being a little bit harder than they really should be, or you're wondering how many moments might be slipping past you without you even realizing it. If that's resonating with you, I've opened up an early access list for this program. And you can go to let's talkfundraising.com forward slash major gifts and join that list. I'll also link to it in the show notes so it's easy for you to find. But for now, even just being aware of this shift, that alone starts to change how you're showing up. Because once you see it, it's really hard to unsee. And when you step back and look at all of this together, the patterns we're seeing across the sector, the way attention has shifted, the moments that slip past us without us even realizing that they were there, it starts to feel a little different. Because this isn't just about tactics, and it's not just about whether an email performs well or whether a follow-up sequence gets a response. It's about whether the way we're working still lines up with the world we're working in. And for a long time, those two things were aligned. The way we were taught to do this work and the way people engaged with it fit together. But that alignment has been shifting quietly, gradually, until you get to a point where something feels off. Even when you're doing everything you know how to do. And that's where a lot of people are sitting right now. You're working hard and you're doing good work, and you're caring deeply about the outcomes, and you're still feeling like it's taking more to get to the same place. And if you don't have language for it, it's easy to turn that inward, to think it's something that you're missing, something that you need to fix, something that you need to get better at. But what if that's not what's happening? What if the reason it feels harder is because the environment that we're working in has changed and the way we're working hasn't fully caught up yet. Because when you really zoom out and you look at how people are moving through the world now, how they spend their time, how they give their attention, how they decide what to engage with, it becomes pretty clear. And in fundraising, we're still sitting in our sandbox asking if anybody wants to play with us. And the good news in all of this is that this isn't something that you have to just sit with. There is a shift happening, and you can start to see it in the organizations that are beginning to find their footing again. Not because they've abandoned what makes fundraising work, not because they've turned everything over to technology, but because they've started to align how they work with how people actually engage now. And when you look at what that actually looks like in practice, it's not complicated. It's just different. They're starting to personalize their outreach in a way that reflects the individual, not just the segment, but they're thinking more intentionally about who they focus on and when. They're paying attention to signals, small changes in behavior and engagement and responsiveness, and they're using those to guide what they do next. And when you see it happening, it doesn't feel like a completely new system. It feels like the work's starting to click again, like things are moving with you instead of against you. And a big part of what's making that possible right now is that we finally have tools that can support that kind of thinking. Tools that can help you quickly sort through large amounts of information, see patterns that would be difficult to catch on your own, get to a starting point faster, and make more confident decisions about what to do next. Not by replacing your judgment, but by giving you better visibility into what's already happening. And that's really how I think about AI in this work, as something that helps you see more clearly. So you can show up effectively. Because when you can see more clearly, you don't have to guess as much. You don't have to sit in that space of wondering, am I missing something? Am I focusing on the right people? Am I moving this forward the way that I should? You can move with more confidence, with more intention, with more alignment with what's actually in front of you. And when that happens, the work starts to feel different. Not easier in the sense that it matters less, but easier in the sense that you're not carrying all of it on your own anymore. You have support, you have structure, you have a way to move forward that actually fits the environment that you're working in now. And at the end of the day, this really comes back to a pretty simple question. It's not an easy one, but it is a simple one. Because the question isn't whether fundraising is changing, it already has. You can see it in the data, you can feel it in your work, you can hear it in the conversations that we're all having. Because at this point, this isn't really about whether this shift is happening. It already is. The question is whether you're going to keep working the same way and feel that gap continue to widen. Or whether you're ready to actually change how you work so it lines up with how people engage now. And if you're ready for that, that's exactly what I've built this program for. You can join the early access list for the AI Advantage for Major Gift Fundraising at let's talkfundraising.com forward slash major gifts. But for now, just start paying attention. Because once you see the shift, it's really hard to go back to working the way you did before. Thank you for being here, my friend. I'll see you again next week. Take care.