Think AI Won’t Work for You? Let’s Talk About That.

If you’ve been listening to this series and thinking…

“This sounds interesting… but I’m not sure it would actually work for me…”

This episode is for you.

Because that hesitation you’re feeling?

It’s not random.

And it’s not a sign that you’re behind.

It’s actually pointing to the exact places where your work matters most, your time, your donors, your relationships, your results.

In this episode, I’m walking through what I’ve been hearing from fundraisers over the last few weeks, the quiet “yeah, but…” thoughts that show up right when things start to feel possible.

Things like:

• “I’ve never used AI before”
• “I don’t think my organization would allow it”
• “I’ve tried ChatGPT… it wasn’t that helpful”
• “This seems complicated”
• “I don’t have time for this”

But instead of pushing past those concerns, we’re going to look at what they’re actually telling you.

Because every one of them shaped how I built The AI Advantage for Major Gift Fundraising.

Not as a theory.

Not as another tool.

But as a system that fits into the reality of your day-to-day work, and actually helps you move donor relationships forward with more clarity, consistency, and confidence.

If you’ve ever felt like AI sounds promising… but hasn’t quite delivered in your actual work yet, this will help you see why.

And more importantly, what changes that.

If you’re ready to take the next step, you can join the waitlist here:
👉 https://letstalkfundraising.com/majorgifts

We’ll be opening enrollment soon, and kicking off our first cohort on Monday, May 4.

💡 Want to take the next small step?

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

→ Course:  The Fundraiser's AI Starter Suite

Transcript

When AI Starts To Click

Keith Greer 0:00

Over the last few weeks, something really interesting has been happening. I've been hearing from a lot of you as you've been listening to the podcast, and there's this moment people are hitting where things start to click. And I can hear it in the way that you're talking about your work because it shifts from, is this even relevant for me, to, okay, wait, how would I actually use this in my portfolio? And that's an exciting place to be because that's the moment where things stop being theoretical and they start becoming possible. But right alongside that shift, there's another set of thoughts that start showing up and they come in fast, almost like your brain is trying to catch up and make sure we're not getting ahead of ourselves. And it sounds a little something like, but I've never used AI before. I don't even know if my organization would allow this. I've tried ChatGPT and honestly, it didn't really do much for me. This feels like it could get complicated really quickly, or I don't have time to learn a whole new system right now. And here's what I want you to notice about that for just a second. Those aren't random thoughts. Those are actually really smart questions because every one of them is pointing to something real about how this work actually happens inside of your day-to-day. Your time is limited, your organization has constraints, your donors matter, and your reputation matters, and you don't get the luxury of experimenting with things that don't actually work. So of course, your brain is going to run those checks. That's not hesitation, that's discernment. But here's the part that really started to click for me when I was building this out in my own work. Because those questions, they're not the reason this doesn't work. They're the reason it has to be built a certain way if it's going to work at all. And once I started looking at it through that lens, my whole perspective shifted. Because instead of trying to push past those concerns, I started building into them. And what that created was something completely different than what most people have experienced when they tried to use AI before. Because we're not doing more complexity and we're not doing more tools or more theory, but we're creating a way of working that actually fits into the reality of your day and starts to give you something most fundraisers don't have enough of. Clarity on what to do next and the confidence that it's actually moving things forward. So today, what I want to do is take those thoughts that have probably been running in the back of your mind and look at them head on. Because once you see what they're really pointing to, you start to realize something. You're not as far away from this as you think. And more importantly, you start to see what this could actually look like inside of your own work. So let's talk fundraising. And here's what tends to happen next. Once something starts to feel possible, once you start to think, okay, this could actually help me, that's usually the exact moment where the yeah, but shows up. Yeah, but I've never done this before. Yeah, but I don't know if I can use this at my organization. Yeah, but I tried something like this and it didn't really go anywhere. And that tension, that push and the pull, that's not a sign that something's off. It's a sign that you're engaging with this the right way. Because if you think about the kind of work that you do every day, you don't get to operate on blind optimism. You don't get to just try things and hope they work out. You're working with real donors, real relationships, and real expectations. And in many cases, real dollars that are going to determine whether your organization can actually do the work, it's there to do. So when something new shows up, of course your brain is going to slow things down for a second. Of course, it's going to start asking better questions, not to shut it down, but to make sure it holds up. And this is especially true in fundraising because this is one of the few professions where how you do the work matters just as much as the outcome. Ethics matter, trust matters, reputation matters. The way a donor experiences you, that matters. So you don't get to shortcut that. You don't get to say, well, this is faster, so let's just do it. It has to fit. It has to align with how you build relationships and it has to support the trust that you're trying to create, not undermind it. Which is why I want to say this really clearly, because if part of you has been sitting there thinking, I just want to make sure I'm doing this the right way, that's not something to push past. That's something to pay attention to because you're not resisting this because you're behind, and you're not resisting this because you don't get it. You're resisting this because you care about doing it right. And that's exactly the kind of person this program was built for. Not someone who just wants the newest tool and not someone who's chasing efficiency for the sake of efficiency, but someone who wants to do this work really well and is looking for a way to do it with more clarity and more consistency and more confidence. And what's interesting is every one of those concerns, every one of those yeah, but moments, they didn't slow this down for me when I was building it. They shaped it. They forced me to ask better questions. They forced me to look at what would actually work in the real world, inside of a real fundraiser's portfolio with real constraints, and build something that could hold up inside of that. So instead of trying to get rid of those concerns, what I want to do next is actually walk straight through them. Because once you see how they connect to how this is designed, you start to realize something really important. These aren't the things that make this harder to use. They're the reason it actually works. So when I hear those concerns, when I hear someone say, I don't know if I can use this, or this feels like it might get complicated, or I've tried things like this before and it didn't really stick. My reaction isn't, oh, you're overthinking it. My reaction is more like, yeah, I've been there. Like I know exactly where that's coming from because when I was first trying to figure this out in my own work, I wasn't sitting there thinking, how do I build something impressive? I was thinking, how do I make this actually work in the reality I'm operating in every day? Because nonprofit work doesn't happen in a vacuum. We've got limited budgets. We've got small teams. Most of us are wearing way more hats than we probably should be. And you're managing a portfolio, you're prepping for meetings, you're writing proposals, you're following up with donors, you're sitting in internal meetings. And somewhere in there, you're supposed to learn AI on top of all of that. That's just not realistic. We don't have the luxury of going out and buying 10 or 15 different tools to solve every little piece of the process. That's not how our world works. But then you look over at the for-profit side, and they've got a tool for everything: dedicated platforms, expensive tech stacks, specialized systems that do one thing really well. And for a while I remember thinking, are we just behind? Like, are we always going to be a few steps behind because we don't have access to all of that? But the more I sat with it, the more I realized that's actually not the problem. The problem isn't that we don't have enough tools, it's that we don't have systems that actually support the way we work. Because even if I gave you all of those tools tomorrow, that doesn't mean they would fit into your day. And it doesn't mean that they would connect to each other. It doesn't mean that they would actually help you move a donor relationship forward. So that's where the shift started for me. I stopped asking, what tool do I need for this? And I started asking, what part of my work is slowing me down right now and how can I support that? And this is where AI started to get really interesting because instead of thinking about it as one more thing to learn, I started seeing it as a leverage point. One platform with one subscription. And inside of that, you can build whatever you actually need. Not what someone else decided you should need, not what some tech bro packaged up and sold to an industry they've never actually worked in, but something that actually fits your workflow, your donors, your organization, your reality. And when that clicked, it was like, wait a second, if I can build what I need, I don't have to wait for someone else to build it for me. I don't have to sit there hoping that some vendor eventually creates the perfect fundraising tool. I can actually solve the problem in front of me myself. And if I'm being honest, a lot of the tools I had tried before, they weren't bad. They just weren't built for this work, the way that my organization worked or the way that I work. They were built outside of fundraising. They were built for scale or marketing or sales, and then kind of adapted into our space, which meant the workflow felt generic, the outputs felt a little off. And the updates for the software, they always felt like they were just slightly behind what I actually needed. So instead of continuing to chase that, I just started building inside of my own work. One piece at a time. Where am I getting stuck? What would make this easier? What would help me move faster without sacrificing the donor relationships? And over time, that turned into something that actually fit, not perfectly, but practically. And that's the part that really matters because when I hear those concerns now, I don't hear them as barriers. I hear them as the exact places where this needs to work. Those are the pressure points. Those are the places where if this doesn't hold up, it falls apart. And that's exactly where this was designed to help. So here's what I've been noticing. When I zoom out and I look at all of these conversations I've been having lately, there are patterns, not in a everyone saying the exact same thing kind of way, but in the way people are feeling their way through this. And it usually shows up in little moments, like someone will say something offhand, almost like they're brushing past it. But you can tell it's actually the thing that's holding the weight. Like Sean, he's on the board of Honor Flight of Northern New Mexico, amazing organization. And early on, he just said, I've never used AI before. I just don't want to cross any ethical boundaries. And I remember thinking, yeah, that makes total sense. Because if you care about your donors, if you care about your organization, if you care about doing this well, of course that's where your mind goes. And what was interesting is he didn't come in trying to be advanced. He wasn't trying to keep up with anything. He was just open. He was curious. He was willing to learn. And then a few weeks into our training, the tone completely shifted. Now it's, I'm so psyched about this, I can't wait to start using it. And that change from I've never done this and I'm concerned about ethics to I can't wait to use this in my own work. That's not about becoming technical. That's about finally seeing how it fits. And honestly, the people who think they're the farthest behind when they start are usually the ones who move the fastest once it clicks. And then on the flip side, I'll talk to someone who has used Chat GPT or another AI platform, and the energy is totally different. It's more like, I mean, I've tried it, it was fine. I didn't really get the hype. And again, I get that because if your experience has been you type something in, it gives you something kind of generic back. You tweak it a little, and then you end up rewriting most of it anyways, and that doesn't feel like leverage. It just feels like more work. Ugh. But what I found is that's usually not about AI as the tool. That's about how AI is being used. Because when it's not connected to anything real, when it's just floating out there without context, it can only go so far. So instead of asking, what can AI do, we started asking, where am I getting stuck in my actual work? And then building from there. And that's when it starts to feel different and actually useful. And then there's this other layer that comes up sometimes, and it's a little quieter, but it's there. It's the, I don't even know if we're allowed to use something like this, which, again, totally fair, because there's a lot of noise around AI right now. Some of it's helpful, some of it's a little dramatic, but underneath all of that, there are real questions about data, about privacy, about what's appropriate. And I think where people get stuck is they feel like it's either we use it fully or we don't touch it at all. And in reality, there's a much more thoughtful middle ground where you understand what you're using. You understand what should and shouldn't go into it, and you use it in a way that actually aligns with your organization because if you think about it, most of us are already working in a cloud-based system, your CRM, your email platforms, your reporting tools. So it's not that this introduces some completely foreign risks. It's that we haven't been shown how to approach it responsibly yet. And once you understand that piece, it stops feeling like a danger and it starts feeling like something you can actually navigate. And then there's the overwhelm piece, which I think is what people are really reacting to when they say, this just seems like a lot. Because when you look at the AI space from the outside, it does look like a lot. There's new tools and new features, and there's new things coming out every week. And it can feel like you're already behind before you even start. But what I found is it only feels overwhelming when you think you have to learn all of it. And you don't. You just need to solve the problem that's right in front of you. Like that's it. Not everything, just the next thing. And honestly, this might be one of the most honest ones of all. I just don't have time for this because your day is already full. Your work already matters. And the idea of adding something else on top of that, it's a hard no, unless it actually makes everything else easier. And that's the difference. Because this doesn't show up as one more thing to do. It shows up in the moments you're already in, when you're trying to figure out what to say to a donor, when you're pulling together research, when you're getting ready for a meeting, when you're trying to figure out what comes next. That's where this lives. And then there's the other end of the spectrum, which I think is kind of fun. The, oh, I use ChatGPT all the time, and I love that. But what's been really interesting is watching what happens when someone who feels really comfortable with it starts using it in a more structured way, because we saw this in the program. People came in thinking, yeah, I've got this. And then halfway through, it was like, wait, I had no idea it could do that. And it's not because they weren't using it, it's because they were using it like a tool and not building with it like a system. And those are two very different things. And then, okay, this one. This is one I hear all the time. Just not always said this directly, but it's there. It's like, I've been to these AI tradings before, and it always ends the same way. You get excited, you see what's possible, and then it's like, great, now go buy all these other tools, go buy my tools to make it actually work. And you're sitting there thinking, like, wait, so I still can't actually do this unless I keep spending money. And especially in nonprofit work, that just doesn't fly. So I made a really intentional decision here. I didn't want this to depend on anything else. No extra platforms, no stack of subscriptions, no, you need this add-on or this piece of software to make this part work. It's all built in one place because it needs to be. And then the last piece, and this is probably the one that I relate to the most, is that feeling of everyone keeps saying what AI can do, but no one is actually showing me how to make it do that. And that's so frustrating because it sounds impressive, but it's not changing the way that you work. And that's the gap that I cared most about closing. Not more ideas, not more possibilities, but actual usable workflows. Like here's the exact thing you do when you sit down at your desk, and here's how you set it up so that it works again tomorrow and the next day and the next day and the day after that. And when you put all of that together, all of these little moments, all of these little yeah, but thoughts, they all start to point in the same direction. It's not that this doesn't fit your work, it's that most of what's out there hasn't been built for it yet. And once you start to see that, it changes how you look at all of this. And when you step back from all of that for a second and you look at all of those thoughts and all of those moments and all of those little hesitations, something starts to become really clear. Every one of those concerns, they're not random. They're not you overthinking, they're not a sign that this isn't for you, and they're definitely not a lack of ability. They're actually pointing to something much more important. They're pointing to the places where your work matters the most, where your time matters, where your decisions matter, where your relationships matter. And those are the exact places where something like this has to hold up. Because if it doesn't work there, it doesn't work at all. And that's why this exists. Not to add something new to your plate, not to give you another thing to figure out, but to support the work that you're already doing in the places where it actually counts. Because if you think about what we've really been talking about over these last few weeks, it's not about AI. It's about what happens when you remove that constant layer of guessing from your work. When you don't have to sit there wondering, am I focusing on the right people? Am I saying the right thing? Did that meeting actually move anything forward? Am I even doing a good job right now? When that layer starts to fall away, everything else starts to shift. You move from guessing to knowing, you move from reacting to leading, and you move from feeling like you're constantly trying to catch up to actually being in control of what's happening inside of your portfolio. And that's a completely different experience of this work. Not because you're working harder, and not because you suddenly became a different kind of fundraiser, but because you finally have something that's supporting how you think, how you plan, and how you move things forward. So this isn't about learning AI, it's about finally having a system that supports how you actually work. And once that's in place, you don't just see your work differently, you show up differently inside of it. So as you think back over this episode and honestly, even over the last few weeks, I want you to just notice where you see yourself in this, where something clicked, where something felt familiar, where you realized, yeah, that's exactly where I've been getting stuck. Because if you can see that, then you can probably also start to see what this could look like if that piece was supported, if you weren't having to figure it out on your own every time. If you had a clear way to move through it, that's exactly what this program is designed to do. The AI advantage for major gift fundraising. This is where we take everything we've been talking about and actually build it into your work, step by step inside your portfolio with your donors, so that when you sit down at your desk, you're not starting from scratch, you're moving forward with clarity. And we're opening this up real soon. And we'll be starting our first cohort on Monday, May 4th. So if you've been listening to this and thinking, okay, I'm ready to actually do something with this, I want to invite you to take that next step. Head to let's talkfundraising.com forward slash major gifts and join the wait list. And we'll make sure you have everything you need when the doors open. Because at the end of the day, this isn't something you need to keep circling around. You don't need to keep trying to piece this together on your own. There's a clear path forward, and if you're ready for it, I'd love to walk that with you. So thanks for being here, my friend. I'll see you again next week. Bye bye.