The Moment I Knew My Fundraising Was Actually Working

For months, I was doing everything I thought I was supposed to do as a major gift officer.

I was reaching out.
I was having meetings.
I was putting in the work.

But nothing was closing.

And the hardest part wasn’t the lack of results.

It was not knowing if what I was doing was actually working.

In this episode, I’m sharing the moment that changed everything, and how I went from second-guessing my work to having complete clarity and confidence in what I was doing.

You’ll hear how I:

• Moved from scattered effort to focused strategy
• Stopped starting from scratch with every donor interaction
• Built a system to prepare for even the most difficult conversations
• Created visibility into my portfolio so I could actually measure progress
• Walked into high-stakes leadership meetings knowing I had the answers

This isn’t theory.

This is the exact process I used to transform my own major gift work, and it’s what I’ve now built into my program, The AI Advantage for Major Gift Fundraising.

If you’ve ever felt like you’re doing everything right but still unsure if it’s working, this episode is for you.

👉 Join the waitlist for early access:
https://letstalkfundraising.com/majorgifts

We’ll be opening enrollment later this month, and the first cohort begins 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

Panic Without Proof

Keith Greer 0:00

There is a point about six or seven months into my first major gift role where I started to panic. And it wasn't a loud kind of panic. It wasn't something that anyone around me could really even see. On the outside, everything was probably looking just fine. I was showing up, I was doing the work, I was having meetings, I was moving things forward, at least on paper. But internally, it was a very different story because nothing was closing. And I remember sitting at my desk one day, looking at my portfolio, looking at my calendar, thinking about all of the activity I had done over the last few months, and realizing I didn't have a single major gift to point to. Not one. And that's when the question started creeping in. Why did I think I could do this job? Can I actually do this work? Was I just lucky in my last role? Maybe those donors were already going to give, and I just happened to be there at the right time to collect the gift. Maybe I didn't actually have anything to do with it. And that spiral, it's a dangerous place to sit in because once it starts, it's really hard to shut it off. And what made it even harder is that when I would talk about it with my supervisor, she would say, You're doing great. And I believed that she believed it, but I didn't feel like it because I didn't have anything that I could point to that showed that I was doing great. There was no clear evidence. There was no signal. There was no way to know if what I was doing was actually working. And whether you're stepping into a role like that for the first time, or you're trying to build a major gift program from scratch, or maybe you're leading a team and trying to figure out if things are actually moving the way that they should, that feeling is the same. You're doing the work. You care about the work, but you can't quite tell if it's working. And that's a really hard place to be because the hardest part of major gift fundraising isn't just doing the work. It's knowing if what you're doing is actually working. So let's talk fundraising. When I stepped into that role, it was actually something I'd been wanting for a long time. Up to that point in my career, I'd been working in smaller fundraising shops, which meant I was doing a little bit of everything. I was managing the annual fund. I was writing appeals. I was handling stewardship and donor engagement. I was planning events, sometimes events with thousands of attendees. I was running galas that raised hundreds of thousands of dollars. I was writing grants. And somewhere inside of all of that, I was also doing major gift work. And for a long time, I was okay with that. Because when you're in that kind of an environment, you stay busy. There's always something moving, there's always something that you can point to and say, that worked, that made a difference, that moved the organization forward. But it also means that you don't have a lot of space to go deep. You're constantly shifting gears, you're moving from one priority to the next, you're keeping a lot of plates spinning, and if I'm being honest, you're doing a lot of good work, but you're not always sure how much of it is actually improving over time. So when I stepped into my first role where my only focus was major gift fundraising, it felt like a breath of fresh air. I finally had the space to focus on one thing: no more bouncing between appeals and events and stewardship plans, just major gifts. And at first that felt like exactly what I needed, until I realized what I had actually stepped into. Because the portfolio I inherited hadn't seen much movement in the three years before I got there. And I remember my vice president saying more than once, the cupboard is bare. And at the time I didn't fully understand what that meant, but I felt it pretty quickly. There wasn't a clear pipeline. There weren't a lot of active conversations happening with the donors. There wasn't this built-in momentum that I could step into and start advancing. It was quiet. And so I did what I thought I was supposed to do. I got to work. I started reaching out. I started setting meetings. I started trying to build relationships and create movement. And on the surface, I was doing all of the right things. But underneath that, there was this growing anxiety because before I had been busy and productive and I could immediately see my results. And now I was focused, but uncertain. And it turns out those are two very different experiences. And that's where things started to get really uncomfortable. Because like I said earlier, I would bring this up with my supervisor, I'd sit in her office, or we'd be on a call, and I'd tell her what I was seeing, or more accurately, what I wasn't seeing. And she would say, You're doing great. And again, I believed that she meant it. She wasn't brushing me off. She wasn't ignoring me. She could see the activity. She could see the effort. She could see that I was doing the work, but there was a disconnect because I didn't feel like I was doing great. And the reason I didn't feel like I was doing great is because I didn't have anything I could point to that showed I was doing great. No gifts had closed yet. There wasn't a clear indicator that the things were moving in the right direction. There wasn't anything tangible that I could look at and say, yes, this is working. And when you're in a role where results average 18 months, sometimes even longer, to materialize, that gap becomes really hard to sit in because you're putting in the effort, but you're waiting on the outcome. And in that waiting, your brain starts to fill in all of the blanks. And it usually doesn't fill them in very kindly. It fills them in with doubt. It fills them in with second guessing. It fills them in with questions about whether you actually know what you're doing. And the more I sat in that, the more I started to realize something. The problem wasn't that I wasn't working hard enough. The problem was that I didn't have visibility into my own work. I couldn't see it clearly. I couldn't evaluate it objectively. I couldn't tell if I was on the right track or if I needed to adjust something. I was just doing the work and hoping it would lead somewhere. And that shows up differently depending on where you are. If you're starting a major gift program from scratch, it might feel like you don't even know where to begin and you're not sure if what you're building is actually the right foundation. If you're managing a team, it might feel like you're responsible for results, but you don't have a clear way to see what's really happening inside each portfolio. And if you've been doing this work for a long time, it might feel like something is off. Like it's taking more effort to get to the same place, but you can't quite explain why. Or maybe you're just sitting there thinking, I'm doing everything I know how to do, so why doesn't it feel like it's working? And that's the moment I found myself in. Because the hardest part of major gift fundraising isn't doing the work. It's knowing if what you're doing is actually working. And it was right around that point when the pressure was really starting to build that something unexpected showed up. Chat GPT launched. And I'll be honest with you, at first it had nothing to do with my work. It was a distraction, a really, really good distraction, because when you're sitting in that kind of uncertainty, when your brain is running in circles, trying to answer questions it doesn't have enough information to solve, anything that pulls you out of that loop for a little bit feels like relief. So I started playing around with it. Not really strategically, and not with some grand vision of how this was going to transform my work, just curiosity. What can this thing do? And in the beginning, I was not good at it. I type something in, get something back, and think, all right, that's not helpful. Or I try to use it for something in my work, and it would give me something so generic that it actually created more work for me and not less. So for a while, it just stayed in that category of, uh, this is interesting, but I'm not really sure what to do with it. But I kept coming back to it. And not because it was immediately useful, but because it felt like there might be something there. And over time, that curiosity started to shift because I stopped asking, what can this tool do? And I started asking a different question. Where am I getting stuck in my work? Where am I slowing myself down? Where am I overthinking something or starting from scratch, or trying to piece things together in a way that feels harder than it should? And once I started looking at my work through that lens, something changed. Because every time I got stuck, I started building something to support that part of the work. And it wasn't perfect and I didn't do it all at once, but piece by piece, and it wasn't that AI suddenly solved everything for me. It was that for the first time in a while, I felt like I had something to actually hold on to, something that could help me move forward instead of just sitting there wondering if I was doing it right. And one of the first places that started to change for me was something really simple on the surface, but incredibly important. I could finally see who I should be focusing on. Before that, I would open up my database, look at my assigned prospects, and it felt like staring at a wall of names. Some of them looked promising, some of them had given before, some of them had capacity. But there wasn't a clear, consistent way for me to say, these are the people I should be spending my time on right now. So I'd bounce around. A little bit of effort here, a little bit of effort there, trying to cover ground instead of creating movement. But once I started building tools to help me analyze that portfolio to look at patterns, to prioritize based on what actually mattered in our organization, that changed. Now I could open my portfolio and say, these are my people. This is where I start. And that matters whether you're looking at a database of thousands or hundreds of thousands of names and trying to figure out where to begin, or you're trying to rebuild momentum in a portfolio that's been quiet, or you're leading a team and everyone is pulling in slightly different directions. Because alignment starts with focus. And once I knew who to focus on, the next thing that started to change was how I reached out to them. Because before that, every time I sat down to write an email or think through my next step, it felt like I was starting from scratch. What do I say? How do I say it? Is this the right approach to even be using? And I would overthink it. I would write something, tweak it, second guess it, come back to it later. And that slows, you know, the whole process down. So I started building structure around that. Not scripts that made everything sound robotic, but systems that gave me a starting point, outreach cadences, sequences that assumed no response and kept the conversation moving, ways to approach different types of donors without having to reinvent it every single time. And what that did is it removed a lot of the friction. I wasn't sitting there trying to come up with something perfect. I had something to work from. And that changes how you show up. Because whether you're trying to start a major gift program from the ground up, or you're trying to increase the number of conversations you're having, or you're trying to help a team be more consistent in how they engage donors, it all comes back to this. Do you know who to focus on? And do you have a clear way to start the conversation? Because once those two things are in place, everything else has something to build on. And once those conversations started happening more consistently, I ran into the next challenge. Because getting the meeting is one thing. Knowing how to move that meeting forward, that's something else entirely. Before this, I wasn't walking into donor meetings blind. I had done my research. I knew their history. I had a general sense of where I wanted the conversation to go. I wasn't guessing, but I also wasn't being fully strategic. I had a direction, but I didn't have a clear plan for how to get there. So I would walk into these conversations thinking, I'd like to move this relationship forward, or I want to explore this area of interest, but I hadn't really defined what success looked like for that specific meeting. And what do I actually need to learn here? Like what signals am I looking for? What would tell me this relationship is ready for that next step? And without that clarity, the conversations would sometimes drift. It would be good, it would be engaging, it'd be a lot of fun, but it wouldn't always create momentum. So this became another place where I started building support. Before each meeting, I would take everything I knew about that donor, our past conversations, their interests, giving history, and I would run it through a system that helped me get really clear on three things. What is the purpose of this conversation? What do I need to understand by the end of it? And what does moving this relationship forward actually look like from here? And that changed how I showed up. Because I wasn't just going in with a general direction. I was walking in with a strategy. I knew where I was trying to go, and I had thought through how to guide the conversation in that direction. But where this really started to shift for me was when I began preparing for the harder conversations. The ones we don't talk about as much, the ones where you have to redirect somebody's interest because it doesn't align with your organization's priorities. Or when you have to say no to a gift because managing it would actually cost more than the value of the gift itself. Those are not easy conversations to walk into. And even when you know what you need to say, that doesn't mean you feel ready to say it. So I started doing something different. I would build AI practice partners, and not just generic ones. I would design them to reflect the donor that I was about to meet with. What is their personality, their interests, even the kinds of objections I thought that they might raise? And then I would make them harder than the real donor, a little bit more resistant, more skeptical, more challenging than I expected that actual conversation to be. And I would practice from different angles, different approaches, different responses, so that by the time I sat down with the actual donor, I wasn't trying to figure it out in the moment. I had already worked through it. And that changed how I showed up in a really fundamental way. Because when you move from walking into a meeting with a general sense of where you want it to go to walking in with a clear plan for how to move it forward. And as I started building out these pieces to support my work, something else began to change that I didn't expect at first. The data I was working with actually became useful. Before this, I was doing what most of us do. I would write contact reports after our meetings. I would enter notes into the CRM. I would try to capture what happened, what we talked about, what might happen next. But a lot of the times those notes were inconsistents. Sometimes they were detailed, sometimes they were rushed, sometimes they were written in a way that made sense in the moment, but not necessarily six months later. And because of that, when I went back to look at that information, it wasn't always that helpful. I had the data, but I couldn't always use it. So I started building these systems. I realized pretty quickly that everything worked better when the inputs were stronger. When the information going in was clear, structured, actually captured what mattered from our conversation. So I built a contact report system that helped me do that. Something that would take my notes, my reflections after a meeting, and turn them into a clean and consistent report that highlighted the key signals. What did we learn? What did the donor care about? What moved forward in our conversation today? What needs to happen next? And once that started to click, everything downstream got so much better. Because now, when I was preparing for the next conversation, I wasn't digging through scattered notes, trying to piece things together. I had something that I could actually work from. And it didn't just help me, it helped everyone around me too. I remember our analytics team looking at the reports that I was putting in and saying, dang, Keith, you're making our jobs so much easier. And that was one of those moments where it really hit me. This wasn't just about saving time. It was about creating clarity, not just for myself, but for everybody in the process. Because when your data is clear, your thinking gets clearer. And when your thinking gets clearer, your decisions get better. And that's when the work really starts to move differently. And this is really where everything started to change for me. Because up to this point, I was improving pieces of the work. I was getting more focused. I was having better conversations. I was capturing better information, but I was still carrying that same underlying question. Am I actually doing this right? And that question shows up in a lot of different ways depending on where you are. If you're newer to major gift work, it sounds like, am I even on the right track here? And if you're leading a team, it might sound something like, can I clearly explain what's working and what's not? And if you've been doing this for years, it might sound like, why does this feel harder than it used to? It's the same question, just different versions of it. And for me, that question didn't go away until I built a way to actually see my work. And that's where the dashboards came in. At first it was simple. I just wanted something that showed me in one place what I had actually been doing. How many conversations was I having? Where those conversations were in the pipeline? What movement had happened over the last month? You know, not vanity metrics, not activity for the sake of activity, but real indicators of whether relationships were moving forward. And when I started looking at my work that way, something shifted because I didn't have to rely on how I felt about my work anymore. I could see it. I could point to it. I could say, this is moving. This is stalled. This needs attention. And then I took it a step further. I started building systems that would actually evaluate my work. Look at my portfolio over a month or over a quarter, and it would ask, where am I creating momentum? Where am I getting stuck? What patterns am I missing here? And when you're managing a portfolio of 100, 150 people, you cannot hold all of that in your head. Things slip, opportunities get missed. And it's not because you're bad at your job, but because there's just so much to track. So having something that could step back and look at all of it objectively with me, almost like a second set of eyes, changed everything. Because now I wasn't guessing anymore. I wasn't waiting for a gift to close to tell me if I was doing a good job. I had proof of progress. I could see relationships moving. I could see where I needed to adjust. I could see where I was doing well. And that's when the identity shift happened. I stopped wondering if I was doing a good job. And I started knowing that I was doing a great job. And that didn't just stay with me. I started sharing those dashboards with my manager, showing her, here's what's happening, here's where things are moving, here's where I'm focusing next. And she didn't just appreciate it. She asked me to share it with the rest of the team. And from there, it spread. Other major gift officers started using these tools. It became something that the organization adopted more broadly and rolled out to everybody. And that was one of those moments where it became really clear to me. This wasn't just helpful for me. This was solving a problem that a lot of us were quietly dealing with. Because when you can actually see your work clearly, you don't just perform better, you feel different doing it. And one of the biggest changes that came from that was what didn't happen anymore. Things stopped falling through the cracks. Because when you're managing a portfolio of 100, 150 donors, even if you're incredibly organized, even if you care deeply about every single relationship, it's just so much to hold. You've got conversations happening at different stages, different priorities, different timelines. And no matter how good you are, things get missed. I mean, we're all human. Things happen. And it's the risk we all carry asking ourselves, what am I forgetting? Who haven't I followed up with? Where did I lose momentum without even realizing it? But once I started using these review systems, stepping back and looking at my portfolio on a monthly or a quarterly basis, that changed. Because now it wasn't just me trying to remember everything. I had something helping me scan the full picture, surface what I hadn't seen, point out where I had gone quiet, highlight where I needed to reengage. And the best way I can describe it is it felt like putting bumpers up at the bowling alley. You might not throw a perfect game every time, but you're not gonna throw a gutter ball either. And in major gift work, that matters because so much of this is about consistency. About staying present in the relationship, about not letting momentum quietly slip away. And for the first time, it felt like I had a system that was helping me do that without having to carry all of it on my own. And that all came to a head in one moment that honestly used to terrify me. Because once a year we would have this really high-stakes meeting. It was me, my dean, my manager, the vice president she reported to, and the president of the foundation all sitting down with the provost of the university to review my work. And if you've ever been in a meeting like that, you know the feeling. All eyes are on you. Every question matters. Every answer is important. And I heard stories from colleagues about how those meetings could go. People getting torn apart, caught off guard, not having answers. So going into my first one, I was bracing for that. But something different happened. They started asking their questions about my portfolio, about specific donors, about where things were moving and where they weren't. And as those questions came up, I realized something. I had already answered all of them. Not in that room, but in the work I had been doing leading up to it, through the dashboards, through the reviews, through the systems I had built to actually understand what was happening in my portfolio. So when they asked, I didn't have to guess, and I didn't have to scramble for an answer. I wasn't trying to piece something together in that high-pressure moment, because I knew. I had answers to every question. And you could feel the shift in the room. Because confidence is different when it's backed by clarity. And after that meeting, my manager said something to me that has stuck ever since. She goes, You're the one employee I never have to worry about. And that wasn't because I was working harder than everyone else. It was because I could see my work clearly enough to lead it. And that changed everything for me. And it took me a little while to fully be able to see that because when you're in it, it just feels like you're solving the next problem in front of you. You're building something to help you prioritize your portfolio. Then you're building something to help you with your outreach. Then something for your meetings. Then something for your reporting. It feels like a series of small improvements, but at a certain point, like I stepped back and looked at everything together and I realized this wasn't six separate things. It was one complete system. It was a way of working that supported every stage of the major gift process, from figuring out who to focus on to starting the conversation, to guiding that conversation forward, to understanding what was actually happening in the relationship, to knowing when how to make the ask, to continuing the relationship after the gift was given. All of it was connected. And more importantly, it was removing something that had been sitting underneath my work the entire time. Guessing. Guessing who to prioritize. Guessing what to say. Guessing how a meeting went. Guessing if I was doing a good job. That quiet layer of uncertainty that most of us carry even when we're doing good work. And in its place, it created something completely different. Clarity. Clarity on where to focus. Clarity on what to do next. Clarity on what was working and what needed to change in my workflows. And once that was in place, everything else started to feel different. It made the work easier because the work was now clearer. I wasn't trying to figure it all out on my own anymore. I had a system that was helping me think, helping me see, helping me move that work forward. And as I started to see that more clearly in my own work, it raised a different kind of question. Not about what I had built, but about where this might be showing up for my fellow fundraisers. So let me ask you this. Where are you guessing right now? Where are you missing a clear way to see what's actually happening in your major gift work? Where are you doing all of the right things on paper? But underneath that, you're still wondering, is this actually working? Where do you feel like you have nothing to point to? No clear signal that things are moving, no way to confidently say, yes, this is heading in the right direction. And that might look different depending on where you are. If you're building a major gift program from scratch, it might feel like you're putting pieces together, but you don't know if you're building the right foundation. If you're leading a team, it might feel like you're responsible for outcomes, but you don't have a clear line of sight into what's actually happening across each officer's portfolio. And if you've been doing this work for years, it might feel like something is just a little off or you're having to start over all the time. Like it's taking more effort to get to the same place, but you can't quite explain why. Or maybe you're heading into a campaign and there's this pressure sitting underneath everything. You need to know where your opportunities are. You need to know how ready your donors actually are, and you need to know if your team is positioned for success. And without that clarity, everything starts to feel heavier. Because you're not just doing the work, you're carrying the uncertainty of not knowing if it's working. And that's the part that wears on you over time. It's not the effort, and it is the ambiguity. So as you're thinking about your own work right now, I want you to get really honest with yourself. Where are you relying on instinct when you'd rather have insight? Where are you putting in effort without a clear way to evaluate if it's actually creating movement? And where would it make the biggest difference for you if you could actually see what's happening clearly? Because once you can see it, you can change it. And this is the point where I can finally say a little more clearly what I've been hinting at over the last few weeks, because everything I've just walked you through, that's what I've been building. Not as a concept or as a set of ideas, but as something that you can actually use in your work. The AI advantage for major gift fundraising. And at its core, it's exactly what we've been talking about today. It's a system that supports the full life cycle of major gift work, from knowing who to focus on to starting and sustaining real conversations, to walking into donor meetings with a clear strategy to actually seeing what's happening in your portfolio, to knowing when and how to move toward the ask, and then continuing that relationship in a meaningful way after the gift. But more importantly, it's built to do one thing really well. It helps you stop guessing or relying on instinct. And it gives you a clear way to think through your work to evaluate it, to move it forward with intention. And this isn't something I pulled from a textbook. It's not something that lives in theory. It's built directly from the work that I've been doing, from the tools I had to create because I needed them, from the moments where I was stuck and had to figure out a better way forward. So when you go through this, you're not just learning about AI, you're learning how to actually apply it inside of your day-to-day work in a way that makes you more effective, more confident, and more clear in what you're doing. And I want to be really clear about something because this is not one of those trainings where you sit through a few videos and get excited for a day or two and then go right back to doing your work the way that you were before. This is designed to change how you work so that when you sit down at your desk, you're not wondering where to start. When you're preparing for a meeting, you're not hoping it goes well. When you're looking at your portfolio, you're not trying to figure out if you're on track, you know. And if you're listening to this and you can feel that gap in your own work, if you can feel where you're relying on instinct or you're guessing, or you don't have a clear way to see what's happening, then I want to invite you to take the next step with me. Go to let's talkfundraising.com forward slash major gifts and join the wait list because later this month I'm going to be opening this up for our very first cohort. And we'll start working together on this on May 4th. And I don't say this lightly, but if you want a clear, practical way to improve your major gift work, this is the most direct path I know how to give you. Because it's the exact path that I walked myself. The goal isn't to work harder, it's to finally see your work clearly enough to move it forward. And if that's what you've been looking for, I'd love to work with you. Thanks for being here, my friend. I'll see you again next week. Bye bye.