If You Wait Until You Feel Ready, You'll Never Start

This is the episode where we stop painting the picture and start talking about what happens next.

If you've been listening to this series for a few weeks and something has started to click, this one is for you. You've recognized the moments. You've said "yeah, that's me" more than once. And now there's a quieter question underneath it all: are you going to do something about this, or keep circling?

Keith opens with a story from earlier in his career, sitting in his supervisor's office, holding a catalog of very responsible reasons to put off pursuing his CFRE. And what his supervisor said that afternoon is exactly what this episode is built around. Because the gap between understanding a problem and fixing it isn't an information gap. It's a decision architecture problem. And this episode is designed to help you close it.

You'll hear a clear and honest walkthrough of what's inside the AI Advantage for Major Gift Fundraising program, including all six modules, the live sessions, the office hours structure, and what the two months of post-curriculum support actually looks like. Keith addresses the most common hesitations directly: not enough time, no AI experience, organizational data concerns, fear of falling behind.

Enrollment for the founding cohort is open now and closes Friday. The cohort begins Monday, May 4.

If something in you just went "yes," that's the right word. Go to letstalkfundraising.com/majorgifts.

💡 Want to take the next small step?

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

→ Course:  The Fundraiser's AI Starter Suite

Transcript

The Decision Moment

Keith Greer 0:00

There's a moment I want to start with today, and it may or may not be the one that you're sitting in right now. But I have a strong hunch that some version of it is close. You are somewhere in your day, maybe you're at your desk between meetings, maybe in your car on the drive home where you're headed to work. Maybe you're at the kitchen table with this playing while you half-answer emails. You've been listening to this series for a while, and for some of you, it has been every episode since I first started talking about this program back in February. For those of you, it is just the last couple of weeks, and somewhere in the middle of all of that, something started to click. You have been hearing your own work described back to you. You have recognized those moments, and you've said, yeah, that's me, more than once. And now there's a quieter question underneath it all, and it does not have a tidy answer. Am I going to do something about this? Or am I going to listen to a couple more episodes and keep circling? If that is the moment you are sitting in right now, I want you to stay with me for the rest of this episode because this is the episode where I want to stop painting the picture and start talking to you directly about what happens next. The first cohort of the AI Advantage for Major Gift Fundraising opens for enrollment is now. Enrollment closes Friday and we begin together on Monday, May 4th, which is coming up fast. And for some of you, that sentence just tightens something in your chest because you can feel the decision coming. So today I want to walk you through it honestly, like a friend would, and help you figure out whether this is yours to say yes to. So let's talk fundraising. I want to take you back a few years to before I built any of these systems, before AI had shown up in any of our work, and before any of this was on my radar. I was sitting in a small office with my supervisor at the time, and he had just finished telling me that he wanted me to pursue my CFRE. And if you've been in this field long enough, you know what that means. It is the certified fundraising executive credential, and it is the closest thing our profession has to a formal stamp of approval that says, you actually know this work and you know what you're doing. There are hundreds of hours of practice to document. There is an application, there is continuing education requirements, and there's a pretty serious exam that goes along with it. None of it is casual. And I remember sitting in his office that afternoon and thinking, I am not ready for this. It was not that I didn't want the credential, it was not that I didn't think that it mattered. I wanted it. I wanted to be the kind of fundraiser who had done the work and had done something to show for it. But sitting there, I could hear a catalog of very responsible reasons to put off. My work was busy. I was in the middle of a gala. I'd not taken a specific class I thought I'd probably needed first. I wasn't sure if I had enough hours of continuing education or the right kind of experience to really be considered ready. And all of those reasons sounded responsible. They sounded like a reasonable version of caring about the work. If you don't feel fully ready, shouldn't you wait until you do? And my supervisor looked at me and he said, something that I've never forgotten. He said, Keith, if you wait until you feel ready, you will never start. And I went home that night and I started the application. At the time, it was a five-year credentialing process, but I worked through it. All of it. And five years later, I sat for the exam, and the part that surprised me looking back was not that I passed. What surprised me was how much of what I used on that exam I had learned in the five years of pursuing the credential itself, and not in the four years of interning in the development office during college. The CFRE did not just confirm what I already knew, it filled in the pieces that I didn't know I was missing. It named things I had been doing on instinct without language for them, and it gave me a structure to hang my experience on. And it did something I didn't expect. It shortened the runway for everything that came after it. I didn't understand until much later what had actually happened in my supervisor's office that day. And it was a decision architecture problem. I had all the information I needed to decide. I had permission to decide. I had support to decide. What I didn't have was a willingness to cross the line from thinking about it to doing it. And he gave me that by saying a hard, true thing out loud. I want to try to do the same thing for you today because if you have been listening to this podcast for any number of weeks, you have all the information you need. You understand the problem and you understand where AI fits in the major gift cycle. You understand that this is not about replacing relationships, it is about removing the friction around them. You understand what the six-week program covers and what you will build inside of it. You know who is leading it. You know what the live components look like. This information is not the missing piece. What's underneath it is something else. And that is what I want to walk through with you today. Let me start here because I think this is the right place to start. You're closer to this than you probably realize. Over the last seven weeks, we have covered a lot of ground together. We talked about the major gift cycle and where AI can quietly support it. We talked about the 30-something hours a week that so many of us spend stuck behind a desk when we want to be with our donors. And we talked about the cost of analysis paralysis and what it feels like to overprepare as a substitute for starting. We talked about how attention is fragmented across the sector and how our outreach has to match the way people actually move through their days now. We've talked about how it feels to work hard for months without closing any gifts and the quiet doubt that creeps in when you can't see your own progress. We've talked about the, yeah, buts and the real concern about ethics and data and whether your organization will even let you do this. And last week we talked about how you bring a clear strategy into every donor meeting instead of walking in with a general direction. And if you've stayed with me through all of that, I want you to hear me say this clearly. That is not small. That's not passive listening. That is a fundraiser already doing the work of getting ready to change how you work. You've been building a readiness you can't fully see yet. And if you only caught the last couple of episodes, I want you to hear this too. You have not missed the window. You are exactly on time. The door is open right now for a reason, and it's open for you. Here is the honest part though, and I want to say it plainly. Listening to a podcast and changing how you work are not the same thing. Reading articles about AI and having a system you use every Monday morning are not the same thing. Agreeing with someone's diagnosis of your problem and fixing your problem are not the same thing. Somewhere along the way, there's a line. On one side of that line, you keep circling, and on the other side, you start building. This program is the structure that helps you cross that line. Let me name the gap that I think is still sitting there for some of you. You can see what I'm describing, and you can picture your Monday morning where you open your portfolio and you know exactly who to focus on this week. You can picture the donor visit where you walk in with a clear purpose and the drive home where the contact report is already drafted before you pull out of the parking lot. And you can picture the review meeting with your manager where you are the one bringing clarity to the room instead of trying to find it in the moment. You can picture all of that. What you might not be able to picture is how you get from where you are now to that Monday morning on your own. And that is a real problem. And I want to honor it instead of wave it away. I built what I built over more than three years. Three years of trying things that didn't work, three years of prompts that came back flat and systems I started and abandoned because they weren't quite right. Three years of learning what to ask AI for and what not to. Three years of figuring out which parts of my work it could actually support and which parts it would make worse if I let it in there. I had the curiosity and I had the time. I had the patience for it because I genuinely enjoy this kind of a puzzle. And even for me, with all of that, it took three years to arrive at something that really works. You don't have three years. You have a portfolio, you have a pipeline, you have a manager asking you what your plan is. You probably have a campaign on your horizon and you have a life outside of your job that also has demands on it. The question is not whether you could eventually figure this out by yourself. You probably could. Many of the smartest fundraisers I know are already trying to. The question is, what is it costing you while you do? Because in major gift work, time is not a neutral variable. Time is the variable. Donor attention moves, timing windows open and they close, and the gift that was available six months ago is not always available now. Every month you spend piecing this together on your own is a month the friction stays in your work. Every month the friction stays, the relationship work stays crowded out. And every month the relationship work stays crowded out, gifts that could have happened don't. This is the reason I built the program that I built. Not because I wanted to teach AI, because I wanted to save my fellow fundraisers three years. That's the real offer. The offer is not six modules. The real offer is six weeks of shortcuts through three years of trial and error with the person who actually made those errors sitting with you while you build it inside of your own portfolio. And I want to say something about the cost of waiting, and I want to be careful with this because I don't want to turn it into somebody that I'm not. You've probably heard plenty of people talking over the years where the energy gets a little frantic in the last week and the urgency starts to feel manufactured. That's not what this is. What I do want to say is honest, and it's this if nothing changes in your work in the next six weeks, the next year of your work, probably gonna look a lot like the last year. The same number of hours at your desk, the same prospects you've been meaning to get to, the same donor you have been nurturing for months without a clear read on whether the relationship is actually moving. The same reporting questions that you are going to try to answer without the data to back them up. The same Friday afternoon where you look at your calendar and realize you only had four donor conversations this week and you wonder where your time went. That's not a failure. That is not a judgment on you. This is the default, and the default is the pattern that you're already in. The default doesn't require a decision. It just requires that you don't make one. And if you're a person who cares deeply about this work, and I know you are because you're still listening to this podcast, the default has a cost that builds quietly. It shows up in the donors that you meant to reach, and it shows up in the performance conversations where you can't quite explain why your portfolio hasn't moved. It shows up in the campaign that is coming up that you already feel a little behind on, and it shows up in the way you feel on Sunday night thinking about your Monday morning. And I don't want to sell you anything out of fear, I really don't, but I also don't want to be so polite about the decision in front of you that I failed to tell you the truth. And the truth is that every year that goes by without a real system for this work is a year of good effort absorbed by inefficiency. And the cohort starting May 4th is the closest and fastest on-ramp I can offer you to a different pattern. So let me tell you what you're actually stepping into if you decide to join us. The program runs for six weeks from May 4th through mid-June, and every Monday at 2 p.m. Eastern, we're going to meet live for the main training session of the week. That's where I walk you through the module for that week, show you exactly how I build each system, answer your questions in real time, and work alongside you while you start to build yours. If you can't make the live session, it is recorded and posted the very next day. So you can catch it that evening or the next morning, because life happens, travel happens, meetings run late, and you will not fall behind because your calendar was full on Monday. But then on Thursday of each week we meet again. This time it's for office hours. This is where you bring me the thing that you got stuck on between Monday and Thursday. Bring me the donor profile your prompt is not quite capturing. You bring me the outreach sequence that is not clicking for your sector. You bring me the contact report format that your team is going to need before they will let you roll this out broadly. Whatever it is, you bring it and we work through it together. Not in theory and not in a hypothetical, inside your actual work with your actual donors. The six modules are these. I've walked through them across this podcast series, but I want to name them once more in sequence so you can feel the shape of what you'll have at the end. Module one is prospect identification. You build a scoring model specific to your organization, your data, and the signals that actually matter in your world. By the end of that week, you are no longer relying on generic wealth screens or gut instincts. You have a focused and defensible list. Module two is prospect qualification and outreach. You build a donor research engine, a donor brief generator, and a 90-day multi-channel outreach sequence with more than a dozen touch points pre-drafted and ready to use. By the end of that week, you are creating what I call inevitable conversations instead of sending one email and hoping for a reply. Module three is donor meetings and conversations. You build a meeting strategy engine and AI role play partner that you can practice difficult conversations with before you're in the room, and a post-visit capture system so your contact report is done before you even leave the parking lot. By the end of that week, you are leading conversations instead of hoping that they go well. Module four is your portfolio intelligence and performance. You build the system that tells you whether your work is actually working. This is the module that, when I built it for myself, changed my entire experience of this job. By the end of that week, you have what you need to walk into any leadership conversation with data, context, and a plan. Module five is proposals and asks. You build the translation system that turns messy thinking into clear and compelling opportunities that your donors can say yes to. And that scales across high volume without killing your time. By the end of the week, you're no longer the person staring at a blank page, trying to articulate the ask. And module six is stewardship and relationship expansion. You build a donor experience system with an impact translation engine and a structured stewardship plan heavily weighted toward the first 180 days after the gift. By the end of that week, you have the tools to turn a first gift into a lasting partnership. That's the module where a donor told me, Keith, you went from an obligation I felt I had to one of the top three charities that matter to me. And that's what module six build towards. After the six weeks of live training ends, you have two additional months of ongoing support. And I want you to hear me say that. You will be in the room while the program is being finalized. You'll have access to me in a way that no future cohort will have because future cohorts will be larger, the curriculum will be more formalized, and the shape of the thing will be set. Right now it's not. Right now, your feedback, your portfolio, your questions actively shape what this program becomes. And that's a specific kind of experience, and it's only available once. I know there are some real questions sitting in your head right now. I've heard them from waitlist members over the past few weeks, and I want to answer them directly because these are the questions I would have myself if I were on your side of this conversation. The first one is usually some version of, I don't have time for this. And I want to take that one seriously because it's real. You do not have extra time. Nobody in Major Gifts has extra time. What I would ask you to do is think about the time you're already losing. Two hours prepping for a visit, you could prep for in 15 minutes. A week digging through the CRM to build a prospect list that you could generate in an afternoon. 30 minutes after each donor meeting, writing a contact report that should take you five. That time is already gone, and the question is whether we get it back. This program is structured so that each week the system you build that week starts saving you time the very same week. You don't have to finish the whole course to see the return. What week one pays for itself. The second one is usually, I've never really used AI before, or I've used it and it didn't impress me. And I want to tell you what Sean told me. Sean is on the board of Honor Flight of Northern New Mexico, and he said, Keith, I've never touched AI and I don't want to cross any ethical lines. A few weeks into the program, he was telling me he could not wait to start using it in his work. He's not more technical than you, and he didn't come in with any advantage. He came in curious and willing. And if you can type into a Google search bar, you have the baseline skills. Everything else, I'll teach you. The third one is will my organization even let me do this? And from the very first module, I walk you through how to set this up in a way that keeps your donor data safe and aligns with your organization's data policies. Most organizations are already working in cloud-based systems. Most of the concern around AI is about using it carelessly, not about using it at all. You'll come out of this program with the language and the setup to have a productive conversation with your IT team, your compliance team, and your leadership about how you are using these tools. You'll not be winging it. The fourth one is what if I fall behind during the six weeks? Every live session is recorded and posted the by the very next day. You can catch up on your own schedule. The Thursday office hours are designed to help people who are stuck on something or who need to catch up, not to punish you. And the two months of support afterwards means you're not racing a clock. Life happens, travel happens, campaigns happen. We've built in for that. And if you have any other questions right now, send me an email at Keith at LetstTalkFundraising.com and I'll get back to you, all right? I want to talk for a minute about the people who have already said yes, because they are part of the reason I can say what I'm saying to you with confidence. The pilot program I ran last summer was the test version of everything you would be stepping into right now. It was not polished, pieces were missing. I was still figuring out how to teach what I already knew how to do. And the fundraisers who went through it taught me an enormous amount about what this program needed to become. I followed up with them six and seven months later to find out what actually stuck. And the answer was almost all of it. Erin Clegghorn is an associate vice president of institutional advancement. She went through the pilot and she said something to me that shaped how I think about this whole program. She said, Keith, you know our business. You are a frontline fundraiser. You're not looking at it from the outside. You've actually been a fundraiser and you are using this in your own work. That authenticity is really meaningful. She said something else that I want you to hear because it gets at what this program actually is. She said, Your course was interactive. You showed us not only how to write the prompt, but what the results were, how to modify them, how to actively do it ourselves. And you gave us the framework. It wasn't just slides and it was us doing it together. That's the program. It's us doing it together. That is what you step into on May 4th. I want to say something a little softer before I wrap up because I think that this matters. And if you have been listening closely to the series, you can probably already tell that it matters to me too. If you've been on the fence, I want you to know you're not behind. You're not. I don't care when you found this podcast. I don't care if you signed up for the wait list two months ago or six hours ago. I don't care if you're five years into your major gift work or 15 or 30. Where you are right now is exactly the place it is reasonable to be in when you're considering something that asks you to change how you work. That's not weakness, that is care. And you don't have to be perfect to say yes to this. You don't have to feel ready. You don't have to have your AI strategy worked out, or your organization's data policies rewritten, or your manager's blessing in your pocket. You don't have to have used Chat GPT more than twice. You have to be willing to show up on May 4th and start. That's all. If the voice in the back of your head right now is saying, I don't want to make this decision under pressure, I want you to hear me say this too. The pressure is the cart closing on Friday, which is real because the cohort has to begin somewhere. And it begins on Monday, May 4th. The pressure is not that if you wait, you've missed your shot forever, I'll run it again. There will be other cohorts. What will be different is the price, the access, and the shape of the thing because the next time I run this, I'll have more people, less one on one time, and a program that is no longer being actively refined with your input. It's not a scarcity trick, it's just a factual description of what this cohort is versus what the next one will be. So the question I want to leave you with is not whether you will ever do this, it's whether you will do it now with this small. Group with me starting May 4th at the lowest price that this is ever going to be again. So if you're ready, here's what I want you to do. Go to letstalkfundraising.com forward slash major gifts, and the link is in the show notes. You'll see everything I just walked you through laid out in one place. You can read it, you can sit with it for a minute, and if it is yours, you can enroll right there. Enrollment closes this Friday, and the cohort begins Monday, May 4th at 2 p.m. Eastern, and we go together from there. But before I go, I want to name who this is for and who it is not because I want to be as honest with you here as I know how to be. This is for you if you are managing a portfolio right now and too much of your week is going to prep, administration, and documentation instead of actual donor conversations. This is for you if you know what a strong major gift works looks like and you don't yet have a consistent system to execute on it week after week. This is for you if you have experimented with AI and nothing is quite stuck because it was not built for the way that you actually work. This is for you if you are staring down a campaign, a performance review, or a board meeting, and you want to walk in knowing exactly where your portfolio stands with the data to back it up. This is for you if you are ready to apply what you learned starting in week one inside your real portfolio with real donors at your real organization. But this is not for you if you're looking for passive content to watch. And it's not for you if you want AI to replace relationship building with your donors, because this program will not teach you that, and I politely refuse to. It's not for you if you're not either building a major gift program or currently managing a portfolio or working with donors, because this program is built around that context. And it's not for you if you want somebody to build your systems for you instead of learning to build and use them yourself, because what you walk away with is not my system, it's yours. You can customize them to fit you and your organization and the way that you work. I'm asking you to come build this with me inside of your real work for the next six weeks, with two months of support on the other side of it.$997 is the investment and Friday is the deadline. Next week, May 4th is the start. Let's talk fundraising.com forward slash major gifts is where you go. If something in you just went, yes, that is the right word. And if you've been waiting for permission, consider this yours. Go to the page, read it, and enroll. I'll see you in the cohort. If you are not there yet, that's okay too. Keep listening, keep thinking, keep building your own understanding of this work and what it asks of you. I'll be here, the podcast will keep going, and the next cohort will come. But I'd rather have you in this one. I'd rather have you here in the room while the program is still being shaped, at the price that will never be the slow again, with a small group and the direct access and the time to really put this into your portfolio. So, thank you for being here, my friend. It has meant more to me than you know to have you in these conversations. Whether you join us in the cohort or not, the fact that you have been listening, thinking hard about your work, and caring this deeply about how you show up for your donors, that matters. And I'm so grateful for you. I'll see you on the other side, my friend. Bye for now.