The Cost of Waiting Until You Feel Ready (Major Gift Fundraising)

There’s a moment most fundraisers don’t talk about.

The one where you know what needs to happen next…
but you’re still trying to get everything lined up before you move.

More research.
More preparation.
More time to “get it right.”

And it feels responsible.

But over time, that moment starts to cost you something.

In this episode, I share a real story from early in my career when I got stuck in that exact place… and what I realized just before it was too late.

We’ll walk through:

• Where “analysis mode” shows up in your work
• What it’s quietly costing your pipeline
• Why waiting to feel ready slows down your results
• And how to start moving forward with more clarity

This isn’t about doing more.

It’s about moving sooner… in a way that still feels thoughtful and aligned with how you do your work.

If this resonated with you…

I’m building a program called The AI Advantage for Major Gift Fundraising to help you navigate these exact moments with more structure and less friction.

You can join the early access list here:
👉 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

A Gala Without A Playbook

Keith Greer 0:00

There was a moment early in my career that I still come back to more often than I probably should. I had just stepped into a new role, I was still figuring out where everything lived, still trying to understand how things worked in this organization. And a few months in, it was time to start preparing for their annual gala. This was the event of the year, the one everyone in the community pointed to, the one that carried the financial success of the year. And I remember being told more than once, this has to be done exactly the way it's always been done. No changes, no deviations, just follow the process. But the problem was, there wasn't a process. There was no guide, no roadmap, just a decade of saved documents organized in a way that probably made perfect sense to the person before me. And absolutely none to me. So I did what I thought I was supposed to do. I started digging, opening files, trying to piece together what mattered, trying to understand how it all fit together, day after day and week after week, just trying to get a place where I felt like I could do it correctly. And the whole time this quiet pressure was building because I knew what came next. At some point, I needed to be out there selling sponsorships, filling tables, bringing this organization's biggest gifts of the year in the door. But I wasn't there yet because I didn't feel ready. I was still trying to understand everything first, still trying to make sure I got it right. And I remember sitting there one day, surrounded by all of these documents and realizing something that I hadn't really let myself say out loud yet. If I stayed in this mode, trying to figure everything out before I moved, I was gonna leave a lot of money on the table. I wasn't stuck because I didn't care. In fact, I cared so much and I desperately wanted to get it right. I wasn't stuck because I couldn't do the work. I'd been coordinating hugely successful galas since I was an intern in my first fundraising job back in college. I was stuck because I was spending my time trying to feel ready for a goal that felt hugely important and nearly impossible to meet. And that blocked me from actually moving the work forward. And if you've ever been in a moment like that where you know what needs to happen next, but you're still trying to get everything lined up first, you know exactly how I felt in that moment. And if that feels familiar to you, if you can think of a place in your work right now where you're sitting in that same tension, trying to get it right before you move, I want you to know that's actually the exact kind of moment I've been building something around. Over the last few months, I've been working on a program called the AI Advantage for Major Gift Fundraising. And at its core, it's really about this. How do you move from digging through information to knowing what your next step is? How do you get to a place where you can start without having to feel fully ready first? If that's something that you've been wanting support with, you can join the early access list at letstalkfundraising.com forward slash major gifts. I'll share more as it develops. And if this is the kind of conversation that feels helpful for you, make sure you're subscribed to the podcast so you can stay with me as we keep building this out together. Because today, what I really want to talk about is what it's actually costing us to stay in that place longer than we need to. So let's talk fundraising. Let's start this off where that analysis mode shows up in your fundraising work most often. And when you're feeling stuck in that analysis paralysis, it's not because you don't care. You're stuck because you're trying to be responsible. And what does that look like? It means that we're showing up, we're being overprepared before we start working on what we're needing to do. Once we feel like we're ready, we might get pulled back into double checking and triple-checking our work and making sure that all of our I's are dotted and our T's are crossed before something ever leaves our desk that actually isn't going out to the donor. And it might be there just to help us have that security blanket. It's trying to get it right before we make any actions that could label us as bad or not doing our job well enough. And it often hides in good intentions. It's the donor research that we're doing, it's preparing our proposals and it's cleaning up our CRM. All of this work feels incredibly productive because we all know that having a great CRM database, that's where we're gonna go in and we are going to find our next potential prospects, our next potential donors. And as it's said over and over again, garbage in, garbage out. So we go in and we clean everything up. And then we do a bunch of research. Is this the right person for us? Are they gonna be the one that's gonna make our next gift? But we can't really tell any of that from the preparation. It's once we actually start moving into that work, once we actually start acting, that we start to see what develops. So if you're telling yourself, I just need a little more information first, catch yourself, because that extra step, it often becomes a pattern in the work that we're doing. I wish it was something that was a one-time pause for us, but it so often becomes a crutch that we can lean on because it feels comfortable, it feels safe, it feels productive, but it's not something that's actually moving those conversations and those relationships forward. It's not the actual work of fundraising that we need to be focused on. So there's a couple signals that I want you to watch out for. And the first one is that you're spending more time preparing than you are engaging in the work that you're doing. So, what does this look like? It means that you're spending more time in your office, more time behind your desk than you're spending in conversations with donors. You might have 50 open tabs in your web browser and dozens of spreadsheets that you're pouring through, trying to set fine sift through everything to make sure that you found the exact next right person to talk to. But there's always, oh, what about this person? Oh, what if there's this other thing? And it gets us stuck because it's comfortable to look through a bunch of templates and it's comfortable to rewrite our donor bios and our proposals over and over and over again. That's relatively low risk work. But if you're only getting in a few conversations every week, that's a real risk of not being able to move the conversations and the relationships and philanthropy forward within your organization. So I want to ask you, where in your work are you preparing more than you're progressing? Is it in pouring through the database, trying to find next potential prospects? Is it in trying to write the perfect brief and make sure you have all the research on a donor before you send that first introduction email, reaching out to them to even find out if they're interested? Is it writing and rewriting and analyzing and evaluating and rewriting your solicitation proposal before it goes out your door? What is that point for you where you're getting stuck preparing and you're not progressing? Because there's a hidden cost to it. And we're going to talk about what it's actually taking from you. Because time, it doesn't actually disappear, it doesn't vanish into thin air, but it gets redirected into things that feel comfortable instead of things that are valuable. Because every hour in analysis is an hour that we're not spending with our donors. And so it's about prioritization, right? We want to spend our time where it makes the most sense. And where it makes the most sense is where it's moving the relationship forward and bringing gifts in the door. And when we have fewer conversations, it means that there's naturally fewer opportunities for us. Because so many of us know that major gift fundraising, yes, it's absolutely about the relationship. But before we can even get to the relationship, it's about a numbers game. Because it's all about how many people are we able to make contact with. Out of those, there's only going to be a small percentage that are capable, ready, and willing to make a major gift commitment. And those major gifts, they don't come from perfect preparation. They come from momentum. So it's important that we have somewhere to start and we're acting quickly before we get to the point where we're starting to make those asks. And when we're not doing that, there's a shift that starts to happen. And it happens really pretty quietly. It's not a dramatic shift. But our pipeline starts to slow. There's not a big failure here. It just means that we're having fewer meetings every week. And that means that we're having fewer steps that we're taking next month. And that means that down the road, there's going to be fewer asks that are being made. And if you look at any one of these metrics all on their own, it doesn't look like a big deal, right? Because we still might be having huge hundred thousand, million dollar, multiple million dollar gifts coming in the door. But if we're not seeing the metrics behind that work progress, that's when there starts to be some real costs that are going to affect us, not maybe tomorrow, but six months, twelve months, two years from now, that's where it's really going to start to impact us. And our timing on making these major gifts asks really matters a lot more than we would really like to admit, because, you know, our donors move and not just outside of our territory, but you know, they move their priorities. Another organization was able to get to them and be able to align their work with the donor's passions. And that window of us to be able to cultivate and work with and move that donor toward a gift that matches their passions and their interests, that window starts to close. And oftentimes we're never even going to get a warning that it's happened. So, what conversations haven't happened yet in your work because you've been focused on getting ready? Because it happens to all of us at some point. And we need to have some kind of an honest reflection and evaluation of where that's happening in our own work before we are able to correct it and resolve it and move forward. And so, why does all of this happen? And it's really kind of deep. And it's there's so much pressure to get it right because the stakes and major gifts feel high because they are. These are huge gifts that are coming into our organizations. And those large gifts come with oftentimes very long timelines. I've been part of gifts that took 10, 12 years between the time that there was that first contact made and the donor making their transformational multimillion dollar gift. I've also been a part of major gifts that have happened in a matter of weeks. But oftentimes they take 18 months or even longer before they're actually able to close. And so when you have those long timelines, there's a lot of pressure to get it right so that we don't lose all of the work that we've done. And with these large gifts, there naturally becomes a lot of visibility in this work that we're doing. Because it's really hard to hide the impact of what a multimillion dollar donation is going to do for our organization and the communities that we're serving. It's a huge impact and it's something that we want to celebrate. And even if the donor is remaining anonymous, the impact is still there, both externally out in our community and internally within our own organizations. People are going to know what we did. And so, with all of this, you are carrying more than just your role as a major gift fundraiser. You're carrying donor trust because our entire profession is based on trust and relationships. And without that, there's no opportunity for these major gifts to come in. There's also the institutional expectations. And those are hugely important and really critical because that's what allows us maybe to keep the lights on next month. If we're in a really great organization, it might allow us to do something transformational with our programs or for our constituents that we're serving. And then we have the outcomes that we're also having to make sure are delivered on by the program side of everything. Because if our donors' expectations aren't met, they're not going to go and talk to the program staff. They're coming to talk to us, the person that sold them that bill of goods on what their gift was going to be able to make possible. So getting it right and be getting stuck in analysis paralysis or getting stuck in preparing becomes a form of protection. And it's protection from making a mistake, whether with the donor themselves or within our organization or publicly out in the community. It's protection from criticism because when you have something that's high stakes, critical to organizational success, and incredibly visible that you're the one in charge of it, all of that feedback comes back to us, directly back to us. And it's also protection from uncertainty, because we can prepare the best offer for the donor to say yes to. And it will meet every single one of their expectations and be exactly what they're wanting to do philanthropically and make the change that they're wanting to see in the world. And they can still say no. Because we there's a million reasons why they might say no, from their finances have changed to maybe they're getting a divorce or a whole other host of reasons that are completely outside of our control. So we stay stuck in getting it right because then there's no risk for them to say no, because we never got there and we were just perfecting it until the point that it kind of slipped away. But that pressure to get it perfect, it also quietly raises the bar for even starting to get momentum because we wait more and we're preparing more and we're wanting to get it exactly right before we start making even a first step. And that leads to hesitation. And so I want you to ask yourself, what does getting it right mean for you and your work right now? Does it mean that you're you know just enough to move forward? Or does it mean that you know everything to the point where there's no chance of them saying no? Where are you on that spectrum? And so then what actually does move our work forward? Because progress in major gift fundraising comes from movement, not from perfection. Because those first visits that we're having with a donor, those identification and qualification visits, those conversations are kind of loosey-goosey. We have a destination we're trying to get to, but the path that we get there with could meander all across the entire donor's lifetime and areas of interest. And so there's not a perfect way that we can prepare for that conversation. We just need to know enough to be able to take that next step, to be able to move forward and to be able to follow up with them in a way that is reflective of what we've done in our conversations with the donors and in a way that continues the momentum that we're starting to build. And when we're starting these conversations, it's small momentum we're looking for. We're looking for areas of interest, we're looking for alignment, we're looking that this is something that they'd even actually consider doing. We're not necessarily asking them on our first meeting to make a$10,000 donation or a$10 million donation to our organization. We're just looking to get some traction before we start this ball rolling. And most of our clarity actually comes after we start, not before we begin, because we're learning through interactions and we're not learning through isolation. We're not learning what we need to know to get that gift to close when we're stuck in our databases, when we are stuck researching, when we're stuck writing a proposal 10,000 times. We get it by meeting with the donors, having those relationships, putting out feelers, seeing what they give back to us, and then responding and adjusting to that movement. Because honestly, our donors, they don't expect perfection, but they do expect presence. And they want us as fundraisers to be thoughtful. They want us to be prepared enough to have this conversation with them. They aren't expecting us to know every single thing in the entire world about all of the ways that this potentially could be addressed and handled in every society, in every context that's out there in the world. But they do need us to be prepared enough to be able to have a thoughtful conversation about it. And they want us to be human in our actions. And you know, humans make mistakes. And some of the best relationships I've ever had with the donors are where I readily admitted to a mistake that I made and come back and give them the correct answer. And I think that when you're able to show up and be human, the trust deepens more than ever before. So the real shift here is that we're no longer waiting to be fully ready to show up. We are showing up ready enough to begin because that's where momentum starts. That's how we get this ball rolling, and that's how we start to get progress in the major gish pipeline. So, what would ready enough look like for you to be able to take your next step? And this is where AI kind of fits into this. It's a tool for being able to start sooner and to shorten that path to action. Because when we're staring at a database with 150,000 potential prospects, where do we begin? But if we can leverage that to help us narrow it down to the 300 who match the criteria of our ideal major gift donor, bingo, we have one and we now have a much stronger place to start than 150,000 names with no idea what to do. It helps us move from a blank prospect research report to a really good starting bio on what we need to know to be able to start those outreaches. And it helps us move from an area where we have no defined tasks in our outreach as we're starting to get to know somebody to a fully engaged strategy. And it reduces the time cost of all of that preparation because it can give us first passes that we can refine to be much stronger. It gives us summaries of huge volumes of information, and it can get us something that is in draft mode much faster than we would be able to produce that first draft for ourselves. And so many of us are much better at reacting to something than we are to creating something from scratch. So it helps you get out of that loop of, you know, there's just one more thing before I want to do before I start. Because now with AI, you have something to react to. You have something that you're able to take action on, and you're not building from scratch every single piece of the pie that you need to be able to build this donor relationship with. And the goal here is not speed for its own sake, because speed without purpose is just fast and pointless. But what we're doing here is we're creating space for more donor interaction. We're going back to that idea of putting our time where our priorities are, because we want to prioritize the work that moves the relationships forward. Being stuck behind our desks and administrative mode is not the work that makes major gifts come in the door. Because we have to make time for what's actually important, for building those connections, aligning our donors with the asks that benefit and prioritize our mission alignment, and then getting them to the point where they are not just ready for the ask, but actually anticipating it because they want to do this work and make it and make a meaningful impact. So with all of this, you know, we ought to think about what is AI's role. And the role of AI is not to replace the work that you're doing. The role of AI is that it can draft it, it can give you a starting point, but it's up to you as a human being to decide if it's ready. Because AI cannot be held accountable or responsible for the actions it takes. So we always have to make sure that whatever we're leveraging, it passes through that human filter first. So, where would having a starting point help you move sooner this week in your work? So I want you to pick one task where you tend to overprepare. And maybe this week it's your donor briefs. Maybe you spend a long time researching them and writing them and refining them and trying to make them perfect before you either. Use them yourself, or you give them to your leadership team to accompany you on a donor visit. Maybe it's that first initial outreach email. Maybe you spend hours researching your donor and trying to find a perfect place that you can say, hey, I noticed this about you. Can I talk to you about that? Maybe it's in your meeting prep. Maybe it's where you're spending a lot of time reviewing all of your notes on everything that you've ever had conversations with with this donor, and you're trying to figure out what are the next steps that I'm going to do to move them forward. Or maybe it's all the way back at the very beginning and you're still looking through your 150,000 prospect database and trying to figure out who is the next person that you're going to reach out to. So pick just one of those tasks where you tend to over-prepare. And I want you to give yourself a really short, uncomfortably short runway because we're testing this out. So what I want you to do is I want you to spend 15 minutes, that's it, just 15 minutes preparing, going through, reviewing, analyzing that. And then you're going to say, after that, I'm going to take a move. I'm going to do an action. I'm going to take a step. I'm not going to prepare for more than 15 minutes and I'm not going to spend multiple hours doing this. And then leverage AI. Of course, make sure that your organization has vetted whatever AI models you're using and platforms you're using because donor data is very important to make sure that we're keeping it safe. But use AI, and if you don't have an AI system already, use a simple structure to get a first draft quickly. Because what you're aiming here is for something that you can react to so that you aren't building from zero. And then I want you to move to action faster. Look at the email and say, is this good enough to send out? And if it is, send it. Reach out to the donor and schedule that next meeting with them. Take the next step. Choose the next prospect you're reaching out to. Because you don't have to get who the next prospect is perfect. You just need to get it in that top couple percentage points because then you're at least within the ballpark of somebody that's going to be really great to reach out to. And then I want you to measure the outcomes differently. We are abandoning this metric of was it perfect? Yes, no, pass, fail. We're abandoning that. We're letting it go. And we're going to embrace this new metric of did I do something that moved the relationship forward? How much did I move it forward? Did I move it forward by leaps and bounds and mountains? Or did we inch forward today kind of like a snail? Either one is okay as long as we're making some movement that takes that relationship to the next point. And now I want to come back to that Gala story from the opening for just a minute. Because eventually I did stop digging through all of the past documents. And not because I suddenly felt ready, I never really did, but because I realized I couldn't stay there any longer. So I put something together and I put together a sponsorship package that made sense to me and a structure I could actually work from. I started reaching out to past sponsors and past donors and table purchasers, and those conversations started happening. Commitments started coming in. Momentum started to build. And no, it wasn't perfect. There were things that didn't match how it had been done before, because remember, there was that expectation of change, nothing. And after the event, during our debrief, I was called out for nearly an hour because I didn't put chargers under the dinner plates of all the things to focus on. And while I was sitting there thinking, this is what you're gonna spend our debrief hour on, because I had just shared at the start of our debrief that we had raised more money than ever with this event. And not by a little amount, but by like 20%, more than they had ever raised before. And ultimately, you know, the part that stayed with me wasn't the silly criticism of something that didn't actually matter to the event success. It was the realization that came months earlier. And it was that the real risk wasn't that I was going to do it differently. The real risk was waiting so long to act that we missed the window. Because people made other plans. The asks never happened, and the money never came in. And I see that same moment show up in our work all the time. And it's not always in galas, but in donor outreach, in preparing for meetings, in figuring out who to talk to next, in making the ask. Because we often spend so much time trying to feel ready first when what actually moves the work forward is starting the conversation. And that's really what today's episode has been building toward. Because the question isn't just can AI help me do this work faster? It's can I move sooner without feeling like I'm guessing? That's what I've been working on inside the AI Advantage with Major Gift Fundraising. It's a way to support your thinking while keeping you at the center of the work, a way to get a starting point you can trust without having to sort through everything on your own first. So that you can take your next step and keep the relationship moving forward, so that you can spend less time trying to feel ready and more time actually moving your work forward. So if that's something that you've been needing, you can join the early access list at letstalkfundraising.com forward slash major gifts. I'll also put a link in the show notes and I'll walk you through it as it develops. And if today's conversation gave you something to think about, something to notice in your own work this week, that's enough. You don't need a complete overhaul because AI is not the strategy. Good fundraising work has always been the strategy. And you just need one place where you move a little sooner. One conversation you don't overthink, one next step you take before you feel fully ready. Because that's where the work starts to change. And more importantly, that's where your time starts to come back to you. Thank you for being here, my friend. I'll see you again next week. Bye bye.