Stop Looking for Unicorns. Start Training Your Fundraisers.

Looking for a unicorn hire who “just gets it” on day one? We’ve all been there—and it rarely works. To celebrate fifty episodes, we pull back the curtain on what truly drives consistent donor results: intentional onboarding that blends benchmarks with belief, practice with coaching, and culture with clarity. We map four levels of onboarding—from isolation and functional quick tours to benchmarked ramp-ups and full alignment—and show how each step changes employee confidence and donor outcomes.

We share lessons from Apple and Disney that any nonprofit can adapt without a Fortune 100 budget: train before public exposure, simulate the hard moments, and coach for strengths as much as gaps. Then we tackle the common nonprofit blind spot—relying on passion while skipping structure—and offer a usable path to shift responsibility from “find the perfect person” to “build the system that shapes great people.” You’ll hear how to define 30-60-90-180 day milestones, create role-specific learning paths for major gifts and grants, and make culture explicit rather than assumed.

AI shows up as a practical ally, not a shortcut. Capture your best mentor’s wisdom, convert it into clear step-by-step playbooks, stress-test your onboarding checklists for missing pieces, and run realistic simulations: skeptical board members, donor objections, stewardship missteps. The results are faster time to competence, lower turnover, and a steadier donor experience across every touchpoint. If passion has been burning out inside your shop, this is your blueprint to protect it—documented processes, consistent coaching, and ongoing iteration that compounds over time.

If this conversation resonates, subscribe, share it with your team, and leave a quick review so more nonprofit leaders can find it. Then tell us: what’s the first process you’ll document and simulate this month?

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Chapters

• 0:00 Milestone And Format Experiment
• 5:06 The Unicorn Hiring Trap
• 6:59 Level 1: Isolation Model
• 11:23 Level 2: Functional Model
• 14:23 Level 3: Benchmark Model
• 19:20 Level 4: Alignment Model
• 24:05 Passion Needs Structure
• 27:20 Shift Responsibility To Leaders
• 30:35 Capture Wisdom With AI

Transcript

Keith Greer: 1:33

Welcome back to Let's Talk Fundraising. Today we are celebrating because this is episode 50. And 50 conversations about fundraising, AI, leadership, structure, and what it really takes to do this work well. And that feels significant, and not just because of the number itself, but because of what it represents. Consistency, experimentation, growth. And if you've been listening since the beginning, you know some of those early episodes were rough. I remember the first couple of episodes I did, I deleted all of the breaths between words, and the episode was a 30-minute run-on sentence without pauses for air. And no, you can't go back and listen to that disaster, because I re-recorded the audio and replaced it with something that actually sounds like a human. And if you've been listening for a while, thank you. Truly, you're part of that growth, and I'm so happy to have you be a part of this. And if you're newer here, I'm really glad you found your way to this conversation. If this podcast has been helpful to you, I'd love to have you subscribe so you don't miss future episodes. And if you'd like a weekly note from me with ideas, reflections, and practical tools, you can sign up at let's talkfundraising.com forward slash subscribe. Now, in the spirit of growth, I am trying something new today. For this episode, I've scripted the intro in the closing, but the middle, it's going to be guided by bullet points. I want to practice speaking a little more off the cuff, less polished, more presence. Because in a time where AI can generate perfectly structured content in seconds, I think there's something meaningful about letting ideas unfold a bit more naturally. So, after you listen, I would genuinely love your feedback. Does this feel different than previous episodes? Is it more connected? Maybe it's less clear. Or hopefully, more engaging. I'm experimenting in public here and your feedback is invaluable. So, alright, let's get into the episode and let's talk about unicorns. When we're hiring in nonprofits, we are often searching for the perfect candidate, the person who already understands fundraising or whatever their role is that they're applying for. They already know the systems. They already live and breathe our mission. They already fit our culture without needing much guidance. We want someone who walks in on day one and just gets it. Somebody who doesn't need much from us. But here's what I've learned over the years. The most successful organizations invest deeply in onboarding because they understand that the employee experience determines the customer experience. It's not enough to just have people in positions. If we want our donors to have an exceptional experience, we have to build environments where our employees can succeed. And today, I want to walk you through four levels of onboarding that I've personally experienced, from the very worst to the very best. And then we'll explore what nonprofits can learn from that and how AI can help us build better systems for the people that we hire. So let's talk fundraising. The first level that I want to talk about is the absolute minimum. It's what I call the isolation model. I just got hired into a new organization, and the onboarding experience went exactly like this. I walked into the office my very first day. They sat me down in the conference room and they handed me the employee policy manual. And it wasn't just one manual. It was, I think, four or five three-inch ring binders filled to the brim, and they wanted me to spend the next 40 hours reading through it to understand what the organization was. Whew. And that was hard because it was the exact same experience for every single position, every single department throughout the organization. Everybody got the employee manual. There was no context in how it applied to our roles. And honestly, because the organization was not a fundraising organization, most of it didn't apply to me. I didn't have any clue why I needed to know all of the information that everybody else needed to know. And they didn't have any context for why they needed to know about fundraising because they weren't fundraisers. There was no conversation from anybody in leadership or from within the organization helping me understand exactly what I needed to do to be not just successful within the organization, but successful in my role. It really felt more punitive, almost like, thanks for being here. Now here's all the rules that you have to follow. And information is not onboarding, it's the difference between getting data or integrating that data into an experience. There is no expectations for what the employee should be doing within their job. There is no goal setting, there's no benchmarking, there's no definition of what culture the organization has. I mean, there was because the organizational culture wasn't great. And that was pretty evident within my first 40 hours there. Uh, just because there was nobody there to help me understand the organization, what our purpose was, what our mission was, why the work that I did mattered to the rest of the organization, and why what everybody else did helped support everybody else too. There was no definition of success. And there was no emotional cost that they were helping to establish within me on why I wanted to be successful within this position, in this organization. So if that's your onboarding model, I want to invite you to explore ways that you can welcome your employees to your organization in a way that actually makes them glad to be there. The next level is what I'm calling the functional model. It's knowing the systems. And I've been through this at several organizations. HR sits down and they walk you through kind of the policies that HR makes sure that every employee knows. Maybe you get some specific training on how to enroll for benefits or how to request time off. Then maybe you get somebody else from another department that's going to come in and teach you how to use the CRM and they'll show you kind of how it functions and what it does. And finance comes in and they'll show you what finance does and how their systems function. Better, but it's still transactional. It's not helping understand how the organization works or what the purpose is, what the mission is. It's very in the weeds of this is what you need to know. But you're still not helping your employees know what success looks like in your organization. So let's go a step further. And this is what I'm calling the benchmark model. It's understanding what's expected of you. And this is a pretty great place to start. Having a 30-day, 60-day, 90-day, and then a 180-day expectation of where you should be in your learning curve, along with some guided outcomes and some deliverables that you as a new employee should be hitting kind of at those benchmarks. It helps establish some accountability, both for what the organization should be teaching you along the way, as well as what you as an employee should be learning about the organization. It helps provide some clarity around what you do, what the organization does, how your role fits within the entire system. But there's still some pieces that are missing. And it's the cultural reinforcement. It's helping people really understand how and why all of this works behind the scenes. So, what would happen if benchmarks were paired with belief? And that's when I compare those experiences to my time at Fortune 100 companies, like when I worked at Apple or when I worked at Walt Disney World. And this is where I start to think about this as the alignment model. Because great organizations don't assume alignment. They actually build it from your very first day. When I started at both companies, they spent an entire day going over classroom style training on the history of the company and the values that it holds, why this company exists, what my role within the organization is, before I even start working out on the floor or with people. They teach you how to handle objections. They teach you how to navigate a lot of the questions and the situations that you're going to be faced with over and over again before you're in the moment and you are practicing on the fly. Because if you get to practice before you're publicly integrating it, you are going to be better. You're going to already meet the level of the company's expectations before you have to do it in real life. They provide coaching along the way. And it's not just negative coaching, but it's positive coaching, reinforcing what you're doing really well as a brand new employee. And then in areas where you're struggling a little bit, it's not about shame or punishment. It's about guiding and gentle nudges back into alignment with what the customers expect. And what this does is it creates an incredible employee experience because that experience that our employees are having determines the experience that our customers, our donors, our program participants are having our within our own organizations. So the donor experience lives downstream of all of that. And without having a great team that's trained really well, the donor experience starts to suffer. And what this does for the employees as we bring them on into the organization is it gives them confidence. It gives them structure, it gives them guidance before they have to practice it in real life. It's about investing in our employees for a great experience before there's this expectation that they have to perform on the fly without any help or assistance or modeling at all. Because in this model, excellence is not assumed, it's trained. What would change in your organization if onboarding felt like this? And this is where I come to the nonprofit's blind spot. Oftentimes we are talking about passion. And passion without structure burns out. We often try to hire for the unicorns, the people who know everything, not just about their job, but about our organization. And they understand how to do it really well right off the bat. And that person, they're generally a myth. There's a reason why they're a unicorn employee. It's because most of the time they don't exist. Mission passion does not mean that they are prepared to be a great employee. Hiring better does not beat training better because the turnover cost is incredibly high when we aren't training our employees to do well. And we need to train the employees because when there is employee satisfaction in their job, they're going to want to stay longer. They enjoy what they're doing. They enjoy where they are. We don't need unicorns. We need systems that help us train employees to be the best that they absolutely can. And this is a responsibility shift. It's transitioning the responsibility of being great from a brand new employee who knows nothing about the organization, about the job, about the mission, about our customers, our donors, the programs that we're leading. And it shifts that responsibility back onto us. Because as leaders within organizations, it's up to us to onboard and train our employees to the best of our ability. And this is about iterative improvement because if you are handing your employees binders of employee manuals, you can iterate off of that and you can improve from here. It's not about being perfect right now, it's about getting better over time. So it doesn't matter where you're starting from in this onboarding experience because we all start somewhere. It's not a failure if you haven't known a better way before or you haven't given the experience much thought until now. What I want to invite you to start thinking about is these shifts that can make the experience of welcoming your employees into your organization even better. And this is where we start talking about how AI can support this section of our onboarding, because we're not looking for unicorns anymore. We're starting to build systems that can support creating those unicorns. Because AI can't replace a mentor, but it can preserve what your best employees know. If you're doing pretty good with your onboarding, you're likely pairing up your new employee with an employee who's been around for quite a while within your organization, hopefully one of your best employees. But if what they're sharing, if what they're training your new employees on isn't written down, that's not training. That's luck that they even get that information. Because if the mentor doesn't transition that information along, nobody knows that it wasn't transitioned. A lot of times in training, we'll just say, ask Susan. She knows how we do that. But then when Susan leaves, so does her knowledge. AI can actually help document that institutional wisdom. It can turn Susan's lived experience into repeatable guidance. So one of the things that we can do is we could document how donor meetings are prepared for. We could document objection handling scripts. We could document how you write board reports, or capture this is how we do things here. Because AI doesn't replace your best people, it helps you scale their best thinking. Because if it only lives in someone's head, it's not onboarding. It's luck that they ever get that information. Because many onboarding systems depend on who's available. Some new hires, they get a great mentor. Others get whoever has the time. And inconsistent onboarding means that we're having inconsistent performance for our employees. So how do we want to use AI? Turn your best onboarding experiences into written guidance. Find out who is the best mentor or trainer of the role that you're hiring for, and have them sit down with AI for a little bit, go into voice mode, and go through the training that they would for a real person. Then ask AI to create a step-by-step guide from that messy documentation, from that brain unload of everything that they said and turn it into something that's going to be useful and structured. So, an example prompt that you could use for this is help me turn these notes into a structured onboarding guide for a new development officer or whatever position you're hiring for. You can use AI to design role-specific learning paths. Because most onboarding is pretty generic, and maybe that's what your day one is, because it's talking about the organization and its mission. But as things progress, fundraisers need different onboarding than program staff. Major gift officers are going to need different onboarding than your grant writers. So what does this look like if we turned it over to AI to help us? You could prompt it with something like, what should a new major gift officer know in their first 30 days? And compare your current onboarding best practice lists to what AI is suggesting and identify some gaps there and start iterating back and forth to create something that's going to be truly resonating and absolutely helpful. Because AI is becoming a second set of eyes here. It's not creating something from scratch, and it's not replacing your thinking, and it's not replacing your current training, but it's helping to integrate a more full set of systems that's going to become a better ground for training your employees. Because AI can stress test your onboarding process in ways that you're not even thinking about. So paste in your current onboarding checklist into AI and ask what's missing. You can ask it, what would make this more experiential? What would make this resonate more with somebody stepping into this role? How could this better reinforce the culture of our organization? And AI is not going to understand or know what's going to reinforce your culture better right off the bat. You need to feed it all of that information. And the more information you give it, the better job it's going to do of reinforcing what your message actually is. So you've got to be a great communicator when you're talking to AI, because you're inviting critique. You are having a dialogue back and forth. You are asking for help. You're not asking it to replace your thinking. Because AI can ask you questions you didn't even think to ask yourself. Because onboarding should simulate the real work before the real stakes. And that's where I want to go back to my time with Apple and Disney. Because in all of my training with them, they didn't just tell us how to have a great customer or guest experience. They taught us how to handle objections. They taught us how to handle people who were upset or angry or disgruntled. They helped us have the right tools before we ever got in the moment that we actually needed to put them into place. And how does this apply in our onboarding of fundraisers? Maybe it means we're going to have some donor meeting simulations with artificial intelligence. Maybe it means we're going to help them have some complete management training. Maybe we're going to do some role play having difficult donor scenarios, or practice responding to pushback. Practice talking to our board members who might have some real big objections about what's happening within the organization. So you could write something like, act as a skeptical board member questioning our fundraising ROI. That's powerful and practical, and it starts to give your fundraisers the tools that they need to be able to have those meaningful conversations because practice builds confidence before exposure. The goal isn't perfection because perfection doesn't exist. The goal here is confidence. Employees stay where they feel equipped. Employees stay where they feel like they're being invested in, where they're bringing value and where they are valued themselves. Because turnover costs a whole lot more than training. If you're going to take one solid week, 40 hours to train a new employee, how much time does it take you to replace that employee? Likely months. AI reduces the time barrier between building that structure. AI helps you bring the employees up to speed much faster than without having any supporting documents at all. Because you don't need a corporate budget to create that corporate level clarity. What you need is to design an employee experience that is going to be reflective of the donor experience that you want. And AI supports that. If you don't train your people, your donors are going to feel it. You're going to have donor inconsistency. You're going to have inconsistency of your messaging, of your tone in whatever you're sending out through the organization's communication channels. You're going to have the inconsistency of stewardship. Some people are going to be thanked really beautifully and really well for their gifts. And others might be completely ignored. You're going to have an inconsistent culture. Maybe some of your fundraisers are going to feel a little bit more car salesman-y, and others are going to feel a little bit more like they're inviting people in to have a philanthropic impact. But this isn't about blame. It's about responsibility. And you don't need a unicorn. You need an onboarding system that turns great employees into your unicorns. Because hiring better doesn't fix your broken systems. Because when you have a great structure in place, a great onboarding experience for your fundraisers, that structure is able to scale throughout the rest of the organization. Because passionate people often join our organizations. But if they don't have the support to do great work, to do really well within the organization, that passion burns out. Having wonderful systems helps protect our people and it helps protect those passions. So if you've used AI this year for nothing else, what if you used it to explore building a better onboarding system? And as we wrap this up, I want to bring this back full circle because this episode is about onboarding, but it's also about growth. It's about the willingness to look at something we've been doing for years and ask, is this actually working? Because it's about recognizing that just because something is common doesn't mean it's effective. And it's about taking responsibility for the systems we build around the people we hire. Today, I experimented in public and I don't quite know exactly. How it landed. We'll see when I edit. But I changed the format of this episode. I stepped away from a fully scripted middle, and I genuinely want your feedback on it. Connect with me on LinkedIn and send me a DM with your thoughts on this episode. Because we're all growing here. And onboarding works the same way. You don't have to build a perfect system overnight. You don't have to leap from level one to level four in a single quarter. But you do have to be willing to experiment. So try something new. Add cultural context where there wasn't any in your onboarding process. Add coaching, where there was only compliance. Add clarity where there was confusion. And then ask the people who just went through your onboarding process what worked? What didn't? And what would have helped you feel even more confident stepping into this role? Because until your process is near perfect, keep iterating, keep refining, keep listening. Because onboarding isn't a document, it's actually a living system. And the same is true for how we approach learning. And conferences are onboarding experiences too. They're onboarding for new ideas, for new tools, and for new frameworks. But without a plan, the inspiration that we get from conferences fades. And that's why I'm so excited about this session that I'm going to be co-presenting with my friend Carissa Kineski at AFP Icon this year. Our session is called From Inspiration to Implementation, Turning Conference Insights into Action. And we'll be in the very first education block on Sunday morning. We're designing that session specifically for people who want to leave the conference with a plan, for first-time conference attendees who don't want to feel overwhelmed, and for the seasoned attendees who are tired of coming home inspired but unsure of how to implement what they learned. So if this conversation about onboarding resonated with you, that session will feel like a natural next step because it's about building systems that support growth, not just consuming ideas. And if this podcast has been helpful to you, I'd encourage you to subscribe so you don't miss what's coming next. And if you'd like a weekly note from me with ideas, tools, and reflections that you can apply right away, you can sign up on my website at let's talkfundraising.com forward slash subscribe. Fifty episodes in, I'm still learning, still refining, and still experimenting. And I see you doing the same thing inside your organizations. I see the pressure you're under, the expectations, the limited resources, the desire to do this work well, even when the systems around you, they're not ideal. And you don't have to be perfect to move forward. You don't need a team of unicorns to be successful. You need intention, you need structure, and you need the courage to keep improving. And I'm here to walk that path with you. So until next time, keep building systems that help your people succeed. And let's keep talking fundraising. I'll see you again next week, my friend.