Let's Talk Fundraising

Behind the Ask: Navigating Your First Major Gifts Role

• Keith Greer, CFRE • Season 2 • Episode 10

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The journey from behind-the-scenes prospect researcher to frontline major gift officer can feel like jumping into the deep end without a life vest. In this illuminating conversation, Matt Stokes, Leadership Giving Officer at Yale University, shares his experience making this challenging career transition and the lessons he's learned along the way.

Matt brings a unique perspective, having spent years analyzing data and identifying prospects before stepping across the table to build relationships with donors directly. He reveals how his background in research has shaped his approach to cultivation and solicitation, providing him with valuable insights that many fundraisers never develop. Most importantly, he discusses the mindset shifts required when moving from data analysis to relationship building – particularly the realization that donors genuinely want to make meaningful impacts through their philanthropy.

Professional development emerges as a crucial theme throughout our conversation. Matt credits scholarships from organizations like AFP and CASE with providing essential learning opportunities when organizational budgets might have limited his growth. He emphasizes the transformative power of mentorship, sharing how two influential leaders in the fundraising community have shaped his career trajectory through their guidance and wisdom. For those early in their fundraising careers, he offers practical advice on finding mentors and accessing professional development, even with limited resources.

Perhaps most valuable is Matt's advice on building confidence in donor conversations, particularly for those new to making solicitations. He reframes these potentially intimidating encounters as opportunities to help donors achieve their philanthropic goals – a perspective that transforms the entire relationship dynamic. His insights on handling donor criticism demonstrate emotional intelligence that fundraisers at any career stage can learn from.

Whether you're considering making the leap into major gifts, are new to frontline fundraising, or are looking to build stronger bridges between your research and development teams, this conversation offers practical wisdom from someone who has successfully navigated this critical career transition.

Connect with us to continue the conversation and subscribe for more insights on advancing your fundraising career!

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Keith Greer, CFRE:

Hey, there, hi, and welcome back ambitious fundraisers. I'm your host, keith Greer, and today we're talking about making a leap. Stepping into a major gifts role for the first time can feel like jumping into the deep end. Our guest went from analyzing data and identifying prospects to sitting across from donors, building relationships and making the ask. It's exciting, it's intimidating and for many fundraisers making this leap, it's a big adjustment. My friend, matt Stokes, knows exactly what that transition feels like.

Keith Greer, CFRE:

Matt started his career in prospect research, spending years behind the scenes helping fundraisers identify and qualify potential donors, but now he's stepping into a principal gift officer role his first time on the front lines of fundraising. Today we're talking about what that shift has been like, what's helped him find his confidence and what he's learned that can make both fundraisers and prospect researchers more effective. We're also diving into the importance of professional development, the role of mentorship and the conferences that have had the biggest impact on his career, including one he's helping to organize later this year. If you're new to Major Gifts, this episode is going to give you insight and encouragement. If you've been doing this for a while, it's a great reminder of what it's like to step into this world for the first time and how you can better support the next generation of fundraisers. So let's talk fundraising. I'm excited to welcome to the pod my friend, matt Stokes.

Keith Greer, CFRE:

Matt has over a decade of experience in philanthropy, specializing in educational nonprofit organizations. Throughout his career, he has collaborated with development teams to secure more than $25 million in funding for education and research initiatives. Currently, matt serves as Leadership Giving Officer at Yale University, where he partners with college alumni across the Mid-Atlantic and Southeast regions to generate essential support for core academics and research programs as part of Yale's ambitious $7 billion that's billion with a B campaign. A dedicated leader in the fundraising community, matt is an active member of the Association of Fundraising Professionals and the African American Development Officers. He chairs the AFP Code of Conduct Committee. He chairs the AFP Code of Conduct Committee, serves on the AADO 2025 Conference Planning Committee and was recently appointed to the AADO Board. Matt, welcome to. Let's Talk Fundraising.

Matt Stokes:

Awesome. I'm glad to be here, Keith. Thank you so much for having me.

Keith Greer, CFRE:

And we got a chance to meet just a few months ago at the AFP Leadership Institute out in Atlanta.

Matt Stokes:

What did you think of that experience? Overall, I had an amazing experience and it was great to be surrounded by thoughtful and talented fundraisers who are doing amazing work in every part of this country, including you.

Keith Greer, CFRE:

Oh well, thank you. I wasn't fishing for compliments, but I agree, everybody there was so incredible. It was nice to be surrounded by people who are leaders and to be counted among those people, because oftentimes I don't think we often think of ourselves in that role, but people like you and me and everybody else there. We were selected to be there for a reason, and so that's really exciting.

Matt Stokes:

Absolutely. I enjoyed the experience and I'm just looking forward to continuing to build relationships with everybody that I met through the Institute?

Keith Greer, CFRE:

Absolutely, and so you've spent years in prospect research, but now you're on the other side of the table as a principal gift officer. What was the biggest mindset shift that you had to make when you stepped into this role?

Matt Stokes:

Absolutely. I will say that there were a few challenges that came with transitioning from doing behind the scenes work to becoming a frontline fundraiser and I think what helped me make the transition was strategically and thoughtfully building relationships with donors, yeah, and engendering trust and empathy through listening more and talking less, and, I would say, knowing the story and not being afraid to debunk myths and challenge assumptions.

Keith Greer, CFRE:

What were some of the biggest myths and assumptions that you felt like you had to debunk?

Matt Stokes:

Absolutely so oftentimes when I meet with Yale donors they think that the university is too well funded, so that gives me an opportunity to educate and inform them about how the endowment actually works and how the money is already earmarked and how we still need support from donors to support core programs across the university, including keeping the lights on.

Keith Greer, CFRE:

Absolutely, and I think that, coming to an institution as big and as prominent as Yale, that's probably something that's a pretty common misconception out there. But one of the things that I've seen in many organizations is that professional development budgets are often reserved for more senior employees, those who are already at the top of the organization. But you, in your role, you've had some great training and support in your role. What has made the biggest difference for you and do you think more organizations should be investing in their employees stepping into these kinds of roles for the first time?

Matt Stokes:

Yes, that's a great question. I think what made the biggest difference for me was having trusted and caring mentors that I can lean on to help me navigate challenges in my career, and I would say that I've had a few people who have pushed me to achieve my short-term and long-term goals. I would say something else that has been instrumental for me is applying for scholarships through CASE and AFP to attend fundraising conferences and making the case for past employers and sponsors to cover everything else outside of registration. I feel like those opportunities really set me up for success. Not only was I able to network with others in the field, I was also able to learn best practices and put those to use to make the organization that I was working with better and to raise more money.

Keith Greer, CFRE:

I think that's a really great point about looking for scholarship opportunities, because I think so often especially people who are maybe new into fundraising they think that, oh, my organization doesn't have the budget for it, so there's no opportunity to be able to go to these conferences or to go to these learning institutes. How did you find out about these scholarships and how do you think other people can start looking for them and finding those kinds of opportunities themselves?

Matt Stokes:

Yeah, I would say that it comes back to networking, knowing people who are leaders in fundraising, who can say to you, you know, via call, text or email hey, you know, this conference is coming up and I think it'll be a great opportunity for you to learn and grow in the field. I think you should apply for the scholarship that covers registration and then we can figure out how to help you with everything else. But I want you to be in the room, how to help you with everything else, but I want you to be in the room. And sometimes I would learn about these opportunities by being subscribed to AFP newsletter so I would get the email letting me know about the scholarships. Also follow AFP and Case on LinkedIn, so when they make announcements in post, I see the opportunities pop up and would explore them and apply and get help, you know, with reviewing my scholarship materials.

Keith Greer, CFRE:

Yes, yeah, I think having your eyes open for those is really important, and having that network of people whether they're mentors or friends or advisors having kind of you in mind and letting people know about that is really important. And so when we were talking earlier, you mentioned how important mentors and advisors have been in your journey. Who are the people that helped guide you and what's the best piece of advice that they gave you?

Matt Stokes:

Oh yeah, I love this question. So two people come to mind immediately. I would say Birgit Smith-Burton, who is the founder and executive director of AADO, and Ken Miller, president of Denali FSP Fundraising and Grant Consultants. I would say that the two of them have been very instrumental in helping me grow as a fundraiser and with Birgit, she's always encouraged me to passionately pursue growth opportunities that align with my goals and values, and with Ken, he's always encouraged me to stop and smell the flowers by celebrating wins, both big and small. And there have been times where I haven't done that, and when I first started working with Ken as a mentor, that was something that he challenged me to do and I'm glad that I listened to his advice because it allows me to, because it allows me to, like sit with what I have accomplished and how I've helped others and how others have helped me, and it kind of helps me think about how I would like to move forward in doing this kind of work.

Keith Greer, CFRE:

I think that's a really beautiful idea to celebrate both the small wins and the big wins, because so often it feels kind of like we're marching along right. It's just one foot in front of the other and there's never an end to the journey, and so it never maybe feels like we're making progress along the way. But when you can take those moments to really stop and reflect on what you have accomplished, you get to see just how far you've come instead of how far you still have to go raising money for your nonprofit. So I love that advice. And for someone who's new to the field, what advice do you have for them to find a mentor?

Matt Stokes:

I would say network, network, network.

Keith Greer, CFRE:

So what should they be doing?

Matt Stokes:

Network, network, network.

Keith Greer, CFRE:

I love it, just in case you missed it the first time.

Matt Stokes:

I would say that it's genuinely good to get to know people and partner with them, to grow your career and be actively involved in advancing the fundraising community through service. I think that's an important part of it too, because I think relationships make the world go round.

Keith Greer, CFRE:

They do, and being of service is really important and it's a good way to start your networking right, and that's kind of what you're doing with conferences and professional development. So what events or workshops have been the most impactful for you? And tell us about the conference that you're helping to organize in September. What makes that really a must-attend event?

Matt Stokes:

Got it. I would say. An opportunity that comes to mind right away is AFP Lead 2022 in Houston.

Keith Greer, CFRE:

Okay.

Matt Stokes:

I had the opportunity to attend that opportunity and it was great, and one of the highlights for me was booking time with a career coach, and he helped me come up with actionable strategies that led to where I am today. So I remember having a conversation with him about pivoting from prospect research to frontline fundraising, and he was very helpful in helping me think through how I could start from where I was and get to where I am now, and I was able to put those strategies into action and they worked. Yes, so the AADO 2025 conference will be held at the Emory Conference Center in Atlanta this September the 15th through the 17th and I think that this conference is a vital gathering for advancing our fields uh and building meaningful connections among professionals. I think that it provides an essential platform for fundraisers of color to have impactful conversations about their career journeys, lift one another up and move their work forward, and I am on the conference planning committee, so we are most definitely looking for sponsorships.

Keith Greer, CFRE:

Excellent. So if anybody out there wants to sponsor the AADO, reach out to Matt. We'll make sure to put his LinkedIn information in the show notes so that you can help out with that conference. What is it that is so special? And about finding that community among people like yourselves, because I definitely feel that importance within the LGBTQ community myself. But what is it that for you? That's really about. Finding people who share that similar background that makes it such an important piece of building that community.

Matt Stokes:

Absolutely. I think a part of it is knowing that I am not alone, and I want to be surrounded by like-minded people who can support me through the good, the bad and the ugly, and I also think it's important to see yourself reflected in leadership. Personally, one of my long-term goals is to one day lead a fundraising shop at a college or university, and through AA and DO, I have met fundraisers of color who have done that, and I have the opportunity, through this vibrant network, to work with them to figure out how I can get there. So I would say that those two things come to mind when I think about why it's important to have these kinds of spaces for us.

Keith Greer, CFRE:

I really thank you for sharing that. The other part for me and I totally agree with everything that you're saying, but a big part of it for me is having somebody who has a shared background with me. They are going to see the world in a different way than anybody else does, and so the way that they're going to approach the problems and the challenges that I'm facing are going to be more aligned and attuned with who I am as a person as well, and so I think having that shared background is just so vital and so important, and so thank you for sharing that. That I wanted to ask was you talked about working with a career coach to find out how to best make the ask and to advance into your next phase of your career, from the researcher into the relationship person who's actually making the ask? And making that ask can be really intimidating, especially for someone coming from a background where they really didn't have to do that before. What's been the most important factor in helping you build confidence in these conversations?

Matt Stokes:

Yeah. Something I want to note is that my fundraising career started in college, so, like most people, I fell into fundraising. It was not something that I thought I would be doing now, and I will say that I am grateful that I had this opportunity, because I have had a fulfilling and rewarding career in fundraising. So while in college I worked for the Oberlin Annual Fund and in the evenings during the week I called parents and alumni to ask for financial aid support, and this very early experience gave me the confidence to now make bigger ask in my current role at Yale. So I think that early experience was very instrumental and, to answer your question, the most important factor is knowing that people want to make a meaningful impact through their giving.

Matt Stokes:

And I enjoy helping them figure out how they want to do that.

Keith Greer, CFRE:

I think so many people who are just stepping into fundraising for the first time, they feel like they might be begging right, like they are imposing on somebody by making the ask. But oftentimes the people who are taking those meetings with you, they know exactly what you're there for and they are wanting to help. Otherwise they wouldn't have shown up right.

Matt Stokes:

Right.

Keith Greer, CFRE:

And so, now that you've been in this role for a bit, what's the biggest lesson you've learned about building donor relationships and making solicitations? Is there anything about major gift works that has surprised you?

Matt Stokes:

Absolutely, absolutely. I would say. The biggest lesson for me is to be consistent and persistent and speak with conviction when it comes to building donor relationships. Yeah, and I would say one thing that has been surprising is that people can be very honest, very honest about how they feel toward an organization, and it's not a personal attack on the gift officer listening to their story.

Keith Greer, CFRE:

Yes.

Matt Stokes:

And I've learned that that honesty can help an organization improve its operations and better serve its key stakeholders. And that was something that was challenging for me at first and it is a challenge that I'm learning to overcome is that I'm not to take what they're sharing with me about the organization as a personal attack, because it's not a personal attack and I think that sometimes donors need to feel seen, heard and understood in order to move forward. So I can say that I've been in meetings where people were very honest, been in meetings where people were very honest and at times it was uncomfortable, but it was exactly what they needed to move forward with their giving at Yale and it helped them get back to a point where they were more responsive and open to meeting and continuing the conversation. But they just needed to feel seen, heard and understood in order to move forward.

Keith Greer, CFRE:

I love what you're saying about making sure that somebody feels seen, heard and understood in those moments where they do air their frustration. When I was young, I worked at Disney World out in Orlando, florida, and one of the things they taught us was about making relationships. Last L-A-S-T and it was when somebody came to you with a problem you would listen to what they're having to say, you would apologize for their experience, solve the issue and then thank them for bringing it to you. And if you're able to do that in a really honest and sincere way, which it sounds like you do, you're able to help transform that relationship from one of anger and frustration to one of mutual respect and support. And so beautiful job on doing that, matt.

Matt Stokes:

Thank you, and I love, I love what Disney taught you. I'm going to put that into practice.

Keith Greer, CFRE:

Last, yes, make those relationships last. And so, now that you've seen both sides of the relationship, let's talk about the relationship between prospect researchers and fundraisers. What do you wish prospect researchers understood about the work of a major gift officer that would make that collaboration easier officer.

Matt Stokes:

That would make that collaboration easier. Yes, and I want to preface this by going back to one of your earlier questions about how organizations can invest in people who are starting in this work, and, I would say, investing in nine-month frontline fundraising programs like the one that Veritas Group does for mid-level and major gift fundraisers. I went through their nine-month program in 2023, and it was one of the best programs that I have ever been a part of. I learned the ins and outs of being a successful major gift officer and I think that that program has most definitely contributed to the successes that I've seen in my current role, and one of the things that I learned through that program is that it's important for major gift officers to create a donor engagement plan for each of their prospects. So, with saying that, I wish prospect researchers understood gift officers' strategies for cultivating and soliciting donors, because I think that that information could inform their research.

Keith Greer, CFRE:

Say a little bit more about that, like how would that impact the way the prospect researcher researches?

Matt Stokes:

Yes. So prior to me going into a meeting, it's important for me to have an agenda and like talking points and to know the purpose of the meeting and what I'm going to cover and what I'm hoping to get out of the meeting. I think providing that strategy to a prospect researcher can help them, help me, prepare for my meeting and maybe find information on the prospect that I wasn't privy to. Okay so it helps like tailor their research to support the work that we're doing together to move the donor relationship forward.

Keith Greer, CFRE:

Perfect. And so then, on the flip side of that, what do you wish major gift officers understood about prospect research, and how can these two teams work better together to really drive fundraising success?

Matt Stokes:

Great question. I wish major gift officers understood that prospect research is invaluable and actionable but takes time to gather into a cohesive dossier for use.

Keith Greer, CFRE:

It's not just at your fingertips. Ready to go, Matt? No, Aw, dashing my hopes and dreams here.

Matt Stokes:

I think prospect research could work with prospect management to identify and research warm leads and feed these potential donors to major gift officers for discovery work. And I think major gift officers could keep the CRM updated as much as possible with donor data from their meetings and interactions with prospects, which gives prospects research a frame of reference for research. I do think that that is very important. A frame of reference for research. I do think that that is very important.

Matt Stokes:

Having done prospect development work at Morehouse College, which was what was very valuable for me in that role was being able to have prior meeting history on a prospect. So if I knew that the vice president of development was going to be meeting with the president of the board, what was helpful for me was to be able to go into that person's record and look at the meeting history and kind of like, follow how that relationship has been developed and use that information as a jumping off point for researching that person to learn things about them that maybe we were not aware of before. That could help the vice president of development as she prepares to walk into that meeting.

Keith Greer, CFRE:

Okay. So question here about putting information into your CRM. What kind of information are you wanting major gift officers to put in there? I'm sure adding in a telephone number or an updated address or email address is helpful, but that's probably not the context that you're necessarily looking for. It's probably more about those contact reports, right, when you're having those individual meetings and you're finding out new details and new information that you might not be able to find on the prospect research side. But it gives you a new lead to follow to try to find that information. Am I hearing you right?

Matt Stokes:

Yes, absolutely. I think what comes to mind immediately is you know, when you're meeting with a prospect and they're telling you that they have like a second home and like where is that second home and how often do they vacation there? Does the prospect have kids? Like where are their kids in their educational journey? Like are they in high school? Like what type of high school do they go to? Are they at a public high school? Are they at a private school? Are they getting ready to apply for college and what colleges are they looking at? When it comes to the donors giving, what are their philanthropic priorities? Like where else are they giving? What types of gifts are they making to those other? Organizations of details can help a prospect research team dig deeper and find more information about a prospect that could be useful to a major gift officer.

Keith Greer, CFRE:

Absolutely, and not just for the prospect research team. But chances are most of us are not going to be in this role of major gift fundraiser for this organization for the rest of this organization's life. There, not going to be in this role of major gift fundraiser for this organization for the rest of this organization's life, there's going to be somebody that comes after us and it's not only great for the prospect researcher but it's great for the person that's coming in next, Because I have certainly stepped into roles where the extent of contact reports is met with donors, discussed gift, talked about family and no further information, and it is supremely unhelpful in figuring out where things are at.

Matt Stokes:

Absolutely, and I would wholeheartedly agree. That was actually one of the things that the Veritas Group program that I did kept, emphasizing how important it is to do the data entry, to get everything into the CRM, especially when it's still fresh in your mind Because, to your point, keith, one day you will leave the role, so it's helpful for the next person coming behind you to know where to pick up with the relationship.

Keith Greer, CFRE:

Exactly, and so, coming from that research background, you've got a really strong foundation in data and analytics. How has that shaped your approach to donor cultivation and solicitation, and have you found yourself using research tools in a new way now that you're on the fundraising?

Matt Stokes:

side research background has most definitely informed the work that I do now in individual giving.

Matt Stokes:

For example, if I can figure out what a donor supports philanthropically, I can think of ways to approach this topic in an upcoming meeting and focus on how he or she might like to realize those philanthropic goals through Yale. And I would say that, like sometimes I use tools like Rocket Reach to find new contact information for donors so that I can set up an in-person or virtual meeting. At previous organizations I used Alumni Finder but I find, like Rocket Reach to be very helpful. If I've tried to contact a donor via phone or email, I'm not getting through to them. Sometimes Rocket Reach will come in handy. Or sometimes, like a basic Google search, like if I can find, if I can see in the CRM where somebody works but we don't have a record of their work email I may be able to find their work email on their employer's website and I may be able to use that email to get in contact with them to set up a meeting so that we can talk about how they would like to support the university through their time, talents and treasures.

Keith Greer, CFRE:

And so our last question that I've got for you, Matt, is for anyone stepping into their first major or principal gift role, what advice would you give them? And if you could go back in time and give yourself one piece of advice before starting this new role, what would it be?

Matt Stokes:

Yes, that is an excellent question. Thank you, keith. I honestly would tell anybody stepping into this work that collaboration is key and I'm going to say it again for the people in the back, collaboration is key. I would say take time to get to know your colleagues, leaders and campus collaborators. They are knowledgeable and can help you get the information you need to make the case.

Matt Stokes:

I can't emphasize enough how my current colleagues, leaders and campus collaborators have been instrumental in me learning about Yale, which is a large university, yale, which is a large university, and they've made you know, tackling the learning curve, that I had easier, and I would tell myself to speak up and ask for help, like there is no shame in asking for help if you need it. If you don't understand something, it's perfectly fine to raise your hand and say you know, I don't understand this. Can somebody explain it to me? I think that's a very healthy way to learn and to foster a growth mindset is to say you know, I may not know this right now, but I can learn it and one day I will have mastery of this skill. And that comes from asking for help and learning from others and, along those lines I would say, to foster relationships with more seasoned fundraisers who can help you learn the process, like they've been doing it for a while and so they can offer you tips and tricks on how to do different things to get meetings, write convincing proposals, write quick talking points, how to jot down quick notes after a meeting so that you can enter them later Because, like sometimes, a lot of us have like a bunch of meetings and so sometimes the meetings start to blend together.

Matt Stokes:

But there's different things that you can do to remember each visit or each meeting that you have in a day.

Matt Stokes:

Can you share one of those quick tips with us to like, between meetings, to take five to 10 minutes to jot down major points that came up during the visit, and then to also just jot down one to three next steps that you want to do to follow up from the meeting, and that could be to thank the person, to send them a proposal about a specific opportunity that they're interested in, or it could be that you learn that the person is expecting a baby or expecting a grandchild, so maybe there are some, there's a bib or something, a nice gift that you can send them to congratulate them on growing their family. To congratulate them on growing their family. Another colleague shared with me that, if you are open to it, you can also do voice notes on your phone and just speak into the phone for maybe three to five minutes, just capturing highlights and next steps, and then you can go back to it later. Just as long as you have it somewhere written down or in a recording, that'll help you with keeping the CRM updated.

Keith Greer, CFRE:

That is such helpful advice. I hadn't used the three to five minutes to take a quick note or to do the voice recording, but for me I just build in five to 10 minutes at the end of my meeting with somebody to just put my notes into the CRM on exactly what we talked about. But I love what you're saying about making sure that you're putting in the next steps too, because I think so often we forget about the next steps and recording those as our next set of actions. So wonderful advice, matt. Thank you so much for being here on the podcast today, for sharing your story and your transition into this new role for you. That's super exciting. Are you going to AFP Icon or AFP Lead this year?

Matt Stokes:

I am currently not signed up to attend either of those.

Keith Greer, CFRE:

Right now I am registered to attend the AADO 2025 conference in Atlanta this fall, and where can people find out more about that conference?

Matt Stokes:

Yes, they can find more information on AADO's website. That website is wwwaadoconferencecom.

Keith Greer, CFRE:

Perfect, and if somebody wants to become a sponsor, we'll again link Matt's LinkedIn in the show notes. Reach out to Matt and become a sponsor of such an amazing program that's going to support so many development officers within our community. So, matt, thank you again for being here and I'll look forward to seeing you, hopefully soon in person and, if not, definitely on our next Leadership Institute Zoom meet.

Matt Stokes:

Yes, I'm absolutely looking forward to it and I thank you again, Keith, for having me.

Keith Greer, CFRE:

My pleasure. Have a wonderful weekend. Bye-bye.

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