Podcast: Navigating Capital Campaigns: Lessons in Leadership and Strategy with Alexandra O’Connor

Season 4, Episode 26
In this episode, Andrea Kihlstedt talks with Alexandra O’Connor about her journey in capital campaign fundraising. From learning the ropes at Community MusicWorks to leading an ambitious endowment campaign at The Gordon School, Alexandra shares insights on donor engagement, strategic planning, and balancing operations with relationship-building.
Tune in to hear Alexandra’s journey and discover practical tips to elevate your own fundraising efforts!
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Andrea Kihlstedt:
You want to hear some stories from the field? Well, today I’ve got a juicy one for you. I am here today with my friend and colleague, Alexandra O’Connor, who is going to tell us about how she cut her teeth with capital campaign fundraising.
I’m Andrea Kihlstedt, as you know. My friend and colleague and partner, Amy Eisenstein, isn’t with me today, but of course she will be back. And now let me just introduce Alexandra.
Alexandra, hi.
Alexandra O’Connor:
Hi, Andrea. It’s so great to be with you today. Thank you so much for having me.
Andrea Kihlstedt:
I know. I don’t get to work with you anymore, but working with you for some period of time was really such a pleasure. Alexandra was the director of philanthropic engagement at Community MusicWorks, which is a community-based music organization in Providence, Rhode Island.
I have spoken about that campaign several times on this podcast, and she really was some of the power behind that campaign up until a certain time when she moved to another organization in Providence, The Gordon School, where she now is. And she jumped from one frying pan, namely a capital campaign in Community MusicWorks into another frying pan, namely a capital campaign at The Gordon School.
A Unique Capital Campaign Journey
So you’ve cut your teeth. You’re now a pro in this business, Alexandra. Welcome, and how do you think about your work and this trajectory of yours?
Alexandra O’Connor:
That’s a great question. It’s funny, when I first saw the job description for Community MusicWorks, I was initially so intrigued. And when I saw the list of folks that I’d be working with and their background, you can’t help but want to work for this organization when you see leaders like Sebastian Ruth and Kelly Reed and Liz Cox.
And they’re just amazing people in the community and the inspiring work behind the mission that I knew I just wanted to raise resources for them. And hearing more about the campaign was really exciting, but I hadn’t had direct capital campaign fundraising experience, so that was a new thing that I was going to be learning.
And as someone who is a lifelong learner and really enjoys the fundraising space, I was ready for my next challenge. And also being able to partner with you, Andrea, and Sebastian, I say this all the time, and I mean with my whole heart, it just was by far the strongest learning experience I’ve had in a professional setting. You two were such visionaries and such thoughtful partners, and while it can be intimidating to go into a capital campaign without knowing a lot about it, we learned as we went together.
Wandering Through the Weeds
And I think that was also a great piece of advice that I got from you is that sometimes you wander through the weeds, and when you do, you often get some of the solutions that you were looking for. So we did a lot of wandering and we got a lot of really great results.
Andrea Kihlstedt:
We did do a lot of wandering, and partly because I just like to wander. I believe in the power of thinking in a way that is not always one step in front of the other. I believe in the power of a little bit of creative wandering, as you say.
But let me go back to the beginning, which is that Community MusicWorks had never done a campaign. It was an organization about 20 years old and decided that it needed a building. So it set about planning for a building. Originally, they thought they might be able to raise between $6 and $8 million. I started working with them with Capital Campaign Pro, and they brought Alexandra on to support all of their fundraising, but also to work with the capital campaign.
Dividing Up the Work of a Capital Campaign
But a lot of that work, and in fact the bulk of the energy and the work for that campaign came from their founder and executive director, Sebastian Ruth, who as Alexandra has said was really just a remarkable human being. He’s just low-key, and so smart and so capable, and together I and Alexandra and Sebastian formed a great team.
Alexandra O’Connor:
It’s so true.
Andrea Kihlstedt:
How did we divide up the work? What do you remember from that?
Alexandra O’Connor:
I remember us talking about the way that we functioned as a team, and oftentimes we would just revel in the fact that we were just so happy that we brought different skill sets that came together in such a beautiful way. So we’d call ourselves this stool, and we each had a leg.
And I would put it in terms of a team of you’ve got Sebastian, who’s the visionary, whose thoughtfulness and unbelievable wisdom, and then also connections with folks was just beyond comparable to what other folks could do. The way that he could light up a room and authentically connect with people in ways that were so meaningful to you and just deeply listen to you knowing that he’s carrying a million and one details but takes the time to spend with each person and just everything he leads or touches is just incredibly thoughtful, so you have him there as this visionary.
And then we have Andrea, who’s been doing capital campaigns for decades and is brilliant in this space and just provided so much wisdom and guidance and ease to us as we just came across different hard questions as we went through this campaign. And things that I remember early on where it seemed like a very simple thing, like it matters what number you asked somebody for. And the number, if it slightly changes, that makes a really big difference. And just having these conversations with Andrea and really going in on those questions that I remember being young and early in my career not really understanding the power that holds.
And then I came in new and eager to learn. And one of my strengths, in addition to relationship building, is really behind operations and data and analytics and seeing that bigger picture and being able to put it in a way that our board was able to digest and understand.
So as you mentioned, we were moving forward with the goal of 8 million, but that quickly changed to 10 and then increased to 11. And one of the charges I enjoyed the most was being able to put together a presentation for our board each time of showing them, with confidence, this is our path to getting to our goal and here’s where it is and showing them in a really thoughtful way of how we could do that with the data that was behind it. So between the three of us, I feel like we just made a really strong team.
Andrea Kihlstedt:
Alexandra, I learned so much from watching you put those reports together because you could see, you put them together for the campaign steering committee and the campaign planning committee and the board. And in your reports you could say:
“Here is the path to our goal. And if we don’t do it this way, if this gift doesn’t come in, here is another way we could do it, and here is the likelihood of our reaching our goals if this happens or if this doesn’t happen.”
And I could see as you presented these really well constructed reports, they were spreadsheets using pivot tables and fancy things, that I could see the people’s confidence rise. That it wasn’t just me or Sebastian saying:
“Of course, we could do this.”
But Alexandra had the ability to actually show real numbers and real assessments of donor possibilities that would lead to that goal and lead to that number. And it made for a wonderful, encouraging, confident sense among all of the volunteers on that campaign. That was really, really remarkable what you did.
Alexandra O’Connor:
Well, thank you. I love that work, and I also just enjoy to have something tangible and to have a guidepost for my work. So while it was so helpful for the board and for steering committees and planning committees as we did those presentations, it also was just the tool that I used every single day to guide my work because it would also show me where our successes were and also where our gaps were so I could easily see, in order for us to get up to our path, we had a handful of donors that we were cultivating say at 500,000, but I needed to move them to the next space, or I didn’t have enough people in my pipeline at a million or 250,000, and just seeing where we could fill certain holes and what steps we needed to take next.
Strategically Addressing Holes in a Capital Campaign
Andrea Kihlstedt:
There’s nothing like seeing where the possibilities are and where the holes are to get you to start thinking strategically about how to address that. And in many campaigns, I don’t see that. In many campaigns, it’s hard for people to do that. They don’t have someone like you who is able to do that kind of systematic analysis and go with that level of details where things were tied to the donor base and you would be able to say:
“Well, we have five real prospects for this gift. If it doesn’t come through, this is what’s going to happen. And if three of them come through, then this is what’s going to happen.”
And that was really, really remarkable. It made Sebastian feel confident. It made board members feel confident and all of the people on the various planning committees feel confident. And in the end, this capital campaign business is, sometimes I call it a confidence game. I don’t mean that in a negative way, but it is about confidence.
Alexandra O’Connor:
Yeah, a thousand percent. Because no matter how many times people have done this and no matter how seasoned a fundraising professional you are, going into a capital campaign will always jolt your nerves. You’re about to do something really exciting and ambitious for your organization that you deeply believe in and that you know this organization needs, and you’re about to make some big asks of people.
So it’s a big moment for the organization, and so you want to feel that confidence because you’re about to embark on a new chapter.
Andrea Kihlstedt:
One of the things that happened with Community MusicWorks, and I think many organizations faced this, is that as they embarked on their campaign, they were also working on the architectural plans and the construction plans and the costing of the project, and this was shortly after COVID and prices were going up like mad. So it seemed that every time we turned around the project, the building was going to cost more.
The Goal Skyrockets to Cover Increasing Costs
So here we were on one side busily asking people for gifts. While on the other side, the goal that we had started with, $8 million, was no longer going to cover the costs. The construction costs went to 8 million and to 9 million, and it became this unnerving spiral. And the question was always, well, can we raise the goal? And we relied so much on your ability to look at the possibilities in the donor pool to say:
“Well, is this just a dream, a fantasy or do we have the prospects that might enable this to happen?”
Alexandra O’Connor:
And I will say I also feel like with that, I learned so much from my very… My first fundraising experience was working for City Year. And so working for a nonprofit who at the time had a budget of $160 million and seeing what they had to implement in terms of their operations to ensure everything was cohesive and sound when you’re working with dozens of sites across the United States and then international sites as well and you’re one 501(c)(3).
It was really a great learning experience to take what they had and know that even though they’re a huge operation, I can take their strategies and their practices and apply it to a smaller nonprofit, and I can apply it to this capital campaign. And I’ve done that now to at my work at Gordon School. It’s just really great strategies and just scaling it to the size of your organization.
Andrea Kihlstedt:
And what are the strategies that you brought with you from your original jobs?
Alexandra O’Connor:
From City Year.
Andrea Kihlstedt:
City Year.
The Importance of Your Donor Database
Alexandra O’Connor:
Yeah, I think for them, so we worked using our database. And for me, one of my rules is that everything needs to go in the database. You need a centralized location for all of your data, and data out is only as good as data in. And so being really thoughtful about every time that I would have a meeting or do a mailing or have a phone call, it was a practice that I would implement where I would make sure to take notes and record it. And knowing that when you’re in a smaller shop, it might not be perfect, and that’s sometimes something that I have to let go of is someone who oftentimes likes to operate in perfection or perfectionism, but just making sure that you have the note that you’ve done something because then you can track things so much better of what was being done.
And so a lot of times, both with Community MusicWorks and with Gordon, it’s been smaller shops in terms of development. Oftentimes it will be just me or one other colleague utilizing our database, so I had to make sure that I really kept those practices strong for myself and abided to them. Then now as our office is growing with our capital campaign at Gordon, just training my team on that as well.
Then I think too with operations, again just similar to relationship management, there’s always more that you could do. So when you’re assessing your pipeline, you could always be going through it and assessing is that the right ask amount, are they rated the right priority, things like that and going through, and you can always adjust those numbers.
So I think having enough checks and balances with yourself where you’re going through and making sure that you’re rating those different things that you have in your database to make sure that it’s still the right numbers.
And then, also finding that really strong balance of not spending too much time on the operation side that you’re not out doing the relationship work, so it’s really important to find that balance.
Capital Campaign Pro: Helping Multiple Campaigns
Andrea Kihlstedt:
Alexandra, at some point at Community MusicWorks I think we had raised about $11 million, something like that, and you decided that you would finally accept an offer from The Gordon School. They had been after you for the longest time. They knew they wanted you to come and work for their development shop, and they finally got you.
So Sebastian and I cried in our tea for a little bit about that, but off you went and you lost me — but you decided to continue on with Capital Campaign Pro and you got one of our other advisors. What was that like?
Alexandra O’Connor:
I did. It’s amazing. And of course, losing Andrea when you’re doing a capital campaign sometimes feels like you’re losing your arm because she was just such a tremendous resource to us. But seeing Capital Campaign Pro grow in the time that we were together and just the incredible quality of the consultants that come through this organization is unbelievable, I knew that I would be in great hands.
And then of course, meeting Paula within the first half hour of our meeting, you just know that she’s going to be this tremendous steady resource who’s so seasoned. And I can’t tell you the number of times that Paula and I are just speaking and I have this, oh yeah, moment of she just says it so beautifully and so, she’s just done this for so many years that there are things where sometimes being newer in your career you might second-guess yourself or you might wonder or you might pause even on I’m not sure if I want to reach out to that donor because I’m either worried about what the response might be.
I don’t quite know the strategy. And Capital Campaign Pro, and specifically the consultants that I’ve worked with, with Andrea and Paula, just take so much ease to it and just offer this piece of advice that it feels so simple, but they’re just such seasoned professionals that they’ve seen this a million times over and can offer you that ease and keep pushing you forward in this work.
Andrea Kihlstedt:
Alexandra, that was one of the principles on which we found in Capital Campaign Pro. That we would bring on people as campaign advisors who had had long careers in this field and who were at the end of their careers. They weren’t building their own businesses anymore. They had had their own businesses. They had had 20, 30, 40 years of experiences in the capital campaign world. They didn’t want to stop altogether. They wanted to keep being useful and doing the work, but they wanted to change gears.
One Way Capital Campaign Pro is Different
And at Capital Campaign Pro, we set it up so that those people could have a sense of collegial identity, so that advisors would come together periodically and so that everybody we brought on had a real, we had real deep expertise in the field, that we set that up as a guiding principle early in this business.
And it’s worked. I’ve been really tickled with that, actually.
Alexandra O’Connor:
It a thousand percent works, and it shines. It absolutely shines through. The number of a-ha moments that I have during this experience is it comes through all the time. And the other thing I’ll share too is both Community MusicWorks and Gordon, again, we’re smaller teams.
And so when we set out our budgets for our campaign, you obviously when you’re working with consultants want to ensure that you’re really getting the return on your investment, and Capital Campaign Pro brings that tenfold. And this is now my second experience doing that.
And I know that because I can see the results and because just of the amazing advice that I’ve gotten and the things that I’ve learned as I’m still navigating this space.
Going from One Capital Campaign to Another
Andrea Kihlstedt:
Well, let’s talk a little about your work at The Gordon School because I hear from Paula around the corner is what’s going on, and I know that you have solicited some of your first really big gifts for the school successfully. So what’s that been like for you?
Alexandra O’Connor:
It’s been really exciting. In order for me to do my work well as a development professional, I have to believe in the work that I’m doing and believe in the place that I’m fundraising for. And I’ve always been mission-driven, and I’ve worked for some incredible nonprofits. And leaving Community MusicWorks was a very hard decision, but coming to Gordon was also very easy.
This is an incredible school that I believe in fully. It’s a nursery to eighth grade school here in East Providence with a deep commitment to diversity, equity, and inclusion and belonging and is just doing things differently. And I can see the potential that Gordon has, especially in regards to raising resources that we need for the school, and that’s what excited me to come into this space and really bring it to the next level.
The Feasibility Study: Half Endowment, Half Facilities
And so for us, we were beginning to embark on a feasibility study. And the thing that Gordon really needs most is ensuring that we’re here for generations to come, and so financial stability is a huge piece of that. And going into an endowment campaign is really the space that we are exploring in our quiet phase.
And before we started our feasibility study, most folks had shared that, our professionals in the space, that an endowment campaign for a nursery to eighth grade school would be a harder sell. And we knew that, but we also knew the school’s greatest needs, and so we tested our capital campaign to be half endowment and half facilities, and we had a very successful feasibility study.
And what was amazing to me is what came out of that is that endowment was the clear ringer. And that’s not to say that there weren’t some folks that had some ideas of different facilities improvements, but it was amazing to me that when you do a feasibility study what you could be surprised by, and it also just really doubled down on how effective feasibility studies are and how essential they are to do before you embark in a capital campaign. So that was incredibly helpful.
And what I love about endowment campaigns is just the legacy that they leave. Before, endowments are new to me too. I mean, before I was doing this work, I hadn’t spent a lot of time working with endowments. And to be honest, what I had heard of them before, to me, just being very new in my career, I didn’t understand as much the purpose when I thought, well, there’s a direct need, why wouldn’t you raise for that? And learning more about what Gordon’s current endowment supports and it was when I started here two and a half years ago, it was at $11 million and already with resources that we’ve raised and then how it’s been invested, it’s up to 14 and a half million. Seeing the longevity of endowments, just the fact that they’re there in perpetuity, and so whatever you support will just be there forever.
And I see these essential programs that we have at Gordon School, whether it’s our Britt Nelson Visiting Artist program or our Karla Harry Visiting Author program or our civil rights trip in eighth grade, which is our capstone trip that year for our middle school students, it’s just amazing to me to know these are programs that are essential to our school, but that will also live on for decades to come.
And so that’s the power in endowment, and I’m so grateful for the board members and the leaders and the people of Gordon’s community that had that foresight back 30 plus years ago to start an endowment for Gordon because that’s what we’re building on. And that’s why I believe in this work, and that’s what I want to leave as my legacy at Gordon so that when there are students sitting at these desks or when there’s leaders out in the community that graduated from Gordon School, they’ll be grateful that the school had the resources it needed because we had been strategic and thought about growing our endowment at this point in time.
Andrea Kihlstedt:
Alexandra, it sounds as though your passion, not only for the school but for the endowment, is what has fueled your conversations with donors. I know you’re actually talking to a lot of donors.
Alexandra O’Connor:
Yes, absolutely. And again, I have to believe in a place in order to raise money for it. And another beautiful tie with Gordon is that two of my three children are here. I would love for all three, but my current is not even a year yet so he is not of age to be at Gordon, but I also see it in my children. I get to watch our educators just so beautifully navigate this space with them, and I have partners in raising my children, and I couldn’t imagine a better place to do it, so seeing it through that lens.
And then I also just truly enjoy connecting with people in this community and hearing about their own Gordon story and why it means so much to them and what they learned from their experience and really how coming to this school has changed their life and has made them stronger leaders, more compassionate learners, and just people out in society that are making a difference and asking the right questions. So I love that space.
And then again, I have really become a huge endowment fan. I mean, I love endowments. I think they’re crucial for an organization. And seeing just the power in endowments has been really eye-opening and it’s been a special thing to see, and I want to secure more resources for Gordon in that space.
Cautionary Words About an Endowment Campaign
Andrea Kihlstedt:
I would be remiss if I didn’t take your enthusiasm for endowment at Gordon and tell people that while there are some institutions that really are set up for that, for many institutions that don’t have these long relationships that have existed, these long, familiar relationships, raising money through a capital campaign for endowment really is a tough slog.
So I don’t want you to listen to Alexandra and decide that your institution should by all means raise money for endowment. It has to be the right institution in order to make that work. And it’s exciting when it happens, and it tells me so much about the culture of the organization. That the organization has deep relationships, deep multi-generational relationships with families who have been engaged with this school, and that’s what sets her up for doing so well with an endowment campaign, but not every institution is well set up to do that.
So like Community MusicWorks, going back to that, they’ve raised a little bit of money for their endowment through the campaign. But for them to say, “Well, we’re going to have a big endowment campaign,” it would’ve been a fool’s errand. It was appropriate for them to raise money for a building. They haven’t been around long enough. They’re not well-enough established to have a big endowment campaign. So I don’t want to lead anyone astray as we think about this.
When it’s right for the institution, it is a powerful motivator, but for many institutions it is not yet right, so let’s be careful with that.
The Intimidation Factor When Working With Donors
Alexandra, before we end, I just want to find out now when you are at Gordon School and you’re really doing much more work with donors than you did at Community MusicWorks, has that been intimidating?
Alexandra O’Connor:
Of course, it could always be intimidating as you start to go more into that space, but I think that’s also the other piece that I love. While I love the operation side, I also just love getting to know people. And especially when you have this tie of loving a place and a community so much, it’s been really inspiring for me to get to know what Gordon means to other folks, to other families, to alumni, to former faculty, to current faculty, and so I love building those relationships.
It is, as you go more into the frontline fundraising, there’s always those moments where you could have a pit in your stomach of am I going to be making the ask or doing, having the right strategy as we go in? And again, I just can’t express enough how helpful it is to have the anchor of Capital Campaign Pro, and having that guidance is so helpful. And I enjoy every week we have. Now I’m guided by my list of who we should talk about and what the strategy should be and what’s going to potentially motivate their gift, and I really enjoy that space.
Andrea Kihlstedt:
That’s fantastic.
3 Lessons Learned Through Capital Campaign Fundraising
All right, let us get down to the weeds here. Alexandra, I wonder if you can think back over your capital campaign career, which is now about seven years old, I think that’s what we calculated. If you were to think about three lessons that you would like to tell other people for as they think about capital campaigns, what would those lessons be?
Alexandra O’Connor:
It’s a great question. I know I touched on this earlier, but I think a really good lesson is not relying too heavily on operations and making sure that you’re doing the relationship work behind it. So it’s important to find that balance. Operations is hugely successful in terms of efficiencies and providing that guiding star. And you just want to make sure that you’re not… I think of Andrea’s voice all the time saying:
“Don’t be sitting behind your desk all the time. You have to be out in front of people and building those relationships and making those phone calls and sitting down with folks.”
That one’s really helpful. That would be my first one.
My second one is really shooting for the stars, and so making sure that you, when you’re talking with folks, that you share what your dreams are and your biggest aspiration is because you have the ability to bring it back if you need to. But being open and transparent about what you really want to do for your organization and getting people on board I think it’s a stronger way to bring in buy-in, and then if needed, you can scale it back.
Then I would say the last thing, which is helpful, is that when working with folks, people, we’re all pretty consistent and we’re all pretty predictable. This is one that I learned from Andrea and I loved it because it stayed true through Community MusicWorks and through Gordon. And I think the important thing, and Andrea would always share with me, she’s like you have to find the patterns with folks, and it takes a lot of strategy to do that. But I love figuring out what is inspiring to folks and what’s really going to drive them, and you can do that by just really understanding their consistent patterns.
Andrea Kihlstedt:
There’s something incredibly reassuring about knowing that people are relatively consistent, right?
Alexandra O’Connor:
Yes.
Andrea Kihlstedt:
It’s like, oh, of course.
Alexandra O’Connor:
You just —
Andrea Kihlstedt:
Pay close enough attention and you see one set of behavior and you watch and if you see it repeat again, you can be pretty sure it’s going to repeat again, and you can start developing your plans based on that. I always loved that. I find it to be true not only in capital campaigns, but in life. It’s a powerful lesson to learn and to apply to all kinds of things.
Final Thoughts
So Alexandra, my friend, what a pleasure to actually see you, and as we sit here on a Zoom together to be reminded of your wonderful abilities and charm. This coming Saturday is the grand opening of the Community MusicWorks building in Providence, Rhode Island.
I am going up to that celebration and Alexandra will be there, so I’ll actually get a chance to give her a big hug and to enjoy being together in person for a little bit while we celebrate the real conclusion of the Community MusicWorks campaign, which by the way, ended up raising a whopping $15 million.
Alexandra O’Connor:
Amazing. That’s amazing.
Andrea Kihlstedt:
Amazing. Thank you, Alexandra. I look forward to seeing you on Saturday.
Alexandra O’Connor:
Can’t wait to give you a big hug. Thank you so much.
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