Podcast: Unsticking Your Campaign: Proven Strategies for Overcoming Fundraising Challenges

Season 4, Episode 7

In this episode, Amy Eisenstein and Sarah Plimpton tackle a common issue in the world of fundraising—campaigns getting “stuck.” Every fundraising campaign experiences ebbs and flows, but the key to success is knowing how to navigate the valleys. Amy and Sarah share actionable strategies to help you get your campaign back on track.

Learn how to turn a stalled campaign into a momentum-building success, all while maintaining strong donor relationships and inspiring your community to achieve your fundraising goals.

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Amy Eisenstein:
If you are worried about your campaign getting stuck, you are in good company, and I’m super excited to share so many strategies today about getting your campaign unstuck.

Hi, I’m Amy Eisenstein. I’m here today, not with Andrea Kihlstedt, but with our other colleague, Sarah Plimpton, who is our director of client happiness. And I am so excited that Sarah is joining me for such an important discussion today on how to get your campaign unstuck or unstalled.

Getting Your Campaign Unstuck and Unstalled

So Sarah, you have tons and tons of experience, unfortunately… Well, I shouldn’t say that. I was going to say with stalled campaigns, but I don’t mean that. Campaigns ebb and flow and every campaign goes through sort of a period of time where things slow down, honestly.

So instead of talking about stuck or stalled, I mean, I don’t want to say that because so many of these campaigns go on to have amazing finishes and go over goal, but there are ebbs and flows. So let’s talk about getting unstuck.

Sarah Plimpton:
Yeah. Hi Amy, and thank you for having me. It’s a pleasure to be with you today. So I think you’ve started off this conversation in exactly the right place, which is to note that every campaign has hills and valleys and the valleys are to be expected in a sense. So that, if and when you find yourself in that valley, rather than freaking out that you are there, reframe it and say:

“Okay, these valleys happen in a campaign, and here we are. And there are always things I can do or we can do as a team to sort of climb back up the hill and get a big win.”

So I think one of the first things to note for our listeners is just sort of the mindset around a valley or being stuck or in a rut, that it’s normal.

Amy Eisenstein:
It is normal. I’m so glad you said that. And I have to say, I’m so thrilled we’re talking about this today and it came about because we have a client who was feeling a little stuck and you had a conversation with her and wrote this brilliant email where you outlined, I don’t know, almost a dozen strategies for her to consider and try and follow. And I just thought, oh my gosh, this has to be something that we share with our podcast listeners because there’s so many good strategies, there are so many things to do when you’re feeling stuck or frustrated.

So we’re going to talk about a few of them today, not every single one that you shared with our client. But let’s talk about some of the ones that we love the most.

Strategy #1: The Low-Hanging Fruit

All right, so what’s your number one recommendation for a development director or an executive director who’s sort of feeling in the doldrums of the campaign?

Sarah Plimpton:
So the first thing that I always think about is sort of the low-hanging fruit, if you will. We know that current donors or past donors at any moment in an organization’s life cycle are the best prospects. So if somebody’s already given to you, they’re more likely to give again.

So this may not come as a huge surprise to people, but I would always keep an eye on and look at donors to your campaign who’ve given one time, so who aren’t pledged out and donors to your campaign who maybe did pledge over a couple of years or three or four years and either paid that pledge off early or their schedule has come and gone and they’re done paying it on the schedule that they anticipated.

Amy Eisenstein:
Yes. So people who finished paying their gifts, whether they pledged or gave a one-time gift.

Sarah Plimpton:
And I think that sometimes people are a little bit anxious about going back to people for a second gift. And I think that you can do this a couple different ways, but one of the ways that I advise clients a lot on is to ask about the conversation. Which is to say, don’t necessarily barrel right into a donor who’s already given and say, hey, would you give again? Would you give another $25,000? But rather set it up by saying:

“We are at X point in our campaign, we’re really looking to close the gap and get to the public announcement or to the goal if you’re in the public phase, and I’m curious about whether at some point in the coming weeks or months you might be willing to have a conversation about a second gift to the campaign?”

Because what you’re doing is you’re asking about asking, you’re not asking. But there’s a little bit of a space there where the donor can give you some feedback and you can protect yourself a little bit if it is too aggressive for the donor. But my experience would suggest that many, many donors are very open to that.

Amy Eisenstein:
Yeah, I mean if you think about it, you use this term low-hanging fruit, which I love to hate. Always makes me laugh thinking about donors as fruit. But think about them as the people that are closest to you, the people that already are supportive and excited, they’re the number one people who want to see this project happen. They’ve already invested in it. So they don’t want you to come up short. They want to see you get to goal. And so they are the likeliest people to give and get out of the mindset of donor fatigue. Don’t worry about it. If there’s an important cause, an important project, and they have the capacity or the power to help you get to the end line, they want to do it.

And so going back to them, I think, and saying, look, we are here. We’re at 60%, we’re at 70%, we’re at 80% wherever you are, and we’re turning back to our biggest advocates and supporters, and you’re one of them. So we’re here to ask if you would want to consider, think about making a second gift. I love the way you’ve said that. All right, excellent-

Sarah Plimpton:
Wait. Can I just say one more thing about that, Amy?

Amy Eisenstein:
Yes.

Sarah Plimpton:
I want to just point out for our listeners, I think it’s much easier for people to say yes to that kind of an ask when they see themselves as one of many. And what you just did in your language there was brilliant in that you framed it by saying, at this point in the campaign, we are going back to several of our earliest friends and supporters to explore the opportunity or possibility of a second gift. Could you see yourself being one of those conversations or one of those people? So that the donor doesn’t feel like:

“Oh my gosh, they’re coming just to me, it’s all on my shoulders. But oh, they’re doing this with all the people who are like me who joined early in this campaign.”

I think that’s a really important little nuance to the way that you phrase it and frame it with donors.

Amy Eisenstein:
Love it. Great.

Strategy #2: Project Plans to Generate Enthusiasm

All right. So what’s another strategy?

Sarah Plimpton:
All right. So I think it’s not uncommon for project plans to be sort of unfolding and maybe construction begins. There’s a groundbreaking early in the campaign effort or midway through the campaign effort, and then that’s unfolding on a parallel track as your campaign. So I think that sometimes organizations think of those two things as to while the campaign is funding the project, the ongoing project development is actually a great cultivation opportunity.

And so the things like hard hat tours, beam signing ceremonies, having meetings, if it’s safe to do so, definitely talk to your construction manager about this, but having meetings around exciting things that are happening in the construction project, maybe having a meeting in this space or I don’t know. Using that project to gin up excitement and momentum with your volunteers who might be feeling fatigued or your donors who might still need more information about the project.

Amy Eisenstein:
Yeah, I think that’s a great idea. And not everybody’s doing construction, so I just want to throw out an idea for organizations that have either the construction hasn’t started or they’re not doing construction, and that is give an update on the project. I mean, you can talk about the project, whether you’re actually able to do a hardhat tour or a beam signing, as you suggested, you can always go and say, here’s where we are in the project planning. This is what’s happening. Because often you’re not going to be stuck, I hope, in the first 6 to 12 months of your campaign, you’re going to be stuck 18, 24 months, in year three.

And so your project plans, whether they’re construction or not, have come a long way in your thinking. You may not have spoken to that person. I mean, I hope this isn’t literally true, but about the project specifically in more than a year or in 18 months. So no matter what phase or stage or project plans are in, you can go give an update and have a conversation about it for sure. I love that as a cultivation strategy.

Anything else you want to add about that specific one? So with beam signings and hardhat chores, it’s obvious excitement, but is there anything that you’re specifically talking about? You’re giving an update, are you asking anything of donors at that point?

Sarah Plimpton:
Well, I think in the conversation that I had with the client of ours who you referenced a little bit ago, we were talking about the way that inviting someone in for a hardhat tour as a precursor to the, hey, could we have a conversation about another gift at some point to this campaign, is a nice pairing. Because you engaged them in a substance of what it is you’re doing and why you’re doing it, and helped them feel part of it and connected to it.

And then you’ve had a conversation about, hey, could we have another conversation? You should be doing that stewardship anyway and cultivation anyway. But to think about it as a way to jigger things with people, to shake up the dynamic, to have a different reference point, to have a different catalyst in your conversation with them to pivot to a new place. Those kinds of stewardship, mid-campaign stewardship opportunities can often shake loose new opportunities for you.

Amy Eisenstein:
Yeah, I love it because as the project develops in progresses in thinking development, whatever it is, it gets more exciting, it gets more real. And so you can share those updates and speak about that. I love it.

Strategy #3: Ask for Advice

All right, so the next strategy you mentioned is talking about or asking for advice, I should say, sort of similar to sharing a project update, but very different. So what kind of advice in the middle of the campaign or in a sloggy part of the campaign might one think about asking donors or talking to potential donors about?

Sarah Plimpton:
Yeah, so I would think about the notion of asking for advice in a couple different ways. First of all, let me step back and say that asking for advice is one of my favorite things to do or tools in a campaign in multiple situations. I just think it is one of the most brilliant things that you as a fundraiser can do.

So when I think about asking for advice in the moment of a stalled campaign, or you’re in a valley and you need to figure out how to get out on the valley, let’s talk about who you might ask. So you might look at your donor list and think about, all right, if we need to close the gap from where we are to the next million, say, keep the numbers easy. If you look at your donor list and think, all right, who on this list is really connected and might have introductions that they could make on our behalf or might have good ideas for us or might even have more philanthropic support they might throw our way if they got a little bit differently connected or engaged here.

So I would look at your current donors. I would look at your prospect list. Go to some of your prospects and say, hey, we’re in this campaign. I would love your thought. Can I just pull the curtain back? No. Just to be clear, I’m not suggesting you share all kinds of confidential information. I’m absolutely not. But just to say this is where we are. This is how we’ve gotten here. These are the strategies we’ve employed. This is the gap. This is our gift range chart. Here’s our case for support. What do you think? Does this resonate? Are there things that we could be doing differently? Are there people not on our donor list that should be, that you can help us strategize about or open doors to? Would you ever consider joining a committee? There are all kinds of things you can ask people about midway through to just generate new ideas and open new doors and connect people or see connections between people differently, which will affect your strategy.

Amy Eisenstein:
Yes, I love that. So I think you’re right to point out that so often… Well, you said you love asking people for advice, and what went through my head is that so many nonprofit staff and volunteers are almost afraid to go to people for advice. But it is the best strategy. It is the best way to engage people and asking them what gets them excited, what philanthropy is in their wheelhouse or realm or friend base or what their friends talk about and are excited about. There’s so many things that you could ask a donor or a potential donor to get them involved and engaged and just to learn more about them. And you know what? You may learn that they’re not interested in your project, and that’s okay. That’s important information too. So don’t be afraid to talk to people.

Sarah Plimpton:
And it might even be a conversation as simple as, hey, person X, we’re in this campaign. I wonder if you might be willing to sit with me and look at a list of names, no other information, just a list of names, and tell me who you know, what you know, who you think might be interested in this project, why they might be interested, and just help me paint a picture of people that we have not yet been able to get to. I’ll just anecdotally say that, Amy, I have worked on a lot of campaigns over the course of my career and without fail, every single one of those campaigns, there were sort of at least three or four prospects, probably more, who am I kidding? Handful of prospects who were sort of enigmas for the whole campaign where we were like, if we could just get in front of this person. How do we get to this person? Or we really think they’d be interested, but we just can’t get there.

And I will say that on more than half of the campaigns, I’m not going to say that we got to all of the people because we never did. I don’t want to false hope. But when we did get to the people it was because we talked about the names and nauseam. Every committee meeting or every other committee meeting, it would be, all right, it’s the time on the agenda. We got to talk about John Smith. What do we know? What do we not know? Who knows who? Let’s review the facts.

And it’s in the constant retelling and talking and talking and talking, it feels brutal and painful, but literally the 16th time you talk about John Smith something’s going to crack or somebody’s going to be like, my cousin’s wife plays golf with him every Tuesday. I might be able to make a thing and all of a sudden you’re in the ninth hole with John Green, whatever his name is.

I mean, so talk about the people all the time. And ask other people to talk about the people with you all the time.

Strategy #4: Look to Your Community Foundation

Amy Eisenstein:
Great. I love it. What’s another strategy?

Sarah Plimpton:
Another strategy? Well, most cities, towns, communities, regions have a community foundation, most of them. If you don’t have a relationship with your community foundation now, there’s no time like the present. Do some research, figure out the org chart or figure out the land of land and make a cold call or ask some volunteers, look at the board, who knows who. How can you get in front of your community foundation?

And what you’re aiming to do really is introduce yourself, introduce your project, and say, this is who we are, this is what we’re trying to accomplish. You are a big driver of philanthropy in our town, city, region, whatever.

• We, A, want you to be aware of us.
• And B, more specifically, we wonder if you are aware of anyone who we should be talking to who might have interest in this. And would you be willing to broker an introduction or how would you recommend that we take those next steps?

Definitely do that.

Amy Eisenstein:
Yes, they might be holding all the donor advised funds and all the other funds in your community of people that they might be willing or happy to introduce you to, or at least mention to their donors that there’s an exciting project going on in town and they want to make people aware of it. I mean, there’s lots of ways.

And listen, whether they’re a little helpful or a lot helpful or not helpful at all, it’s a strategy. And what we’re doing here today is giving you several strategies. Some are going to work better than others, but when you’re feeling stuck, you need to try something different. You need to get out of that rut. And so saying, okay, this week I’m going to try and get a meeting with XYZ program officer or the president of the community foundation or my board member knows a board member at the community foundation. It’s just more list sharing, talking to people, awareness. I love it.

All right. One thing we haven’t talked about… Oh, do you want to say anything else about community foundations? Go ahead.

Sarah Plimpton:
No, I think I know where you’re going next though —

Strategy #5: Challenge Gifts

Amy Eisenstein:
Okay, I want to talk about challenge gifts.

Sarah Plimpton:
Challenge gifts, yeah.

Amy Eisenstein:
That is such a great strategy that can be deployed multiple times throughout the campaign. But let’s talk about a challenge gift for when you’re feeling stuck or as a motivator.

Sarah Plimpton:
So I love a good challenge gift and, okay, here’s what I want to say about challenge gifts. They are motivating for donors. We see this over and over and over again. When you are soliciting for an effort and you have the horsepower of being able to say, and your gift will be matched or you will help us unlock dot, dot, dot funds, that’s a huge motivator.

It is also though, a huge motivator and incredibly meaningful for the challenger. And this is something that I think often gets overlooked. Asking somebody if they will issue a challenge or will allow you to use their philanthropy meaningfully and authentically to inspire other people is a tremendous cultivation stewardship feel-good moment for that donor. So when we think about looking back at donors where you might go back for a second gift, think too about anyone in our universe might want to be the challenger.

Amy Eisenstein:
So there’s two sides to every challenge gift. I love that. So let me say this about challenge gifts. I think too often when I talk to development directors, their image of a challenge gift is whatever dollar amount, and then you blanket everybody. So in the public phase that you would put on social media and send an email and do direct mail, but that’s not what we’re talking about here at all. So I want you to give an example of the way a challenge gift might work in the quiet phase or to get you out of a rut, not a public phase challenge, not a broad-based challenge, not asking everybody and their brother to give a little bit. That’s one kind, it’s one kind of challenge gift, but that’s not what we’re talking about here. So what are we talking about?

Sarah Plimpton:
No. Okay. So I’ll give you a real-life example. So I worked on a campaign once where we had some mega donors at the top of the gift range chart who were ready and willing to step in there, and then we had sort of a vacuum in the middle. So the low-six figure, mid-six figure range, we had a lot of prospects and suspects, but they were not quite as ready or as convinced to jump in at those levels as we might have hoped. So in this campaign, we went to the top donor and this was I believe it was like a $8 million campaign, we went to the top donor and said, would you make a gift of $2 million. 1 million outright, give it, it’s not part of the challenge. And then another million that you give when we receive at least 10 gifts at the 6 figure level.

So we were then able to go back and say to the mid-tier of the gift range chart and say, we have a million dollars on the line. We need 10 gifts at the 6 figure level. Now we deployed this strategically in that we did not blanket the whole universe with this. This was a very targeted approach and it was sequenced. Who we went to, it was sequenced. I’m not going to get into all the nuance there because there were some people that we wanted to give more than a $100,000. Floor was not $100,000. But it was an incredibly effective way for people to feel like, oh, there’s already skin in the game.

Somebody has committed a million dollars that’s in and that’s above me, which feels really good. If I lump up a little bit, I can help this organization leverage another million. And part of the sequencing there was to go to those 10 donors and say to the first woman we went to, you can help the next nine dominoes. And so the next one saying, you can help the next eight dominoes. So there was a real trickle-down effect, if you will.

Final Thoughts

Amy Eisenstein:
Strategy. Yes. Campaigns are all about strategy, and I think that that’s what lots of people who haven’t done campaigns before aren’t aware of that. I mean, it is, it’s hard work and it’s a little bit of luck, but you make your own luck.

Sarah Plimpton:
You create your luck, 100%.

Amy Eisenstein:
I love that. So listen, if you’re listening and you’re worried about getting stuck, I mean, truthfully, our clients get stuck less when they are set up for success from the beginning. So if you’re thinking about a campaign, you’re getting ready for a campaign, you’re not sure if you’re going to hire expertise or do it yourself, we’d love to talk to you about all of our resources and ways we might be able to help you make sure that you don’t get stuck. But of course, when you do and you are our client, we are here for you. You’ve got Sarah and her whole team’s absolute brilliance at your beck and call for all these unstuck strategies.

So Sarah, I just love it. We talked about donors, going back to donors who have already made a gift, who might consider a second gift and how to think about that. We talked about using your project plans as cultivation tools and asking for advice of course also. We talked about going to your community foundation and we talked about challenge gifts, which I love, and we’ve got other close the gap strategies also. But I think that is what we have time for today.

So thank you so much for joining me and sharing your wisdom. Thank you to our listeners for listening. Thank you for being here, and we hope to see you next time. If you want more information or to talk to us about your campaign, we would love to hear from you, visit us at capitalcampaignpro.com.

Thanks, Sarah. See you next time.