Cindy Wagman Shares Fundraising Tips For The Reluctant Fundraiser

cindy wagman

Fundraising can seem like a daunting task. Fear, panic, nervousness take over and you feel like fundraising just isn’t for you, but the truth is you do have the potential to be an excellent fundraiser. 

Cindy Wagman is the President and Founder of The Good Partnership, a values-driven, social-justice informed consultancy that is working to unlock the potential of small nonprofits through fundraising. She is the host of The Small Nonprofit podcast, Canada’s #1 podcast for charities and author of Raise It! The Reluctant Fundraiser’s Guide to Raising Money Without Selling Your Soul.

Cindy joins the show to discuss Raise It, and give tips on how to build confidence as a reluctant fundraiser. 

Cindy’s Top Tips

  1. Redefine what you consider fundraising. Good fundraising can look different for small organizations and we often think of fundraising as standing in front of someone asking for money. There are so many different ways to do it, and it’s up to you to figure out what good fundraising means for your organization. It’s all about being authentic and connecting with people in some type of way. 
  2. Reflect on the mental obstacles that may be standing in the way of your success. Ask yourself why you feel a certain way about something and how your past experiences are impacting your present thinking. Use this knowledge to re-train your brain and creative habits that align with your fundraising goals. 
  3. Value being curious over making a pitch. Look to listen rather than "sell” your nonprofit to a donor. Focus on listening, engaging and connecting with people to find those who really care about your work.

Our Favourite Quotes 

(1:53) Most organizations don't have fundraising shops in-house, they don't have dedicated fundraisers, and the people who are responsible for fundraising don't want to do it. And so that is really where I feel like as a sector, we've kind of failed or sort of let people down.

(11:38) You're not pitching, you're learning and you don't have one shot to get it right. The best ask comes from listening and engaging and connecting and building a relationship.

(14:30) You have to go in imperfectly and you have to be comfortable knowing that competency and confidence comes from practice over and over and over again. I look at my kids learning to read or learning talk. They don't stand up one day and get great at walking, they do it over and over and over again. But they're not worried that they're not going to take perfect step or that they're going to fall on their

They know they're going to fall on their butt and they do it anyways. And that's how we build confidence in fundraising.


Let's learn about fundraising for the Reluctant Fundraiser with Cindy Wagman.

Hello, and welcome to Driven's Fundraising Superheroes Podcast. I'm your host, Sabrina Sciscente. And if you're not familiar with our team at Driven, we are innovators and nonprofit technology looking to help you unlock your true fundraising potential. You can visit Trust to learn more about how we can help with your donor, volunteer and member management.

So how do you fundraise when you don't see yourself as a fundraiser? It's tricky, right? Many organizations are struggling with fundraising because of this.

Cindy Wagman is the President and Founder of the Good Partnership, a value-driven social justice informed consultancy that is working to unlock the potential of small nonprofits through fundraising. She is the host of the Small Nonprofit Podcast, Canada's number one podcast for charities and author of Raise It, The Reluctant Fundraisers Guide to Raising Money Without Selling Your Soul. I am so happy to have Cindy on the show to talk about reluctant fundraising and her new book Raise It. So thank you, Cindy, for joining me.

Thank you for having me. I'm so excited to be here.

So your new book Raise It focuses on teaching non-fundraisers how to fundraise. So why did you decide to focus on this specific market?

I love that question because I could talk for days about how we teach fundraising as a sector, and usually it's through professional associations or things that we're talking to, people who are chosen fundraisers, professional fundraisers. But if you look at the makeup of the charitable sector in Canada, the United States, pretty much anywhere. Most organizations don't have fundraising shops in house, they don't have dedicated fundraisers, and the people who are responsible for fundraising don't want to do it. And so that is really where I feel like as a sector, we've kind of failed or sort of let people down.

In terms of those. In my experience, those small organizations, our grassroots are doing really important work, very often social justice-based. And for the good of all of us, we need them to know how to fundraise well. And we don't right now. So that's why I chose to focus on this sort of reluctant group of fundraisers who would really rather do anything but fundraisers. But they do it because their organization really requires it of them. Yeah.

That's definitely what resonated with me when I was reading the book and I was listening to your excerpt on your podcast was that I am definitely one of those people. It terrifies me to go up to somebody and ask for money. So I'm really excited to share with our listeners some tips, because I know that this is definitely a common struggle. There's a lot of anxiety that comes with fundraising.

Yeah. And part of that is also what we think of as fundraising, which is actually usually wrong. And I don't want to tell you that you're wrong, but there's sort of these stereotypes or these narratives of what we think of as fundraising. There are stories in our minds of what we picture when we think about fundraising, which, as you brought up, we think of, like standing in front of someone and asking for a lot of money, and that is a small fraction of fundraising that your organization may or may not do.

We also often think of corporate asks pitching, which, again, actually is not as big or common as other types of fundraising. We have a lot of false narratives in our brains around fundraising that prevent us from actually doing the work to learn what good fundraising actually looks like for small organizations, which most people actually are. They're naturally talented at it because it's relationship building. And even whether we're introverted, extroverted, nerd, divergent or neurotypical like, all of us have some capacity to connect with other people or in our way.

And most of all, good fundraising is authenticity. So we all have the capacity to do it. And actually, maybe I'll blame our sector or blame those professional associations or groups that have put up these sort of walls around, like, how do we have to do it this way? Or you have to be a professional. You have to get certified. I say this like I've spoken to professional associations. I am a certified fundraising executive. I have all that, but I've seen how it can create a bit of a barrier between the people who do this every day or the people who do this off the side of the desk.

Yeah. It almost makes it seem bigger than it actually is. And I guess that's kind of where the anxiety comes in because you're so hyped up on and you mentioned this in your buck. I need the perfect pitch. I need a really strong marketing plan. I need all these things at the end of the day. You just got to do it. You got to take that chance.

Yeah, but it's hard, and this is also a bit of a bone to pick with how we teach fundraisers. Like, yes, just do it. And I've been around board tables, and I was just, like, just sell five tickets to our event or just pull out your LinkedIn profile and let's look at who. You know, the acts are not hard. It's not complicated, and it's not hard to do. In fact, it's surprisingly simple, but our brains are preventing us from taking that action. And this is not just true of fundraising.

This is how our brains work in the world. We often know what the good things are to do or good decisions, but that doesn't mean we do that. We make bad decisions all the time, and we have bad behaviour. I don't want to call behaviour bad, but unhealthy behaviour or behaviour that isn't aligned with our goals, and we still do it. And that's because our brains operate on autopilot. And unless we change autopilot those simple tasks, will always feel insurmountable.

It is definitely a mental game, and you have to start shifting that mindset. It's that self-fulfilling prophecy. People who tell themselves are not good fundraisers are not going to be good fundraisers. But how do you begin to tackle that mindset shift? How do we start identifying those negative triggers?

Yeah. So the first thing is to just start to bring awareness to how you feel and what your beliefs are around fundraising. What happens in our brain is the more we experience something or repeat something, we create these little neural pathways. They're shortcuts that make decisions really quickly. There's a bunch of patterns to what kinds of shortcuts to make. So there's, like, we have negativity bias where we overemphasize negative things, confirmation bias, like there are all these biases where we might have heard of they're also called heuristics.

So there's patterns to this. But fundamentally, the idea is if we are exposed to something over and over and over again, our brain makes that a shortcut. So it requires less mental energy to just go through the world and make all these little decisions. The first thing is we have to become aware of what those shortcuts are. And the best way to do that is to reflect. How does that make me feel? What are my underlying beliefs in this situation? So it could be around doing a face-to-face ask.

Right. So it could be what am I worried about? I am worried about rejection. Maybe I'm worried about the fact that the donor maybe doesn't actually care about this work, or they're going to feel coerced into giving. And so much of it is very personal reflection, because while I see a lot of trends, these are your own life experiences, right? It could be our experiences growing up and how we talk about or don't talk about money in the home or value of things. Or it could be things around the value of nonprofit work that I've seen.

A lot of people think that we shouldn't be paid a lot because this is charitable work, and that's just part of the part of the so for each of us, we actually have to start to think, okay, what's this fundraising situation that I'm coming up against? And let's take minute to just pause and maybe even write down, like, what am I thinking? What am I feeling? What are my fundamental beliefs that underlie that? So do I believe that people fundamentally don't want to give to charity?

Do I believe that this work is less than or not professional enough? There's so many things that come up with people, but fundamentally, we have to do a little bit of self-reflection, and I guarantee you that all of us, even professional fundraisers, have some stories that we're telling ourselves that keep us stuck in around fundraiser at any other behaviour. So we need to bring awareness to that. And then we can start to look at activities to change those beliefs, which also happens through repetition and creating new shortcuts in our brains align with what we want it to be.

Yeah, I would love to hear your thoughts, because there's that mindset part, and then there's the actual presenting in front of your donor. So how do you display a passion for your cause? How do you get really excited about pitching when you're, like, super nervous or you just.

So the first thing is you're not pitching. If you're going into a meeting with a pitch, you're doing it wrong. And again, this is a story that we've built in our sector. Actually, I would say that the for-profit sector has imposed on our sector around what strong fundraising is. And it's the idea that we have 30 seconds strong, nail it and that's it the reality is, and so that's a belief or shortcut or even a mental model around what fundraising is. We can start to unpack that the best way to feel confident going into meaningful conversations with nurse is to be curious.

You're not pitching, you're learning and you don't have one shot to get it right. The best ask comes from listening and engaging and connecting and building a relationship. I just had a conversation with someone else. I call it like a path of mini yeses where we start to develop and understand. Okay, what is a good ask look like for you? How does that align with the priorities of the organization? Is there an overlap? Let's figure that out first.

Is this the right fit for organization? Because if it's not stop wasting your time. There are definitely donors who don't align with your mission. Just move on to the next one. I guarantee you there are people who care about your work. So first, how do you find the people who care? How do we engage them and understand why they care what impact they want to have, how that connects and bring them into learning how our organization is doing those things? Sometimes education that has to happen there.

I've been having a lot of conversations around that. Like, how do we edge the donors? Because sometimes they might not align, but they're close and they are open to learning, and sometimes they're not. We always want to surround ourselves with donors or the right fit. And then we have to say, okay, what is the right ask? And that comes out from conversations I had a conversation with today. They said, we just need a really good pitch deck. I said, I don't want you to put anything because I guarantee you it's going to be wrong.

It is not what's going to resonate with that donor. If you put something, it should be after having multiple conversations with potential donors so that you understand what the right messaging is. Almost always project our own feelings and beliefs and get the messaging wrong. Part of it is just like thinking about what that fundraising process looks like, and then the other is because fundamentals, as I said, shortcuts in our brains through rapid, and we often misattribute fundraising success or what makes someone successful fundraising. Very often I will hear people look at a fundraiser and say they're so successful fundraising because they're really confident or they're really outgoing or they're really extroverted.

And in fact, they're confident because they have the experience. And so you can't wait or fake the confidence. You have to go in imperfectly and you have to be comfortable knowing that competency and confidence comes from practice over and over and over again. I look at my kids learning to read or learning talk. They don't stand up one day and get great at walking, they do it over and over and over again. But they're not worried that they're not going to take perfect step or that they're going to fall on their butts.

They know they're going to fall on their butt and they do it anyways. And that's how we build confidence in fundraising.

Exactly. Yeah. You have to fall in order to learn how to get back up and recover and keep knocking. Yeah. The thing about striving for perfection is that it often leads to procrastination or progress not being done. People feel like we said before that there's so much that you have to do in order to present themselves in front of a donor. How can you learn how to take a step back and recover when things aren't going exactly how you want it to? Especially in the beginning. How do you recover from a no or maybe a time when you are in the middle of an ask and you just feel those nerves coming on.

I want to just say that you can fundraise really successfully without ever doing a face to face ask. That might be controversial, but it is very true, especially in small organizations. Chances are you're almost never in front of someone pitching or making an ask. Usually you're sending emails direct appeal, but I still want you to engage with your donors because the more you get to know them what's right or how to approach them or what fundraising strategy is right for your organization. But there will be times you do have to sit down with someone face to face or present something.

And so for me again, I go back to this idea of, like mini Yes's, or like course correction, where I almost never just go with a hard ask. I learn what first of all, I have a fundraising backround, right. The fact that I'm a fundraiser so that people know the nature of our relationship, and then usually what I would do is look at okay, we have conversations that help me figure out what the right ask is, how do we build that? And actually, because they know I'm a fundraiser, we're going to talk about what programs you're interested in or what kind of work it is. Through that I'm like ok they are clearly not interested in this, or they might be really interested in that.

So let's talk about the program, learn more about it. And when I do major gifts, I will actually get buying or permission to ask. And so what it looks like is we've been talking about this program, and maybe I'll reach out and say, hey, Sabrina, we've been talking a lot about this program. I'd love to come and preview you with an offer to support it financially or like to make a donation towards it. Are you available? Blah, blah, blah. So when I book that meeting to ask, I'm very clear that that is the purpose of that meeting.

So the donors not caught off guard. They have time to think and prepare, and I can't sort of chicken out. They know what the purpose is. And then when we do have the meeting, chances are, if they say yes to that meeting, they're not going to say no to a gift. Maybe we talk a little bit about what the gift looks like or what the amount is or when it's made. But it's not a yes or no answer. And that, to me, is one of the biggest learnings I've had in doing major fundraising or corporate sponsorship, I think are very similar in that approach where you're not going in with a yes-no.

And by the time it comes to like, let's say, put pen to check, it's not a yes. No question. It's how do we make this work? What's the right opportunity here? That's a lot easier. You're not going to get rejected meeting with you for a potential donation. You save there's very little line. So again, I just want to reiterate that so much of fundraising is not at all that it's building the relationships. It's understanding who you're talking to. It's communicating with people through email, video mail, social media and engaging them and not thinking of it as a one way conversation.

But how do you engage people through those mediums so that you can still build relationships with lots of people of the time. Yeah.

Because at the end of the day, it really is just connecting with people. And there's so many people like you said, donors that really want to support you. You just got to find and learn how to pick up on the cues of who that is. So yeah, I totally agree. I think that's a really good perspective to have. And when it comes to major gifts asking permission, I feel like that's 100%. It's a lot easier to go in and be confident when you know that they are already accepting of your presence.

Exactly. So don't hide what your goal is. Just tread fully, build trust and figure out why I always start with, like, why do they care? What do they get out of giving? What are they excited about? Not at the expense of our work? Again, there are donors who are not right for you. And that's okay. But when there's alignments, then how do you really make it meaningful for both the organization and the donor?

And we touched on this kind of in the beginning of our conversation. But I'd love to go in a little bit further. So there is a lot of information out in the world geared towards people who, like you said, they're fundraisers by profession. They went in, they knew that's 100% what they wanted to do with their career. And here we're talking about the reluctant fundraiser. So why is it important that small nonprofit don't compare themselves to other larger organizations or focus on so much of the best practices or what's kind of being marketed to them as fundraisers?

Mostly, we don't see the full picture. We only talk about it as an iceberg because we all stand, you see the tip of the iceberg, the bulk of that is underwater. And that's what we see when we look at organizations. We see celebrity endorsements, big galas, fancy marketing campaigns. And we don't see the work that's going on behind the scenes to get there. And we can't necessarily just reverse engineer it without a lot of resources. And again, it's this idea of, like, I think I have to start there and be perfect out of the gate.

It's much more effective to start where you are, be humble, be authentic, leverage what you already have in your organization and focus on those strengths and those opportunities and build organically will get you so much further than spending all this time and usually not taking much action to develop a brand campaign or develop these big things back in the day, it was like the next ice bucket challenge. Those things just are not necessarily attainable, or they take a lot of work that we don't understand. And fundamentally, I think why we look at them that way is that it feels like an escape or an easy out or something like that.

We'll never get there. So we don't have to try that hard. We don't have to put ourselves on the line. And it's sort of a distraction more than anything. And again, like, it comes down to mindset, our brain. It's core functions to protect us and keep us safe and to help us get through the world alive. And so what happens is when we fix it. If we're a small organization or reluctant fundraiser and we fix it on these things that are so unattainable, that's our brain saying, I'm not going to let you do the things that are going to be successful because we're just going to focus on those other things and you're never going to take the right actions to get there, and it's keeping us safe.

And so instead start to build a fundraising habit that might be a little less safe, but certainly not outrageously. So, again, you're probably not going to go ask for a million dollar gift face to face with someone. You're going to start where you are. You're going to build community. You're going to build broad base of supporters or focus on a couple of key activities that are going to be meaningful for your organization and fundraising. And that will get you so much further. But to jump that huge divide is virtually impossible.

I don't want to say never.

But yeah, you always have to focus on what you can control in the ice bucket challenge. I mean, it took off, but to go viral like that, I feel like one in a million.

It rarely rarely happens. And I guarantee you the excuses I hear for why organizations are not raising money. They're very common, and they're almost always wrong. So I hear organizations say we don't know anyone who can give. You might not know anyone who can write a check for $10,000, but that's not the only way of giving. And certainly that's not the only amount of giving. Or I don't have corporate connections. Again, corporations make a small percentage of donations in our sector. There are so many that we hear over, and we need to brand first.

We need to rebrand. We need to raise awareness before we can ask anyone for money, because no one's heard of us. If no one has heard of your organization, I just don't believe it. I don't believe that there's no one out there who's aware of your work. If you were actively doing work, you have community. You have people around you start where you are instead of trying to again, like, cross this divide, that will just not it will prevent you from taking any action.

Exactly. Well, before we go today Cindy, I'd love for you to share with our audience how they can get in touch with you, where they can learn more information about your work.

Yes. So you can connect with me. The website's social handles are the same. The good partnership. I think it's a little different on Twitter, but you can find me Cindy Wagman and you can get. So I recently wrote a book called Raise. It The Reluctant Fundraiser's Guide to Raising Money Without Selling Your Soul. It talks a lot about what we covered today, plus a bunch of other stuff that's available at And I think we have a promo code. So for any listeners, if you use the code driven, you will get 10% off.

So only if you buy through our website, not if you buy through Amazon or anything like that. Please do connect with me.

Thank you again to Cindy for coming on to the show. And that is all for today's podcast. I have linked all of our resources in the description box below. And if you are interested in purchasing Raise It like Cindy mentioned, you can use promo code driven for 10% off through purchase on her website only. So make sure you do visit that link in the description box and get your copy of Raise. It is a fantastic resource for those of us who have a little bit of anxiety when it comes to fundraising.

And if you want to stay updated on everything, Fundraising Superheroes and Driven give us a visit at There you can listen to past podcast episodes, get access to a ton more resources, and also sign up for our monthly newsletter. We would love to have you join the Driven family. Thank you so much for listening to today's episode, and we'll see you next time on the Fundraising Superheroes Podcast. Bye.

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By Trust Driven on Dec 16, 2021, 12:00 AM


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