The Art of Asking:

Strategies for Successful Annual Campaigns

Fundraising Professional, Philanthropy Educator, and Nonprofit Leader

Bob Hopkins is a veteran philanthropy professional, nonprofit executive, educator, publisher, and Certified Fund Raising Executive with more than four decades of experience helping charitable organizations build stronger relationships and sustainable fundraising systems. He has served as executive director of the Texas Neurofibromatosis Foundation, published Philanthropy magazine, and founded PAVE, an organization dedicated to advancing philanthropy education and engagement. Known for his practical, relationship-centered approach, Bob teaches nonprofit leaders that successful fundraising begins with listening, trust, and the simple truth that people give to people. He is a valued member of the SynerVision Community and contributes his experience through the Nonprofit Prosperity Council: Philanthropy Redefined, in alliance with C-Suite Network.

 

Episode Summary

In this special live-audience episode of The Nonprofit Exchange, Hugh Ballou welcomes longtime fundraising professional Bob Hopkins for a practical conversation about annual campaigns, donor relationships, and the art of asking for support.

Drawing on more than four decades of experience in philanthropy, Bob explains why individual donors remain essential to nonprofit sustainability. His central principle is simple: people give to people. Successful fundraising begins long before the request is made, through genuine relationships, careful listening, consistent communication, and a clear understanding of what matters to each potential supporter.

Bob defines an annual campaign as an organized, multi-month process rather than a single event or one-time appeal. He describes a typical fall sequence: introduce the campaign in September, make the formal request in October, follow up and collect gifts in November, and celebrate and thank supporters in December. The purpose is to build predictable support for the coming year and establish an annual rhythm that donors come to recognize.

The conversation also addresses the importance of preparing a focused contact list, maintaining a clean and current database, involving board members and volunteers, and communicating the results donors can help achieve. Bob emphasizes that organizations do not need thousands of names to begin. A smaller list of people with authentic relationships can be more valuable than a large list of disconnected contacts.

Throughout the episode, Bob encourages nonprofit leaders to listen more than they speak, learn about a donor’s interests, and connect the mission to those interests before making an invitation. He also reminds leaders that fundraising should never be treated as the work of one person. Strong annual campaigns engage a team of people who can reach out through their own relationships.

The episode offers an accessible starting point for nonprofit executives, board members, development professionals, and emerging leaders who want to replace reactive fundraising with a thoughtful, relational, and repeatable annual campaign.

Key Takeaways

• People give to people, so trust and relationship come before the ask.
• An annual campaign is a planned process, not a single event or email.
• A smaller list of genuine relationships can be more effective than a large, impersonal database.
• Listening helps leaders understand what potential donors care about and how the mission connects with their values.
• Boards and volunteers should participate in fundraising through their own relationships.
• Consistent communication, follow-up, gratitude, and celebration are essential parts of the campaign.
• Annual campaigns help organizations build more predictable support for the year ahead.

Closing Principle

“People give to people.”

The Interview Transcript

Hugh Ballou: Here we are. Welcome to the Nonprofit Exchange. This is Hugh Ballou, your host. And today is really different than episodes we’ve done before. We’ve never done one for a live audience. So we have our regular weekly meeting of the community, Center Vision Community, which is in association with the C-Suite Network, Nonprofit Prosperity Council. And it’s redefining philanthropy. Bob Hopkins has been a dear friend for years and he made a presentation recently. I said, Bob, let’s dig deeper into this. So, Bob, I’m going to let you introduce the topic and then we’re going to have a dialogue just to work through some of the major themes and then we’re going to give people some real reason to say, hmm, it’s time that I change what I’m doing because I’m not getting the success that I want. So, Bob, welcome to The Nonprofit Exchange and tell us what you’re going to talk about today.

Bob Hopkins: Hello there, everyone. Glad to see you. Am I going to be on the screen? I don’t see myself on the screen.

Hugh Ballou: You are front and center, my friend.

Bob Hopkins: I am so glad. Anyway, hello, everyone. For those of you who don’t know me, I’m an old man. And I have been around for a long time. And I’ve been for 45 years doing philanthropy work. And I like to tell a secret about my success. I stopped drinking alcohol. that was the beginning of my decision to do something else with my life besides hang out in bars with the people that did too. So I actually joined the National Council on Alcoholism as a volunteer. And I was finally the executive director because of the fact they liked what I was and who I was and what I was doing. They sent me to fundraising school back in 1982, 84. And my goodness, I learned so much because you know what? I had a desire to be a giver and a getter. In other words, I liked raising money from people, but I didn’t know how to do it. And there is a who, what, where, when, why reason that we do it in certain months and we don’t do it in certain months. And there are three different options of fundraising. One is who do you go to? You can go to corporations, I don’t, because only 5% of all the money raised in America comes from corporations. You could go to foundations with grants, and Tony Rokas can tell you this, only 6 or 7% come from foundations, and foundations won’t even look at you. unless you have three to five years of experience and you can show them your information, your financials, etc, etc. And so the best place to go and what I’m going to talk about today is people.

Hugh Ballou: People. People. So Bob, this is the biggest track for nonprofit fundraising across the whole sector. This is the biggest percentage. So let’s start with generosity. You know, the spirit of generosity, the myth is I don’t want to bother people talking about money. So what experience in your understanding about generosity and what does it mean that people want to give and why people give?

Bob Hopkins: Okay, well, we are Americans, that’s number one, because of the fact we have a culture of giving. Now, I know that all religions and all cultures tell you that you must give back to society. But in America, we have an organized fashion in how to do that, and that is through the nonprofit sector, 501c3s. But also many countries, and I have somebody from Africa here, they have NGOs, non-governmental organizations, but they’re not quite as sophisticated and organized as is the 501c3 sector that we have in the United States. So even in Africa they have 501c3s because they realize that if they take on the American system that it’s going to be a lot easier for you to not only raise money but also to distribute it to those organizations that you need to. So people, people give to people who have a good cause. Hello? People give to people who have a good cause. So anyway, if I don’t know somebody, I’m certainly not going to say, hi, how are you? My name is Bob Hopkins and please give me money for my cause because I belong to the Texas Neurofibromatosis Foundation. Oh, you’ve never heard of that disease before? Oh, well, let me get started. No, I don’t do that. I usually try to create a database of people that I know on a daily basis because every day I meet new people and there’s a difference between meeting them and having a relationship with them and for them to finally end up being a giver to your non-profit organization. So therefore, all of you here today, and I know most of you here today, have family members, you have good friends, you have people that give to people. And by the way, generosity is key in the United States of America. 73%, they say, of Americans do give something to a nonprofit organization or to a cause of some kind. And even if you don’t have a 501c3, you have a cause. Everybody wants something different to happen. They want a solution to a problem, whether it be hunger, or whether it be housing, or homeless, or whatever it may be. Whether it be the arts, whether it be religion, whether it be education, whether it be health, all of us have something that we want to change. And we could do that if we had a system, an organized system to do that. And in America, we have what is called an annual campaign.

Hugh Ballou: Ah, that’s the topic. So dig into that. You know, we think it’s a big deal. We think it’s a whole lot of work. We think it’s just a lot of wasted time. But it’s really an essential part of what we do, isn’t it?

Bob Hopkins: Well, we do, but unfortunately, most nonprofit organizations don’t know about this topic. So therefore, 40% of nonprofits fail every year because number one, they don’t have a system of raising money and they don’t know how to do it. And by the way, folks, I have lots of volunteers in my organizations and lots of people who want to volunteer hours and time. And that’s wonderful, wonderful, wonderful. But there’s also an important asset that we have to give as a resource to our nonprofit organizations, and that is dinero. And that is a check, that is money. And it could be $5 and $5 a month or $10 a month or once every three months or something. And each organization can create their own system of how you collect money from people. So I want to give $500, but I can’t give it all at once. But I could give it $100 for five months. I could give $50 for 10 months. And all of you need to be thinking along those lines, too, when you decide to go on your annual campaign. So an annual campaign is an opportunity for all of those folks that you are connected with that know you and you know them to ask them finally for a contribution to your nonprofit organization. And by the way, a 501c3 has obviously an organizational aspect to it, which means that there’s a lot of expenses that goes into creating a 501c3. So if you’re going to start one, you make sure that you understand you got to pay for telephones, you got to pay for office space, you got to pay for people, you got to pay for materials, you got to pay for books. You got to pay for a telephone, on and on and on. And so many people start something and they don’t realize that they’ve got to have a lot of expenses that goes along with that. And so if they don’t have a plan, they just might fail, which means they’re going to say one day, we got to close the doors because we can’t pay for the rent anymore. So that’s where I come in.

Hugh Ballou: So let’s talk about, we decided we’re going to do it. So let’s pick up from where you are. So I decided I want to do it. What do I do now? And then how do I create the messages? Cause people don’t like paying for telephones, but they like paying for results. So talk about where do we plan and how do we create the messages?

Bob Hopkins: Okay, Hugh, this is a whole nother topic at one another another point, but you’ve got to create a board of directors. You have to have at least three people when you start one. You have to have a person who starts it, which may be the president. You have to have a treasurer, and you have to have a secretary. And these people are board members and a board can be any number of people that you want. And some people say we need to have five. Some people say maybe 10, some people 20, 21, whatever. I think 55 is too many. I think one or two or three or four is too few. So therefore, when people get on a board of directors, they have a responsibility and it’s fiscal, which means they are responsible for the organization fiscally. which means money-wise. So when you have a board meeting, I hope the first thing you talk about is money. Don’t put it at the very end and say, okay, let’s have the treasurer’s report. Well, we don’t have time, see you all later. But money needs to be talked about from the very beginning. Otherwise, if money is not an issue to you all, then you’re not gonna be along for the ride for very long. So anyway, back to annual campaign. When do people feel the best about who they are? And I could ask that question to many of my students who are in the audience here and they would already be able to tell you that the fall, October and November, they say is the best time we all feel good about who we are. And there’s all kinds of reasons and we can go at that at a later date. The second best time that we feel good about ourselves is in the spring. And that is usually in March and April. And regardless of the fact that we have We have income, we have to pay our income taxes on the 15th of April. April is still, March and April are good months for when people feel the best about themselves. And there’s all kinds of reasons for that. So that’s why we are talking about an annual campaign in the summer when it’s hotter than hell in Dallas. It’s 106 degrees today. We are inside and we’re in air conditioning and we don’t care about getting out and running around the block six or seven times or playing tennis or even sometimes golf. So what we do during this time is we plan, and now’s the time to plan, and that’s what we’re doing today, and that’s what I have been doing in Dallas for the last couple of weeks because of the fact that I am teaching a face-to-face course here, which is a five-session course, which is two hours long each time, and some of my students are here already, so they’ve heard some of this information before, but you know what? It’s good to hear it again, and it’s good to hear it again, and by the way, I never, hear enough about how to fundraise because everybody’s got new and different ideas than I do. But one of the things I want to talk about is, OK, so I got a friend and he needs and he needs an outlet. He needs something to do. He needs something in his life. And unless I ask, he’s not going to call me up on the telephone and say, oh, by the way, Bob, I don’t have anything to do and I’d like to be part of your group. Because people aren’t like that. They want to wait until somebody says, you know what? You’re a great person. You’re a good friend. I’d like you to consider being a volunteer for our organization. So you have to ask. And the question that many people, Hugh, don’t know how to do is they don’t know how to talk to people, especially about something like this. And I teach speech, and I have many students say, Bob, when you get into a group, what do you say? And you know what, I understand that concept because most of my students, especially those high school students who had to go through a pandemic for two years and didn’t get a chance to socialize with people, don’t have the skill of being able to just carry on a conversation with two people, except on the telephone. And the telephone is a different thing than face-to-face. I try to do everything face-to-face as much as I possibly can. I like to gather people together. I like to smell them. I like to touch them. I like to hug them. I like to hold their hands. I like to say and look them in the eyes. I love you. I think you’re wonderful. I’d love for you to be part of our organization. So it’s an interpersonal relationship, Hugh, that we have to form with people. And by the way, you and I have known each other for two or three or four years. I don’t know how long, but obviously the first month we were getting to know each other. Are you think five years? It seems like a hundred, but I thought it was two. So anyway, it took me a while to get to know Hugh enough to even have a conversation with him and tell him my personal information about who I was really as a person. And I have a list of 350 people in my database. You’d think I have a thousand, but I don’t. I have 350. And why do I have only 350? Because these are the people that I actually have a relationship with. I have written two books, they happen to be in my books. I happen to belong to C-suites as I see Susan Younger there and with the big smile on her face and those big glasses. And she and I have a relationship and I feel like we have known each other for a long time and we have for a couple of years because I’ve been a part of C-suites and she’s been a leader at C-suites for all these years. So I’m going to put Susan Younger on my list. Guess what folks, she’s gonna get a letter from me. And it’s gonna say, dear Susan, I love you and you love me. Now let’s talk serious stuff and let me tell you about what I need and who I am and what I’m all about. And she already knows what I’m all about. She knows that I have an organization called the Texas Neurofibromatosis Foundation. She already knows how to pronounce it and she knows what it is. And now it’s time for her to actually make a contribution besides just a volunteer time. It’s now time for her to be a giver in money. But you know what? I announced that I’m going to be asking you all for money many months in advance, like today. I’ll be asking you for money in October, which is only two months away, by the way, since we’re already into August.

Hugh Ballou: This is great. This is great. Can I hone in on something here? We’re going to learn how to ask people for money. So after this recording, we’re going to dig in with people and have some case studies and maybe some rehearsal, how we do the ask. But Bob, in the context of, you said you had 350 people on your list. That was a game changer for me. We’re all thinking, oh, we need thousands of people to be able to do an annual campaign. So talk about size. If we have 10, we have 100, do we need lots of people? And how do we then start putting, you’re taking us to the final thing, how do we ask for money, but how do we have people in the room and how do we build this system where people are gonna want to support us?

Bob Hopkins: Yeah, well, Janet Smith is probably in the audience. She’s got 8,000 people on her list. Okay, I don’t. She’s been around a long time doing a lot of things. I’ve been around a long time too, and I know more than 350 people, but I have 350 people who I feel comfortable enough to put on my list to be asking them for money because of the fact they’ve had some relationships with me. Now, I’ve got 50 people there that I’ve just met the last year. but I’ve had some responsibility in being their friend by calling them and talking to them and seeing them at events and joining the same organizations that they have joined. I just joined the Lions Club for the first time. I’ve been there only a month, but I’ve already made some great friends who are gonna be on my list because of the fact that I’ve known them before I joined Lions Club. So I’ve had some responsibility of relationships then before I even decided that they would be on my list. Okay, now listen to this very closely because I didn’t learn this until late in life. The winner of a conversation is usually the listener. I want to say to you, Susan Younger, I have an organization of neurofibromatosis and I tell you about 10 minutes and I can’t stop talking because I love it so much. I’ve not even asked Susan how she is today. I’ve not even said, Susan, let’s have a conversation. How are you doing? What’s going on in your life? And then I will say to her, and by the way, you know, I have an organization called Neurofibromatosis and I could go on and on and on about that. But first of all, why don’t you tell me about you and your giving? Are you interested, by the way, in a disease like mine, or do you have something else that you would prefer to be a donor to, but you just don’t have the opportunity? And then I have asked her a question, and now what? She gets to talk. And I need to listen, and I need to listen, and I need to ask more questions, and I need to listen, and I need to ask more questions. And by the way, I don’t have the last word. She has the last word, and I’m the winner. because I have given her the time to tell me who, what, where, when, why about her self and about her life and about her feelings and what it is that she is interested in before then I say to her, now, Susan, I’m gonna send you some information. Please give us a gift of some kind because she’s told me you’re interested and I’m gonna let you make the decision of what that gift should be.

Hugh Ballou: This is perfect. This is perfect. So in the last five minutes of this interview for the nonprofit exchange, talk to us about the next steps for, you know, clean your email list. You know, how do you do the next steps for the annual campaign in our last five minutes here?

Bob Hopkins: Okay. I talked to a lot of people about this over and over and over again. So every time you’re going to talk to Bob Hopkins, you’re going to listen to neurofibromatosis. In some way or another, because you’re going to say, how are you today? What are you doing? Well, I’m doing this for neurofibromatosis. Do you have any idea what it is? I talk to him. I take him to lunch. I take him to dinner. We end up talking about what I care about a lot in my life. And so do you. And I just talk about neurofibromatosis. So it’s not something that I spring on you all of a sudden and say, oh, by the way, This is time for you to be giving to me and I’ve got an organization called neurofibromatosis. If you don’t know how to spell it and you don’t know how to pronounce it, it’s not time for me to ask you for a contribution to it.

Hugh Ballou: So define what an annual campaign is. Is it an event? Is it an email system? What is an annual campaign?

Bob Hopkins: It’s a three-month process. You start it in September and you end it in December before Christmas. In fact, you tell people about it in September. You actually send information and ask them in October. You collect the money and remind them in November and you celebrate in December. And what it is, is money for the year coming up, 2027. So it’s not like you’re gonna put the money and use it this year, it’s for next year. Now, I know you need it for this year and you can go ahead and use it for this year, but you know, when you do this every single year, you’re gonna have a plan and people are gonna know, okay, I’m gonna expect a letter from Bob because this is another year. And if I don’t get something from him in October, there’s something wrong. He’s either closed the place or they’ve cured neurofibromatosis.

Hugh Ballou: So start early, be very specific with your messaging, and then the follow-up piece. You know, you’ve got to send them more than one message. We’re afraid of sending more than one message, but you know, most people don’t open every email. And if they do, they might not read it and act on it. So in our last couple of minutes, what’s the next sequence? The follow-up, and then after the event, follow-up.

Bob Hopkins: Okay, by the way, I don’t do anything by myself, Hugh. I gather people together, and I’m looking at the screen right here, and I see Humberto Gallegos. He’s a good friend, and he’s part of me. So what I’m going to do is tell him, I want you to assist me, Humberto, in contacting my folks. I know Susan Younger. Susan, I want you to assist me in contacting my friends and my people. Now, I don’t know Elijah as well as maybe some of you don’t even know who he is, but he’s from Africa. I’m not going to ask him to do anything yet, because you know what? I’ve not seen him face to face. I’m going to see him in February though, and next year he will have a part in my annual campaign for sure. And so I’m looking at some of you other people that I do know, for instance, and I don’t want to leave anybody out, obviously, but Dr. Janet Smith Warfield, we work together. I’m helping her with her campaign and she’s going to be helping me with mine. And so we have a relationship. She knows all about me. I’ve listened to her. She’s listened to me. So now it’s time that Janet makes a contribution, but I don’t have to even tell her anything more because of the fact we’ve been talking about this for two or three months. And I could go on and on with all of you here.

Hugh Ballou: We’re going to go on. So, the people on the podcast, you can find this episode on thenonprofitexchange.org, thenonprofitexchange.org. And you can go to Center Vision Community and you can log in and join us one time and see what it’s like to be part of this energy field. So, as a closing thought for this section, Bob, We’re going to go on and have a lot more conversation with the audience here. What’s one principle you want leaders to remember whenever they ask someone to support their mission?

Bob Hopkins: That people give to people. OK, period. They don’t give to the cause. It might be polio, it might be neurofibromatosis, but the end of the day, it’s gonna be, they’re gonna give to you. Maybe you aren’t the best person to go to that person. Maybe there’s somebody that’s closer to you than me. Therefore, I will ascend probably Humberto Gallegos to go talk specifically to his people instead of me going to his people. So that’s where he fits in and they’re gonna give to him because he’s the one who came to do the asking and he’s the relationship. that they have.

Hugh Ballou: This is great. So people, if you didn’t get all these good talking points, there’ll be a transcript for this in the place for the Nonprofit Exchange, and there’ll be an analysis of this. And, you know, we invite you to join us sometime because Bob’s part of this community, and we learn from Bob all the time. Bob and I, those years, I’ve learned about the true meaning of philanthropy, and I’ve learned more about fundraising than I ever thought I needed to know. So here we are. Thank you, Bob, for being the guest today on the Nonprofit Exchange.