Asking
We have a prospect list. We’ve qualified it. We’ve decided on a strategy, and we’re moving forward with a list of people. Now is the time to ask.
I’ve been on both ends of countless pitches from nonprofits. All (well, ok, most of them) were brilliant organizations trying to change the world. But very few of them took the time to listen to me before they started telling me their story.
How to Listen
Listening, not speaking, is the most crucial skill a solicitor can develop.
I can always tell when I’m on the phone with a good fundraiser because we have this fun little professional tug-of-war - I try to get them to talk about themselves, and they try to get me to talk about myself. Fundraising conversations are like watching judo - great fundraisers shift the energy back to the people they’re trying to solicit.
Learning when to listen and speak is challenging because it’s as much about mindset as anything else. You can take the adage “you have two ears and one mouth for a reason” literally, but if done without sincerity, it is easy to spot what it is — a ploy.
The best advice I’ve ever received for this skill came from a podcast that the renowned journalist and interviewer Ira Glass recorded with Jesse Thorn. Ira said; before he dived into a conversation, he took a moment to look into the eyes of the person sitting across from him and “fall in love.” This lesson was profound for me - it’s a practice that will transform your relationship with your donors.
Buddhists have a version of this practice “metta” (lovingkindness) meditation. When developed, it suggests a profound connection and understanding with the universe that can easily precede any meaningful conversation with a little practice.
I won’t feel like you’re waiting impatiently to speak if you love every word I say. By fully opening ourselves up with compassion, we open our hearts, and they open theirs. We acknowledge their humanity, unique journey, and viewpoint of the world. We are not treating them as subjects to be questioned but as equals sharing this human experience. This connection paves the way for an atmosphere of vulnerability and authenticity, providing a platform for sincere and profound conversations.
Many fantastic fundraisers I know spend their time honing their questions very carefully. Do the same - keep a list of the questions you ask that are most impactful. But the efficacy of our questions is contingent on the strength of the connection we establish with the people with which we engage. Absent this connection; our questions might appear robotic or disingenuous, devoid of the depth and subtlety that genuine understanding mandates.
The skill of conversation extends beyond merely framing the right questions – it involves connecting with others on a profound level. When we gaze into someone’s eyes and metaphorically “fall in love,” we create an environment conducive to meaningful dialogue, empathy, and comprehension. In this process, we build bridges of connection and empathy that rise above our differences, drawing us closer in our shared human journey.
Don’t force conversation; reveal it. The art of listening is more than merely hearing words; it’s about tuning in to the speaker’s emotions, intentions, and subtexts.
When we usurp conversations, we risk interrupting or overshadowing the speaker, curtailing their thoughts, or discarding their viewpoints without genuinely grasping them. Conversely, when we invite discussion, we foster an open, safe space for the speaker to voice their thoughts and feelings freely, without fear of judgment or interruption.
The art of listening demands patience, empathy, and an open mind. It involves being wholly present and engrossed in the conversation, actively endeavoring to comprehend the speaker’s perspective. Such listening bolsters our understanding of others and enriches our lives by exposing us to the varied perspectives and experiences of those around us.
I always think of the book Primary Colors, which describes the main character as exhibiting “the most aggressive listening the world has ever known: aerobic listening.” This descriptor signifies the attentive, inquisitive, curious, flexible, and aggressive listening our world calls for—a skill that requires years of practice.
Poor listeners tend to be competitive, using their listening to pinpoint reasoning or logical errors. To them, silence is merely a tactic to prepare their subsequent remarks. People’s perception of their listening ability often mirrors their assessment of their driving skills—most adults consider themselves well above average.
Improving listening involves intention and repetition. Before every conversation, set your intentions—demand excellence from yourself. Deep, open-ended queries will come to mind as you listen, stimulating curiosity and insight. By gently probing and occasionally challenging, you can broaden the discussion (“What about…”) or refine it (“How might we…”) in each of your conversations.
Good listeners are like trampolines. They allow the donor to bounce ideas off of you and amplify and clarify their thinking. This dynamic interaction drives innovation and deepens mutual understanding, underscoring the critical role of listening in effective communication.
How to Ask
To paraphrase the famous sales trainer Zig Ziglar, a skilled fundraiser would never sell ice to an Eskimo, but he could sell them a darn good heater. That’s because a fundraiser’s role is to connect the donor’s vision with the organization’s needs. Good fundraisers don’t exploit or manipulate - they connect the dots. We discuss storytelling later in this book but should speak of persuasion now.
Persuasion aims to equip fundraisers with tactics to weave compelling narratives that trigger action. Harnessing the power of persuasion can enable nonprofits to build deeper connections with donors and rally support for their noble causes.
Although I’m sure you will find plenty of ways to use fear or greed in your persuasive narrative, I strongly caution against this. Not only will it burn you out as a fundraiser, but it is also akin to the story of the boy who cried wolf — when the time comes for your donors to be scared, they will ignore your cries for help.
Instead, I look to the ancient past for persuasive inspiration. Aristotle, a forefather of rhetoric, identified three modes of persuasion to influence others: ethos, pathos, and logos. Each method holds unique implications for nonprofit fundraising and can be employed to craft compelling appeals.
Ethos is building credibility and trust. Ethos refers to the character and credibility of the speaker, playing a crucial role in the persuasiveness of an argument. Establishing a solid ethos is paramount for earning potential donors’ trust in fundraising. Nonprofits can bolster their ethos by demonstrating real expertise, showcasing impactful accomplishments, building a board or advisory board with a stellar reputation in the field, and adhering to ethical standards in their actions and communications. In other words, ethos is building viability.
Pathos is the way we engage emotions. Pathos is the “heart story” your nonprofit tells. Pathos seeks to arouse emotions in your audience, persuading them to support a viewpoint or action. Nonprofits can share compelling stories, images, and testimonials that spark empathy, compassion, or outrage. You can tell stories from the heart, which put people in the mindset to care profoundly and inspire action.
Logos is the “head story,” logic, and reason. Logos relies on evidence to convince the audience. Often, it is pathos that drives us toward a decision, but logos that confirms it. We can deploy logos for nonprofit fundraising by offering clear, data-backed explanations of the problem and the proposed solutions’ effectiveness. By presenting persuasive evidence, you can appeal to donors’ rationality and underscore the significance and impact of their contributions. Charts, graphs, and many page reports this is where those resources will live. The story you tell about your nonprofit should include all three of these critical elements.
Now that you have a persuasive speech, you’ll want to use it. First, choose a channel. Remember, the more personal the approach, the greater the likelihood of a positive response. You want to make it challenging for people to say no. The more vulnerability, the greater your odds of success: Emails < Texts< Phone Calls < Video Calls < Events < 1:1 In-Person Meetings.
Make them exceptionally comfortable for a greater chance of success in your in-person meetings. Meet at the donor’s home or a private club. The more critical the ask, the more carefully chosen your environment should be. And, of course, try to include both halves of a couple whenever possible. Most couples make big financial decisions together.
Conversations will usually begin with a few minutes of preliminary chatter. This initial time is an excellent place to ask a few light catch-up questions about their lives - their kids, their hobbies, and even the weather can be a good topic of conversation. Always begin by thanking the donor for meeting you. If you are in a highly well-kept home, it can be tempting to compliment the donor’s decor or sense of personal style. I recommend against it - as much as possible, you want to appear as though you are used to being in beautiful spaces, plus it can accidentally make your donors feel uncomfortable.
The same is true for challenging areas - I have fond memories of an Oklahoma oil baron who worked out of a trailer in the middle of nowhere with nothing but an AM radio and a folding chair (and no air conditioning). No matter how outrageous the surroundings, appear comfortable in them.
Your physical appearance should be well-kept but not noteworthy. Your first impression should appear both friendly and powerful. I’ve noticed that some people naturally seem more friendly, and some appear more powerful. Powerful people should make efforts to appear friendly and vice versa. After the preliminaries are complete, you will open by setting the tone for the conversation. Your full presentation should be over in fifteen to twenty minutes, so plan accordingly.
In major gifts you will rarely ask for money in your first meeting. Instead, you will usually have several cultivation meetings where you gauge the donor’s interests and desires before making an ask.
But when it’s time, I usually like to open by setting the tone immediately. “I’m here today because I want to discuss you making a significant financial commitment to [PROJECT X] that you care so much about. This is a profound opportunity to impact generations to come. Here’s what I mean…” This is important, because it removes the awkwardness of sneaking in the ask at the end of a friendship conversation.
The opening is also a great time to reconnect over any common ground you share with your donor. Then you will come to the presentation. Here is where you will talk about the project itself. Things get tricky in this section because you risk lecturing your prospect to death. People have very short attention spans - far shorter than you might realize. It’s elementary for any donor to put on a polite smile, and you may not even realize that they stopped paying attention to you a few minutes into your speech.
Combat this by focusing on benefits. It’s never “building a library”; it’s “giving 100k families access to education”. It’s not “legalizing marijuana”; it’s “making sure families stay intact, and no one goes to jail for having a little weed in their pocket.” Keep the benefits short and compelling, and don’t be afraid to ask questions if things get stuck.
Clearly articulate the impact of the prospect’s donation on your organization and its mission. Don’t get lost in the weeds here — keep the conversation high-level and inspiring. Demonstrate how their contribution aligns with their values and resonates with their interests.
Many fundraisers delve straight into the functional aspects of the organization. However, donors are primarily interested in the impact of your work rather than its operational details. They’re more intrigued by the difference their contribution can make rather than the internal workings of your organization. Be prepared to answer their nuts and bolts questions of course, but always emphasize the ‘why’ over the ‘how.’
Paint a compelling picture of a future where your organization realizes the donor’s desires. About halfway through, the time will come for you to ask for the gift. The ‘ask’ should naturally evolve into a conversation that reflects the donor’s deepest desires. It should never feel forced, only revealed. The surrounding meeting should build up gracefully to that pivotal moment.
Ask for something specific — not a range. When you ask, I prefer to use this language: “Would you consider a personal commitment (or leadership gift) of ______ by ________ date?”.
When making your request, specify the amount and the terms of the gift. A distinct amount or timeframe increases the chances of receiving your desired donation.
Afterward, I pause and give them a chance to answer. That pause is hard, and it takes practice. A few seconds can feel like a lifetime.
I always phrase my questions “Would you consider” to combat most people’s biggest fear — what if they say no! By starting my ask with “Would you consider” I have an easy trampoline response when someone says “no.” “Well,” I say, “what would you consider?”. It’s short, sweet, and effective, and I’m spared the awkwardness of a back-and-forth negotiation. It gives me opportunities to answer any objections. And most importantly, it allows me to keep my soul intact.
I hope they say yes, but I’m always a little disappointed if they say yes too quickly. I like shooting for a “stop and think” amount of money. You’ve probably hit the nail on the head if there’s a slight pause before their affirmative response.
The worst possible answer is “maybe.” So much time is spent by development directors fruitlessly chasing yet another “maybe” for months. I far prefer a “no.”
After you ask, address their queries and apprehensions thoughtfully and respectfully. Be willing to adjust the donation amount or terms if necessary but avoid haggling—it’s not a business transaction; it’s an inspiration for a generous act. After your request, thank them for considering your case and answer any additional questions they may have. Maintain a balance of confidence and humility throughout the conversation. These traits may sound contradictory, but great leaders can hold both in paradox.
Fundraising often involves navigating objections. Donors may hesitate due to budget constraints, trust issues, or a lack of perceived value in your cause.
However, resistance isn’t a dead end. With the right strategies, objections can become opportunities for dialogue, understanding, and gaining support.
Objections are seldom outright rejections, often expressions of concern, skepticism, or misunderstanding. Instead of seeing them as obstacles, consider them as invitations for further information or opportunities to deepen the relationship with your potential donor.
After comprehending their objections, respond empathetically. Validate their concerns and offer relevant information to alleviate their doubts or worries. The aim isn’t to bulldoze the complaint but to foster an open dialogue where the donor feels valued and comfortable.
Counter objections with clear, factual, and compelling information about your nonprofit. If a donor questions the impact of their donation, illustrate how their support could make a tangible difference. If they’re apprehensive about financial transparency, explain your organization’s procedures for managing and reporting contributions.
Remember that the “customer (donor) is always right” for our conversation. It doesn’t mean they’re actually correct, of course. But it does mean that you can offer new information without insulting their current beliefs.
Reinforce to potential donors that their contribution is more than money; it’s about partnering with your organization to make a difference. This perspective can make donors feel more engaged with the process, and it’s easier to overcome objections when you’re building the project together.
And, of course, respect the “no.” Acknowledge a donor’s right to decline. If they maintain resistance after you’ve addressed their concerns, it’s appropriate to take a step back. This respect can fortify your relationship with the donor and open the door for future support.
Designing solutions that truly resonate with our donors requires an intimate understanding of their fundamental desires, values, and motivations—their “deep needs.” By addressing these needs, we can create donation experiences that engage not just the pragmatic but also the emotional and psychological aspects of giving. Unearthing these deep needs, shrouded in layers of thought, emotion, and behavior, is the crux of our cultivation work.
Empathy is vital to this journey. Through active listening, careful observation, and immersive experiences, we can understand the complex tapestry of our donors’ lives, unveiling their hidden values. These values, like “the need to feel love” or “the need to be validated,” can often feel very personal. But we know that giving can help fulfill many of these profound needs appropriately and successfully. Armed with such profound insight, we can craft experiences that resolve surface-level issues while cultivating emotional bonds, enriching the lives of our beneficiaries. Understanding deep needs thus steers us towards a future that enhances our donors’ experiences and programs.