Socratic fundraising

Socratic inquiry uses questions. But just asking questions isn’t enough. To be Socratic, the questions must guide toward a goal.

In fundraising, the “one big thing” is always the same: Advance the donor’s hero story. Socratic fundraising can do this.

The hero story steps

In the universal hero story (monomyth), a guiding sage often kicks off the hero’s journey. The sage challenges the hero with a choice. It’s a challenge to

In the donor’s hero story, the fundraiser is the guiding sage. This guiding sage challenges with a choice. This happens at the ask. A compelling fundraising challenge

The hero story cycle

The hero story progresses through

A box and arrow diagram where "Original identity" links to "Challenge" links to "Victory" links to "Enhanced Identity"

In three words, this is: identity, challenge, and victory.

A circular diagram where "Identity" (bottom left) links with an arrow pointing to "Challenge" (top middle) which links with an arrow pointing to "Victory" (bottom right) which links with a backwards arrow pointing back to "Identity"

In fundraising, including each step makes the ask compelling. Completing the cycle advances the donor’s hero story. Let’s look at the ideas underlying each step.

Original Identity → Challenge

In other words, “I am the kind of person who makes gifts like this.” Why?

i.e., “People like me make gifts like this.”

i.e., “Giving to this cause or charity fits my values.”

i.e., “Giving to this cause or charity fits my life story.”

Victory → Enhanced Identity

In other words, “I want to be (or be seen as) the kind of person who makes an impact like this.” Why?

i.e., “This impact helps (or is supported by) people like me (or with me).”

i.e., “My values make this impact meaningful to me.”

i.e., “My life story makes this impact meaningful to me.”

Challenge → Victory

In other words, “The gift will make this tangible (visualizable) impact.”

The tightening spiral

In Socratic fundraising, the donor tells his story. But the goal is to get the donor to tell his story about these steps: identity, challenge, and victory. The steps in this story cycle aren’t just a one-time process. They’re an ongoing, repeated, circular narrative.19

Socratic fundraising progresses from general to specific. The circle becomes a spiral. It moves from broad to narrow. The process can start with wide-open, sweeping cycles.

This might first elicit the donor’s identity elements. This includes

Questions can connect these identity elements to giving (i.e., the challenge) and to impact (i.e., the victory). This completes the circle. It connects identity, challenge, and victory.

Then the circle becomes smaller.

It connects these identity elements with a specific cause or charity.

Then the circle becomes smaller.

It connects these identity elements with a specific project or work within the charity.

Then the circle becomes smaller.

Just before the ask, the proposal reviews and confirms each step in the cycle.

Finally, the smallest circle is the challenge phrase itself.

The ask itself references each step in the cycle.

The process is like a tightening spiral or mandala. The three-step cycle is our guide: identity, challenge, and victory. If our questions are building these three connections, they’re advancing the story. Otherwise, we’re just making conversation.

Step-by-step

The compelling challenge requires these three links. Socratic fundraising can help. It can build these links through the following steps.

  1. Justify asking questions.

  2. Ask questions that

  1. Ask questions that make the challenge.

The first step is to justify asking questions. For example,

The next step is to ask questions that connect with the donor’s identity and define a personally meaningful victory. This includes

  1. Ask opening questions.

  2. Ask follow-up questions.

  3. Ask confirmation questions after reflective statements.

  4. Spot solutions while repeating these steps.

The final step is to ask questions that make the Challenge. This includes

  1. Ask for permission to ask.

  2. Connect the gift with the full story cycle.

Restate and confirm the identity connections. (Original Identity → Challenge; Victory → Enhanced Identity). Make the case for support. (Challenge → Victory).

  1. Ask for the gift.

These theory concepts show up in real-world practice. They match the questions that the best fundraisers often ask. Next are about two hundred examples quoted from top fundraisers. Use them verbatim or create your own. But the key is to understand the cycle.

There isn’t just one “magic” question. Different questions work for different people at different times. Questions become powerful when they’re part of the full story cycle. They’re not just random conversation. They move towards a destination. They advance a story. They advance the donor’s hero story.

Part I: Identity

The following are examples of opening questions and phrases. These connect the donor’s original identity (history, people, or values) with the charity, the cause, or philanthropy.

Identity: Life history

Cause or charity origin story

“When did you first get interested in [this cause]?”20 “Would you mind telling me how you became connected to the organization?”21 “How did you first find out about us?”22 “What first brought your attention to our organization?”23 “How did you first get involved with the organization?”24 “How did you get connected to this organization?”25 “Can you tell me what brought you to [this charity] in the first place?”26 “How did you get [or come to be] involved with our organization?”27 “How did you decide to first start supporting ABC Charity?”28 “What first made you interested in supporting this hospital?”29 “What got you started as a donor to this organization?”30 “What led you to make your first gift to the organization?”31

Philanthropy origin story

“Where did you learn to give?”32 “How did you learn to be generous?”33 “What is your first memory of when you knew it was important to give back and help those people or organizations in need?”34 “What is your first memory of an act of generosity?”35

School or camp origin story

“What are your best memories of your time at ABC Charity?”36 “What experiences were most meaningful to you during your time as a student?”37 “What were your favorite moments as a student.”38 “What’s your favorite place on campus?”39 “What was the best thing about your experience at our school?”40 “Did you participate in any activities while a student?”41 “Tell me about your favorite faculty member.”42

Post-origin story journey

“Tell me about your journey since you graduated from the university.”43 “Tell me about your journey since you were first diagnosed.” “Tell me about your journey since you first became involved in [this cause].”

Cause or charity life history review

“How has [this cause or charity] been important in your life?”44 “Tell me your ABC Charity story.”45 “How has [this cause or charity] impacted your life?”46 “How has the organization’s work affected you personally?”47 “What have been your past experiences with the organization?”48 “If you were to tell others about your care at the hospital, how would you describe it?”49 “What have been your most positive experiences at our charity?”50 “What is the most meaningful experience you had through your involvement?”51

Identity: People

Cause or charity people connections

“Have others in your life been affected by [this cause]?” “Is there anyone in your family who also cared about [this cause]?” “How has [this charity] impacted your family or loved ones?”52 “Have any of your family members or close friends been involved with our charity?”53 “Is your giving your decision or do you decide together with someone else? What is their connection to [this charity or cause]?”54 “Do you have a favorite doctor or staff person at the hospital?”55 “Do you know any of our leaders, board/committee members, staff, volunteers, or other supporters?”56

Philanthropy people connections

“Did your parents or other family members support any charitable causes?” “Can you tell me a bit more about who taught you to be generous or where your generous spirit comes from?”57 “When you were young, was there anyone whom you considered a role model for giving?”58 “Who are your philanthropic role models?”59

Identity: Values

Values underlying giving motivations

“What inspires you to give?”60 “What inspired you to make this gift?”61 “What inspired your first gift?”62 “Broadly speaking, what is your rationale for charitable giving?”63 “What inspired you to create your donor advised fund / private family foundation?”64 “How does your giving reflect your values, your feelings, and your aspirations?”65

Values underlying causes supported

“Tell me about a few other causes you support: why do you support them?”66 “Would you mind telling me about the causes that are most important to you?”67 “Do you typically give to the same nonprofits each year?”68 “Why do you support them?”69 “Where else do you give, and why?”70 “Where does [this charity] fit in your overall philanthropic priorities?”71 “Where does our charity fall on your list of charitable priorities?”72

Values attributed to others

“What do you think are the most important factors to donors who make a major gift to our institution?”73 “What is the single most important reason that you believe someone would support the project?”74 “How can we make giving to this charity more compelling for other donors?”

Identity: Open-ended (history, people, or values)

Connections

“Do you mind if I ask, what is your connection to our mission [or organization]?”75 “How could we connect with you better?”76 “How would you like to be more involved?”77 “Is there any area within the organization where you could see yourself becoming more involved?”78

Why us?

“Why do you give to this organization?”79 “Why do you support us?”80 “What’s motivated you to be such a consistent supporter [of this charity]?”81 “Why have you been such a loyal donor?”82 “Why have you been so loyal?”83 “Why does what we do interest you?”84 “Why do you serve on X committee?”85 “Why does this cause matter to you?”86 “What’s the key thing that persuaded you to join our cause?”87 “Why do you care so much that you would sacrifice your precious time and invest your limited dollars to move this mission forward?”88 “When you think about programs such as ours, what motivates you to support them?”89 “I understand you haven’t supported our cause significantly in the past; tell me more about that.”90 “Of all the charities you could support, why do you support us?”91

Sidenote: A caution about “Why?”

In the previous questions, we often want to learn “why?” But using this word is risky. “Why?” or “Why did you do that?” can feel like an attack.92 It’s what we say when a person has done something stupid. It can cause defensiveness. So, be careful with this word. Where possible, consider a substitute.

Part II: Victory

The following are examples of opening questions and phrases to define a meaningful victory.

Victory: Defining the broadest victory

Global victory

“What changes do you believe would make the world a better place?”93 “If you could change the world, what would you do?”94 “How would you like to make a difference in this community? In this world?”95

Legacy victory

“What would you like to pass on to future generations?”96 “As you look out to the future, what is the legacy you would like to leave?”97 “What positive difference do you want to make?”98

Victory: Defining a giving victory

No limits victory

“If there were no restrictions on you, what would you like to do philanthropically?”99 “In the best of all possible worlds, what would you do to support our charity?”100 “If you could do anything for [this charity], if the sky was the limit, what would that look like to you?”101 “If money were no object, what would you like to see happen with our program?”102 “If money were no object, what would we be doing that we’re not now doing?”103 “If money were no object, what kind of an impact would you like your giving to have?” “What would be your dream gift?”104

Overall victory

“What change do you want to see because of your giving?”105 “What do you want to achieve with your charitable donations?”106 “What do you hope to achieve with your philanthropy?”107 “What would you ultimately like to accomplish with your philanthropy at our charity?”108 “What are your goals for your Donor Advised Fund / Private Family Foundation? How long do you want it to last?”109 “What are you trying to accomplish with your philanthropy and how might we help?”110 “As you think about making a difference with your philanthropy, what appeals to you most?”111 “What kind of impact would you like to have on [this cause / these beneficiaries]?”112 “Do you have any lifetime charitable goals? Tell me about those.”113 “What would you like to accomplish with your money / giving / philanthropy in this cause or at this charity that would be meaningful to you?”114

Single gift victory

“What are your goals for this gift?”115 “What kind of impact do you want to make with your gift?”116 “[If the donor has a current scholarship, endowment, etc., ask] what kind of impact do you ultimately want it to have?”117 “Have you thought about how you would like your planned bequest gift to be used?”118 “A year from now, how would you know that you made a wise move with your philanthropic investment in us?”119 “If you were going to make a significant investment in the hospital, a gift in the million-dollar range, what would you like to accomplish with that gift?”120

Victory: Defining an organizational victory

Organizational change victory

“If you could change anything to better [this charity], what would it be?”121 “You’ve been such a loyal member of the ABC Charity family, and have supported ABC Charity’s mission for so many years, what are your dreams for where you’d like to see ABC Charity go in the future?”122 “What are your long-term hopes for our charity and its mission?”123 “If you had the ability to enhance or expand ABC Charity’s mission in a specific way, what would it be? What could we do to be more effective in the future?”124 “Where do you think we could improve our services or programs?”125 “Are there any thoughts you’d like me to take back to share with our CEO/ president/ executive director?”126 “What are the most critical results you expect our organization to produce?”127 “What could we do better in your opinion?”128 “If you could change anything about [this organization, issue or project], what would it be?”129 “If there was one thing you could change about our charity today, what would it be?”130

Organizational interest victory

“What areas of [this charity] are you most interested in?”131 “What interests you personally about the problem we are addressing?”132 “What excites you the most about our organization’s work in the world?”133 “What means the most to you personally about what ABC Charity does?”134 “What were your impressions of the tour? ... What intrigued you most?”135 “Is there a particular program, project, or area of outreach [scholarship fund, award, etc.] that interests you most?”136

“If you were to make a significant commitment, is there a particular area you would want your gift to support?”137 “Based on what you have told me about your experiences, memories, wishes, etc., if I can help you find a way, what at our nonprofit would you most like to support financially?”138

Organizational strengths victory

“What do you think we do best?”139 “What do you think is the best thing about what our non-profit does?”140 “What contributions to the community does the organization make that are important to you?”141 “What’s the most exciting thing you’ve heard about our institution recently?”142

Victory: Defining a victory with gift options

Victory with a single gift option

“What do you think about this opportunity?” “What is most compelling to you about the project?”143 “Could you ever see yourself being involved in a project like this?”144 [After an event describing a project ask] “What were your impressions of the event?”145

Victory with a menu of gift options

“Which of these projects would be most meaningful or important to you?” “If you had to choose between making a gift toward the new building, the scholarship fund, or our endowment, which would you select? Why?”146 “If you could have your family’s name on something like a building, scholarship, lectureship, what would be most meaningful to you?”147 “After outlining the various projects to be funded by a campaign, ask, ‘If you had the money to fully fund any one aspect of the project, what would it be?’”148

Victory: Defining a victory with gift implications

Personal implications

“What if [this goal was accomplished]? What would that mean to you?” “What would it mean for you to make a personal impact in saving, or extending, the lives of women living with breast cancer?”149 “What would it mean for you and your family to have an enduring impact in improving cancer therapies while assuring your own family’s financial future?”150 “What are your thoughts about naming facilities or programs after benefactors? ... But what about you? How would you feel about associating your name with this project?”151 “Does your philanthropy give you joy?”152 “What philanthropic gift has given you the greatest joy? How?”153 “What makes giving a rewarding experience?”154

Community implications

“Why do you think this project is important to the community?”155 “What would the world look like in ten years, if the women who died of breast cancer last year, hadn’t? How would families and communities be different because of the accomplishments those women would have made?”156

Victory: Defining a victory that would overcome a barrier

“What would have to happen for you to say yes [to a gift request, invitation to serve, etc.]?”157 “So [, yes,] I do understand why you stopped supporting us. What can we do to bring you back into the fold?”158 “What would motivate you or your business to invest in a nonprofit organization?”159

Victory: Defining a victory with past giving

“Tell me about some meaningful gifts that you have made.”160 “How do you know when you have made a ‘good gift?’ Share a couple of examples of ‘good gifts’ with me. Why did you feel they were good?”161 “I understand you made a significant gift to X at our institution a while back; How do you feel about how we used your funds?”162 “When you look at all of your giving, be it time or money, what captures your heart and your attention?”163

Part III: After the opening

Follow-up questions

Opening questions start the conversation. But the conversation needs to continue. Follow-up questions can help. These can be open-ended. For example,

“Would you tell me more about that?” “How do you mean?” “How so?” “How did you feel about that?” “How did you feel when that happened?” “What happened next?” “Really! Tell me more.” “What else?” “Can you give me an example of that?” “What led you to that?”164

Even better is when the questions are reflective. This shows you’ve been listening. Reflective follow-up questions include,

“Tell me more about ….” “What happened after you …?” “What’s an example of …?” “How does … fit into the picture?”

Reflective summary and confirmation question

The donor has been talking. Hopefully, we’ve been listening. We’ve been listening for links that connect to a challenge. We’ve been listening for identity connections. We’ve been listening for victory connections. In the next step, we summarize and confirm the donor’s connections.

The goal isn’t just to show we’ve been listening. It’s to highlight these connections for the donor. This happens in three steps.165

  1. Reflective transition

“So, what you are saying is …” “It feels like you are …” “It sounds to me like …” “So, you are thinking about …” “So, what I’m hearing is …” “I’m picking up that …” “I’m noticing that …” “So, your experience has been …” “I’m getting the sense that …” “I think what I heard is that …” “Would I be correct in saying that …” “So, you’re saying that …”

  1. Reflective statement

Summarize, highlight, or repeat key statements that support a connection.

  1. Confirmation question

“Do I have it right?” “Is that it? Is that right?” “Is that what happened?” “Does that sound right?” “Am I getting it right?” “Is that the right idea?”

Spot solutions

We’ve been listening. We’ve been identifying connections. We’ve been confirming those connections. Now we match these with donor experiences or gift options.

Consider possible experiences. What experiences would strengthen these connections? Are there particular programs, areas, or projects that match? What employees, beneficiaries, or other donors should they meet?

Consider possible gift options. What peers should be present at the solicitation? Are there giving instruments that match? These might be

Ask for the next step

Typically, initial conversations don’t end with a donation request. But they do end with a request. This might simply be a request to share the next experience. For example,

“Can we set a time so I could show you one of our facilities?”166 “Do you think you have time for a tour sometime in the next two weeks?”167 “Would you be interested in attending [this event]?” “I think you would be a fantastic addition to our [board, committee, or group]. What are your thoughts on that?”

Part IV: Challenge

The final step moves towards and then makes a compelling ask. The following are examples of questions and phrases that do this.

Ask for permission to ask

At some point, things progress to a fundraising ask. But the ask shouldn’t be a surprise. (At least not for any significant request.) This isn’t an ambush. Instead, we want permission. We want permission to present an ask.

The ask, however, is described in terms that highlight value. We don’t just want to ask for money. We want to share helpful options. Example phrases include,

“Would you be open to exploring ideas to …”168 “Would you be interested to hear more about how you could …”169 “Would you like to hear about some possible ways to …”170 “We would like to show you some ways that you can … Would you be open to hearing some of these ideas?”171 “My job is to put together personalized options for you to consider. Would you mind if we set a time to look over some of those ideas together?”

The options we want to share are valuable. They might address problems or barriers for the donor. Example phrases include,

“What if it was possible to make a gift and still [address financial objection]? Would you like to hear about these options?”172 “If we could show you a way to … would that be of interest?”173 “There are simple ways to … Would you like to know more about those?”174 “Can I tell you about a gift option that would …”175

The options we want to share are useful. Other people like the donor agree. Example phrases include,

“Others in your situation have ... Would you like to hear more about how this works?” “You remind me of another donor. Do you mind if I share her story? She was able to … Is that something that might be useful for you?” “Some of the people I meet with are interested in hearing about ways to … Is that something that might interest you?” “Others who share your feelings have established perpetual funds here as a way of giving back to ‘dear old State.’ Would you like to hear more about setting up such a fund, perhaps in honor or memory of a beloved family member?”176

Once we get a yes, we just need a date. Example phrases include,

“Would your calendar allow us to meet this Thursday or next Tuesday?”177 “How does next Tuesday work for you to meet?”178

The ask meeting

Fundraising needs an ask. But the fundraising ask shouldn’t be just a “naked” challenge. It should be part of the full story cycle.

A circular diagram where "Identity" (bottom left) links with an arrow pointing to "Challenge" (top middle) which links with an arrow pointing to "Victory" (bottom right) which links with a backwards arrow pointing back to "Identity"

The challenge comes from the donor’s identity. It leads to a meaningful victory. The victory is meaningful because it connects with the donor’s identity.

This ask or proposal meeting presents this full cycle. It will describe and confirm the donor’s identity connections:

The “case for support” then shows

This step may use a formal proposal document. It will answer,

Why is the project needed?

[It will define a victory.]

Why now?

[It will show the challenge comes from a threat or opportunity that forces a choice.]

How exactly will it work?

[It will show how Challenge → Victory.]

What’s it going to cost?179

[It will define the challenge.]

Make the story cycle ask

Finally, the ask itself can present the story cycle one last time.

A circular diagram where "Identity" (bottom left) links with an arrow labeled as [1] pointing to "Challenge" (top middle) which links with an arrow labeled as [3] pointing to "Victory" (bottom right) which links with a backwards arrow labeled [2] pointing back to "Identity"

[1] Identity → Challenge sentence

“You have … [here describe a connection with the donor’s identity].”

[2] Victory → Identity sentence

“You understand … [here describe how the victory would be meaningful to the donor].”

[3] Challenge → Victory sentence

“Would you consider a gift of $______ to … [here describe the promised victory]?”180

Then, be silent. An ask might sound like this:

[2] “You understand how a new regional history collection would preserve our shared heritage.” Victory → Identity.

[3] “Would you consider a gift of $50,000 to lead the campaign to make this a reality?” Challenge → Victory.

[2] “You understand more than anyone how lives can be changed by offering free early screening.” Victory → Identity.

[3] “Would you consider a gift of $100,000 to help fund next year’s screening clinics?” Challenge → Victory.

[2] “You understand how this new exhibition could make a real impact for other art lovers like you and our whole city.” Victory → Identity.

[3] “Would you consider a gift of $50,000 as our lead campaign donor to make this happen?” Challenge → Victory.

[2] “You understand how important scholarships are in helping others like you become proud alums of the future.” Victory → Identity.

[3] “Would you consider a gift of $100,000 to fund a permanent named scholarship giving students the chance for an education?” Challenge → Victory.

Conclusion

There may not be one magic question. Use whatever works for you. But there is a magic journey. It connects,

The magic journey is the hero’s journey. It’s also the donor’s journey. Questions can help advance that donor-hero’s journey.