Start with three questions: What would you most like your philanthropy to accomplish? What do you most enjoy about your giving, and what feels harder than it should? and Who in your family is involved in your giving, and would you like anyone else to be involved? Together, they move a conversation from purpose, to experience, to participation.
These are discovery prompts, not a script that guarantees agreement or a particular charitable vehicle. They help wealth advisers, family-office professionals, attorneys and other trusted advisers hear what a family is trying to do before discussing grants, governance, tax structures or measurement. A contribution by Kris Putnam-Walkerly published on October 5, 2026, presents the three opening questions; the frameworks below show how to use the answers responsibly.
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Why begin with questions instead of a giving strategy?
Families often arrive with a practical symptom rather than a clearly stated goal. Someone may say, “Our giving is all over the place,” “We want to involve the kids,” or “We have money in our DAF and no real plan for using it.” Another family may ask, “How do we know whether our giving is making a difference?” Each statement points to a different issue: unclear purpose, family participation, an unused structure or uncertainty about learning.
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The prompts work best when the adviser listens for the words beneath the answer. “We want to help locally” might conceal a concern about accountability, a family story, a desire for visible results or a wish to build children’s responsibility. The adviser should reflect what was heard, ask permission before offering options and avoid treating any answer as a commitment.
Question 1: What would you most like your philanthropy to accomplish?
This question changes the starting point from where do you give? to why do you give? It invites a family to describe a desired difference before debating organizations or tactics. The answer can be broad at first: improving an opportunity, strengthening a community, honoring a person, responding to a crisis or helping future generations develop shared values.
Use follow-ups that make purpose concrete
- “Why is that important to you?” surfaces the experiences, values and relationships behind the goal.
- “What would success look like?” asks the family to describe observable progress without forcing a numerical target too early.
- “If your philanthropy could make meaningful progress on one issue over the next five or 10 years, what would you want that to be?” tests whether the family wants focus and a longer time horizon.
- “What makes that difficult?” identifies constraints such as disagreement, limited time, a crowded request pipeline or uncertainty about effective approaches.
Do not turn a five- or 10-year prompt into a promise. It is a way to reveal appetite for focus, patience and learning. A family may prefer several smaller commitments, emergency response or unrestricted support. The adviser’s job is to clarify the choice, not to imply that concentration is always superior.
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Separate the goal from the vehicle
Once a purpose is named, ask what kind of contribution could advance it: money, relationships, expertise, advocacy, convening or patient support. A donor-advised fund, private foundation or direct grant is a structure; it is not the purpose itself. If a family has money in a DAF but no plan for using it, the conversation should first establish the intended difference, decision rules and a realistic grant cadence. The structure can then be evaluated against that plan.
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Question 2: What do you most enjoy about your giving, and what feels harder than it should?
This paired question makes room for both satisfaction and friction. Asking only what is difficult can make philanthropy sound like an administrative burden; asking only what is enjoyable can hide bottlenecks that prevent good intentions from becoming useful grants.
Listen for the specific source of friction
The prompt can uncover too many requests, difficulty deciding where to make grants, uncertainty about whether giving makes a meaningful difference or family members with competing interests. Each requires a different response.
| What the family describes | What to explore next | Possible next step |
|---|---|---|
| Too many requests | Whether the family wants a focus area, an eligibility screen or a scheduled review period | Create a short decision rubric and a channel for declining requests respectfully |
| Difficulty choosing grants | Which criteria matter: urgency, evidence, local knowledge, relationships, equity or unrestricted need | Agree on two or three primary criteria before reviewing proposals |
| Uncertainty about results | What outcome matters, what the organization can reasonably measure and what learning would change a future decision | Request proportionate information or fund useful assessment rather than imposing a large reporting burden |
| Competing family interests | Where interests genuinely conflict and where a shared value can connect them | Define separate discretionary lanes alongside a small set of shared commitments |
Turn enjoyment into a design clue
Enjoyment is not merely a feel-good detail. A family that values meeting community leaders may prefer site visits or structured conversations with people served. A family that enjoys mentoring may want to contribute expertise in addition to money. Someone who values quiet, unrestricted support may prefer a streamlined approval process. Preserving these sources of motivation makes a plan more sustainable.
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Question 3: Who in your family is involved in your giving, and would you like anyone else to be involved?
This question opens discussion of values, wealth and responsibility without assuming that more participation is always better. A family may want a couple to make decisions privately, involve children in learning but not approvals, invite grandchildren to recommend small grants or include non-family trustees with relevant expertise.
Clarify the desired level of participation
- Information: Who should receive updates about grants, finances and results?
- Learning: Who wants exposure to community issues, nonprofit operations or due diligence?
- Recommendation: Who may suggest organizations or causes?
- Decision: Who has authority to approve a grant or change a policy?
- Leadership: Who will steward the work when current donors reduce their involvement?
Ask each participant what role feels meaningful and what role feels burdensome. Involving children can mean a family conversation, a site visit, a small grant budget or a formal board seat; these are not interchangeable. Age, interest, geography, privacy and preparation all matter. A clear role is more useful than a vague instruction to “get the kids involved.”
Make disagreement discussable
Invite the family to name decisions that are shared, individual or unresolved. A written process can allow personal giving alongside collective giving, set a threshold for consensus and identify who breaks a tie. The process should be revisited as children become adults, marriages change, wealth transfers or the family’s priorities evolve.
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Use the answers to build a giving plan
After the three questions, summarize what you heard and ask the family to correct your understanding. The summary should distinguish an aspiration from a decision. This simple map keeps a conversation from collapsing into a premature product recommendation.
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| Conversation finding | Decision it informs | Evidence that the decision is ready |
|---|---|---|
| A desired social or community outcome | Focus area, time horizon and types of support | The family can explain why the outcome matters and what progress would look like |
| A recurring source of friction | Decision rules, meeting rhythm, delegation or specialist help | The family can identify the bottleneck and the change that would relieve it |
| A preferred participation pattern | Roles, authority, education and succession | Participants agree who recommends, decides, learns and communicates |
| A question about impact | Learning agenda and proportionate information requests | The family can state what information would change a future choice |
If the answers reveal a need for philanthropic advising or family giving-plan support, present that as an option tied to the stated need, not as an automatic next step. A family seeking clarity may need a facilitated process; a family seeking evidence may need issue research; a family struggling with participation may need governance design.
Add an impact lens without losing the family’s purpose
The University of Pennsylvania’s Center for High Impact Philanthropy offers three complementary questions: What difference do I want to make? Is that difference meaningful to the population I hope to serve? and How will I know if I am moving closer to making that difference? The second question is a crucial check against defining success only from the donor’s perspective.
Impact has no single definition that fits every person or situation. Invite people served to shape the definition through direct engagement, representation in organizational leadership or participatory impact assessment. Listening is not a ceremonial add-on: it can change which outcome matters, which trade-offs are acceptable and what a respectful partnership looks like.
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The Center describes high-impact philanthropy as starting with a social-impact goal, using the best available evidence, considering cost alongside impact and learning continuously. That sequence links the family’s purpose to practical choices without pretending that a single score can rank every charitable effort.
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Measure what is useful and reasonable
Match the question to the organization’s control
Ask what outcomes a nonprofit can reasonably measure and attribute to its own work. A food pantry may track reach, reliability and participant experience; it generally cannot claim sole responsibility for a household’s long-term economic mobility. Asking for distant outcomes outside an organization’s control can produce misleading numbers and divert staff from service.
Use existing evidence when it is strong
When credible evidence already links an approach to the desired impact, activity and nearer-term outcome measures may provide useful assurance. Every grantee does not need to recreate a full study. Ask what evidence exists, how closely it matches the local context and what uncertainty remains.
Resource new assessment instead of shifting the cost
If evidence is weak and a new assessment would help, funders should provide dedicated support and consider whether the nonprofit or an intermediary is better positioned to do the work. Duplicative reporting requirements can consume a small nonprofit’s capacity. Agree on a small set of questions, a realistic schedule and how the findings will affect future funding.
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Complete the sentence, “If we learn X, we will consider Y.” If no plausible finding would change a decision, the requested metric may be performative. A useful learning agenda might test whether a pilot reaches the intended population, whether unrestricted support improves resilience or whether a program is ready to expand.
A practical first-conversation workflow
- Set expectations. Explain that the meeting is for listening and clarifying purpose, not selecting a charity on the spot.
- Ask the purpose question. Let the family answer fully before offering examples or categories.
- Probe for success and difficulty. Use one or two follow-ups, then reflect the answer in the family’s own language.
- Ask about enjoyment and friction. Separate an emotional preference from an operational problem that needs a process change.
- Map participation. Identify who wants information, learning, recommendation, decision authority and future leadership.
- Apply the impact lens. Check whether the desired difference is meaningful to people served and what evidence could support learning.
- Agree on one next action. Examples include drafting a one-page purpose statement, interviewing grantees, setting a family meeting or defining a small pilot.
- Record and confirm. Send a short summary of aspirations, open questions, roles and the agreed next step; invite corrections.
Adapt the spirit of the questions for funder–grantee conversations
The Trust-Based Philanthropy Project describes General Service Foundation’s verbal reporting prompts: “What do you want us to know about your work over this last period?” “What are the strategic questions you are grappling with?” and “How can we help?” They are asked by phone or in person, with notes kept to track grantee progress.
This is an adjacent example, not a substitute for the family-adviser questions. Its value is the same posture: invite the other party to set the agenda, surface strategic uncertainty and make the funder’s role useful. A family can use that posture when speaking with prospective or current grantees, while still respecting the organization’s boundaries and expertise.
Pitfalls that weaken the conversation
- Turning prompts into an intake form. A checklist can suppress stories and disagreement. Follow the answer that carries the most meaning.
- Assuming focus is always best. Concentration can increase learning, but some families intentionally balance local, urgent and long-term giving.
- Equating participation with succession. A young person may learn without joining a board; a non-family adviser may provide continuity without controlling values.
- Demanding perfect attribution. Social outcomes often have many causes. Ask for credible contribution and useful learning rather than impossible certainty.
- Ignoring burden. Reporting, site visits and family meetings consume time. Match each request to a decision it will inform.
- Recommending a vehicle too early. A structure should serve a purpose and process already clarified, not become the topic that replaces them.
A strong opening conversation ends with greater clarity about the difference the family wants to make, the experience it wants to preserve or improve, and the people who should participate. It does not need to end with a grant recommendation. The next decision can be modest, explicit and testable, giving the family a sound basis for learning and adjusting its philanthropy.
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