Most advisors want to have better philanthropic conversations with their clients. The 2026 TPI study makes clear that clients want them too. What often stops these conversations from going deeper is not lack of interest on either side. It is that the conversation opens in the wrong place.
The default opening is technical. Do you have charitable intent this year. Are you thinking about a donor-advised fund. Would a foundation make sense for your family. These are competent questions. They arrive early in a lot of client meetings, often as part of an annual planning check-in, and they get responses that let the meeting move along. But they rarely open anything. They ask the client to make a decision inside a framework the advisor has already chosen, and the framework is a structural one.
Most clients who want to give meaningfully are not, at the start, asking a structural question. They are sitting with something quieter and less finished. What they most need from the first question is not a set of options. It is permission to think out loud.
The question that opens that door, more reliably than any other I have found, is this:
What do you hope your wealth makes possible?
The question is spacious on purpose. It does not assume the client has giving priorities identified. It does not assume they know how much they want to give, or when, or through what vehicle. It does not assume the wealth is destined for charity at all. It simply asks what the client wants the wealth to do, in the widest sense, and lets them answer in whatever register feels true.
That register is often personal. Sometimes it is about family. Sometimes it is about a place, a memory, a debt, a fear, a hope for someone the client loves. Sometimes it is about something the client has never quite said out loud, and the question is the first invitation they have been given to try. What makes the question work is that it takes philanthropy off the table as a category and puts wealth on the table as a subject the client already thinks about, in language they already use.
By contrast, "do you have charitable intent?" is a narrow question, and it presumes the answer is a yes or no. Most clients who would give meaningfully will not describe themselves as having charitable intent. That phrasing sounds like something a tax attorney says, and clients respond by answering the tax attorney's question. "How much do you want to give?" comes too soon for many clients. The number is the last thing to settle, not the first. Asked before the meaning is clear, it produces guesses that the client will later revise, second-guess, or resent.
When you ask what a client hopes their wealth makes possible, prepare to sit in silence for a moment. This is a real question, and thoughtful clients will treat it as one. Some will look out the window. Some will start slowly and get more specific as they go. Some will begin somewhere unexpected, like a story about a parent, or a place they visited, or something they wish they had done differently. That is the work happening. Resist the urge to fill the silence with a follow-up prompt too soon.
When the client does answer, listen for a few things.
Listen for what the answer is really about. It may name a cause, but the deeper content is often about family, legacy, responsibility, or repair. A client who says they want their wealth to help their grandchildren "understand what they have" is telling you something quite different from a client who says they want to fund cancer research at the hospital that treated their father. Both answers matter, and both point toward different next conversations.
Listen for what is not in the answer. If a client talks at length about causes but never mentions their spouse or children, that is information. If a client talks about their family but avoids the word community, that is information. If a client's answer is entirely about the past, and never touches the future, that is information.
Listen for how much the client trusts their own answer. Some clients speak with quiet certainty. Others sound like they are figuring it out as they go, sometimes for the first time. The second group often needs more time and less structure. They are not looking to be steered. They are looking to be accompanied.
A few follow-up questions tend to open the conversation further, without narrowing it prematurely:
Where does your current giving feel most alive?
Are there causes, places, or communities you feel responsible to?
Who in your family needs to be part of this conversation?
Are there values you want your wealth to express more clearly than it does now?
What kind of giving would feel more honest to you?
That last question is often the one clients did not know they were waiting to be asked. Honest giving is a phrase most people have never encountered in a planning meeting. When it lands, it lands.
At some point in this conversation, you may notice that it has moved past the scope of a planning meeting. The client is asking questions about family dynamics you are not staffed to hold. They are wrestling with values in ways that are not going to resolve in a follow-up call. They are describing an interest in an issue area you would need to spend a month researching to advise on well. That is not a failure. That is the conversation working. It is also the signal that a philanthropic specialist can strengthen what you are already building.
Bringing in a philanthropic advisor at that moment is not a handoff. It is an extension of the trust the client has just placed in you. Your role does not shrink. The client's team gets deeper, and the work you are building for them gets served by someone whose job is precisely the questions the client has now arrived at.
For advisors who want a place to start, though, start here: what do you hope your wealth makes possible? Ask it in a real voice, at a real moment, and then let it do its work.
Shanon Solava is a Certified Impact Philanthropy Advisor and the author of Giving Without Grasping. She advises families, family offices, and foundations on the human side of philanthropy: purpose, values, family dynamics, and long-term stewardship. She holds two facilitation certifications from the Interaction Institute for Social Change and works with clients across the country from her home in Pennsylvania. Reach her at [email protected].