There is a version of the philanthropic conversation that happens in most advisor offices, and it goes something like this. A client sits across the desk. Their portfolio has grown, or their business has sold, or their estate plan is due for its annual review. The advisor raises charitable planning. The client agrees, in principle, that charitable planning matters. A donor-advised fund gets funded. A trust structure gets discussed. Everyone leaves the meeting having done responsible work.
And then, sometimes months later, the client says something to a spouse, or a friend, or their own advisor in a quieter moment, that sounds like this: I'm not sure any of this is really doing what I hoped it would do.
The Philanthropic Initiative has been tracking a version of this pattern for over a decade. Their 2026 study of the philanthropic conversation confirms what many of us in the field have long suspected: HNW clients want these conversations with their advisors. They also increasingly report that when the conversation happens, it stops short of what they actually wanted to talk about. A rising share say their philanthropic needs exceed what their current advisors can meet on their own, and most would welcome being referred to a specialist. (Worth verifying the exact figures before publishing.)
The temptation is to read that finding as an indictment of advisors. It is not, and it should not be.
The gap is not a competence problem. It is a training problem, and a scope problem. Financial planners, estate attorneys, and CPAs are trained to solve technical problems well, and the problems they are trained to solve are real. Tax efficiency matters. Trust structures matter. Titling and beneficiary designations matter. What is harder to see from inside the technical work is the moment when a client's question stops being technical and becomes something else entirely.
Because the questions underneath charitable planning are almost never technical. They are questions like:
What is this wealth for?
What do I owe, and to whom?
What do I want my children to understand about how we got here, and what they should do with it?
What kind of ancestor do I want to be?
What harm has this wealth touched along the way? And what, if anything, might repair look like?
These are not questions an estate plan can answer. They are barely questions a single conversation can hold. They are the questions that make some clients go quiet mid-meeting, or start bringing up their adult children unprompted, or ask an oddly specific question about a nonprofit they visited last summer. They are the signals that the conversation has moved past the vehicle and into the meaning.
No advisor needs to become a philanthropic facilitator, a family systems specialist, or a program officer with issue-area expertise. What advisors do need is the ability to recognize when the conversation has crossed that threshold, and to know that a client who has crossed it has not become someone else's client. They have simply arrived at a place where the depth of the conversation now exceeds the scope of the meeting.
That is the moment when bringing in a philanthropic specialist strengthens the advisor relationship rather than threatening it. The client experiences it as their advisor going deeper, not handing them off. The specialist works alongside the planning team, focused on the questions the plan cannot answer. When that work is done well, the technical work an advisor built ends up serving something the client can articulate, believe in, and pass forward with confidence.
For advisors who want to test whether a client's charitable planning conversation is ready to open up, a few questions tend to move it there without forcing anything:
What do you hope your wealth makes possible?
Are there values you want your giving to express more clearly than it does now?
Who else in the family needs to be part of this conversation?
Where does your current giving feel alive, and where does it feel automatic?
Any one of those questions can shift a meeting. Not because they are clever, but because they signal to a client that this is a room where the deeper question is welcome. Most clients have been waiting to be asked.
The philanthropic conversation gap is real, but it is not a tax problem, and it is not a failure of care. It is the moment when the technical work an advisor is trained for meets a set of questions no training prepares anyone for. That moment does not have to be uncomfortable, and it does not have to be handled alone.
That is what specialists like me are for. I work alongside advisory teams as the person focused on the questions beneath the plan: what the wealth is for, what the family wants it to say, and how everyone stays committed to it over time. If you have a client sitting on questions the plan cannot answer, I would welcome the conversation.
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].