What a governance structure can’t do is tell a donor who they actually are as a giver
Here’s a scenario that plays out more often than the sector likes to acknowledge.
A high-net-worth individual, let’s say a successful entrepreneur or a second-generation family wealth holder, decides they want to give more intentionally. They reach out to a lawyer, an accountant, or a financial planner. They’re advised to establish a private foundation or a donor-advised fund. Documents get signed, a vehicle is structured, and tax efficiency is achieved.
And then, not much happens. Or what happens can feel very, very thin. A few grants go out the door, a charity gala gets a table, the annual disbursement quota is met. But the donor (if you ask them) will honestly tell you that they don’t feel like a philanthropist. They feel like they have a philanthropic structure. Those, unfortunately, are two very different things.
The financial and legal infrastructure of strategic giving is necessary, and I’m not arguing against any of it. But it isn’t sufficient, and the sector’s tendency to conflate the two is, in my experience, doing real harm to donor experience and to the organizations that ultimately depend on major gifts.
What a governance structure can’t do is tell a donor who they actually are as a giver. It can’t surface the experiences, communities, and values that should drive their philanthropic decisions. It doesn’t create the relationship between a donor and a cause that makes giving feel meaningful rather than obligatory. And, it certainly can’t build the kind of donor who stays engaged for decades; who invests in organizations rather than just funding programs, and who eventually brings the next generation into the work.
That is the work of a philanthropy advisor, and it’s a discipline in its own right.
When I begin working with a new client, the first thing we do isn’t reviewing their portfolio or their tax position. Instead, we talk. We talk about where they came from, about the moments in their life when they felt most connected to something larger than themselves. Sometimes, we talk about the communities that shaped them; the Northern Ontario town, the mid-sized prairie city, the immigrant neighbourhood, and what those places need now.
This is what I call “discovery,” and it’s the foundation of every philanthropic strategy I build—not because it’s a nice values-clarification exercise, but because it’s the most reliable way I’ve found to surface what a donor actually wants from their giving, as opposed to what they think they’re supposed to want. This difference matters enormously.
A donor who gives because they genuinely feel called to a cause gives differently than one who gives because it’s expected or tax-advantaged. They give more consistently, more generously, and with more strategic intelligence over time. They’re also, frankly, a better partner to the organizations they fund.
One of the most underused tools in the philanthropic advisor’s kit is experiential engagement. It’s not found at a gala, nor a site visit where the donor gets a polished presentation and a gift bag at the end. A real encounter with the work is often what moves the needle, and it can look very differently across different types of people. It could be a morning of volunteering at a funded organization, a conversation with a program participant, or an afternoon in the field with a frontline team member whose dedication drives progress forward.
I’ve watched those encounters change people. Not in a sentimental way, (though emotion is often part of it) but in the way that any real experience changes how we understand something. The donor who has sat across from a family that used emergency housing services thinks differently about what it means to fund housing than the one who’s only read the need statistics. Their giving becomes more specific, more patient, and inherently more effective.
Designing for those moments is part of the advisor’s job. It means having relationships with the organizations in a client’s portfolio that go beyond the grant agreement. It means knowing which executive director will make a donor feel genuinely useful (not just welcomed) and which volunteer program will create authentic connection rather than managed distance.
This is worth naming directly, because too often the conversation about donor experience gets framed as something the sector does for donors. In fact, it’s something the sector does for itself.
Connected donors are better donors. They give to operating costs. They give during difficult periods, not just when things are going well. They refer their networks. They offer skills and relationships, not just money. And they stay—which, in a major gifts context—is just about everything.
The most durable charitable relationships I’ve witnessed have one thing in common; the donor doesn’t experience their giving as a transaction. They experience it as a relationship with a community they care about. That shift, from transaction to relationship, is what good philanthropy advisory actually makes possible.
It’s also, I’d argue, what the sector needs more of. Not more giving vehicles. More givers who feel genuinely connected to the work.
Keith Z. Brewster is the Founder and Principal of WAVE Philanthropy, where he helps individuals, families, foundations, and organizations turn generosity into meaningful impact. Drawing on a unique background in scientific research, entrepreneurship, business development, and philanthropy, Keith brings strategic thinking and lived experience to every engagement. Known for his innovative and experiential approach to giving, he helps clients create purposeful, lasting legacies through thoughtful governance, community engagement, and transformational philanthropy.
