Who Do You Trust?

By: Leslie Gross, Senior Advisor

On isolation, being burned, and why the most powerful thing in philanthropy might be a room where you can admit you were wrong

Here’s something that rarely gets said in philanthropic settings.

This work can be profoundly lonely.

The kind of lonely that comes from being surrounded by people and still not knowing who you can trust.

It happens in family governance meetings where old tensions find new contexts, at conference tables where you’re being assessed as much as included, and in site visits where genuine connection competes with the weight of who controls the check.

These are vital relationships, but each carry their own baggage.

They come with dynamics that make full honesty expensive: the grantee-grantor power differential that shapes what people will say to your face, the sibling or spousal friction that predates the foundation, the intergenerational handoff that nobody fully agreed to.

To hold your values, set real limits, and show up as an effective funder, you learn to protect a version of yourself that almost no one in your philanthropic life actually knows.

This matters enormously as the projected $124 trillion wealth transfer accelerates. A significant share is moving through family foundations and donor-advised funds managed by Gen X women who are taking their philanthropic stewardship seriously.

What the data doesn’t capture is how many of them are doing that work without anyone they can fully level with.

That’s not a personal failing.It’s the architecture.

What Is a Peer Community for Philanthropists?

High achievers in other fields have what researchers call a personal board of directors: a deliberately assembled group of people who serve different functions, cover different blind spots, and offer different kinds of value at different moments.

The evidence is clear: your support network, not just the quality of any single advisor, is one of the strongest predictors of sound decision-making over time.

No single person has the bandwidth, the range, or the objectivity to fill every role.

For philanthropists, the peer accountability circle is that board. It is a small, consistent group of fellow philanthropists who convene regularly to share real challenges, test their thinking, and hold each other to their own stated intentions.

Unlike conference programming or content-focused networks, peer accountability circles are built around reciprocal disclosure: what you bring is a real question you are carrying, not a polished update.For family foundation leaders, high-net-worth donors, and anyone navigating the weight of inherited or earned wealth, a peer accountability circle offers something the broader philanthropic field does not: a room where you can be honest without consequence.

The Trust Problem in Philanthropy No One Talks About

There is a specific kind of wariness that comes with having resources in a world that wants them.

You have been in rooms where someone was warm and attentive, and you eventually understood that the warmth was calibrated to your checkbook or your connections, not to you. You have shared a genuine concern about your foundation’s direction and watched it surface later as a talking point. You have learned what happens when you open up in the wrong room.

So you become careful. You get comfortable performing confidence you do not always feel, because the cost of being seen as uncertain can be high.

This is not cynicism.

It is an entirely rational response to a real pattern built on accumulated experience. This is why the Women’s Philanthropy Institute at Indiana University has found that women’s philanthropic networks function at their best when built on genuine shared values and mutual accountability, not on proximity to resources.

The gap between those two things is exactly where the wariness lives.

Conferences Offer Contact. Trust Requires Something Else.

In some of these spaces, you are the walking ATM. The networking is not neutral, and you can feel it. In other contexts, you are the student, there to receive expertise from onstage voices with credentials and frameworks. The dynamics of a philanthropist navigating sibling conflict, spousal disagreement about giving priorities, or an intergenerational transition at a family foundation are not what the breakout sessions were designed to address.

But even in the best conference rooms — those with good programming and genuine goodwill — there is a structural failure that no agenda can fix.

A single encounter cannot build real trust.

Psychologists Roy Lewicki and Barbara Bunker identified three stages of trust that unfold sequentially over time. The first is calculus-based: a surface-level calculation that this person seems credible, that sharing a little seems safe. The second, knowledge-based trust, requires repeated interactions that build genuine familiarity and predictability. The third and deepest stage, identification-based trust, is where people have internalized each other’s values and intentions enough to function as real allies.

A meta-analysis of 39 studies on trust in professional relationships confirmed what the model predicts: trust increases consistently with the duration and frequency of contact. A conference encounter, however meaningful in the moment, reaches the lobby of stage one. What philanthropists navigating real decisions actually need is stage three.

What Trust in a Philanthropist Peer Group Actually Requires

Genuine trust in a peer context requires something specific: the reasonable belief that you can be wrong in this room without paying for it later.

That means being able to say you made a grantmaking decision you now regret, and having the people around the table respond with curiosity rather than judgment. It means changing your mind about something you said with confidence three months ago and having that treated as evidence of growth rather than inconsistency. It means having access to what researchers describe as an emotional anchor: someone who can hear the full version of what is happening, not the polished one, and help you think more clearly because they have done the same kind of work themselves.

The most powerful thing about these spaces is not the advice. It is the permission to not have it all figured out.

Confidentiality is the foundation on which everything else rests. Without the genuine belief that what is said in the room stays in the room, the conversations that matter most will not happen.

It requires time, reciprocity, and a container held with enough consistency that people come to trust not just the individuals in the room but the structure itself.

What Grows Inside a Philanthropic Peer Community

I’ve watched something happen over time in peer accountability circles that I did not fully anticipate when I first began facilitating them.

People who you would never have imagined in the same room find each other. The woman who chairs a multi-generational family foundation and the woman three years into stewarding a first-generation DAF. Philanthropists whose politics lean in different directions, but who share a genuine commitment to getting the work right. They become, over time, some of each other’s most trusted advisors — and in the fullest sense, each other’s board.

For many philanthropists, particularly those who came to it through inheritance, the work can feel like an obligation at best and an identity crisis at worst.

Sitting in a peer community with people who understand the specific weight of it changes the relationship to the work.

The Peer Community Women Philanthropists Have Always Built

The peer accountability circle is not a new idea. It is a very old one that has been formalized.

Women have been building deliberative community for one another for as long as communities have existed: in mutual aid societies, in church benevolent associations, in the informal networks that organized civic life before institutions were willing to.

The giving circle model, which the Women’s Philanthropy Institute at Indiana University identifies as one of the defining developments in contemporary women’s philanthropy, is a direct descendant of this lineage.

Women who maintained connection to peer giving communities during the pandemic sustained their philanthropic engagement at higher rates and directed it more strategically than those navigating the same pressures alone. The Stanford Social Innovation Review reached the same conclusion. The future of philanthropy is female, and the infrastructure driving that is not institutions, but relationships built in rooms that do not make the agenda.

Community is not supplemental to good philanthropy. It is load-bearing.

The Question Underneath the Question

The question of who you trust is not really about individuals.

It’s about whether you have a structure that makes trust possible.

That kind of trust has to be built deliberately. It requires time, reciprocity, safety, and a shared commitment to each other’s clarity.

It does not happen at conferences. It does not happen in one-on-one advisory relationships, however skilled the advisor. It happens in rooms that are built for it, with people who have decided together that honesty is worth the risk.

For Gen X women in philanthropy right now, carrying the weight of the great wealth transfer, navigating family dynamics no one briefed them on, making decisions that matter in isolation they did not choose, the question is not whether they need those rooms.

The question is whether they have one.

About Grant Philanthropic Advisors:
We’re an independent firm helping clients to focus and maximize their philanthropy—in turn, strengthening the fabric of our communities. Founded in 2019, we help donors move from responsive patterns of giving by assisting clients to identify values and become more strategic in their philanthropy. Our goal is to help donors to become more effective as change-makers. We work with foundations (large and small staff teams), donor advised fund holders, multi generational families, individuals, philanthropy supporting organizations and corporations to design philanthropic strategies.