A successor trustee called me eighteen months into the job, technically with a question about an investment account.
We spent ten minutes on the account. We spent an hour on everything else.
She was administering her mother’s trust for herself and two siblings. On paper, she was the obvious choice — organized, trusted, the one who’d always handled things. In practice, she was coming apart. Every distribution turned into a referendum. One brother thought she was being stingy; the other thought she was being reckless; her sister thought she was playing favorites. She’d begun second-guessing decisions she knew were right, because three people she loved were pulling her three directions and she could no longer tell where her own judgment ended and their anxiety began.
She didn’t need a statute. She needed to know she was allowed to hold the line without losing the family.
No one had prepared her for any of it. We’d named her in an afternoon, years earlier, and handed her the weight at the worst possible moment — while she was grieving — never mentioning that the hard part wouldn’t be the accounting.
The question we never ask
When we help a client choose a trustee, we run through a predictable list. Is this person responsible? Good with money? Will the other beneficiaries trust them? Likely to be around long enough to see it through?
All reasonable. None of them predicts the thing that actually determines whether a trustee survives the role: can this person stay themselves when the family’s anxiety floods the room?
Because that’s the real job. The arithmetic can be hired out. What can’t be delegated is standing in the middle of a grieving, frightened, sometimes divided family and making steady decisions anyway — holding a boundary with a sibling you love, saying no without going to war and yes without being run over, absorbing a great deal of emotional pressure without either caving to it or hardening against it.
That’s a capacity, not a credential. And it’s invisible on the résumé we usually screen from.
Differentiation, in a word
Murray Bowen, who spent his career studying how families behave under stress, had a term for this capacity: differentiation of self — the ability to stay connected to the people you love and still think for yourself under pressure, to feel the pull of the group without being governed by it.
Every family runs on two forces at once: the pull toward togetherness and the pull toward individuality. Under stress the togetherness pull spikes, and the least differentiated person in the system gets absorbed by it. A well-differentiated trustee can be fully present to the family’s grief and still make a clear decision. A poorly differentiated one gets metabolized by the anxiety and starts making decisions to manage everyone’s feelings instead of the trust’s purpose.
The rabbi and family therapist Edwin Friedman called the mature version of this a non-anxious presence — the person whose steadiness lowers the temperature of the whole room, not by going cold or checked-out but by staying warm and clear while everyone else escalates. That is exactly what a good trustee provides, and exactly what we never think to look for.
You see the two failure modes constantly. The over-fused trustee can’t say no to anyone, absorbs every complaint, and slowly bends the trust to keep the peace. The cut-off trustee does the opposite — goes rigid, stops returning calls, hides behind the document, and lets the relationships rot. Both are differentiation failures. Both were predictable, if anyone had been looking.
What the role actually is
James Hughes, who has written as thoughtfully as anyone about wealth across generations, describes the trustee not as a technician who moves money but as a steward — someone whose real work is the flourishing of the people the trust was built to serve. That’s a far bigger job than we describe when we hand it over.
And none of it starts with the document. It starts with self-knowledge. You cannot steady a system you can’t see yourself standing inside of. The trustee who knows their own reactivity — that they tend to cave, or to harden, or to need everyone happy — can manage it. The one who doesn’t gets managed by it.
We hand people the weight in an afternoon and check the box. The preparation — the part that decides whether they can actually carry it — we almost never do.
The practical move is small and almost never made. Before you finalize the appointment, ask the differentiation question out loud: can this person hold a boundary with the beneficiaries and keep the relationship? Have they ever, in this family, said the hard thing and stayed connected? And after the appointment, prepare the person, not just the paperwork — a conversation about what the role will actually feel like, explicit permission to hold the line, and a standing place to bring the hard calls.
Over to You
When a client names a successor trustee, how much of your attention goes to whether that person can stay steady under family pressure — versus whether they can read a statement and keep good records?
And for the trustees already serving in your clients’ plans: who’s checking on how they’re carrying it?
Originally published on LinkedIn on 2026-08-14. View the LinkedIn version.