About fifteen years ago, fairly early in my career, I was brought in to handle the estate planning for a family that owned a successful business. I hadn’t found them on my own — their longtime CPA and financial advisor had introduced me. I was the newest person at the table, the one the others had vouched for, and I was very aware of it.
The plan had a centerpiece everyone treated as settled: the oldest son would take over the business. It wasn’t presented as a question. It was the foundation the rest of the plan was built on — the buy-sell, the voting shares, the way the other children were equalized with assets outside the company. When it came up, it came up the way a fact comes up. Of course he takes over the business.
I had a quiet question I never asked.
I’d spent a few hours with this family by then, and nothing I had seen told me the son actually wanted the business. He answered for his father in meetings. He deferred on every operating question to a younger sibling who clearly ran the day-to-day. When the succession came up, he nodded — but he never once spoke about it like a man describing his own future.
I noticed all of it. And I said nothing.
Part of it was the ordinary fear of making things awkward. The bigger part was that I’d been introduced by the other advisors, and questioning the one assumption the whole plan rested on felt like stepping on their toes — like the new attorney making things complicated when everyone else had already moved on. So I told myself what’s easy to tell yourself in that seat: they know this family far better than I do. They’ve thought about this. Who am I, three meetings in, to reopen the one thing nobody is questioning?
We built the plan around the assumption. It got signed.
A few years later, I learned how it played out. The father stepped back, the son stepped in, and within two years the business was struggling — not because the son was incapable, but because he had never wanted the job and had never found a way to say so. The younger sibling who had actually been running operations left rather than report to a brother in a role everyone had assumed into existence. The family fractured along the exact line nobody had been willing to look at. The plan did precisely what it was drafted to do, and that turned out to be the problem.
The CPA who had brought me in — the same one whose toes I’d been so careful not to step on — said something when it unraveled that I still think about. “I always wondered if he really wanted it. I figured someone would say something if it were a real problem.” We had both been waiting for the other person to be the one to ask.
I’ve thought about that family a lot. Not because the documents were wrong — they were clean — but because the most important question in the entire engagement was one I could see and chose not to ask.
Two lessons have stayed with me.
The first is that the estate planning attorney has to actually run the estate plan. When a family arrives through their CPA or financial advisor — as good families often do — it is tempting to treat the plan as a set of instructions to be drafted while the “real” relationship lives somewhere else. That is backwards. The other advisors are essential, and I am not diminishing them. But the person drafting the plan is responsible for whether it holds, and that responsibility cannot be exercised from the passenger seat. Deferring on the human assumptions because someone else owns the relationship isn’t respect. It’s abdication.
The second is that the uncomfortable question is not an intrusion on a good plan — it is often the thing that decides whether the plan is any good at all. A successful plan is not “the documents matched the client’s stated instructions.” A successful plan is one that does what the family actually needed it to do. And you frequently cannot know that without asking the question you are most tempted to leave alone.
Which brings me to a book, and a three-word phrase, that reframed how I think about all of this.
Enter the Danger
Patrick Lencioni is a management consultant and writer, best known for his work on teams and organizational health. In his book Getting Naked, he lays out a model for what makes a trusted advisor genuinely trusted, built around a counterintuitive idea: the willingness to be vulnerable with a client — to risk the relationship in service of the client — is the very thing that earns the relationship. The phrase at the center of it is three words long. Enter the danger.
The moment you most want to avoid — the awkward observation, the question that might embarrass someone, the thing you can see that nobody is saying — is the moment of highest value you can add. Stepping back from it protects you. Stepping into it serves the client.
Lencioni names three fears that keep advisors out of the danger. They are worth stating plainly.
Fear of losing the business. The advisor senses the client doesn’t want to hear it. The relationship is going well; the work is flowing. Raising the hard question introduces friction. The unspoken calculus is: if I say this, they might not come back. So we stay quiet, or we soften the observation until it has no edge, and we tell ourselves we were being diplomatic.
Fear of being embarrassed. The advisor isn’t sure they’re right. They think they see something, but they don’t have the full picture. If they name it and they’re wrong, they’ll look foolish. So they stay silent until they’re certain — and by the time they’re certain, it’s too late for the observation to matter.
Fear of feeling inferior. This one is the most uncomfortable. The advisor worries that raising the concern will mark them as less sophisticated than the client — that it will reveal they don’t understand something everyone else does. The client is a senior executive, or a major philanthropist, or someone with a long and successful track record. Who is the advisor to question them?
Every one of those fears is understandable. And every one of them, when it wins, costs the client something. In my succession story, all three were in the room at once — and the referral relationship that introduced me made each of them louder.
Ask the Dumb Question
Another of Lencioni’s principles: ask the dumb question. The one you’re sure everyone already has an answer to. The one that feels like it would embarrass you to ask because it’s so basic. Ask it anyway.
Most of the time, the “dumb” question is the one that reveals an assumption nobody has tested. Does the child you’re handing the business to actually want it? Are we sure your son is ready to manage this money? Do your daughters know what you’re planning? Have you actually talked to your spouse about what would happen if you went first? Is your successor trustee even aware they’ve been named?
These questions are “dumb” because the stated answer is usually yes. But when you ask them — slowly, with genuine curiosity, leaving room for the answer to be complicated — a surprising number of clients pause. Sometimes they say, actually, no. Sometimes, we haven’t talked about that in a while. Sometimes, that’s a good question, and then they change the subject — which tells you something too.
The advisor willing to ask the dumb question does more for a client than the advisor who is exquisitely technical and never goes near the soft place.
Tell the Kind Truth
There is a difference between honesty and cruelty, and Lencioni draws it cleanly. Telling the kind truth means saying the hard thing in a way that is clearly in service of the client — not in service of the advisor’s need to be seen as smart, or right, or brave.
“I want to name something I’ve been thinking about, and I could be wrong — tell me if I am.” That’s kind.
“I think this might be a mistake, and I want to make sure you’ve considered it before we execute.” That’s kind.
“I notice we haven’t talked about this in the months we’ve been working together. Can we spend a few minutes on it?” That’s kind.
The kindness isn’t in softening the content. It’s in the framing — in making clear the observation comes from care, and that the client has room to disagree, reject, or sit with it without having to defend themselves.
Always Consult, Never Sell
The last principle I want to name is this: always consult instead of sell. Even before a client has engaged you, even when the relationship isn’t established — act like the trusted advisor. Give the honest assessment. Raise the hard question. Point out the thing they should consider. Treat the conversation as if you were already serving them, not auditioning to.
Most advisors do this backwards. They sell during the courtship and consult only once the engagement is signed. Lencioni’s observation is that the reverse is far more powerful: you demonstrate the value of the relationship by providing it, not by describing it.
Every month or so I am in a preliminary conversation where I realize, within fifteen minutes, that what the prospective client thinks they need isn’t what they actually need. Sometimes I tell them and it reshapes the engagement. Sometimes what they need isn’t something I do, and I refer them out. Sometimes the honest observation costs me the work. And every time, I have the sense that the conversation built something more valuable than the engagement would have been.
The Hero Complex
One thing Lencioni doesn’t dwell on, but I think is worth naming: entering the danger has to be for the client, not for you.
Some advisors get a charge out of the hard conversation. They like being the one who says the thing nobody else will. They start entering the danger in a way that makes the room about them — their courage, their insight, their willingness to speak truth. That isn’t service. It’s performance, and clients feel it.
The real work is quieter. You notice the thing. You weigh whether it matters. You find a way to name it that leaves the client’s dignity and decision-making authority intact. You don’t need credit for having said it. You just need to have said it.
Enter the danger because the client needs someone to — not because you need to be the one who did.
Over to You
Think about the last time you stayed quiet in a room where you should have spoken. What were you afraid of — and was it really about the client, or about you?
And if you had entered the danger, kindly and specifically and on the client’s behalf, what do you think would actually have happened?
Originally published on LinkedIn on 2026-06-19. View the LinkedIn version.