Early in my career, I built a plan that did exactly what my client asked for and almost nothing she actually wanted. The whole gap came down to a single word.
She was in her late sixties, very successful, deciding what to leave her children, and she told me she wanted them to be “independent.” I nodded. I wrote it down. I thought I understood her, because I knew what the word meant to me.
It took a few meetings to realize I had never actually checked. For her, independent meant her children should never have to rely on anyone — not on each other, not on her, not even on the trusts she was creating. She wanted the inheritance to sit quietly in the background as a last resort, something they were not supposed to count on or plan around.
That is nearly the opposite of what the word meant to another client I worked with not long after — a man in his fifties, using the same word about his own kids. For him, independent meant they would have the freedom to choose their lives without money dictating the answer. The inheritance was a foundation to build on, not a safety net to forget. To him that freedom was the entire point; without it, his children would be trapped in the same scramble he had spent his life trying to escape.
Same word. Nearly opposite plans. Early on, I would have heard “independent” and quietly filled in my own definition — and built the wrong plan without ever realizing I had. I nearly did exactly that with the first client.
What I do differently now is the subject of this issue.
The Script
We all carry scripts. A script is a deeply held, mostly invisible way of understanding something — a word, a relationship, a situation — that we have built up over a lifetime and rarely notice we are using. When a client uses a word, they are reading from their script. When we hear it, we are reading from ours. Most of the time the two are close enough that the conversation works. Sometimes they are not, and the mismatch stays invisible until something goes wrong.
Family. Security. Fair. Enough. Success. Legacy. Responsibility. Trust. These words appear in almost every estate planning conversation, and every one of them carries a different meaning for every client — and for every advisor.
The practitioner failure isn’t disagreeing with a client’s script. It’s assuming your script is theirs.
Two Parts of Every Script: The Value and the Rule
A few years ago I picked up a distinction I first heard framed by Tony Robbins, and it gave me language for something I had been fumbling toward for a long time. It is the difference between a person’s values and their rules.
A value is the state a person is actually after. Not the asset, not the document — the feeling underneath it. Security. Freedom. Belonging. Being respected. Knowing they mattered. When a client says they want their children “taken care of,” the value is rarely the money. It’s the state they imagine the money producing.
A rule is the private, usually unspoken set of conditions that has to be met before that person will let themselves feel they have the value. And rules are where the real complexity lives, because they are almost always invisible — to us, and very often to the client.
Here is what makes this so easy to miss. Two people can hold exactly the same value and have completely different rules for satisfying it. A husband and wife both say they want a plan that keeps the family close. They are not, in fact, in disagreement about anything that matters — they share the value. But his rule for “close” is everyone gathers, no one drifts, we stay one unit. Her rule is each of them is free to live their own life and still knows the door is open. Neither has ever said the rule out loud, because to each of them it isn’t a rule — it’s just what the word obviously means. They have been married thirty years operating from two different rulebooks for the same word, and the first time the difference surfaces is in your conference room, over a question about how the trust should distribute.
When you can see that, you stop refereeing a disagreement that isn’t really there. The couple doesn’t need to be talked out of opposing values. They need someone to notice they share one and are colliding over the rules underneath it.
Your Values Set the Weather You Live In
There is a second thing the values-and-rules distinction explains, and it took me years of client (and personal) work to really absorb. A person’s values, and the rules they attach to them, do more than shape what they want from a plan. They set the emotional climate that person already lives in — the default state they wake up inside of, before you or anyone else enters the picture.
A client whose highest value is security, with strict and demanding rules for when she is allowed to feel secure, does not live in security. She lives in vigilance. A client whose highest value is freedom lives, quietly, with one eye on the exit — alert to anything that might tie him down. You are not arranging assets for a neutral person. You are doing your work inside a weather system the client brought with them, and the plan you draft lands in that weather whether you account for it or not.
This is why a technically excellent plan sometimes fails to give a client any peace. If her rule for feeling secure is I never have to depend on anyone and nothing can ever go wrong, there is no trust on earth that satisfies it, because the rule itself is built to be unsatisfiable. The plan was never the problem. The plan was being asked to do something only a different rule could do.
When What They Say and How They Live Don’t Match
Now the part that confused me longest, because on its face it looks like hypocrisy and it almost never is.
People will tell you, clearly and sincerely, what they value — and then live, and plan, in direct contradiction to it. A woman tells me nothing in the world matters more to her than her children staying close to one another, and the distribution scheme she insists on would quietly set them against each other for the rest of their lives. A man tells me he wants above all to be generous to the next generation, and every gift he describes comes with a leash attached. You can see the value plainly. You can also see they are living the opposite of it.
I used to think the job was to point out the contradiction and correct it. It isn’t. The contradiction is information, and there are usually two things hiding inside it.
The first is a self-defeating rule. The woman who wants her children close may have an unspoken rule that close means they depend on me — and a plan built to keep grown children dependent on a parent is a plan almost guaranteed to breed the resentment and rivalry that drive them apart. Her rule is sabotaging her value, and she can’t see it, because the rule is invisible to her.
The second is a competing value running underneath the stated one — and it is very often a fear. Robbins would call it a “moving-away-from” value: the state we organize our lives to avoid, which usually has more power over our behavior than the state we say we’re moving toward. The generous man with the leash on every gift may value generosity, truly — but he values not being taken advantage of more, or not becoming irrelevant to his children, and that quieter fear is the one actually writing the plan. He is not lying when he says he wants to be generous. He is telling you the value he is proud of while a value he is not proud of does the steering.
So how do you understand it, and how do you help? You get curious about the gap instead of trying to resolve it for them. You say something like: You’ve told me how much it matters that they stay close — and I notice the plan you’re describing would put them in competition with each other. Help me understand that. Then you stop talking. Most of the time the client has never seen the gap you just named, and naming it — without judgment, as a thing you’re puzzled by rather than a thing you’re correcting — does more than any redraft could. You are not catching them in a contradiction. You are showing them a rule, or a fear, they had been operating from without knowing it was there.
The Rules No Plan Can Satisfy
And then there are the clients who hand you a set of rules that no document, however well drafted, can ever satisfy.
I want them provided for, but not entitled. Protected, but free. Equal, but rewarded according to who deserves it. Generous to charity, but with nothing left on the table. And I’d like to set it all up once and never have to think about it again.
Every one of those wishes is reasonable on its own. Held together, several of them directly contradict each other. If you treat that as a drafting problem — and it is so tempting to, because drafting is what we’re good at — you will build an ever more elaborate instrument, layering in conditions and contingencies and trustee discretion, and the client will sign it and still feel vaguely unsettled. Because the unease was never in the trust. It was in the rules. You cannot draft your way out of a contradiction the client is holding inside themselves.
The most valuable thing you can do here is the thing that feels least like lawyering. You name the contradiction and you hand the choice back to them. You can build a plan that protects them or one that frees them. The place where those two pull against each other isn’t a drafting question — it’s a decision, and it’s yours, not the document’s. Sometimes the real deliverable in that meeting is not a revised plan. It is a revised rule. The client leaves having loosened a condition they didn’t know they were imposing on everyone, including themselves — and only then can any plan you draft actually do its job.
The Postures We Default To
So far this has all been about the client’s invisible operating system. Here is the part that took me longest to see, because it is about mine.
Every advisor I know has a default way of being in the room — a characteristic posture they fall into, usually without noticing, because it is simply the one that feels most natural to them.
Some show up as the expert. They know the rules, they’ve seen the patterns, they have the answer. What they offer is clarity and competence, and it is exactly right when the client needs answers. Some show up as the protector — careful, watchful, focused on making sure nothing bad happens to the client. What they offer is diligence, and it is exactly right when the client is exposed or overwhelmed. Some show up as the problem-solver, drawn to the hard case the one other professionals walked away from; what they offer is creativity under pressure, exactly right when the client has a problem nobody else would touch. And some show up as the companion — present, unhurried, willing to listen — offering the feeling of being genuinely heard, which is exactly right when the client needs to think out loud before they can decide.
None of these is wrong; each is valuable in the right situation. The trouble is that most of us show up the same way no matter what is in front of us — because our default is invisible to us. The client who needs to think out loud doesn’t need the expert handing them answers. The client who is drowning doesn’t need the companion nodding along. The client who needs to be slowed down before a mistake doesn’t need the problem-solver spinning up something clever.
The advisor who knows their own posture can choose when to use it. The advisor who doesn’t is used by it. It is the same lesson as the client’s rules, turned on yourself: the operating system you can’t see is the one running you.
Knowing When to Change Hats — and When to Refer Out
There is a harder version of this that I had to learn slowly.
Sometimes a client doesn’t just need a posture that isn’t my default — they need one I have to step into deliberately, for the length of an engagement, and inhabit for real. The client who needs to think out loud doesn’t need me to be a companion by nature; they need me to put that hat on, genuinely, while we work together. Most of the time that is entirely possible, and recognizing which hat the moment calls for — then being willing to wear it even when it isn’t the one I reach for first — is most of the job.
But not always. Sometimes what a client needs is something I cannot give them well. Not because I lack the technical skill, but because the relationship they are looking for isn’t one I can authentically provide, or because the work sits in a place I am not the right person to hold. The honest move there is not to force the hat on and hope. It is to recognize the mismatch and point them toward someone built for exactly what they need.
So before I take on a client now, I try to answer one question honestly. Can I put on the hat this engagement requires — not as performance, but for real — and serve this person well, even though it isn’t my default? If the answer is yes, the work is staying aware of it so I don’t slide back into my reflex the moment they need something else. If the answer is no — if what they need is genuinely beyond what I can do well — then the most valuable thing I can offer is to say so early and send them to someone who can.
Neither answer is a failure. Pretending you don’t know which one is true — that is the failure.
The Diagnostic
I’ve ended up with three questions, two I ask myself and one I ask the client.
What does this word mean to them, and what does it mean to me? I pick the one word the meeting will turn on — legacy, security, family, fair — and make myself hold both definitions before I sit down. Not to predict the client, just to stay aware of my own assumption.
What posture am I in right now, and is it the one this client needs? When I am tired or stressed or coming off a hard conversation, I am far more likely to fall back into my most natural mode whether or not it fits. The question interrupts the autopilot.
And the one I ask out loud: What would have to be true for you to feel that? Whatever the value is — secure, taken care of, fairly treated, at peace with the plan — I keep asking some version of this until we reach the actual conditions underneath it. That single question surfaces almost everything that matters: the rule the client is using, whether it’s a rule any plan could meet, and whether a quieter fear is sitting behind the value they named. It is the closest thing I have to a master key, and it costs nothing but the willingness to not assume I already know the answer.
None of these takes more than thirty seconds, except the third, which sometimes takes the whole meeting and is worth every minute of it.
Your Clients Are Doing It Too
Your clients are reading from scripts as well — running their own values and rules, mostly unaware of either. So is their spouse, from a different rulebook. So are their children, who will read the plan someday through rules that may not even be written yet.
Naming all of this isn’t only for your own awareness — it is work you can do for the family. When a husband says legacy and his wife clearly hears something else, you are the person in the room who can notice it, slow the conversation down, and ask: can we spend a minute on what that word means to each of you, and what would have to be true for each of you to feel we’d gotten it right?
Most of the time, the couple never has. They have been married thirty years, using the same words, assuming the same meanings, never once comparing the rules underneath. The first time they actually do it is in your conference room — and that conversation, the one that looks like a detour, often turns out to be the most important one you have with them.
Over to You
Pick a word that comes up in almost every planning conversation you have. Family. Security. Legacy. Trust. What does it mean to you — and just as important, what would have to be true for you to feel you had it?
And when you hear a client use it — do you check, or do you assume?
Originally published on LinkedIn on 2026-07-02. View the LinkedIn version.