What They Worry About and Hope For

Imagine a tutor named Grace Pereira who visits Mrs. Lin at home to talk about her son, Owen. He starts his last year of high school in the fall. Mrs. Lin mentions that Owen’s grades slipped in the spring. Grace has another student across town at five, so she keeps the meeting moving.

Near the end, Mrs. Lin asks, “Do you give homework between sessions?”

“Yes, about an hour a week,” Grace says, and she moves on to her rates. Mrs. Lin thanks Grace and says that she will think about it. Two days later, Mrs. Lin writes that she has hired a tutor who checks Owen’s work every week.

Suppose instead that Grace thinks about why Mrs. Lin is asking before she answers. “I set Owen one task after each session and check it at the start of the next, so you’ll know each week whether he did it,” she says. “It comes to about an hour a week.” Mrs. Lin books Grace for two sessions a week through the school year.

Grace gives the same homework both times. Mrs. Lin’s question is about homework, but her worry is whether Owen will work when nobody is watching. The second answer speaks to that worry first, with a fact Mrs. Lin can check each week. Then it gives the hour.

Wealthy clients share a few common worries

Surveys of wealthy people point to four worries that come up often, and each worry has a hope on its other side:

• Their children. In Bank of America’s 2026 study of wealthy Americans, 61% of the richest group worried about how motivated their children are. That group had more than $25 million to invest. The hope on the other side is that their children will do well on their own.
• Their health. The same study surveyed people with at least $3 million to invest. Of them, 94% said they were already taking steps to improve their health and live longer. The hope is a long and healthy life.
• Their privacy and safety. In a 2025 Chubb survey, online security was the top worry of people with at least $1.5 million to invest. Their biggest concerns were cyberbullying and identity theft. The hope is a home and family that stay private.
• Keeping what they have. In a 2015 UBS survey reported by Funds Society, half of the people worth $1 million to $5 million shared a fear. They were afraid that “one major setback,” such as losing a job or a crash in the markets, would hurt their way of life. The hope is a family that stays secure.

A fifth worry comes up when a client cannot judge what your work is worth. A client who is new to having money is one example. That client may worry about paying too much.

Keep these five worries in mind when a client asks you something, because any one of them can shape the question.

A worry often sits under an ordinary question

In the course’s view, a client who has just met you may not want to say a worry out loud. A practical question is easier to ask, so the worry comes out as a question, such as Mrs. Lin’s question about homework. When your answer speaks to the worry, the client knows that you heard what they meant.

The course suggests two rules for that answer. First, use a fact the client can check, such as a schedule or a number. A fact can be tested, and a general promise cannot. Second, do not say the worry out loud. The client chose not to say it, and naming it tells them that their worry showed.

Here are some questions a professional might hear. Next to each is the worry or hope that may sit under it, and an answer that speaks to it first:

The question	What may sit under it	An answer that speaks to it first
An event planner hears, “How many events do you have that weekend?”	Will my daughter’s wedding get your full attention?	“Yours is my only wedding that weekend, and I will be on site from eight in the morning until the last guest leaves.”
A home organizer hears, “Who else will be in the house?”	Can I trust the people who see our things?	“Everyone who comes into your house has signed your confidentiality agreement. That is me and Ana, who has worked with me for four years.”
A photographer hears, “Where will these photos end up?”	Will pictures of my children end up online?	“Nothing goes on my website or social media without your written yes. Your gallery is private, with a password only your family has.”
A specialist realtor hears, “What if prices drop after we buy?”	One bad year could hurt our way of life.	“Here’s what similar houses on this street did in the last downturn. We’ll set a price you’d be comfortable holding through one like it.”
A private chef hears, “Can you send the receipts?”	Am I paying more than I should?	“Every receipt is marked with the meal it was for, so you can see what each dinner cost. I send them each week.”

Once you know a client’s worry, the course suggests that you keep answering it. One good answer shows the client that you heard them once. A regular update shows it every week. After the booking, Grace sends Mrs. Lin a short message every Friday without being asked. A typical one says, “Owen did Tuesday’s task. It took him 40 minutes.”

Why naming the worry out loud goes wrong

Imagine a personal trainer named Luis Ortega who meets a new client, Mr. Webb, at the gym at six. Luis’s next client is already warming up. Mr. Webb asks, “Do you work with people my age?”

Luis wants to show that he is listening. “Of course,” he says. “I can tell you’re worried about getting hurt.”

Mr. Webb laughs, a little stiffly. “I’m not worried,” he says. “I just wondered.” He tells Luis that he will think about it, and he does not call back.

Suppose instead that Luis answers the worry without naming it. “We start with a check of your joints before we add any weight,” he says. “Most of my clients are in their sixties and seventies.” Mr. Webb asks when they could start, and he books a first session for Thursday.

Luis has the right guess both times. In the first version, he says out loud what Mr. Webb chose not to say, so Mr. Webb has to deny it. In the second, the facts answer the worry, and Mr. Webb does not have to admit to anything.

How to hear the worry and answer it

1. When a client asks a question, ask yourself what worry or hope might sit under it. Check your guess against the five common worries: children, health, privacy and safety, keeping what they have, and paying too much.
2. If you cannot tell, ask what is behind the question, and let the client decide how much to say. For example, you can say, “Can I ask what’s behind the question? I want to make sure I answer the right one.”
3. Answer the worry in your first sentence, with a fact the client can check. Do not name the worry itself. For example, a coach who is asked, “Do you coach anyone else at my company?” can start, “Nothing you tell me reaches anyone at your company.”
4. Then answer the question they asked. For example, the coach can go on, “You’d be the only person there I coach.”
5. Write the worry on a page under the client’s name, in a notebook or a notes app. Then choose one regular update that keeps answering it, as Grace’s Friday message about Owen’s work does.

Next: You will see why asking good questions closes the gap between your world and a client’s, and pretending does not.