Stay the Adviser After Years With One Client

Imagine a life coach named Sabine Kettering who works with people at a turning point in their lives. Four years ago, Conrad Whitlock sold the software company he founded. He hired Sabine to help him decide what to do next. He is 56. He pays her himself, and they talk by video every other Tuesday.

In the first year, Conrad started a foundation that pays for music teachers in public schools. By the third year, it has a director, Mia, and it runs without him most weeks. Along the way, Conrad has told Sabine what he does not tell anyone else. He worries that his two grown sons see him as a bank. Without the company, he does not know what to say when someone at a dinner asks what he does.

Conrad also expects a great deal. His assistant moves their calls to fit his week, and Sabine makes room every time. He introduces her to his friends as “practically family.”

Sabine is fond of Conrad, so she lets the calls carry on as they are. Each Tuesday, they talk about whatever is on his mind. One week it is the foundation’s board, and the next it is an argument with his younger son. She notices that he no longer talks about what he hired her for. She says nothing, because the calls feel like time with a friend.

In March of the fifth year, Conrad’s assistant writes to Sabine. “Conrad has asked me to let you know he’ll be pausing his coaching for now. Please send a final invoice.” Sabine writes to Conrad himself and hears nothing back. At a dinner, a friend asks Conrad whether the coaching helped. “Sabine was wonderful when I sold the company,” he says. “Lately we just chatted.” The friend hires a different coach.

Suppose instead that Sabine keeps one call each March, the month Conrad hired her, for a different conversation. In the third March, she says, “When you hired me, the question was what you’d do after the company. You’ve answered it. The foundation runs, and Mia runs it. So what would you like our work to be for this year? Or are we done?”

Conrad is quiet for a moment. Then he says that what he wants now is for his sons to come to him for something other than money. They agree that this is the work for the year, and that they will talk on the first Tuesday of each month.

In the fourth March, Conrad tells Sabine that his elder son asked him to read his first business plan. They agree that the work is done, with a last call in June. “I’ll call you when I need you,” Conrad says. Two years later, he joins the board of a public company, and he calls Sabine that week. At a dinner, the friend asks whether the coaching helped. “Every March, Sabine made me say what I was paying her for,” Conrad says. “The year I couldn’t, she said we were done.” The friend asks for her number.

Sabine coached Conrad with the same care both times, and he told her the same worries. What changed was whether the work kept a purpose. In the first version, the work outlasted the question Conrad hired her for, and nothing took its place. Sabine became “practically family,” which was a place Conrad gave her and could take back through his assistant. In the second, they agreed each year what the work was for. When it was done, they both said so, and Conrad came back when he needed her.

So in a long relationship with a powerful client, stay the adviser they hired. Once a year, agree with them what the work is for, as they change. Here is why the work drifts, what a Manhattan tutor saw inside wealthy families, and what two live-in tutors in Moscow found.

A client who grows needs the work to change with them

Here is the course’s view of what happens over years with one client. A coach, a tutor, or a consultant is hired for a question. It might be what to do after selling a company, how to raise a grade, or which colleges to apply to. When the work goes well, the client answers the question. From then on, the client is not quite the person who hired you.

Three changes come together. The client grows, so the question they hired you for is answered or stops mattering. The client tells you more, including what they hide from the people around them. The client also expects more of you, because you have been good for years.

Each change pulls the work away from a purpose. Once the question is answered, the calls go on from habit. Once the client has told you their worries, the relationship starts to feel like friendship, or like family. That can feel like success. Even so, a coach who is family is no longer the outsider the client hired. A place in the family is also the client’s to give, and the client’s to take back.

This is a different problem from a client who stays from habit while the work stays the same. A new idea inside the old work does not help when the work itself no longer fits the client. The client needs a new question, or an end.

A closer relationship is still welcome when the client chooses it. Answer each step they take at its own size, and keep the work on the same terms as before. What the client tells you in those years is the most private part of the work. Keep it to yourself, the way you keep every client’s business.

A Manhattan tutor was dazzled by her families at first, then saw how afraid the parents were

Blythe Grossberg spent years teaching at an elite prep school in Manhattan and tutoring some of New York’s wealthiest families. In 2021, she told NPR’s Michel Martin what she saw in their homes.

At first, she said, “I was very taken in by this glittering veneer.” She described going to the families’ houses and seeing the children’s endless clothes. One student collected limited-edition sneakers. “But I quickly realized that was just a very thin veneer,” she said. “And underneath the surface, the parents were extremely fretful about their children.”

What drove the parents, in her view, was “a fear that their kids would not measure up to what they had achieved.” To help the children along, she said, the parents ran their lives the way an investment bank is run. The children had benchmarks to meet on a regular basis. “So the kids really became, like, products rather than people who have failings and setbacks and reversals and everything that kids have on their way to growing up.”

Measured against this lesson, Grossberg’s first view of the families was the houses and the clothes. Time showed her the fear underneath. That fear is part of what a long-standing client trusts you with. In her account, it was also what lay behind the parents’ demands. So when a long-standing client starts asking for more, ask what worries them before you agree to more work. That step is the course’s own, drawn from her account.

In Moscow, one live-in tutor described being cut off, and another is still in touch

In 2016, The Moscow Times reported on the young tutors who live with wealthy families in Barvikha, a suburb of Moscow. Most of them are British, and the paper calls them governors and governesses. The families hire them to prepare their children for life in the West, before the children go to school abroad. The tutors are on call around the clock. “They make the rules and you are always wrong,” said one of them, a 22-year-old English teacher the paper calls John.

How the work ended differed from tutor to tutor, and two of them spoke about opposite endings.

The tutors grow close to the children, the paper reported, and many families cut ties abruptly. One tutor spent three years bringing up a child. Then a personal assistant phoned to tell him that he was not needed anymore. “One day you’re part of the family, the next day you’re nothing to them,” said Emma, a governess who would not give her last name. The experience, she said, had “hardened” her.

John looked after a Russian boy for two years. Unlike many of the tutors, he is still in touch with him. “He’s in a boarding school in England, I’m really proud of him,” John said.

Live-in work is closer than a weekly coaching call. The step to a coach or a private tutor is the course’s own. Here is the step. Emma’s sentence describes a place in the family, which the family gave and could take away in a day. John’s pride is in the boy, who reached the kind of school abroad that the families hire tutors to prepare for. Nobody could take that from him with a phone call. So build a long relationship on the work you were hired for, and on what the client becomes through it.

Why answering every new request with more work goes wrong

Imagine a private tutor named Philippa Dray who teaches reading and math to children at private schools. She has taught Clio Ashcombe on Mondays since Clio was seven. Clio is now 10, and next year she will take the entrance exams for the school her mother went to.

In September, Mrs. Ashcombe asks for a second session each week. In October, she asks for a practice paper every Friday, with the score sent to her and her husband. In November, she asks for a third session before the exams. Philippa has room in her week, and she wants to keep a family she has taught for three years. So she says yes each time.

By January, Clio is tired. Her scores are where they were in September, and each Friday’s score brings another email from Mrs. Ashcombe. In February, Clio cries before a session and tells her mother that she hates Mondays. The Ashcombes stop the tutoring that week. They hire an exam tutor another parent recommends, and later they send Clio’s younger brother to the new tutor too.

Philippa’s mistake was saying yes to each request without asking what lay behind it. Each request made sense on its own. Together they turned Clio’s tutoring into a weekly score. Behind them was a worry Mrs. Ashcombe had not said aloud.

The version that works asks before it agrees. In September, when Mrs. Ashcombe asks for a second session, Philippa says, “I can do that. Before I do, can I ask what worries you most about this year?” Mrs. Ashcombe says, “I went to Wexley. I don’t want Clio to be the one who didn’t get in.”

Philippa answers the worry with what she sees. “Clio’s reading is already where Wexley wants it, and her math is close. A second session on math until Christmas should cover it. I’d rather not add weekly scores, because Clio does her best work when she isn’t being graded.” Mrs. Ashcombe agrees. In March, Clio takes the exams and gets a place. The next September, the Ashcombes send her younger brother to Philippa.

Asking whether the work is done is not inviting the client to leave

Many coaches and tutors hold back from a yearly conversation about what the work is for. Asking whether the work is done can feel like inviting your best client to leave.

A long-standing client may already be asking that question in private. In the first version, Conrad decided the work was over without telling Sabine, and his assistant told her. Many of the families in Barvikha ended things abruptly too, one of them with a phone call from an assistant. When you ask the question, the client decides it in the room with you. When the work is done and you both say so, the client has a good ending to tell friends about. They also have a reason to call you again. Conrad called Sabine the week he joined the board. A client who decides alone tells friends, “Lately we just chatted.”

How to keep a long relationship working

1. Choose a month for a yearly conversation with each client you have worked with for more than a year. The course suggests the month they first hired you. That ties the conversation to when the work began, not to a problem. Tell the client now. For example, a business coach can say, “Every September, I’d like to use one of our calls to look back at the year. Then we can agree what our work is for in the next one.”
2. Before the conversation, write three notes on the page you keep on the client. Write the question they hired you for, what they have done since, and what you see now. For example, a career coach might write that her client hired her to help him make partner, and he did in May. What she sees now is that he dreads managing the associates.
3. In the conversation, tell the client what they have done, and ask what the work is for now. End with an agreement on the question for the coming year, or on the fact that the work is done. For example, an executive coach can say, “You hired me to get you through your first year as chief executive, and you’re through it. What would you like our work to be for this year? Or shall we stop here?”
4. When a family hires you for a child, ask the child as well as the parents. The child is the one who does the work. For example, a Latin tutor can ask a 15-year-old, “What would you like Latin to do for you this year?”
5. When a long-standing client asks for more, ask what worries them before you agree. Then answer the worry with what you see. For example, a public speaking coach whose client wants an extra session before every board meeting can say, “I can do that. Before I do, what worries you most about the board this year?”
6. When the work is done, say so, and agree on a last session. For example, a parenting coach can say, “I think you’ve done what you came to me for. Let’s have our last session in June. If something new comes up, call me.”

Next: You will see how to charge for a long relationship with a retainer or a package, instead of by the session.