Questions Without an Interrogation

Imagine a personal stylist named Hanna Lindholm who meets Mrs. Pryce about a speech in May. Mrs. Pryce’s message said that her old school has asked her to speak at its graduation. Hanna has a page of questions she asks every new client, and she starts at the top. What do you wear most days? Which colors do you avoid? What size are you in jackets? What is in the closet already? What is the budget? Who else will see the outfit before the day?

Mrs. Pryce answers each one in a few words. Hanna writes each answer down and asks the next question. After 15 minutes, Mrs. Pryce has answered 14 questions, and she feels as if she is filling in a form out loud. She says she will think about it, and she hires the stylist a friend uses.

Suppose instead that Hanna opens with the detail in the message. “Your note said it’s your old school. When were you last there?” Mrs. Pryce says she has not stood in that hall since she was 18. Hanna says, “Thirty years, then, and the whole school looking at you.” Then she asks, “What did you wear the last time you gave a speech?”

Mrs. Pryce says a navy suit that felt like armor. Hanna says, “Armor gets you through a morning.” Then she asks whether Mrs. Pryce wants armor again in May, or something else. Mrs. Pryce thinks, and says she wants to look like someone who left that school and did well. That sentence is the whole job. The sizes and the budget come out in the last five minutes, when Mrs. Pryce asks what the outfit would cost. The colors come out in the closet. Mrs. Pryce books her before she leaves.

Hanna needed the same facts both times, and she left with the same facts both times. What changed was where each question came from and what sat between them. In the first meeting, every question came from the page, and nothing sat between them. In the second, every question came from the answer before it, and Hanna said one sentence about the answer first. Here is why the second meeting felt like a conversation to Mrs. Pryce, and the first felt like a form.

A question that picks up the last answer is the one that shows you heard it

In 2017, Karen Huang and four colleagues at Harvard published three studies of conversations between strangers. The people who asked more questions were liked more by the person they talked with. The questions that counted most were the follow-up questions, the ones that pick up what the other person just said. When people were told to ask more questions, their partners found them better at listening and understanding. That is where the liking came from.

Those were strangers in a study, and the step to a client’s front hall is the course’s own. Here is the step. A follow-up question cannot be written down in advance, because it does not exist until the client has answered. “What did you wear the last time you gave a speech?” was only possible after Mrs. Pryce said she had not been in the hall since she was 18. A page of questions is the opposite. Every question on it was written before the client said a word. So none of them can show the client that an answer was heard. Fourteen good questions in a row, each written in advance, add up to a form.

The sentence between questions is the course’s own suggestion, and here is the reason. A question says nothing about what you made of the answer. Suppose your only reply to an answer is another question. Then the client hands you a fact and gets nothing back but the next question. A sentence about the answer tells the client what you took from it, and it gives them something to answer back. So the next question arrives as part of a conversation. That sentence is about the client’s answer. It is not the short fact about yourself, which has its own place in the meeting.

A wedding planner says a list of questions makes the meeting an interview

Jessica Dum runs a wedding coordination business in Indianapolis. In a post on first calls for other planners, she writes that her coaching clients “get worried about the exact questions they need to ask.” Her advice is to let that go. “There is no need to have a huge list of ‘getting to know you’ questions,” she writes. “This will help it feel less like an interview and more like grabbing coffee with a friend.”

She gives an example of what to do instead. If the couple wrote on the inquiry form that a friend sent them, “start by talking about said friend and how small of a world it is that you two know them.” Measured against this lesson, that example is the method. The friend is a detail the couple gave her. Her first move is a sentence about that detail, not a question from a page. She also says what the call is for. “Your consultation should be focused on listening,” she writes, and not on talking.

A coaching school tells its coaches to ask one question and stop

Bay Area Executive Coach Training, which trains executive coaches, published a post in 2023 on a habit it calls stacking. The writer had watched an interview in which one person “asked the author several questions at once.” Stacking “comes naturally to people who are quick thinkers,” the post says. They end up “blurting out a few questions in a row.”

The post says what happens next. The writer finds that “the person being asked usually just answers the last question and sometimes the one before it.” Most people have heard the reply the post gives next. “Tell me again what was your first question?” Its first reason for asking one question at a time is what two questions do to the client. “If we ask two questions or worse, a third one, then we cause our client’s mind to speed up as they consider all questions asked and decide which one to answer.”

The post’s other reasons belong to coaching, where the hour is meant to feel unlike an ordinary conversation. Your meeting with a client is meant to feel like one, so take the first reason and leave the others. A client asked two questions at once answers one of them, usually the last. If the one you needed was the first, you have to ask it again, which is one more question. The post also asks where the space went “between the response and the next question.” That space is where your sentence about the answer goes.

A travel adviser follows the sardines, and the client books him

Imagine a travel adviser named Tomasz Wrobel who meets Mr. Ferraro about a trip in September with his brother. Mr. Ferraro’s message said that the two of them have not traveled together since they were students. Tomasz asks where they went then. Mr. Ferraro says Portugal, on a rail pass, eating sardines out of the tin.

Tomasz says, “So the sardines are coming on this trip.” Mr. Ferraro laughs and says his brother will insist. Tomasz asks what his brother will not put up with now, 30 years on. Mr. Ferraro says stairs, and anything before nine in the morning. Tomasz says, “Then the days start at ten, and the hotels have lifts.” Then he asks which of the two of them picks the restaurants.

The conversation runs for 20 minutes like that, and Mr. Ferraro does most of the talking. When he asks what the trip would cost, Tomasz asks the four questions he still needs. He asks for the dates and the number of nights. He asks whether the brothers want one base or three, and what Mr. Ferraro spent on his last trip. It takes two minutes, and Mr. Ferraro answers all four at once, because by then he is planning the trip with Tomasz. He books the following week.

Tomasz had the four questions written down before the meeting. They came last, in two minutes, as a check. Everything before them came from Mr. Ferraro’s answers, and each answer got a sentence before the next question.

Why a run of good questions still goes wrong

Imagine a tutor named Kerem Demir who meets Mrs. Quennell about her daughter, Isla, who is 14. He has 20 minutes before his next session. He does not have a page of questions, and each question he asks comes from her answer. “Which subjects?” Math and chemistry. “Since when?” The spring. “What did the school say?” That she has stopped handing work in. “Has she had a tutor before?” One, last year. “What happened with him?” He did not come back after the summer. “What does Isla say about it?”

Mrs. Quennell answers every question, and each answer is shorter than the one before. After 15 minutes she says she will talk to her husband. That evening she tells him that the tutor “asked good questions, but it felt like being cross-examined.” She hires the tutor a neighbor uses.

Every question Kerem asked was a follow-up question, and the meeting still felt like an interrogation to Mrs. Quennell. The reason is what was missing between them. She gave him six facts, and each one got another question back. The version that works has Kerem say one sentence after “she has stopped handing work in.” For example, “So the work is getting done, and it’s the handing in that has gone.” Mrs. Quennell can agree or correct him, and either way she has heard what he made of her answer. Then he asks what Isla says about it. A description of his method or a story about another student would take the subject away from her. The sentence is neither. It is one sentence about her answer.

Leaving the page in your bag is not leaving without the facts

A professional who has used a page of questions for years has a reason for it. The page is how they make sure they leave with the sizes, the dates, and the budget. Without it, a first meeting can feel like a pleasant hour that ends with nothing to quote from.

The page still exists, and it does its job at the end. Hanna got the sizes and the budget in the last five minutes, when Mrs. Pryce asked about the cost. Tomasz asked his four questions in two minutes, and Mr. Ferraro answered all four at once. Most of what is on the page comes out on its own, in the client’s answers, when the questions follow those answers. What is left is a short check. A client who has been talking for 20 minutes answers a check without noticing it. Dum tells her planners the same. “Don’t worry too much about having the perfect list of questions to ask them.”

How to ask what you need without running a list

Before the meeting, write the facts you must leave with on one page. For most work that is the dates, the size of the job, the budget, and who else will have a say. Then put the page in your bag. It is a check for the end of the meeting, not the order to ask them in.
After your opener, build each question from the answer you just heard. The test is whether you could have written the question before the client spoke. If you could, hold it. For example, an event planner hears that the last party at the house ran out of ice. She asks what else went wrong that night.
Before each question, say one sentence about the answer you just got. It says what you took from the answer, and it is not your method or a story of your own. For example, a music teacher whose client says the boy taught himself three chords from a video can say, “Three chords is most of the songs he knows.” Then she asks which songs.
Ask one question and stop. When a second question is already in your mouth, keep it until the client has answered the first. For example, a dog walker who wants to know how far the dog walks and whether he pulls asks the first. He asks the second after the answer.
When the client turns to the work or asks what it costs, take out the page. Ask for what is still missing, and say that you are checking. For example, a private chef can say, “Two things before I can give you a price. How many nights a week, and is anyone allergic to anything?”
Afterward, count the questions you asked that you could have written before the meeting. If more than a few were, the page was in your hand and not in your bag. Write the count on the client’s page, and read it before the next first meeting.

Next: You will see what a client learns about you from the shape of your email before they have read what it says.