Using “Tell Me” as the First Question in Every Negotiation

Excerpted from Chapter 6 of “Ask for MORE – 10 Questions to Negotiate Anything” by Alexandra Carter

“Tell me” works as a first question not just in a formal business setting when you don’t know the other person well, but also across virtually every kind of negotiation.

When Jamie, a successful family photographer with a social work background, prepares to do a photo session with a family she hasn’t met before, the first question she asks is “Tell me about your family.” She told me, “You’d be surprised at what you learn when you ask that question. Sometimes one parent is nervous about posing for pictures and may want some coaching, sometimes the kid has a neurodevelopmental issue that makes it hard for them to look at the camera. When I start with this question, I get the most information possible, and that helps me get to know this family and what they are hoping for from their photos.”

Likewise, Amy, an experienced physical therapist, uses “Tell me” to gain a patient’s trust and define treatment goals. She explains, “Lots of people are scared about physical therapy. They’re worried it might hurt, or they’re intimidated by the work of rehabbing from a surgery or injury. So to start out a conversation with a new client, I might ask, ‘Tell me about your day-to-day,’ or ‘Tell me about yourself.’ If they say they like to read and enjoy going to the library, but they’re having trouble getting there, okay, we can work on that. The most important thing is to gain their trust. Because then we can work together. I know they’ll be more likely to tell me if something hurts, or if they feel they’ve overdone it one week. It’s important for me to know what they enjoy, what motivates them. Because if we link the work to something they love, it all becomes that much easier.”

Using “Tell Me…” with Loved Ones

It takes practice to ask “Tell me…” of the people closest to us. Even as a trained mediator, I realized in shame one day that I had been coming home every day and asking my spouse, “How was your day?” Sometimes the response I got was, “Pretty good,” and other times only a shrug as he sorted through the day’s mail. Why? I was asking him a completely closed (not to mention rote) question! The day I finally decided to practice at home what I preached in the office, I arrived home from work and said, “Tell me all about your day.” I was surprised at how much he opened up. He was wrapping up a difficult work project and stressed about it. The trains had been late getting into the office, but he ran into one of our classmates from law school and got a chance to catch up. He’d had a good morning workout and was feeling strong. And so on. These days, “Tell me…” is the number one question I ask my spouse, on almost every occasion.

I’ve also used this prompt with my eight-year-old daughter and remember a specific occasion when her answer to this question took me by surprise. I had taken her to a swim meet at the local pool. After a long day of swimming, she came out of the locker room in the evening in tears. I asked her what was wrong. She said, “Mom, at this pool you need to share showers. Another girl came in while I was showering. It was so awkward!” I paused for a moment. Internally, I wondered, “Could she be feeling awkward about her body? Are we at the point where she wants more privacy?” But I stayed in the moment with her, and simply asked, “Can you tell me what made it awkward?” She huffed at me. “Mom, isn’t it obvious?” I said, “I’m not sure. Tell me what made it awkward for you.” She responded, rolling her eyes, “We wanted our shower at different temperatures.” “Tell me…” allows us to hear what our partner or kids are actually thinking, instead of suggesting the answer we think is right. When sincerely asked, it also registers as genuine in a way that encourages an actual answer.

Your Turn: How to Ask This Question

Now that we know why we are asking this question—to learn more and build better relationships—we’re going to work together on how to ask it.

You’re going to ask the other person to tell you their perspective on the situation you’re discussing. How exactly you pose the question depends on the type of negotiation. Here are some examples of what “Tell me…” can look like depending on the situation.

When You’ve Initiated the Negotiation

If you’ve initiated the negotiation, you will want to frame the issue first, and then ask the other person to tell you their perspective. Before you ask the question, you will explain the reason you asked for the conversation, as briefly as possible, and let the other person know the issue on which you’d like to hear their perspective.

For example, Brittani has asked the CEO of her start-up company to meet with her to discuss compensation. She has been with the company for a year as the VP of sales for her region, and has wildly exceeded every sales benchmark, winning several major deals that have set her company up to raise even more money. With her company heading into meetings for its next round of investors, Brittani has telegraphed to management that she’d like to discuss her results and a larger equity stake in the company. So her Window conversation may start as follows: “Thanks so much for making time for me today. I asked for a meeting because, as I think you know, I’d like to discuss my progress at the company and compensation package going forward. When I signed on last year, we had an agreement that we would review my terms after I’d been with the company for a year and we had some results to discuss. I’m very pleased with how things have gone and I’m eager to make my long-term home here. But before we get down to discussing the future, I’d love it if you could tell me, from your perspective, how things have gone this past year.” In this way, Brittani has framed the issue in a way that sets herself up for success, but also provides an open space for her CEO to share information to round out the picture.

When Someone Else Has Initiated the Negotiation

For a meeting with a boss, client, or family member where you’re not sure of the topic, you might begin by saying something like: “You asked to meet with me today. Tell me what’s on your mind.” Or “Tell me your hopes for this meeting.” When You’ve Both Agreed to Discuss a Particular Topic If you are sitting down with someone by mutual agreement, with a specific topic in mind—for example, your performance at work or a difficult argument at home—you want to ask the broadest possible “tell me” question about that topic: “Tell me your perspective on what’s been happening recently.” “Tell me about the position you’re looking to fill.” “Tell me your thoughts on the settlement.” When in doubt, a great way to start the conversation can be something as simple as “Tell me your perspective.”

Land the Plane

Here’s where you start to put it into practice. Landing the plane means that you ask your “Tell me…” question and then wait. Landing the plane is critically important for this question! This is your first Window question, and it’s meant to be extremely broad.

Don’t add another question on the end. I have seen countless people say things like, “Tell me what’s brought you here… Have you made an offer yet?” You’ve taken a great open question and completely closed it. Instead of staying open to what the person had to say about their situation as a whole, you’ve now told them you’re just here to talk numbers. Ask your question and then keep your lips closed.

Enjoy the Silence

Often we are scared of silence. We fear that we won’t be prepared for what’s on the other side of that silence. We fear the other person may feel pressured or burdened by the pause in conversation. But “Tell me” is a big, important question. It may take time for the other person to consider their answer. Give them that time. If you’re nervous, try counting in your head while you maintain eye contact and a positive expression. Challenge yourself to see how high you can go before you break the silence. If you’re on the phone, you can take this moment to stretch or just fix your gaze out the window.

You know who often requires the most time to answer this question? Kids. The first time I asked my daughter, “Tell me all about your day!” I waited for her to answer. And when I tell you I waited, I mean I waited minutes while my daughter doodled in a notebook, walked around the kitchen, and then started playing with some slime she had made at summer camp. For a moment, I thought to myself, Well, that flopped! But I stayed silent.

Then, slowly but surely, the trickle of information started. She’d had a substitute counselor. The sub told the kids to be quiet a lot. Someone got in trouble. She ate pizza for lunch. Could we work together on an art project?… And just like that, we were off to the races. Silence works.

Follow Up

If my favorite question is “Tell me,” can you guess my second favorite?

“Tell me more…”

That’s right. Let’s say you’ve asked someone, “Tell me,” and heard a bunch of information in response. After you ask someone to tell you their perspective on a situation or topic, you then will want to follow up and get more information about any valuable topics or insight they offer in response. So once you’ve heard the person out, you’ll want to continue by summarizing what they said and then asking “Tell me more” questions about aspects of what they told you.

For example, in a conversation with a direct report about changes they’d like to make to their position at work, you might say, “So you’re seeking more client contact as well as the greater feeling of autonomy you had in your previous position. Can you tell me more about that prior position?” By asking “Tell me more,” you keep the person talking and get more detailed information without resorting to yes-or-no questions that shut the conversation down.

Imagine you’ve gone fishing off the coast of your favorite body of water. You’ve cast your net wide and hauled in twenty fish, along with seaweed and some other stuff. You’re going to take a minute to sort through your catch and separate the fish from the stuff you’re going to throw back or away. And now I want you to look at those twenty fish. Each of those fish is valuable. When you ask this question and hear some valuable information, I want you to treat each topic as a “fish” you’ve hauled into your net. For each topic where you’d like more information, you’re going to follow up and ask the person to tell you more about that topic.

So let’s say, for example, that you’ve asked me to tell you about my last trip to India. In response I say, “It was great! We held a Peace Summit in which we convened together ambassadors from a number of countries with Indian government leaders and some CEOs of private companies to talk about public-private partnerships for peacebuilding. My students did a fantastic job with the research and also assisted in the teaching. We stayed at a lovely hotel that had these gorgeous gardens; I tried to spend a few minutes there every day. I managed to call home every day, but sometimes my daughter was too tired to talk. That was rough, because I missed her a lot, especially in the last days of the trip. Toward the end, we spent a couple of days traveling to the Taj Mahal. Hopefully we’ll be able to do this summit again every year.”

Okay, you’ve just heard a lot of information in response to this question. Some of the things I talked about were:

•  This year’s Peace Summit

•  My students

•  The hotel and gardens

•   My sadness at missing my daughter

•  The Taj Mahal

•  My hopes for the future of the summit

Let’s say for purposes of this conversation that you’re interested in talking more about the work aspects of my trip. You would then pick those topics and say, “Tell me more about the summit this year,” or “Tell me more about your students’ roles on the trip.” If you were interested in some of the non-work parts of my trip, too, you might also ask me to tell you more about the Taj Mahal.

The purpose of “Tell me more” is to continue to keep the conversation open for as long as possible. Sometimes, people do a great job asking an initial open question, and then they narrow it precipitously in the second round. For example, you might ask me to tell you about my trip to India, and then follow up with: “How many days did the summit run?” That’s a really narrow question that doesn’t get you nearly as much information as “Tell me more about the summit.”

If you stay with the conversation and ask “Tell me more” for the information you uncover, you’ll get the most out of this question and set yourself up for success in the rest of your negotiation.

Note from Bob:  Almost everything in life in negotiable.  And having to negotiate is often part of all of our lives – even if you would wish otherwise!  The Good News is that negotiating does not have to be dreaded – it is something you can do successfully by simply learning to ask the right questions.  And “Ask for MORE – 10 Questions to Negotiate Anything” by Alexandra Carter will help you suceed!  Order your book to day by clicking HERE

Alexandra Carter


Alexandra Carter is a clinical professor of law and director of the Mediation Clinic at Columbia Law School.  She is a negotiation trainer for the United Nations, as well as to Fortune 500 companies, government agencies, nonprofits, and more.  Alexandra graduated with honors from Georgetown University, was a Fullbright Scholar in Taiwan, and received her law degree from Columbia Law School.  In 2019 Alexandra was awarded Columbia University’s highest teaching honor.  She lives in Maplewood, New Jersey, with her husband and daughter.


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