Turning Around Tough Conversations

Published: Jan 24, 2019
Modified: Mar 25, 2020

By Andrew Sobel

We’ve all experienced moments when we’re at a loss for words. Your boss criticizes your work. A customer demands a discount. Your presentation gets off on the wrong foot. Tempers flare. Later, you’re left thinking, I wish I had been able to think of just the right thing to say to that person! When there’s a lot on the line, it’s not just about finding the right thing to say—it’s about asking the right questions.

No interaction, regardless of how tough, is ever completely lost. You can transform tough conversations—and the relationships they affect—by learning how to ask what I call “power questions.”

Power questions allow you to turn a conversation around, shift the focus back to the other person and give you some valuable time to gather your thoughts.

Here are tips for using power questions to handle eight of the toughest, most awkward conversations:

  1. Your boss criticizes you.

    Your boss pulls you aside and tells you, “You’re not a team player. You need to collaborate better.”

    When this happens, you should immediately ask him or her two important questions. First, “Could you help me understand what I’m doing wrong by sharing a couple of examples where I have collaborated poorly with others?” And second, “Can you make some specific suggestions for how I could be a better team player?” Your openness to criticism and willingness to improve will make a good impression on your boss, and, hopefully, you’ll leave with some specific action steps.
  2. A customer demands a discount.

    When a customer asks for a discount, that’s a strong “buying signal”!  You can shut the conversation down by simply saying “no.” Or, you can open up the discussion and learn more about your customer.

    You could start by asking, “I’ll be able to respond to your request more effectively if I can understand what’s behind it. Can you tell me something about why you need a discount or feel our price is too high?” Next, you might say, “I can reduce the price if the scope of the proposal is also cut back—or if we could agree to a long-term relationship with guaranteed volume levels. Would you like me to develop an option to do this for you?”

    By using power questions, you can delve more deeply into the customer’s needs. You might find another way to show him the value he wants. In the long term he’ll view that much more positively than a one-time discount. It’s also a much better option than turning him down completely.
  3. A potential customer is indifferent or hostile

    Especially in this economy, buyers can afford to be standoffish. The right questions, however, can help you connect with even a defiant prospect. If a potential customer won’t engage, consider asking, “What would be the best way for us to spend this time?” or, “I know you are busy—what interested you in taking this meeting? Do you have a particular challenge that we could discuss while I’m here?”

    As many companies are still pinching pennies, it’s quite possible your customer will say to you, “We have no need for your services now. I’ll call you when we do.” How should you respond? Try this: “You’d be surprised how many of my best customers said that to me when we first met! Do you mind if I ask you one or two questions? When things do pick up for you, in which areas are you going to make your very first new investments?” If you can follow up with a few more thoughtful questions, you may just start building a relationship—and learn about a current need you can help with.
  4. A conversation turns to anger or goes off the rails.

    You’re just a few minutes into a presentation at work, and it all goes wrong. You are being angrily confronted, or your information is being irrationally challenged. Tempers flare. What do you do? If you’re like most people, you keep on talking—faster and faster—to try to persuade your audience.

    A better option is to hit the “reset button.” Ask, “Do you mind if we start over?” Then, shift the focus to the other people in the room by saying, “We probably should have talked before I put this presentation together. Before I go on, can I ask—what’s your perspective on the impact of these new regulations?” or, “You’ve alluded to some data I have not seen. Can you tell me more about that and where it came from?” Those magic words—“Can we start over?”—can salvage a tense situation at work and also at home. But you must use them early in the conversation.
  5. You’re turned down for a job.
    In this job market, you are going to hear “No, thank you” far more often than “You’re hired.” “If you’ve had only a single screening interview, it’s unlikely you’ll get any feedback at all out of the firm that rejected you. But if you went through a longer interviewing process, you ought to try and learn something. Here are two questions you should ask your interviewers if you are turned down for a job: “What are you looking for that you did not see in me as a candidate?” and “What advice can you give me, as I apply for other positions, about how to best represent my experience and skills and to handle the interviewing process?”
  6. You’re introduced to someone you don’t know at a work or social event.

    “Hi, I’m Andrew Sobel.” Then what? If the other person is a gregarious extrovert, you may not have to do or say anything—he or she will carry the ball. But chances are, there will be an awkward silence. Or at best, a bland “How are you?”

    When you first meet someone at an event, start with some easy, non-threatening questions. For example: “Where are you from?” or “So what’s your connection to our host?” or “How are you enjoying Atlanta?” and so on. Then you should quickly dig a bit deeper: “Where did you grow up?” “How did you get started in your field?” and “So when you’re not shaking things up at the office, how do you like to spend your time?”

    Don’t waste 20 minutes engaging in purely superficial chitchat, but on the other hand, don’t dive in with inappropriate questions like “If you had only a month to live, what would you do?” Rapport starts with identifying commonalities and similarities, not shocking the other person.”
  7. A prospective customer asks, “Tell me about your firm. What’s different or special about you?”

    Even the best salespeople seem to choke when they are asked this question. Usually, they spout a bunch of unconvincing statistics, talk about all their offices around the world, and tout their unique, “collaborative” approach—the same stuff anyone else can and does say. A better response—one that will engage your prospect—is to first seek additional information. You might ask, “I’m curious, have you had any past experience with our company?” or “What particular aspect of our business would you like me to talk about?”

    Often, prospects have something specific they want to know about you or a doubt they harbor, and this second question will help draw it out. This way, you’ll focus in on what’s most important to that particular customer. Finally, you should add, “The best way to talk about our firm is to share a couple of examples of recent work we’ve done with clients in your industry. Would that be helpful to you?”
  8. A customer is unhappy and calls you to complain.
    The CEO of a major bank told me, “When you have a customer crisis, there is rarely an easy solution—the solution actually lies in how rapidly, energetically, and sincerely you respond to their complaint. The quality of your response is the solution.”

    Just as surely as the sun rises each morning, you will receive calls from unhappy clients and customers, all of them saying in their own way, “You’ve let us down!” The first principle to remember is that when people are upset, emotions are like facts. Don’t—repeat, don’t—start arguing with your customer about what really happened and whose fault it is! An unhappy customer who tells you he is unhappy is a gift, because most dissatisfied customers never express their anger—they just vote with their feet.

Ask the unhappy customer:


  • “Thank you for raising this with me. Can you tell me any other facts or background information about what happened?”
  • “Can you tell me more about that?” (This demonstrates your interest and helps explore the problem more deeply.)
  • “How do you think things got to this point?” (This may uncover the origins of the problem, including things the customer may have done to exacerbate it.)
  • “This is extraordinarily important to me. How soon can we meet to discuss the problem and how we can best respond to it?” (This shows the customer he is your number one priority right now.)

And finally, don’t forget to apologize!

Few situations are more awkward than a tough conversation. When you find yourself in the midst of one, asking the right questions will help you salvage the moment. The bonus is that you’ll open yourself up to having a very vibrant conversation that will pave the way for more authentic and productive relationships in the future.

About the Author(s)

Andrew Sobel is a widely published author on client loyalty and the capabilities required to build trusted business relationships. He is the author of the best-selling Clients for Life. His other books include Making Rain and the award-winning All for One: 10 Strategies for Building Trusted Client Partnerships. His latest book is Power Questions: Build Relationships, Win New Business, and Influence Others (Wiley,  2012). For more information, visit http://andrewsobel.com