From Confrontation to Calm: How to Ask Your Way through Ten of the Toughest Conversations You’ll Ever Have

At work, at home, with friends, and even with perfect strangers, it isn’t uncommon to find yourself suddenly entrenched in a tough, tense conversation. Instead of trying to stutter and mutter your way out of it, and risk permanently damaging an important relationship, Andrew Sobel suggests you ask your way through it using key Power Questions.

Hoboken, NJ (June 2012)—We’ve all experienced moments when we feel at a loss for words. Your boss criticizes your work. A customer demands a discount. Your presentation gets off on the wrong foot and tempers flare. Every time, you’re left thinking, I wish I had been able to think of just the right thing to say to that person! What should I have said? Andrew Sobel says that no interaction, regardless of how tough, is ever completely lost. He suggests transforming tough conversations—and the relationships they affect—by asking a few power questions.

“In these situations, when there’s a lot on the line, it’s not all about finding the right thing to say—it’s about asking the right questions,” says Sobel, coauthor along with Jerold Panas of Power Questions: Build Relationships, Win New Business, and Influence Others (Wiley, February 2012, ISBN: 978-11181196-3-1, $22.95). “By posing just one or two thoughtful questions, you can turn even the most difficult conversation around, shift the focus back to the other person, and give yourself invaluable breathing room to gather your thoughts.”

Read on for a look at ten of the toughest, most awkward conversations you’ll ever have, and the powerful questions that will help manage them with ease.

1. 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 conversation 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 say 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 deeper into the customer’s needs,” says Sobel. “You might find another way you can show him the value he wants. In the long term that will be viewed much more positively than a one-time discount and is a much better option than turning him down completely.”

2. 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,” says Sobel. “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 information you can act on.”

3. Someone attacks your beliefs or values.
Nothing chokes us up emotionally and angers us like an attack on our beliefs, values, or practices—especially with regard to religion, politics, and childrearing! Say you’re having a discussion about healthcare and the other person says, stridently, “Oh come on, you’re not going to tell me you think the government can do a better job running healthcare than efficient private companies! Please!” How do you respond? Your first reaction is to vigorously defend your position. This will most likely lead to an angry escalation.

“Instead, try first asking a few questions,” advises Sobel. “For example: ‘I’m curious, what things do you think the government should get involved with?’ or, ‘That’s a fair point. What kind of grade would you give the private healthcare companies for their performance?’ or, ‘What do you think should be done to help people who are uninsured or cannot afford private insurance?’ You could also ask, ‘What’s the worst service you’ve ever received? Was it from a for-profit company—a restaurant or an airline?—or from the government?’ When you’re attacked, come back with questions that help you learn more about the other person and understand their anger—and that also help put your ideas into the mix in a non-confrontational manner.”

4. 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,’” notes Sobel. “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!”

5. 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—trying harder and harder to persuade your audience.

“A better option is to hit the reset button,” says Sobel. “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.”

6. You’re turned down for a new 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,” explains Sobel. “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?’”

7. Your job interview is almost over, and the interviewer asks, “Do you have any questions?”
If you’ve got only a few minutes left, try to make an emotional rather than intellectual connection with the interviewer. Ask, “What do you love most about working here?” or, “As you look ahead to the future of your business, what are you most excited about?” You could also ask about culture—for example, “What types of people thrive here, and on the other hand, what are the most common reasons why new hires don’t work out?”

“Questions that are thoughtful and personal in nature will put a smile on the interviewer’s face,” says Sobel. “End with a complicated question about business process reengineering, however—or a superficial one about vacation benefits—and they’ll be grimacing as you leave. Remember, if you want to be noticed by recruiters, don’t talk more. Instead, ask better questions! You’ll soon find yourself answering the best question of all: How soon can you start?

8. 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—they’ll 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 have you come in from?”; “So what’s your connection to our host?”; or “How are you enjoying Atlanta?” and so on. But 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,” advises Sobel. “On the other hand, don’t dive in with inappropriate questions like ‘If you had only a month to live, what would you do?’ Remember: Rapport starts with identifying commonalities and similarities, not shocking the other person!”

9. A prospective customer says, “Tell me about your firm. What’s different or special about you?”
Even the best salespeople seem to choke up 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—which 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,” says Sobel. “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?’”

10. 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!’” says Sobel. “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 they are unhappy is a gift, because most dissatisfied customers never express their anger—they just vote with their feet.”

Here are some of the key questions you must ask when this happens:

  • “Thank you for raising this with me. Can you tell me any other facts or background information about what happened?”
  • “Can you say 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,” Sobel adds, “don’t forget to apologize!”

“Few things can make us feel more awkward than a tough conversation,” says Sobel. “When you find yourself in the midst of one, asking the right questions is a great way to salvage the moment and give yourself breathing room to think. The bonus, of course, is that you’ll actually open yourself up to having a very vibrant conversation and will pave the way for a more authentic and productive relationship in the future.”

About Andrew Sobel:
Andrew Sobel
is the most widely published author in the world on client loyalty and the capabilities required to build trusted business relationships. His first book, the bestselling Clients for Life, defined an entire genre of business literature about client loyalty. In addition to Power Questions, his other books include Making Rain and the award-winning All for One: 10 Strategies for Building Trusted Client Partnerships.

For 30 years, Andrew has worked as both a consultant to senior management and as an executive educator and coach. His clients have included leading companies such as Citigroup, Xerox, Bank of America, Hess, Cognizant, Ernst & Young, Booz Allen Hamilton, Towers Watson, and many others. His articles and work have been featured in a variety of publications such as the New York Times, Business Week, and the Harvard Business Review. Andrew is a graduate of Middlebury College and earned his MBA at Dartmouth’s Tuck School. He can be reached at

About the Book:
Power Questions: Build Relationships, Win New Business, and Influence Others (Wiley, February 2012, ISBN: 978-11181196-3-1, $22.95) is available at bookstores nationwide and all major online booksellers.