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Bar News - August 17, 2012

How to Ask Your Way through Tough Conversations


Here are six of the toughest, most awkward conversations you’ll ever have, and the questions that will help you easily manage them:

A client demands a discount

When a potential client 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 fees are too high?" Next, you might say, "I can reduce the fee if the scope of the proposal is also cut back—or if we could agree to a long-term relationship. Would you like me to develop an option to do this for you?"

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."

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."

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?"

A prospective client says, "Tell me about your firm. What’s different or special about you?"

Even the best rainmakers 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 firm?" or, "What particular aspect of our practice 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 on what’s most important to that particular client. 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?’ Skip the boring facts and figures and go right to engaging examples that will capture your prospect’s imagination."

A customer is unhappy and calls you to complain.

The CEO of a major company 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 and leave."

Here are some of the key questions you must ask when this happens:
  1. "Thank you for raising this with me. Can you tell me any other facts or background information about what happened?"
  2. "Can you say more about that?" (This demonstrates your interest and helps explore the problem more deeply.)
  3. "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.)
  4. "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!"

Andrew Sobel is the author of Clients for Life, Power Questions, Making Rain and the award-winning All for One: 10 Strategies for Building Trusted Client Partnerships. Sobel is a graduate of Middlebury College and earned his MBA at Dartmouth’s Tuck School. He can be reached at

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