Questions You Should Never Ask

You have finally gotten the meeting you sought with a top executive at a prospective client. You prepare well for the session, researching the company and the individual you’re meeting with. After the small talk dies down, you ask your “killer” question:

“I’d like to get a better understanding of your issues. So, what keeps you up at night?”

Terrible question. Awful. Clichéd. One of my clients, the CIO of a large bank, told me that he literally kicks people out of his office when they pull out that question.

I’ll get back to why it’s a bad question to use with a prospect you don’t already know well, in just a minute.

Good questions can be incredibly powerful. In fact, my new book, which will be published next January by John Wiley & Sons, is called Power Questions. It’s all about some very special questions that can transform conversations and people. But just as there are powerful questions, there are lousy ones. Here are some of the questions you should avoid:

1. Closed-ended questions.

Anyone who has ever had to sell something knows that closed-ended questions are the least productive type of question you can ask. If you are trying to build a relationship with someone, and understand how they think and what their issues are, you want to move as quickly as possible from closed-ended to open-ended questions.

  •   “What’s your market share?” …Better: “What are the main reasons you’ve gained market share in the last three years?”
  • “When did you start your new job?” …Better: “What’s the most rewarding part of your new job?"
  • "How long do you want the training session to be?"…Better: "Why do you want to do a training workshop?"

2. Judgmental questions.

Some questions are really just hidden judgments. For example:

  • “You didn’t really mean to do that, did you?”
  •  “Why do you think you always arrive late?”

3. Sarcastic questions.

Sometimes we ask questions that aren’t really questions—they are just vehicles for sarcasm and anger, a blunt instrument to beat up on someone. I once heard a parent, for example, ask their high school junior, “Why do you think a competitive college is going to admit you with those kinds of grades?” Other examples would include questions like “You’re so moody, why would anyone want a relationship with you?” and “Do you seriously think that is going to be acceptable?”

4. Clichéd questions.

“What keeps you up at night” is a cliché. Every salesperson on earth has been using that question for at least 20 years. In reality, most people aren’t going to share with you what really keeps them up at night. Furthermore, it’s a “problem” question, and most really top executives have delegated the operational problems to their subordinates to solve—they are more focused on growth and innovation than problems. If you know the person well already, it may be a perfectly good question to use—“So, Brad, what’s keeping you up at night these days?” might be fine for an ongoing client.

Another cliché is “What has surprised you?” (The president of Lewis & Clark college recently wrote an OpEd column in the Wall Street Journal on why this is a terrible question. See Barry Glassner’s "The What’s Surprised You Trap"). Another one is, “What question haven’t I asked you?” This one smacks of “I am very cleverly trying to get you to be my advisor on what questions to ask,” and again, it’s been over-used. Finally, there’s the old saleman’s chesnut, "I know you’re happy with your current suppliers, but what could cause your management to bring on a new vendor?"

Better versions of these–or different, more appropriate questions altogether–are:

  • What keeps you up at night? …Better: “How is your new international strategy impacting your area?” or “How are you reacting to the new regulatory framework?” (e.g., approach it indirectly) or "What are your most important initiatives for this year?" or "How will your leadership assess your performance at the end of the year?"
  • What has surprised you? …Better:  “What have you been especially focused on accomplishing during your first three months at your new job?”
  • What question haven’t I asked you? …Better: “Are there any other issues, that we haven’t discussed, that you think are relevant to the problem?"
  • What could cause your management to bring on a new vendor? …Better: "Can you share with me in which areas your current vendor is strong, and in which areas they play less well?" or "When was the last time there was a shakeup of your suppliers? How did that happen?"

5. Self-aggrandizing questions intended to show how smart you are.

At a dinner party a few years ago, a retired college professor sat across from me. He fulfilled every stereotype I’d ever had about excessively intellectual academics, right down to wearing a bowtie and tweed sports jacket. He had the obnoxious habit of posing questions and then answering them. “I’ve asked myself many times,” he would begin, “Why is it that people so often say one thing and do another? I think this has to do with our tendency towards self-deception…” It was appalling.

6. Leading questions..

Leading questions are like the one used by the apocryphal prosecutor, who asked the defendant in court, “When did you stop beating your wife?” Leading questions are formulated to get someone to admit to something or to drive home a particular point. They are, like the false questions described earlier, inherently dishonest. Other examples of leading questions include:

  • “When did you realize that you would never make it as a professional musician?”
  • “How did you cope with the disappointment of not getting that job offer?”

Remember, good questions are sincere. They reflect a genuine curiosity. They are open-ended. They get at the "why" of things. They explore implications. They challenge assumptions. They help you connect on a personal level. They demonstrate, indirectly, your familiarity with the issues.

(See my earlier article on asking good questions, "Ask Questions Like a Client Advisor")

Andrew Sobel is the leading authority on client relationships and the skills and strategies required to earn enduring client loyalty. The most widely published author in the world on business relationships, he is a consultant, educator, and coach to major services firms worldwide. Andrew is the author of the recently released All for One: 10 Strategies for Building Trusted Client Partnerships—which was voted one of the top 10 professional services sales and marketing books of the decade—as well as the business bestsellers Clients for Life and Making Rain . He has contributed chapters to four books on leadership, marketing, and human resources management; and his articles and work have appeared in publications such as the New York Times, US Today, Strategy+Business, and the Harvard Business Review. He was a Senior Vice President and Country Managing Director for Gemini Consulting, where he served on the European Executive Committee, and for the last 15 years he has led his own consulting firm, Andrew Sobel Advisors, Inc. He can be reached at (Tel: 505.982.0211).


Back to top