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