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Sales Tips: Never Ask a Prospect These Questions By Andrew Sobel

You finally got 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 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 know well in just a minute.)

Good questions can be incredibly powerful. 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 want to understand how they think and what their issues are, you want to move as quickly as possible from closed-ended to open-ended questions. Some examples:

Instead of: “What’s your market share?” Try: “What are the main reasons you’ve gained market share in the last three years?”

Instead of: “When did you start your new job?” Try: “What’s the most rewarding part of your new job?”

Instead of: “How long do you want the training session to be?” Try: “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?”

Judgmental questions stop the conversation dead in its tracks. They shut the other person down.

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. Salespeople have been using that question for as long as there have been things to sell. In reality, most people aren’t going to share what really keeps them up at night until they develop some trust in you. Client executives tell me this is a lazy question because it shows you haven’t done your homework and thought about the conversation in advance.

Furthermore, it’s a “problem” question, and most high-level 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, 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?” (Barry Glassner, President of Lewis & Clark College recently wrote an OpEd column in The Wall Street Journal on why that is a terrible question. See The ‘What’s Surprised You?’ Trap). Another one is, “What question haven’t I asked you?” That 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 this old salesman’s chestnut: “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:

Instead of: “What keeps you up at night?” Try: “How is the new international strategy impacting your area?” or “How are you reacting to the new regulatory framework?” (e.g., approach it indirectly) or “What are the two or three initiatives that you’re putting the most resources, time, and attention into this year?” or “How will your leadership assess your performance at the end of the year?”

Instead of: “What has surprised you?” Try: “What have you been especially focused on accomplishing during your first three months at your new job?”

Instead of: “What question haven’t I asked you?” Try: “Are there any other issues we haven’t discussed that you think are relevant to the problem?”

Instead of: “What could cause your management to bring on a new vendor?” Try: “Can you share with me areas in which your current vendor is strong and areas in which 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 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 your familiarity with the issues.
Andrew Sobel is a leading authority on client relationships and the skills and strategies required to earn enduring client loyalty. He is the author of the business bestseller Making Rain: The Secrets of Building Lifelong Client Loyalty, among others. You can contact him through his website www.andrewsobel.com