Here is an excerpt from an article (“Client Loyalty, No. 76) by Andrew Sobel that is featured at his website. To read the complete article and sign up for his free online newsletter, please click here.

*     *     *

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 [in four of six categories] 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 Q: “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 Q:  “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 Q: “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 Q: “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?”

[To read the complete article, please click here.]

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.

*     *     *

Andrew Sobel is the leading authority on the skills and strategies required to build clients for life. The author of three acclaimed books on business relationships, he works with major services firms worldwide. His most recent book is All for One: 10 Strategies for Building Trusted Client Partnerships.