Eight Cringeworthy Questions You Should Never Ask

I’ve heard this a hundred times: “There are no bad questions.”

Sorry, but there are indeed bad questions. And, there are good questions that go bad when used at the wrong time. For example: “Why?” It can be a great question—or a critical, negative one if used improperly.

Here are eight questions you should avoid:

First: What keeps you up at night? If you’re meeting for the first time with a prospective client, this is a lazy question that shows you haven’t done any homework or preparation for a meeting. It’s also a cliché, in that salespeople have been asking it for last 25 years. You’ve got to be more creative than that, e.g., “How are you reacting to…?” or “What are the priorities are you are investing significant personal time on right now?”

Second: What has surprised you? This is often asked of someone who recently took over a new job. It’s a poor question because there is no good answer. If someone tells you, “nothing”, then they risk coming across as overconfident and unaware. If they tell you they were “surprised” by a bunch of things, then they appear to have been uninformed and unprepared for the role. Instead, ask, “Have you identified your longer-term priorities yet?” Or, “How have you focused your time during these first few months?”

Third: What question haven’t I asked you? That’s an old salesman’s trick, to get your prospect into the position of being your coach and sitting, in effect, on the same side of the table. As if, “We’re in this together!” But sophisticated executives see right through that one. Ask instead, “Are there any other issues we haven’t discussed that you think are relevant to this topic?”

Fourth: What would it take to get your business? Ouch. I still see this question in books on selling. You get someone’s business by building a relationship of trust and demonstrating that your product or service can add value and solve a problem—not by asking this crude question.

Fifth: Related to the last one is this old chestnut, If I could show you a way to save a substantial amount of money, would you be interested in a proposal from us? Please, you insult the other person’s intelligence when you ask something like this. That might be appropriate if you were selling scrap metal or remaindered encyclopedias. Better: “We recently worked with a firm in your industry on this issue and were able to reduce their customer acquisition costs by 20%. Would you be interested in hearing the story of how they accomplished that?”

Sixth: What does success look like? Look, per se, there’s nothing terrible about this question. Except, the fact that it’s become a cliché. It’s the same question that every outside provider has been asking your client, all day long. Nowadays, I cringe when I hear it. Instead, be specific: “What exactly will your people be doing differently when this initiative is successfully implemented—what new or changed behaviors would you like to see?” Or, “How will your customer experience be different a year from now, if you are successful?” Or, “What financial results do you expect to see from this change?”

Seventh—and a lot of people do ask this: How can we do a better job for you? (or, “How can we add more value?”). Here’s the problem with this seemingly earnest and caring question: Most of the time, clients cannot answer it. They either mumble something like, “Keep up the good work” or “Please don’t mess this project up”. You have to figure out how you can do a better job. You learn how by spending time with your client, learning their business, and understanding their frustrations, needs, goals, and priorities. Only you can make the connection between those client needs and your particular product or service. Don’t expect your client to put the two together—they rarely will. There are many better questions you can ask that will help you understand how to do a better job!

Eighth—leading questions like Would you say you are fed up with the underperformance of your sales force? Or, Do you now feel ready to make a change? These are clear attempts to get the other person to say “yes” and agree with you, or to “lead” them to a particular answer. Questions like this are manipulative and can feel coercive. Better: How are you reacting to/how do you feel about the underperformance of your sales force?

Here’s a bonus bad question:

Ninth—if you are speaking to a teenager or young adult: Why did you… (Why did you stay up so late the night before your exam? Why did you leave your knapsack in the car—you know there have been break-ins in that neighborhood? Why were you speeding on route 25?) I actually like “why” questions when you’re trying to get to the higher-level strategy and goals that are driving a client action. But with young people, it’s code for “Why were you so stupid?”

There are hundreds of great questions you can ask. Avoid these stale, clichéd ones. They can make the other person feel bored or insulted. And, they make you sound unoriginal and uninspired.

(PS: There are 337 thoughtful questions listed in my book, Power Questions).