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“What Keeps You Up at Night” and Other Pitfalls When Asking Open Ended Questions

There is one question that comes up in virtually every Richardson Sales Performance sales training session that I have conducted over the past 23 years. It is part of an activity in which teams practice coming up with and asking open-ended questions to buyers. This is the question that participants love to ask buyers — “What keeps you up at night?”

This was new, innovative, and fun back in 1997. Now, it is a cliché. It is a salesy question. If a buyer is interviewing four different companies to find the right partner, he/she can hear that question four times. In my training sessions, I work really hard with participants on asking open-ended questions that avoid this trap. The goal is to come up with classic questions that never go out of style. “What are your biggest worries when it comes to switching advisors?” If I am a buyer and you ask me a worry question, I’ll talk about my worries. You don’t have to make it a cliché about what keeps me up at night.

Another pitfall that I encourage sales professionals to stay away from involves trading questions: “If we are able to do X and Z for you, will you agree to do Y?” Asking open-ended questions with “If”; is a manipulative construction. Buyers see that you are trying to get them to say yes to something before they are ready. They hear the start of a negotiation designed to get a premature commitment from them. And, they know that even if they answer the question and make a commitment, they do not have to keep it.

Sales professionals also falter by asking something so open-ended that the buyer doesn’t even know how to begin to answer it. “Tell me about your business.” What specifically do you want to know? In today’s world of easy online access to information, don’t ask about business basics that can be found on the buyer’s website. A better approach would be to ask something like, “Tell me where your business is headed over the next two to three years,” or, “Talk to me about the top initiatives that your company is instituting this year.”

Asking open-ended questions can backfire, too, if they’re focused on fact-finding instead of encouraging dialogue. “What percentage of your business is in Asia?” “How long have you been with the company?” The answers will be numbers. The goal should be to strategically think through 1) what kind of information you want to get, and 2) what is the best wording for a question to get to the heart of that subject.

Think of it like this: If I am the buyer, my favorite subject is me, my business, or my company. I can be very happy to talk about these things. The only people who rush through these dialogues are sales professionals. Often, they want only the facts so that they can close the deal vs. trying to really understand what is important to the buyer before offering a solution. They make assumptions based on their tenure in the business and the work that they’ve done for similar organizations. The biggest pitfall is assuming the buyer is like all of the other buyers who have come before.

What I tell sales professionals is this: If you listen to and understand the buyer, you have a much better shot of the buyer listening to you and taking the next step in the buying process with you. And, the quickest way to get there is to asking open-ended questions and then let them talk.

The person doing the most talking in sales dialogues should be the buyer. As a sales professional, you should be asking thoughtful and strategic questions that, in the explore phase, keep the buyer talking 90% of the time. That means asking good, open-ended questions 90% of the time to discover and explore the buyer’s needs. The remaining 10% could be closed-ended questions to get additional facts.

The biggest aha! moment that I get in training sessions is when participants begin to understand questioning strategy. They will say, “I never thought about those kinds of questions. I never thought to ask about that.” After the training, they will come back to me and say, “I feel so much more prepared to have a really meaningful discussion — and to not leave any gaping holes in the knowledge that I have of my client and what they are really looking for.” Some of the veterans will say, “Where were you 20 years ago when I started in sales?”

I remind them of a simple foundation of consultative selling is questioning and understanding buyers: know what you know; know what you don’t know; fill in the gaps.

About the Author

Dennis Grieco, a 20-year veteran at Richardson, is a Master Training Consultant that acts not only a top-level and highly skilled facilitator for world-class sales organizations across industries, but he also takes responsibility for the development of all Richardson Senior Training Consultants to ensure they are able to meet the high standards our clients have come to expect. As a versatile trainer, Dennis facilitates programs based on clients’ needs, delivering training strategies and developmental programs in support of corporate business goals. In the classroom, he improves the skills of individual participants by utilizing his real-life experiences to provide relevant and memorable learning points