Avoiding Interrogation

To find the opportunity with a new customer, you’ve got to make yourself teachable.

You’re not teachable if you’ve already decided what the opportunity is. You’re not listening if you’ve already decided what the customer should buy or fixed on what you want to sell them.

If you’re asking lots of yes-no questions, testing them against some pre-determined hypothesis, you’re probably annoying them.
No one wants to be qualified for your solution before you’ve really understood their business and what they’re trying to do.

Closed-ended (yes-no, fill-in-the-blank or multiple-choice questions) make a customer feel diagnosed and interrogated.
In initial conversations, customers prefer open-ended questions — what, how, who and why — questions that invite them to share perspective and tell their story. Thoughtful open-ended questions build a relationship faster.

If you’re used to troubleshooting, it will take practice to pry open your closed questions, but it’s worth it. You’ll quickly discover that the open-ended versions are the quicker route to the sale.


Are you using automated tools to track your inventory?

How big is your IT team?

Would you like to spend less time on maintenance?

Is [Competitor] working out for you?

Are you having trouble with X?

Are you using Windows or Linux?


How are you tracking your inventory now?

Who manages your system today?

What do you want your IT people to be doing?

What do you like about [Competitor]?  What else would you like it to do?

How do you manage X?

Tell me about your OS.

You can convert any yes-no question to a friendlier open-ended version by assuming the answer to the original question is “yes” and asking the follow-up question.

Instead of…

Are you going to add capacity to
your data center?

Try this…

How do you plan to increase your capacity?

Yes-no questions are particularly annoying when they’re leading — that is, when you’re using a question to express your point of view. You’ll usually get better information by stating the point directly. Provocative statements encourage customers to ask questions.

Instead of…

YOU: Would you like to automate that process?

Try this…

YOU: A lot of our customers get big savings from automating that process.
CUSTOMER: How do they do that?

If you really want to annoy a customer, ask multiple questions at once: “Are you having thermal issues in your data center? Any hot spots or trouble controlling airflow or issues like that? Would you say that’s been a problem?”

Compare that with this version: “How’s the temperature in your data center?” Full stop. You’ll get a much better response from customers when you ask one question, then be silent and really listen to their answer.

If you’re listening, the customer will keep trying to teach you how to sell to them.

Sometimes customers do that by giving you an incomplete clue, something that sounds promising but isn’t explained. Take the bait. Always prompt them for more:  “Tell me more about that.”

CUSTOMER: This approach to storage would connect well with our new XTR initiative.
YOU: Tell me more about that initiative.

When a customer uses a vague, general term or a buzzword — flexible, interoperable, scalable, user-friendly, consolidated, streamlined, integrated — always ask, “What do you mean by that?”

CUSTOMER: This solution has to be very flexible to work for us.
YOU: What does flexibility mean for your organization?

CUSTOMER: We’re trying to make this scalable.
YOU: I’d like to understand that better. What does scalable mean for you?

Opportunity hides behind buzzwords.

Don’t interrogate customers. Engage them. As you ask open questions, make provocative statements and follow clues, they’ll teach you their business. You’ll see which of your messages are relevant. You’ll learn how to express your value in their language.


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