Great Question!


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I really enjoy someone telling me I’ve asked a great question.  Even with all these years of selling and consulting, it doesn’t happen that much when I’ve not prepared questions in advance.  But when I do, I’m able to build some real credibility just by the nature, content, and delivery of my questions.  I’m proud of that skill.

A few years ago, I tried to organize a webinar on questioning skills.  My guests were going to be a New York City detective and an investigative reporter from the Wall Street Journal who had interviewed me (and gotten me to share some things I wasn’t particularly interested in appearing on the front page of Section 2 of the Journal).  She wasn’t able to get permission from the paper to participate in the webinar.  It never came to pass.  Too bad.  It would have been fun and a great learning experience for all of us in sales.

The idea for the detective came to me years before when I was in the emergency room at my local hospital with a nasty kidney stone.  While I was in agony, waiting for the shot of Demerol to take effect, I heard two detectives introduce themselves to the patient in the next bed.  Evidently he had been beaten up by two “assailants” less than an hour before.

The first question one of the detectives asked is where anyone would start.  It didn’t yield any clues.

Do you know who did this to you?


But from that point on, even as the Demerol took hold, I was amazed at the path of the interrogation.

Where did this happen?

Parking garage at work.

See the men who did this?

Had stockings over their faces.

Can you tell us anything about them? Size, clothing? The victim went on to provide a few scant details about the two men.  Too few for me.

They say anything to you or each other?


You married?


Girl friend?


How long?

Three months.

Your girlfriend ever talk about her old boyfriend? [Great question, detective!]


What did she say?

With that, in ten more minutes the detectives had zeroed in on the boyfriend who had the threatening combination of being quite jealous, prone to violence, and wanting his old girlfriend back.  This wasn’t TV.  It was real and I was transfixed.

Know where we can find him?

I think he lives on North Broadway.

We’re gonna have a conversation with the old boyfriend.  We’ll get back to you.  Feel better.

From that point on, from a questioning point of view, I wanted to be like those detectives—have the ability to ask questions that got to the truth, even when the answer wasn’t apparent to the person I was asking the questions of.

I thought about questioning a lot.  I learned what’s most important to get to the answers you want. You don’t just start asking questions.  You need a plan.

Photo credit: © Tomasz Trojanowski, Fotolia

Republished with author's permission from original post.

Dave Stein
Dave specializes in helping his clients win critical B2B sales opportunities as well as helping them hire the best sales talent.Dave is co-author of Beyond the Sales Process. He wrote the best-selling How Winners Sell in 2004.


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