I always feel a small rush of pleasure when someone tells me I’ve asked a great question! Even after years of selling and consulting, I find I don’t hear it all that often—unless I prepare my questions in advance. When I spend time proactively anticipating what I may need to know before I’m in the discussion, I find myself consistently able to build real credibility simply by the nature, content, and delivery of my questions. I’m proud of that skill, even when it’s unacknowledged. And, asking questions is indeed a skill.
A few years ago, I attempted to organize a webinar around questioning skills. I wanted two experts to participate—a New York City detective and an investigative reporter from the Wall Street Journal who had interviewed me recently (and somehow gotten me to share a few things I wasn’t particularly interested in revisiting in the publication or on the website). The journalist, unfortunately, wasn’t able to get permission from the paper to participate, and the webinar never came to pass. Too bad. I think it would have been fun, a great learning experience, and a different perspective for us sale professionals.
The idea to include a police detective had come to me years before when I was in my local ER with a nasty kidney stone. While I waited in agony for a shot of Demerol to take effect, I heard two detectives introduce themselves to the patient in the next bed. Apparently, my hospital roommate had been beaten up by two “assailants” less than an hour before. Momentarily distracted from my pain, I was riveted to the conversation taking place five feet away.
The detectives started with the first question that anyone would be likely to ask.
Do you know who did this to you?
No.
Undaunted, they pressed on. Even as the Demerol took hold, I was completely fascinated at the path the interrogation took.
Where did this happen?
The parking garage at work.
Did you see the men who did it?
They had stockings over their faces.
Can you tell us anything about them? Size? Clothing? The victim provided a few scant details about the two men. Nothing particularly noteworthy.
They say anything to you or each other?
No.
You married?
No.
Girlfriend?
Yeah.
How long?
Three months.
Your girlfriend ever talk about her old boyfriend? [Great question, Detective!]
Yeah.
What did she say about him?
Boom! In fewer than twenty minutes, the detectives zeroed in on the ex-boyfriend who had a the classically dangerous combination of being prone to jealousy, having a penchant for violence, and an ongoing desire to get 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.
I never learned how that life drama turned out, but I have little doubt that those detectives were able to find their culprit, and ask him some very meaningful questions. And elicit responses that would be helpful to solving their case.
From that point on, I wanted to be able to ask questions like those detectives did. I wanted my questions to lead to the truth, to reveal the as-yet unknown, to bring forth answers that might not even be apparent to the person I was interviewing.
Clearly, those detectives knew what they needed to ask before they walked into that hospital room. The WSJ reporter who got me to say more than I intended must have also understood in advance what she wanted from me. Their conversations may have seemed spontaneous, but the questions they chose guided them to the information they sought.
I’ve given a lot of thought to questioning, and I’ve had a great deal of practice. There’s no doubt that it’s a skill that requires forethought. You can’t just start asking random questions and expect to get useful responses. You need a plan. Then, if you listen carefully and keep an open mind, you’ll usually find that the answers take you directly to where you need to be: knowledgeable!