How to Ask a Question: It’s More than Who, What, When, Where, Why and How

The title seems either simplistic or insulting: “How to Ask a Question?” Who needs to know that?

Turns out, plenty of people do, and the post below will walk you through some ways to make your questions, and your time, both more valued to others and valuable for you.

While we all learned (or should have learned) the grade school lesson of the 5 W’s and 1 H, the reality is that asking good, effective questions that surface information and quickly cut to the core of an issue is part art, part science. In other words, it’s more than Who, What, Where, Why, When and How. [Updated: And if you’re looking for another take on the same subject, check out Mark Suster’s post from Sunday, June 6 called Asking Questions More Effectively.]

Like many things in life, figuring out how to ask a question starts in itself by answering one simple question for yourself: what are you trying to do?

Trying to promote a point of view? Think Terry Gross, or a number of talking head types on radio or TV (Rush Limbaugh, Rachel Maddow, Glenn Beck, etc.) . While I listen to Terry’s show Fresh Air, she’s not the best interviewer around. Why? Most of her questions have a “Isn’t it true?” orientation. It’s great for promoting a point of view, and surfacing facts you want confirmed. That point of view approach is not so hot for surfacing unknown information, or for casting a broad net of possible subjects. Effective though, when you want to expedite a conversation along a certain path of conversation – such as hosting a talk interview program and have just so much time for the conversation.

Trying to confirm details? The inquisition model where you want one simple fact confirmed: the “Did you?” question, great for surfacing a yes or no. Think Perry Mason, and highly effective when you have most of the pertinent data in hand and are looking to confirm things. It’s the basis of the 5 Ws and 1 H and perhaps why it’s overused. Not so effective? When the person being questioned lies (think Bill Clinton’s famous “That depends what the meaning of isresponse to the grand jury investigating him for sexual harassment ) or can evade the intent of a question by answering honestly. Did you eat the candy? No (but I ate the candy.) And asking Why? As noted here frequently gives you  a rationalization – it’s far better to ask “How did you happen..? or “What caused you. . ?” when you want deeper information.

Trying to collect information? From interviewing job candidates (and prospective employers) to interviewing national presidential candidates, “Tell me about” is the simplest and easiest way to both cast a wide net, as well as drill down deep. Think Tom Brokaw who reminds us that it’s not the question that gets you into trouble, it’s the answer. Downside of the question? You need to have the ability to digest the information that’s being provided: if you can’t connect the dots, not so helpful to ask the question. But for avoiding showboating to getting data rich information, “Tell me about” is hard to beat. As my colleagues Johanna Holldack and Jo Whitehouse noted this week over dinner, the best VCs, the best candidates, and the best would-be collaborators keep it simple and laser focused by leading their questions with that one simple question: “Tell me about” or its cousin, “Tell me more about.”

Knowing what information you’re seeking – e.g. just what are you’re looking for – should be the first thing you think about when asking any question. It reduces your time, and makes the information you get more valuable: it’s true ordering at a restaurant, interviewing a candidate, negotiating financing, or looking at a role with a firm.

Life Back West is an occasional set of writings focused on ways people, teams and organizations can be both more effective (doing the right thing) and more efficient (doing the right thing well). More about executive, career and team / leadership coaching services can be found at the “About J. Mike Smith and Back West, Inc.” sidebar or the “Hire Me” tab above. You can also read an online interview with me at WhoHub, as well as participate in my learning community courtesy of KnowledgeCrush.