THE ONE CONVERSATIONAL TOOL THAT WILL MAKE YOU BETTER AT ABSOLUTELY EVERYTHING

Guest Post by Shane Snow

Great insight moves your career, organization or business forward.  The Problem?  Most people are terrible at asking questions.  Learn from the pros how to do it right.

Ask yourself: If you could interview like Oprah Winfrey, would you get more value from your meetings? Would your mentors become more valuable? Would your chance encounters with executives in elevators and thought leaders in conferences yield action items and relationships?

The answer is yes.

“As someone who had little to no experience in business–outside of running my own one-man freelancing operation–all that’s really saved me (so far) from madness are the skills I used as a journalist,” says Evan Ratliff, who wrote for magazines like The New Yorker before founding his startup, The Atavist. One of those skills, he says, is “being able to formulate questions that deliver useful answers, whether from advisers or clients or whomever.”

Good questions can move your business, organization, or career forward. They squeeze incremental value from interactions, the drops of which add up to reservoirs of insight. Of all the skills innovators can learn from journalists, the art of the expert Q&A is the most useful.

The problem is, most of us ask terrible questions.

We talk too much and accept bad answers (or worse, no answers). We’re too embarrassed to be direct, or we’re afraid of revealing our ignorance, so we throw softballs, hedge, and miss out on opportunities to grow.

But we don’t have to.

The following advice can make you a much better interrogator, not to mention conversationalist:

Don’t Ask Multiple-Choice Questions

When people are nervous, they tend to ramble, and their questions tend to trail off into series of possible answers. (“What’s the most effective way to find a good programmer? Is it to search on Monster or to go on LinkedIn or to talk to people you know or … uh… uh… yeah, is it to, um…is there another job site that’s good …?”)

You’re the one with the question; why are you doing all the talking? Terminate the sentence at the question mark. It’s OK to be brief.

On that note, learn to be comfortable with silence. Allow your respondent to think; don’t jump in with possible answers after a few seconds pass. You won’t get answers if you keep talking, and you’ll rarely learn anything if you offer all the answers.

Questions that start with “who,” “what,” “where,” “when,” “how,” or “why” have high probability of thoughtful responses, whereas those that begin with “would,” “should,” “is,” “are,” and “do you think” can limit your answers. (Of course, if you’re trying to limit an answer to “yes” or “no,” you can do that, but if you’re seeking advice or stories, opt for open-ended questions.)

Good: “What would you do?”
Bad: “Would you do X?”
Terrible: “Would you do X or Y or Z or Q or M or W or … ?”

Adding a simple “what” to a bad question beginning with “do you think” is all it takes to generate an open-ended response. Practice asking questions that begin with the 5Ws (and H) to turn duds around.

Don’t Fish

“The really ‘bad’ questions are leading ones–the questions where you’re fishing for a particular answer,” says veteran journalist Clive Thompson, who writes for Wired and The New York Times. “You have to avoid those at all costs.”

First of all, if you know the answer, why are you asking?

If you’re seeking confirmation on something you already suspect, ask objectively, and ask directly. You’ll come off as confident (and less of a chump), and you’ll get more honest answers.

Good: Do you like Spotify’s new discovery feature?
Bad: What do you think of Spotify’s terrible new discovery feature?

Interject With Questions When Necessary

“Stopping a conversation to ask the right questions is far superior to nodding along in ignorance,” Ratliff says.

A good journalist will steer a conversation by cutting in with questions whenever they need to. This helps rein in ramblers and clarify statements before the conversation gets too far ahead to go back. Notice how great interviewers like Larry King or Jon Stewart maintain control of their conversations; it’s almost always through polite interruptions–not with things they want to say, but with questions that keep the Q&A on course.

Mature people will rarely be upset by interruptions that let them continue talking. To the contrary, additional questions make people feel like they’re being listened to.

Field Non-Answers By Reframing Questions Later

Journalists are used to speaking with publicists and well-rehearsed business people with whom it’s often hard to pin down to get a straight answer. Sometimes non-answers are delivered deliberately; often they’re the results of simple rambling. (How many times have you forgotten the question halfway through your response?).

In these cases, you can follow up with either a direct question (“So, how many dollars per month will this cost?”) or by slipping in a variation of the question later into the Q&A. Journalists often have to probe from multiple angles before unlocking the information they need. As long as you are sincere, you won’t come off badly if you ask clarifying questions about the same sorts of things. You won’t come out as empty handed either.

Repeat Answers Back For Clarification Or More Detail

If you’re getting vague responses–or complicated ones for that matter–restate the answers in your own words. (“So, your software will email me any time there are important news stories in my industry?”)

This will typically yield either a definitive “that’s correct,” or a clarification with extra detail. Either way, it’s useful for getting a precise answer.

I know some people who deliberately misparaphrase respondents’ answers in order to incite quick, and often less careful, responses–or in some cases catch someone who’s lying. (Be your own judge of when and whether you feel comfortable employing such tactics.)

Don’t Be Embarrassed

The worst kind of question is the one left unasked.

“There’s typically no point in pretending you know something when you don’t,” Ratliff says. “As a reporter the goal is to gather information, not to impress your subjects. You’d think it would be different in business, but it’s not.”

People are much kinder than we often give them credit for.

“I don’t let questions from entrepreneurs drive me crazy,” says Fred Wilson, partner at Union Square Ventures, a man who is frequently mobbed by entrepreneurs at events. “They are all trying so hard to get where they want to go. I just try to give them the best answer I can.”

And if you ask a bad question from time to time, it’s okay. It happens to the best of us. Legendary business thinker Seth Godin writes, in response to my query about how to ask good questions: “I’m not sure I have a useful answer for you!”

Shane Snow  is a New York City-based technology journalist and web entrepreneur. Co-founder and Chief Creative Officer of Contently. You can find more of Shane‘s writing here.