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The One Conversational Tool That Will Make You Better At Absolutely Everything

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 Walter Cronkite, 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 advisors 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, 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 businesspeople 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!"

Get more expert advice on topics that will help your career in the Fast Company newsletter.

—Shane Snow is a New York City-based technology writer and cofounder of

[Image: Flickr user Daniel Vucsko]

Add New Comment


  • Shane, I've recently discovered a few articles and posts you've written and I have to say, I'm a fan! Thanks for this insightful post. As a career salesman I learned long ago the value of asking open ended questions to find the pain in someone's life or business for which the product or service I sell is the solution. Thanks for your insight, great stuff!

  • Mike Byrnes

    Don't you just hate "questions" from politicians sitting on a dais? Do the opposite!

  • CottonCory

    I do all these things in everyday life whenever I'm asking questions. Good to know I've been doing it right, haha.

  • Sarah Clayborne

    This answers my question about how... Thank you so much for your unselfish sharing....
    May the rest of your LIFE be the Best of your LIFE...

  • Jimmy Santa Cruz

    -Food For the Brain

    We develop a skill by trial and error. You can't always hit the homeruns your first day, practice elevates. Being open to suggestions and learning to form a technique can help you reach to the next level. Often, when you are given a responsability, you can be challenged with goals that seem unpractical. Take control and work the necessary steps for accomplishing these factors. Take a lead and allow yourself to see the advantages, make them useful, book your resources and find yourself making practice with them. When you approach a similar situation, you will find yourself in sync. Choose the right tools that suite your needs, they allow you to have proper guidence. Why suffer through the many complications? Break it down and take some time to understand the building blocks. I went through many challenges in school jumping ahead of the good stuff. How would it feel to always do the right way the first time? When you practice the right way, you do the right way. So learn the right way.

    -Jimmy Santa Cruz

  • Lewis LaLanne - NoteTakingNerd

    This article got me thinking about a course I believe all leaders would have a high interest in.  It's called "Conversational Magic". It was a three-day seminar (I have the recorded audio from it) where the Neuro Linguistic Expert who studied with the founders of this modality, Robert Dilts coached a group of professionals and therapists how to really see behind and into the answers to strategic questions you ask with the outcome of helping people overcome beliefs they have that are un-resourceful.

    The bad news about that one is that for anyone interested in it, it is hard to find but googling Robert Dilts and contacting him via email should lead one in the right direction.

    The other resource I would direct people to is a little darker and has to do more directly with the "Interrogate" part of asking questions that Shane referenced. It's a book titled . . . 
    "The Interrogator: The Story of Hanns Joachim Scharff: Master Interrogator of the Luftwaffe" Description of the book here on Amazon:

    For those looking to dive deep on the topic, it my understanding there is almost no better resource available. I learned about it from another Neuro Linguistic Programming master by the name of Dr. Joseph Riggio and it turns out he's another master of communication I would direct any would be leaders to as he is massively accomplished in the arena of coaching people into leading themselves first and then others to brilliance.

  • Dabon Joseph

    Great tips. I hope those lucky enough to hold the microphones shall learn from these. In more than countless occasions I bristle that the stupid questions these people ask. As if they are trying to get the interview done fast, regardless if it was productive and useful to the listeners or viewers. 

  • Discover Auctions

    Great post Shane, and thanks to CopyBlogger for recommending it to me.

    As the saying goes "Silence Is Golden" and once you've asked the question, one should be quiet and listen to the answer. If this is a new acquaintance you are questioning, if you listen intently, they usually will say a word or a term in their answer that gives you additional questions or topics to touch on, further enhancing the engagement. This also usually works well with difficult customers to get them to open up so you can find answers/solutions for them and hopefully turn them in to a good customer.

    On the other hand, if you are the one being questioned, I totally agree with Chris. If the questioner constantly talks over you and all about themselves, you are probably wasting valuable time, move on.

  • Othello27

    Shane; great insight.  I'm particularly interested in your style of writing and how you draw from other sources.  Keep up the great work!

  • K.Singh, London

    Great tips. I often come across people who ask me a question but also include an answer in the same question. As you have pointed out, when asking questions it is very important not to lead the person to a specific answer. Otherwise you will never get to know their true expert opinion.

  • Rory

    I think a good place to start is recognizing that there really are "stoopid questions." Somebody told us that here's no such thing as a "stoopid question" and we believed them. Bunko. A whole buncha questions are simply disruptive.


  • maureenolivia

    Actually a better question than "Do you like Spotify's new discovery feature?" is "What do you think of Spotify's new discovery feature?" because you will probably learn more then just a simple confirmation of like and dislike.

  • Batesdon1

    Advice I heard years ago that has held me in good stead, both in friendships and business relationships: Make statements, don't ask questions, whether speaking or writing.  By making statements, you express your opinion openly and let the other person respond with advance knowledge of your position.  On the other hand, asking the other person "What do you think?" in the absence of a statement generally puts the other person in a defensive position.  Worse case, they answer and you say "Well, I don't agree with you"  or "That's silly" or something equally offputting.  The other person feels set up and misused.  Alternatively, in the event you really don't have a position, you might say, "What you you think of (this or that). I ask because I honestly don't know and want to know what you think." 

  • Anika Davis

    Most common ingredient in evaluating, is the combination of listening and willingness. Evaluators may quite useless if somebody showed an ignorance. However ignorance may deserted if the evaluators shows an interest and sincerity in his work because sometimes successful questions is based on the personality of evaluators and successful questions is great if there is a better interaction of both part.

  • Steve Cowie

    The problem with restating the answers *in your own words*. is taking away the interviewee's original meaning and imposing your meaning onto them. Take care with that. 'It's just semantics' won't wash. Meaning is everything.

  • ivipul

    great article..thanks for the advice..
    On reading, you realize, how many "would" and "should" questions you really ask. I just went through a recording of an interview I had just taken today and realized the room to improve..

  • reycarr

    Unfortunately, this article has a few misleading examples that don't actually demonstrate the point the author is making. In addition, he holds up one of the worst interviewers, Larry King, as an example of an excellent question asker. Nothing could be further from the case.

    An anecdote about an interaction that Johnny Carson had with Burt Reynolds might illustrate the point. Burt had been on The Tonight Show with Johnny many times. Most of his appearances were to promote some recent work. This is the case of almost everyone who appears on these late night talk shows. They are pumped to talk about their project so regardless of what question the interviewer asks, the performer just spills out an answer that is part of their own agenda to mention and typically way more than the performer was asked by the host.

    Burt was quite aware of and experienced with of this type of celebrity interview, so one night as he was appearing on The Tonight Show, he secretly told Ed McMahon that he would only respond to the exact question Johnny asked him and not elaborate.

    Johnny would say, "Well, Burt, you have a new movie out."

    Burt: "Yes."

    Johnny (a bit flummoxed): "What's it called?"

    Burt: "Smokey and the Bandit."

    Johnny: "Is there a clip?"

    Burt: "Yes."

    Johnny: "Can we show it?"

    Burt: "Yes."

    Johnny: "Can you set it up (explain what the clip will show)?"

    Burt: "Yes."

    Well, you get the point. After a few of these exchanges (and the audience increased its laughter after each one as they seemed to catch on faster than Johnny), Johnny finally tuned in and was able to do the things he was so great at: spontaneously respond and join in with the joke.

    In Shane's example under the heading "Don't Fish" the question he asks as a 'good' example is just another bad example. The question would have been better if it just asked, "What do you think of Spotify's new discovery?' not Do you like it?

    Larry King never really listened to his guests. His agenda was much more important and his questions continually cut off a guest's opportunity to give more depth.