The Impossibility Question

Excerpted from Chapter 12 of Just Listen with the permission of the author Mark Goulston

Birds fly, but people can’t. You can’t record music. You can’t market a Pet Rock. And you certainly can’t become a multimillionaire by selling books on-line. Why? Because everybody says so . . . or at least everybody used to. Of course, that was before somebody did each of these things.

If you’re that somebody— the Thomas Edison, Wilbur Wright, Gary Dahl, or Jeff Bezos who’s trying to transform a vision into reality— your biggest problem isn’t realizing that your goal is possible. It’s talking other people into seeing that it’s possible.

It’s getting your coworkers, your clients, your employees, your boss, your investors, or your family to go from “we can’t do it” to “maybe we can do it” to “let’s do it.”

Years ago, Dave Hibbard, the co-founder of Dialexis, taught me one of the most powerful tricks for turning a situation around if you’re being held hostage by people who can’t get past “can’t.” He calls it the Impossibility Question, but I like to call it “kicking but.”

The Impossibility Question works with a person who’s somewhere between resisting and listening, but not ready to move to considering. Typically, the person is wavering between fear (“ this is a threatening idea, and it will fail and ruin me”) and apathy (“ this may be a good idea, but it sounds like too much effort on my part”). If you’re lucky, there might be a flicker of interest in there somewhere (“ Hmmm . . . could it work? Who knows.”). But without a shove, your idea is going nowhere. That powerful shove is the Impossibility Question.

Here’s how it works.

YOU: What’s something that would be impossible to do, but if you could do it, would dramatically increase your success?

OTHER PERSON: If I could just do ____ , but that’s impossible.

YOU: Okay. What would make it possible?

That’s it, just two quick questions:

“What’s something that would be impossible?” and, “What would make it possible?”

What’s so powerful about those two questions? They move a person from a defensive, closed position or a selfish, excuse-making stance into an open, thinking attitude. And they make the person picture your vision as a reality and cooperate in thinking strategically about reaching that reality.

When you ask people to tell you something that’s impossible, you are in essence getting them to say something positive: “I believe this is impossible.” Thinking and saying that shifts their minds into a positive (agreeing) movement toward you. Once they’re in that “Yes” vs. “No” or “Yes, but” mode and you agree with them but add the twist—” What would make it possible?”— they’re poised to cooperate.

This approach is a little like the martial arts ploy that uses an opponent’s offensive move against the person by pulling the opponent off balance instead of striking back. It works because rather than resisting that movement you mirror it and invite it, causing the other person to go off balance. Once this happens, the person moves from resisting or thinking to considering, and you have traction.

That doesn’t mean the person will buy in instantly. Sometimes, the first reply will be snarky or hostile: “Well , give me a million bucks and a staff of eighty people and that deadline would be possible.” But wait quietly, and the person’s mind will take hold of the question you posed and feel compelled to give you an answer. In effect, you’ve created a mental itch that needs to be scratched, and the only way to scratch it is by answering the question. When you get that answer, you’re in.

Several years ago, I used the Impossibility Question with a segment producer on the television show, The View. He’d done a capable and competent job of preparing me for a segment in which I was the guest expert, and we got to talking about his dream of being an executive producer. He was smart and creative and talented, but I could see he was still stuck in “can’t”— as in, “I can’t do what I want because there’s too much competition and it’s a cutthroat business and I don’t have the edge I need.”

So I asked him: “What is something that would be impossible, but if you could do it would rapidly accelerate your career wish to become an executive producer?”

He was hesitant at first, but then he responded with: “If I could find out where Chandra Levy is” (this was before she was discovered dead in Washington, DC) “and arrange an exclusive interview with Barbara Walters, that would put me on the radar screen and greatly help my progress toward doing what I want to do.”

I replied: “So even if you don’t do that, if you can arrange for an exclusive interview by Barbara with a highly sought-after guest, you could accomplish the same thing. Correct?”

“Correct,” he replied and as he was about to leave the green room he stopped, turned back to me and said: “I’ve been doing this kind of work for over ten years and never has a guest asked me such a helpful question. Thanks.” Without planning it, I’d succeeded in also accomplishing the impossible for myself— that is, becoming memorable to a producer who must deal with hundreds of guests like me in a year.

How can you use the Impossibility Question in your own life? The power of this question lies in its flexibility: it works in any situation, business or personal, where improvement is vital but people say “It can’t be done.”

Here are two quick examples.


SALESMANAGER: What’s something that would be impossible to do, but if you could do it, it would dramatically increase your sales?

SALESPERSON: If I could get Company X to try our payroll management system, which is much better than the one they’re using now, it would get us to a new level of clients.

SALESMANAGER: Okay, what would make that possible? SALESPERSON: What if our CEO found a way to speak to the CEO of Company X, since the two of them are pretty equal in stature? And, hey . . . maybe our marketing person could figure out a way to invite a few CEOs of other companies to a meeting— maybe something fun that our CEO and company could host .

SALESMANAGER: Hmm, not a bad idea. It wouldn’t be easy to do, but it’s not impossible.

#2: The Impossibility Question in Customer Service

SENIOR MANAGER OF A CUSTOMER SERVICE DEPARTMENT FOR A COMPANY THAT SELLS BUSINESS SOFTWARE: What would be impossible to do, but if we could do it, it would dramatically increase our customer’s satisfaction with our products?

CUSTOMER SERVICE TEAM MEMBER: To be able to read our customers’ minds and predict who’s going to be a pain in the rear after they buy a product, because they’re the ones who tend to badmouth us to everyone they know.

SENIOR MANAGER: What would make that possible?

TEAM MEMBER: What about asking customers when they buy one of our products if we can call them a week later to check with them on how the product is working for them and to walk them through additional tips on how to get even more out of it? That way we can find out who’s having problems, and get them back on track.

SENIOR MANAGER: Great. Let’s do it.

It’s that simple, and it works in any dynamic: coworker to coworker, boss to employee, even employee to boss. But don’t keep the Impossibility Question locked in your drawer at work, because it’s a hell of a tool for changing things at home, too.

For instance, ask your partner, “What would make it possible for us to spend more time with our kids and put in less overtime and still be okay financially?” Or ask a teenager, “What would make it possible for you to be safe and still be able to do many of the things you really want to do?” Or ask an aging parent who’s living with you, “What would make it possible for you to feel less unhappy about giving up driving?”

When you do this, the people you connect with will solve problems you thought were unsolvable. In fact, they’ll stop being the problem, and start being the solution— and the possibilities will be endless.

Usable Insight:

Invite people to tell you what they think is impossible, and they’ll lower their guard to consider what’s possible.

Action Step:

Ask someone at home or work to name an impossible goal the person would like to accomplish or achieve.

Note from Bob:  Asking the “Impossibility Question” has become one of my favorite questions!


Mark Goulston


Mark Goulston, M.D.,is a psychiatrist, consultant, business coach focusing on founders, and is the author of Just Listen,  Get Out of Your Own Way and most recently,Talking to Crazy.  He is a contributor to Harvard Business Review, Huffington Post, Business Insider, Fast Company and Psychology Today.  He is frequently quoted or featured in The Wall Street Journal, Fortune, Forbes, Newsweek and others, and on CNN, NPR, Fox News, and BBC-TV.  Mark lives in Los Angeles with his wife and three children.  For more information visit: contact him:


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4 thoughts on “The Impossibility Question

  1. Pam Smith says:

    This is a keeper! Just put this on the agenda for an upcoming meeting.

    1. Bob Tiede says:

      Pam please report back to share with us how your team responded when you asked them the “Impossibility Question?”

  2. Pam Smith says:

    Feedback from using the question: I left a half hour of the hour long meeting for this exercise and it was not at all enough time to enjoy the level of excitement and great thinking that the question generated. Each member of the team had gems to contribute and there were at least five great ones that we will continue to work on.

    1. Bob Tiede says:

      Pam thanks for reporting back – Do you know how encouraging and motivating your comment is?

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