Using “constraint questions” to free up the imagination

by | Questionology

In the new edition of A More Beautiful Question, I compiled an A–Z index of all the types of questions I define throughout the book. I was fascinated to count nearly 60 different types of questions or inquiry methods.

One of my favorite categories of questions is “constraint questions”—a hypothetical question in which you temporarily shift reality by removing or imposing a constraint. A popular version of a constraint question originated decades ago with the American pastor Robert Schuller, who used it in inspirational sermons and books. Schuller liked to ask his followers:

What would you attempt to do if you knew you could not fail?

It exemplifies a beautiful question in its ability to inspire and spark the imagination. In this case, the constraint being removed is “failure.” The question gives you permission to think big.

The question was picked up years later by Silicon Valley innovators, including the former DARPA director Regina Dugan, who used it in a widely circulated TED speech. It has also been championed by the influential Google X founder Sebastian Thrun, who has quoted it on Reddit and elsewhere.

When using Schuller’s classic constraint question for sparking Silicon Valley innovation, often another constraint is removed: Money—as in, What if money were no object? What would we do then?

Constraints aren’t always removed; adding on a constraint can be just as effective. So instead of imagining having unlimited funds, one might ask, What would we do if we only had one-tenth of our actual budget?

I’ve heard about product designers asking the team working on a project, If we only had a small amount of money to spend, how might we design this product differently? Or, that same designer might play with the constraint of time. On a project with a deadline of 6 months, the team might be asked: What if we only had a week to get this done?

By using these artificial constraints, you can shift the way you or others think about a challenge. Imposing a constraint can cause you to be more focused, more resourceful, or more efficient. Removing a constraint can open your thinking so that you begin to consider more ambitious or expansive possibilities.

A simple constraint question that propelled Motown Records

One of the stories I tell in A More Beautiful Question features Berry Gordy, the visionary founder of Motown Records. During Motown’s heyday sixty years ago, Gordy’s label pumped out one hit record after another. Ever wonder how they did it (besides pure talent and productivity)?

In Motown’s early days, Gordy regularly used a constraint question as part of their weekly “all hands” production meetings (which included the marketing and writing-and-performing personnel). When the Motown team would review the many fledgling demos churned out by the studio the prior week, trying to decide which few deserved to be released as singles, Gordy would ask the group: If you had only a dollar to spend and you were hungry, would you buy this record or a sandwich?

Most prospective records lost to the sandwich; at one meeting 68 singles were considered, and only one was approved as sales-worthy. But the ones that made the “last dollar to spend” cut were extraordinarily likely to become huge hits—as was the case with more than two-thirds of the 500-plus songs released by Motown in the 1960s.

How might life plans change when they encounter a constraint question?

Perhaps the most famous of all constraint questions is: If you only had (X) amount of time to live, what would you choose to do? By imposing a time constraint, the question encourages you to focus on life priorities.

Variations on this question are widely used in the financial and life-planning industries, thanks in part to George Kinder, an influential advisor who heads the Kinder Institute of Life Planning.

Kinder actually uses three different constraint questions as the centerpiece of his life-planning approach. He asks the three questions, in sequence, as a way to help clients think more clearly about future goals and plans. (The questions below are taken verbatim from Kinder’s “Three Questions” Youtube video).

Question 1: “I want you to imagine that you are financially secure, that you have enough money to take care of your needs, now and in the future. The question is… how would you live your life? Would you change anything?”

Question 2: “Now imagine that you visit your doctor, who tells you that you have only 5 to 10 years to live. You won’t ever feel sick, but you will have no notice of the moment of your death. What will you do in the time you have remaining? Will you change your life and how will you do it?” 

Question 3: “Finally, imagine that your doctor shocks you with the news that you only have 24 hours to live. Notice what feelings arise as you confront your very real mortality. Ask yourself: What did you miss? Who did you not get to be? What did you not get to do?”

Notice that Kinder starts by removing a constraint (money); then adds a time constraint of five years; then tightens that constraint, to 24 hours. He’s using the questions to open up people’s thinking, and then to get them to focus on priorities and take stock of their lives.

“For most people, reflecting on these questions wakes them up with a jolt of recognition—that there’s something in their life they haven’t accomplished,” Kinder says. “There is a surge of energy that comes out of this.”

(Hat tip to Jonathan Clements’ excellent blog, where I first learned about George Kinder’s questions.)

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