How Might We ... ?

Jeremy Utley, Perry Klebahn

October 26, 2022

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The more questions you have lined up, the longer you’ll be able to sustain ideaflow. Always prepare a hefty stack before beginning the ideation process.


When answers run dry, ask a better question.

A good question is specific. The more specific the frame, the stronger the flow of ideas it will inspire. A good frame stokes curiosity. Once your interest is piqued, your brain gets to work on solving the problem in earnest. Ideaflow increases. A juicy question can make it difficult to stop thinking of new possibilities. A dull one leads nowhere. You simply can’t fake curiosity.

Sometimes a frame is literal. The legendary artist and educator Corita Kent had her students create what she called a “finder” to “take things out of context.” A finder is simply a frame made of cardboard. It “allows us to see for the sake of seeing, and enhances our quick-looking and decision-making skills.” You can use your phone’s camera as a finder or even something as specialized as a cinematographer’s viewfinder. But a square made of cardboard will do. Try looking at your problem—the product, the store, some aspect of a physical experience—through a finder and watch how a frame can make the hidden visible.

This isn’t just about getting people in a room to generate a million possibilities in one go. Group sessions are helpful from time to time, but develop a habit of framing interesting problems for yourself and keeping them in the back of your mind to fuel your Idea Quota. Collect compelling, specific questions and review them frequently. If you keep interesting things simmering, your brain will always be at work for you in the background, searching for inputs to power world-class creative output.



Nearly every good frame begins the same way: How might we … ? A good HMW question allows for plenty of exploration while leaving enough structure to keep the discussion focused. A question like, “How might we create an ice cream cone that doesn’t drip?” doesn’t leave room for the unexpected. It directs your attention toward a very specific and narrow engineering issue. A laser-focused question generates laser-focused fixes. A prompt can also be too broad: “How might we reinvent dessert for a new generation?” For the owner of an ice cream store, this isn’t going to lead anywhere useful. You need constraints. The brain doesn’t know how to “reinvent dessert”—that’s clearly too abstract. Yet companies try to “reinvent communication” or “reimagine urban transportation” and wonder why nothing happens.

The goal is a large portfolio of different frames. You’re never looking for one, perfect question—a single frame limits your thinking no matter how well it’s designed. Each prompt opens a different set of possibilities to explore. Introducing a good question spurs curiosity even when everyone at the table is certain they’ve thought through all the possibilities around a given problem. The more questions you have lined up, the longer you’ll be able to sustain ideaflow. Always prepare a hefty stack before beginning the ideation process.

There are several ways to craft useful HMWs around a problem or insight.

SCALE. Play with the zoom knob. In their classic short film Powers of Ten, Charles and Ray Eames show a man and woman enjoying a lakeside picnic before zooming out at an exponential rate, revealing the surrounding park, then the city of Chicago, then the Earth, the solar system, and so on. Once the magnitude of the entire universe is revealed, the camera zooms back in, down to the planet, the city, and the couple, before continuing the zoom into the man’s hand, reaching the scale of skin cells, molecules, and atoms.

Scale changes everything. There is always both a bigger picture and a smaller one. Each degree of magnitude reveals something unique that can’t be seen at any other level of magnification. What happens to your problem if you narrow in on one, small aspect? What happens if you widen your frame to include more surrounding context? Play with scale and watch more ideas flow.

QUALITY. Take a positive aspect of your starting insight and double down on it. Or, explore questions that suggest cheaper, faster, more imperfect approaches to the problem. Deliberately seeking “bad” ideas relaxes perfectionistic tendencies. Aerosmith, the best-selling American hard rock band of all time, holds weekly “dare to suck” meetings where every member of the band brings ideas they consider terrible. Often, the results really are terrible, but now and then they get a hit like “Dude Looks Like a Lady.” If it weren’t worthwhile, would they still be doing it after all these years?

Likewise, Second City, Chicago’s legendary improvisational comedy theater, devotes one day a month to ideas they would normally never do. On “Taboo Day,” improvisers are encouraged to propose outrageous, expensive, and impractical ideas that would normally be (not) laughed off the stage. Kelly Leonard, a leader at the storied organization, told us that a deliberate effort to suggest the “wrong” thing nearly always generates rich and useful material.

So turn the quality knob all the way up and all the way down. Either way, relax your sense of “should” and allow for silly, weird, surprising, or outrageous instead. What’s the worst that could happen?

EMOTION. What emotions does your insight inspire, and where might those lead? Consider the full spectrum here, not just positive emotions like happiness and joy but also sadness, loneliness, even fear. Whatever emotions you assume are appropriate to the situation, dial the knob the other way. It’s surprising how often this simple flip unlocks new directions.

STAKES. Try both raising and lowering the stakes of the situation to shake up your perspective. Sometimes, seemingly trivial aspects hide something profoundly meaningful. On the other hand, levity and lightness can be found in some of the most serious contexts.

EXPECTATIONS. What are you taking for granted about the problem? For this dial, it can be helpful to make a list of all the assumptions you’re making about how the product should work or how the solution should otherwise function. Then swap each assumption with its opposite.

SIMILARITY. Analogy is one of the most powerful creative tools. Consider parallel contexts at one end of the dial and completely unrelated ones at the other. To think of good analogies to try, start with the intended outcome. Want to make ice cream faster? “Who or what is built for speed?” Want to delight your customers? “Who or what delights people?” The brain solves new problems in this way, using its understanding of a familiar topic to grapple with one that appears very different on the surface.

You might apply the lessons of high school football to your first job managing a team, or transplant one of Napoleon’s battlefield strategies to a product launch. Consciously or unconsciously, we distill principles from observations and then see where else they might fit.

HMW questions can be silly or serious. The important thing is to seek a middle path between too specific to generate divergent possibilities and too broad to generate any.

Generating HMWs should happen separately from generating the solutions themselves. Resist the impulse to start ideating. If a compelling solution does come to mind as you’re generating questions, it can easily anchor you, cutting off the flow of good problems. To return to a divergent mindset, spell out the problem implicitly being solved by your existing idea as a new HMW. Ask yourself, “What would it actually do—for the user, customer, company—if we made this idea a reality?” Then, ask yourself, “What are other ways we achieve the same thing?”

HMW questions keep your energy up and spur divergent thinking during the ideageneration process. Make a habit of establishing, exploring, and discarding frames to keep ideaflow steady. Each frame, each question, represents another vein of ore to mine. Most will run dry quickly, but a few will astonish you with their depth and richness. You never know until you start digging.


Adapted from Ideaflow: The Only Business Metric That Matters.
Copyright © 2023 by Jeremy Utley and Perry Klebahn.
All rights reserved.



Jeremy Utley is the Director of Executive Education at Stanford and an Adjunct Professor at Stanford’s School of Engineering. He is the host of the’s widely popular program, “Stanford’s Masters of Creativity.”

Perry Klebahn is a co-founding member of Stanford’s faculty. He is an Adjunct Professor and Director of Executive Education at Stanford He has served as COO for Patagonia and as CEO of Timbuk2.

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