11 Questions Legendary Inventors Ask

Inside a smoky control room a few hundred feet from the Berlin Wall, a group of musicians sit slumped on chairs, couches, and amplifiers. One has his head in his hands. Another picks at a guitar without really playing it. It’s 1977, and they’ve spent the whole afternoon on a track that refuses to come together. These are seasoned, successful musicians, and they’re out of ideas.

The producer doesn’t say anything. He walks over to the mixing desk, opens a small black box, and shuffles a deck of cards inside it. He pulls one, reads it silently, and then turns it around so the band can see. It says: “What would your closest friend do?”

The guitarist reads the card twice, then stands up, walks back into the recording room, and plays the simple part he knows his best friend would have played. The song finds its shape before dinner.

The producer was Brian Eno, the British musician who would go on to shape records for David Bowie, Talking Heads, and U2. A few years earlier, Eno had started writing down prompts and questions to ask himself whenever a session stalled. He wrote each one on a scrap of card, and whenever “writer’s block” hit, he shuffled the stack and trusted whatever card came up.

His friend Peter Schmidt, a German-born British painter, had been doing the same thing in his own studio, nearly word for word. In 1975 they combined the two sets and printed them as a deck called Oblique Strategies. Eno kept the box on the desk through Bowie’s Berlin records, and the deck is still in print today.

Eno built a tool for summoning inspiration, and questions were a key component.

So many legendary inventors I’ve studied carry their own unique version of that deck, a handful of questions they return to over and over.

Here are 11 I’ve collected. Some come from people I admire; others come from my own toolkit. Steal whichever ones fit, and use them to start your own custom Oblique Strategies deck.

1. “If I had no constraints or execution risk, what would the ideal solution look like?”

Sketch out the answer you’d build if budget, politics, and technology weren’t limiting factors. Then start adding the real-world constraints back in one at a time and see how much of the ideal version you can keep. Usually it’s more than you’d expect.

2. “Does this help with one of my favorite problems?”

Richard Feynman, the famed American physicist, kept a list of about 12 unsolved problems running in the back of his mind at all times. Every time he learned something new, he checked it against the list. His colleague Gian-Carlo Rota said that when a particular piece of Feynman’s work succeeded, people called him a genius, and Feynman said it was just a habit.

This one is less about the question and more about the list behind it. Most of us have never written our “favorite problems” down. Write down the problems you’d want to crack if you had a free year, and you’ve just created a new source of inspiration.

3. “What would we do if we had to launch this by Friday?”

A fake deadline puts things into perspective and often compels you to remove the unnecessary. It’s another way to tap into the power of constraints.

4. “Why?” Five times in a row.

Taiichi Ohno, the Japanese engineer who built the Toyota Production System, devoted a section of his 1978 book to a habit he called asking why five times. His own example: a machine stopped. Why? Because a fuse blew. Why? It overheated. Why? Poor lubrication. Why? The pump is worn. Why? Nobody checks the filter. By the fifth why, you’ve found the real problem. (Side note: my kids are REALLY good at this one!)

5. “Who has already solved a version of this in a totally different field?”

In The Find a Way Field Guide, we call this the Borrowed Idea. Doctors at Great Ormond Street Hospital in London were making too many errors in the handoff from surgery to intensive care, so they flew to Ferrari’s headquarters and rebuilt the process around a pit stop. Technical errors dropped 42%. Whatever you’re struggling with, somebody in a different industry has already solved a version of it.

6. “Are there constraints? What are they?”

In a 1972 interview, a French museum curator asked Charles Eames, the American designer behind some of the most iconic chairs of the last century, whether design had limits. His answer was that design depends largely on constraints, and that the designer’s first job is to name as many of them as possible. It’s the opposite of question one in this list, but just as useful depending on the context. Constraints often promote creativity rather than hindering it, and being intentionally aware of them is the first step to tapping into their power.

7. “What if we did the exact opposite?”

This is another technique from The Find a Way Field Guide called the Judo Flip. Write down the way everyone in your industry does it, then draw a line and write the polar opposite next to each one. The undesirable last-row seat on an airplane becomes a privacy-enhanced premium add-on. A salon that charges per haircut becomes a monthly subscription for unlimited cuts. Pushing yourself to explore the exact opposite of the traditional approach awakens your creative intuition, and it can judo flip your biggest challenges into audacious new inventions.

8. “If we weren’t already doing this, would we start it today?”

Peter Drucker, the Austrian-born American management thinker, asked this about every product, process, and standing meeting. Sunk cost makes us loyal to things we’d never choose to begin in hindsight. Research suggests that the best innovators excel at both knowing which experiments to start and which to kill (my team at Platypus Labs and I cover this in depth in the next edition of the Innovation Quotient, which comes out on Wednesday).

9. “How might we…?”

I’ve taught this reframe for years, and I’m far from the first. It traces back to a creativity researcher at Procter & Gamble who used it to break a team out of a dead end. “How do we” demands an answer, while “How might we” invites people to shout out ideas that feel unexpected or even a little too wild, and that’s often where the good ones come from.

10. “What would make this 10 times simpler?”

Not 10 percent. 10 times. Strip the thing down to the bare essentials. Best-case scenario (and it happens more frequently than you think), this is the version you end up using. Worst-case scenario, you see the idea/project/problem in a brand new light.

11. “Have I asked enough questions?”

A self-explanatory reminder. You don’t have to stop at 11 questions, or limit yourself to this list. Still stuck? Keep asking.

None of these require a big budget or a fancy job title. Write down the three or four that fit how you think and keep them close. The next time you’re stuck, pull one. And if you’re inspired to be like Brian, keep them in a little black box.