Creative questions are the most under-taught skill in professional life. Coding gets proposed as a fourth literacy alongside reading, writing and arithmetic, which is an odd argument to be having in the age of no-code tools.
Something else deserves teaching from an early age, and I would add public speaking as a second. Whether you are selling, innovating or, more prosaically, trying to charm somebody, knowing how to ask a question is a capability that remains largely ignored.
You do not need a podcast or an interview channel for this to concern you. The quality of the question decides the quality of what follows, in a business and in a laboratory, and two of the most valuable companies of the past forty years exist because their founders changed the question.
| The inherited reflex | What it produces | The shift that transforms |
|---|---|---|
| Creative questions, and why they matterTraining, meetings and performance systems reward producing an answer quickly. Creative questions are the skill of holding a problem open long enough to work out whether it is the right one. | A good answer to the wrong questionRushing to a solution produces work that is competent and misdirected. The failure surfaces months later, and it gets attributed to execution rather than to the question nobody examined at the start. | Problem finding beats problem solvingResearch at an art school found that students who spent their time exploring what to draw produced work judged more creative than those who decided fast and refined. Six years later, the same students had the careers. |
Two companies that arrived by changing the question
Starbucks and Instagram are both the second version of their founders’ original project. Each began with a question that turned out to be wrong, and each survived because somebody was willing to replace it rather than defend it.
Starbucks, from Milan to Seattle
The story starts with curiosity, which is one of my recurring preoccupations. A salesman selling equipment to the hospitality trade, named Howard Schultz, received an unusually large order from a small Seattle coffee shop.
Surprised by the size of the order relative to the size of the customer, he went to Seattle to meet them. He found a small business specialising in coffee beans, roasting its own, serving at the counter and selling high-end brewing equipment. Schultz, Seattle, coffee: you have already worked out that this was Starbucks.
Schultz resigned his sales job and took over marketing and communications for the business. What interests me is what happened next. In the spring of 1983 he was sent to Milan for an international housewares trade fair, looking for new coffee equipment Starbucks could resell.
Walking between his hotel and the convention centre, he passed an espresso bar and went in. Opera played in the background, a single employee called a barista worked the machine like a performer, and that barista knew the customers by name and by preference while they drank standing at the counter.
Schultz cut short his supplier visits and spent the rest of the trip visiting other cafes across Milan. Some were expensive and some were working class, and all of them functioned as living community places. In one of them he heard somebody order a caffè latte, ordered one himself, watched it made, and concluded that nobody in America knew about this.
He returned to Seattle with an irresistible creative challenge: how do I recreate the Italian caffè in the United States?
Starbucks’ three owners rejected the idea. Business was good and they had no interest in turning their shops into cafes. They did agree to provide start-up capital and to supply him with coffee, so Schultz left in 1985 and opened his own place in Seattle’s business district in April 1986.
He called it Il Giornale, the newspaper. The decor recalled Italy, the menu was laid out as a newspaper page carrying Italian words, opera played, the baristas wore white shirts and bow ties, and there were no chairs. Three hundred customers came on the first day, and it was already obvious that the Italian model did not fit Seattle.
Some complained about the opera, others wanted somewhere to sit, and almost nobody knew what the Italian cured meats on the lunch menu were. Even pronouncing the shop’s name was awkward.
So Schultz asked himself a new question: how do I create a comfortable, relaxing environment for good coffee that suits the culture of Seattle? That was a considerably better question.
Once he dropped the opera and the Italian menus and added chairs, Il Giornale began drawing up to a thousand customers a day, which funded two more sites. A little over a year after opening, the three shops were approaching 1.5 million dollars a year, and in August 1987 he was able to buy Starbucks, his own bean supplier, and rename his cafes after it.
From Foursquare to Instagram
A more recent example, from 2010. Location was the fashionable capability, GPS let smartphones tell you whether friends were nearby, and Foursquare had launched a year earlier with users checking in to let their friends know where they were.
A young programmer named Kevin Systrom wanted a share of that action. He had worked at Google and on an early version of Twitter, and he was ready to go alone.
Drawn by Foursquare’s success, he started from one question: how do I build a location-sharing app? A few months of programming produced a simple iPhone app that let you check in, make plans, earn points for time spent with friends and post photos. A thorough copy of Foursquare, which is worth remembering next time somebody praises the originality of startups.
Because Systrom liked Kentucky bourbon, he called it Burbn, and it flopped badly. The app was hard to use, tangled with a mess of features, which is the condition since named feature creep, where too many capabilities make a product unusable.
A second programmer, Mike Krieger, joined at that point, and the two of them analysed how people were actually using Burbn. Users were not declaring their location. They were posting and sharing photographs constantly.
Systrom and Krieger abandoned Burbn entirely and started from a new question: how do we build a simple photo-sharing app? They studied the popular photography apps and identified two main competitors. Hipstamatic had excellent filters and made sharing difficult, and Facebook was unavoidable while its app offered no photo-sharing function.
They saw the space between the two, and built for it. Starting from Burbn they removed every core feature except taking and sharing photos, commenting and liking. A few months of experimentation and prototyping convinced them the key was making the app simpler, and the final version let you post a photo in three taps.
They renamed it Instagram and launched on 6 October 2010. Twenty-five thousand users signed up on the first day and a million within three months. When Facebook bought Instagram for a billion dollars in April 2012, the answer to the second question had produced tens of millions of users.
Instagram succeeded because its founders were willing to go back to the first step and ask again. They studied their own failure, worked out what users were actually doing, examined the competition and formulated a different question. Silicon Valley calls that change of direction a pivot, and the psychologist and creativity researcher Keith Sawyer calls it a zig zag.
Finding a problem beats solving one
In the 1970s a number of psychologists argued that creativity was simply another name for problem solving. We now know it goes considerably further, and that it starts as a staged process where the first stage decides most of the outcome.
The study that separated the two styles
Mihaly Csikszentmihalyi, whom you may know for his work on flow, spent a year at the School of the Art Institute of Chicago with the psychologist Jacob Getzels, trying to understand how creative work comes into being.
They set up an experimental studio with two tables. One was empty, the other loaded with assorted objects including a bunch of grapes, a steel gear lever, a velvet hat, a brass horn, an old book and a glass prism. Thirty-one art students were asked to choose objects, arrange them on the empty table however they liked, and draw the arrangement.
Two distinct approaches appeared. One group took a few minutes to select and place their objects, a few more to sketch the overall composition, and spent the remaining time refining, shading and adding detail. They formulated a visual problem quickly and invested their effort in solving it, and the researchers called them problem solvers.
The second group could not have been more different. They spent five or ten minutes examining the objects, turning them to see every angle. Having chosen, they frequently changed their minds, went back to the table and swapped one object for another.
They would draw their arrangement for twenty or thirty minutes, then sometimes change their minds again, rearrange, erase and start over. After an hour of that, they settled on an idea and finished the drawing in ten minutes. The researchers called them problem finders.
Which group produced the more creative work
Five professors from the Art Institute rated the creativity of each drawing without knowing anything about the process behind it. With few exceptions, the problem finders’ drawings were judged considerably more creative than the problem solvers’.
That result deserves a moment. The exploring group left themselves far less time for the final image, and the final image was all the judges saw. The most creative students were the ones who worked on getting the question right rather than rushing to a solution and rendering it well.
Six years after graduation, Csikszentmihalyi tracked the students down to see who had succeeded and who was respected by critics. About half had stopped making art altogether, a quarter were scraping by, and the remainder had some recognition. The most successful, working in major galleries and represented in permanent museum collections, were on the whole the students who had been problem finders at art school.
The quote worth keeping, and the one worth dropping
Einstein wrote that the formulation of a problem is often more essential than its solution, which may be merely a matter of mathematical or experimental skill. He added that raising new questions and new possibilities, and regarding old problems from a new angle, requires creative imagination and marks real advance in science.
That passage comes from The Evolution of Physics, written with Leopold Infeld in 1938, and it says everything this article is arguing.
The other line, the famous one about spending fifty-five minutes on the problem and five on the solution, is not his. The earliest known version appeared in a 1966 article on manufacturing management, credited to an unnamed Yale engineering professor and split forty minutes to twenty. It attached itself to Einstein around 1973 and has been circulating ever since.
I mention it because using a fabricated quotation to argue for rigour is an uncomfortable position, and because the real one is better.
Field note
A good answer to the wrong question, in Sydney
Not every founder gets a subtle clue. When I launched my recruitment consultancy in Sydney, I went several months without a single client in a market that was expanding fast. What corrected me was not a signal I picked up along the way. It was a punch in the mouth.
The HR director of a large technology company told me, in those words, that my offer was a good answer to the wrong question. I was answering how do you recruit talent from their CV, and the question worth answering was how do you identify behaviours and values that never appear on a CV.
That single sentence reorganised my whole practice. It led directly to recruiting on values, and from there to everything I have since done on engagement. The business had not been badly executed. It had been aimed at a question the market had already stopped asking.
Before improving how you deliver something, check what question your offer answers, and check whether anybody is still asking it. Months of effort can be technically excellent and pointed at nothing.
Four ways to become a creative questioner
Questions are keys that unlock information, and they open a person’s trust as readily as they open their thinking. So when somebody shares an idea with you, what should your first reflex be? Accept it, criticise it, say nothing until you have tested it, or ask where it came from?
Build an environment of trust first
Google’s Project Aristotle set out to define the characteristics of the perfect team and found psychological safety at the front of every high-performing, innovative team it studied. People develop more creative solutions when they trust the person across the table.
Good questions combined with genuine listening are what get a group off the well-worn path. Try asking from a different angle to make everybody’s cognitive muscles work.
Ban questions starting with why
When you are asking questions to support creativity, resist opening each one with why. It looks like the obvious question and it undermines your ability to connect with the person answering.
Instead of asking why that did not work, ask whether the failure surprised them, or what happened next. Why puts people on the defensive. It forces them to produce a simple answer to a situation that may be complex, and it fails to show that the person asking cares about their situation.
Use how and what to open new thinking
Avoid closed questions that call for a single answer and that lead you, without meaning to, towards the answer you were expecting. Open questions such as what surprised you have a far less predictable ending.
Because there is no precise answer waiting, you can learn something deeper and more startling than a set of facts that lead nowhere. The question does the exploring rather than the confirming.
Bet on curiosity and authenticity
Your questions have to be sincere rather than a checklist to work through. Ask with the intention of actually understanding, because everybody can tell when somebody is genuinely interested in what they are saying.
This is why I always encourage anybody asking questions to start from how the other person felt. What did you feel when that happened, or what was the first thought that crossed your mind, both show that the answers are not the only thing that interests you.
Sincere questions tell the person they can be themselves and answer without fear. People rarely remember the exact conversation they had, and they remember how they felt during it.
Which questioning format fits your situation
Four formats get used to work a question in a professional setting, and each one suits a different stage. Choosing by habit rather than by stage is how a team ends up refining an answer to something nobody checked.
Four formats compared
The deciding question is whether you are still looking for the problem or already committed to it. Formats built for solving will close down a problem that deserved another hour of examination.
| Format | What it is for | Where it fails | Use it when |
|---|---|---|---|
| Problem framing session | Producing several candidate questions before choosing one | Feels unproductive to anybody measuring output per hour | The brief arrived already phrased as a solution |
| Open interview | Learning what somebody actually experiences | Collapses into confirmation if the questions are closed | You need the customer’s or the team’s real situation |
| Structured brainstorm | Generating volume once the question is settled | Produces confident answers to an unexamined question | The problem is agreed and options are missing |
| Peer review group | Testing work in progress against people who have done it | Turns into a decision meeting if anyone present holds authority | Work exists, is imperfect, and needs an outside eye |
Signals that you are solving the wrong problem
Four signals tell you the question needs reopening. Each of them appears well before the results do, which is the only useful time to notice.
- Your solution keeps getting better and the numbers stay flat, which usually means the execution is fine and the target is wrong.
- Customers use your product for something other than its stated purpose, which is exactly the signal Systrom and Krieger acted on.
- The brief arrived phrased as a solution, which means somebody skipped the question before you were involved.
- Nobody in the room can state the problem in one sentence without using the name of the proposed solution.
Put your unfinished work in front of people who have done it
A better question rarely arrives alone. Discover how to run a Braintrust like Pixar, the peer format built to reopen a question without anybody in the room being able to overrule you.
How I can help you ask better questions
I work with teams on the stage before the solution, which is the stage almost every process skips. The work runs from a keynote through to facilitating the sessions where a brief gets taken apart and rebuilt as a question.
Workshops and problem framing sessions
A framing session takes a live brief and produces several candidate questions before anybody is allowed to answer one. Teams routinely discover their brief was already a solution wearing a question mark.
Interview and questioning training suits managers, salespeople and anybody running discovery, and it is closer to a practical rehearsal than to a course.
Keynotes and creative leadership programmes
A keynote suits an organisation whose people are competent and keep producing work that lands on nothing. The art school study does most of the persuading, because it is uncomfortable and it is evidence.
Longer work sits inside my broader practice on creative leadership, and the questioning methods connect to the wider set in my piece on the six thinking hats.
Conclusion: creative questions decide what you build
Schultz built an Italian cafe in Seattle and it half worked. Systrom built a location app nobody wanted. Both survived because they went back to the first stage and asked again rather than defending the answer they already had.
The art students who explored produced work judged more creative, and they had the careers six years later. The formulation of the problem is often more essential than its solution.
So before you improve your answer, check your question. Creative questions are a skill nobody taught you at school, they can be practised at any age, and they decide most of what you will build.
Frequently asked questions about creative questions
What is problem finding, and how does it differ from problem solving?
Problem solving formulates a question quickly and invests the effort in answering it. Problem finding spends the time working out which question is worth answering. Research at the School of the Art Institute of Chicago found problem finders produced work judged significantly more creative.
Why should you avoid questions starting with why?
Why puts people on the defensive and forces a simple answer to a complex situation. Asking what happened next, or whether the outcome surprised them, opens the same ground without the implied accusation and produces a more useful answer.
Did Einstein say he would spend 55 minutes on the problem and 5 on the solution?
No. The earliest known version appeared in a 1966 article on manufacturing management, credited to an unnamed Yale engineering professor with a different split, and attached itself to Einstein around 1973. His genuine line, from The Evolution of Physics in 1938, makes the same point.
How do you know you are solving the wrong problem?
Your solution improves and the results stay flat, customers use the product for something other than its purpose, the brief arrived already phrased as a solution, or nobody can state the problem in one sentence without naming the proposed answer.
