Even if you succeed, sometimes it’s worth trying again.

If you don’t succeed the first time, the old saying goes, try, try again. Good advice, for the time being. But let me suggest a modification: even if you succeed, try again. As tempting as it is to declare victory and move on, in many endeavors there is much to be said for rethinking a seemingly satisfying formula.

Consider tips for interviewers in Talent, a new book by economist Tyler Cowan and venture capitalist Daniel Gross. They suggest asking a common question, such as “Give me an example of a time you solved a difficult problem at work.” Then ask for another example. And another.

The standard answers will quickly run out, and the candidate will have to start improvising, digging deeper – or perhaps admitting that he has reached a dead end. “If a candidate does have 17 significant job successes,” write Cowan and Gross, “you might want to hear what the number 17 looks like.”

One way to describe this tactic is that the interviewer asks for answers in parallel rather than sequentially. Instead of putting together a logical sequence of 17 questions, the interviewer asks for 17 different answers to the same question.

This is paradoxical advice, but its logic is clear enough and seems easy to implement. So why don’t we do it? First, we feel uncomfortable. Second, requiring 17 different answers to the same question may seem silly or fruitless.

While this approach is unconventional for job interviews, it is common practice among designers. They often make several separate attempts to complete a given task instead of immediately focusing on what seems like the best idea. In doing so, designers force themselves to explore the full range of possibilities in order to avoid the risk of prematurely adopting a concept that seems attractive but may ultimately turn out to be a dead end.

Researchers Stephen Dow, Alana Glassco, and others at Stanford University explored the idea by asking participants in an experiment to use simple software to design web ads for a magazine. Half of the participants worked sequentially: they sketched out five advertising prototypes, receiving feedback after each. The other half worked in parallel: they sketched three prototypes, then received feedback on all three, and then sketched two more before getting feedback.

Dow and his colleagues asked experts to rate the quality of the final ad and tested it online by measuring click-through rates. They appreciated the variety of advertising and also asked participants to show trust after the process was completed. In every way, the ad for the parallel process was better: the final design looked better and attracted more clicks; the initial drafts covered a wider range of ideas; and aspiring amateur designers gained confidence from parallel prototyping.

A prime example of parallel engineering is the creation of the Windows 95 startup sound. Microsoft was looking to showcase the growing audio capabilities of computers of the day, so, somewhat implausibly, it commissioned Brian Eno, whose previous employees were David Bowie, Talking Heads, U2, Devo, and Roxy Music.

Eno recalls receiving an assignment that required the music to be “uplifting, sexy, driving, provocative, nostalgic, sentimental. . . there were about 150 adjectives. And then at the bottom it was written “and no more than 3.8 seconds.”

Eno describes himself at the time as “completely devoid of ideas”. He found the summary both hilarious and inspiring. He ended up composing over 80 tiny pieces of music. The end result is a musical signature that has stood the test of time, and a liberated Ino. “It really broke the deadlock in my own work,” he told the San Francisco Chronicle.

No doubt this was in part a response to the hard limit of 3.8 seconds of a piece, but it was certainly also a creative response to an attempt at 83 tracks. When it would be easy to stick your nose into a mixing console obsessed with the slightest variations in tone and rhythm, Eno forced himself to explore the possibilities.

Bill Burnett and Dave Evans in their amazing book Designing your life, suggest an exercise in which you sketch out a vision for the next five years of your life. What will you do? Where will you live and with whom? Are you hoping to run a marathon? Start a business? To write a novel? Marry?

It’s often a simple act of the imagination, but what makes the exercise harrowing is what happens next: Burnett and Evans want you to do it again, only this time it’s different – the idea behind the plan is completely forbidden. Return to the drawing board. And then a third time.

I have tried this myself and have seen others try it. People are writhing. They protest. Sometimes they cry. And then, sooner or later, ideas start pouring out. We contain many, all of us. But we don’t always let them see the light. Perhaps we should try to generate responses in parallel more often. Even if you succeed, try, try again.

Written and first published in Financial Times June 3, 2022

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