‘Think Ambitious Experiments’; Valuing Failure and Coaxing the Best Ideas From Colleagues

It’s interesting how we create our best work. I recall as a young Washington Post sports reporter being told by my editor that a tennis article wasn’t good enough, and then angrily writing something much, much better. John Kander, the composer of Cabaret who just passed at age 96, told a similar story about writing the wonderful song New York, New York with partner Fred Ebb, after Robert DeNiro told him their first attempt wasn’t good enough for the film. “What does he know?” Kander recalled asking.

But you can’t go to that well too often, as they say. From talking to a lot of industry folks, one thing becomes very clear: The importance of giving people the space to try, fail and try again. Here are some examples:

Normalize talking about failures. “Working with metrics is all about trial and error, adjustment and retrial,” Elizabeth Gamperl wrote in her Reuters Institute report. “Every failure is a step closer to success.” Said one editor: “We have as many open conversations about when things haven’t worked as possible without everyone getting really upset. That is not easy because people work incredibly hard in the newsroom. What lessons can be learned?”

Make failure safe. “You have to have the ability to put yourself out there and be willing to fail,” Heather Farley, CEO of Access Intelligence and a confirmed speaker at BIMS 2024, once told us. “Fail fast and fail forward is my favorite motto.” What was one of the first things you did when you became CEO of Match? Sam Yagan was asked. “When I took over Match, I realized that they use data, but the expectation—which was always data-driven—was that tests will all succeed. It wasn’t built in a culture of failure. I compare never failing with not having ambition. [So the question became,] how do we let ourselves test out our intuition? The intuition has to inform what data you get.”

Learn lessons in success and failure. “If something [messes] up, you can look at your stats and figure out what went wrong,” said Kate Lucey, a former digital editor for Cosmopolitan UK. “Try new ideas—if they work, how can you expand them? If they fail, why did they fail and what have you learnt about your audience that you can apply to future work? It’s constant learning, constant adapting—and a constant headache… but it’s FUN.”

“Create a culture to build trust and collaboration, and breaking down silos…” Tim Hartman, CEO of GovExec said at one of our conferences. “Think ambitious experiments and trust each other. If you look around and don’t see that, you have a problem.”

Don’t let the quiet ones stay quiet. “Have a think tank where you can bring people to brainstorm,” Elizabeth Petersen of Simplify Compliance told us once. “Every person has ideas but you need to coax them out. I like to brainstorm on the fly. I have introverts [on staff], and they need to be encouraged. To have a structured agenda is a great way to get people talking.”

Set benchmarks. “One of the biggest barriers to innovation is fear of failure,” Petersen added. “The information industry is changing so rapidly and there are so many unknowns. Even the most thoroughly researched product may not gain market traction. The key to developing a humming new product development engine is to be comfortable with risk and to set measurable (and transparent) benchmarks for product success.”

Allow for turbulence. “Embracing failure is easier said than done,” Anita Zielina, former director of news innovation and leadership at the Craig Newmark Graduate School of Journalism at CUNY, told us at BIMS a few years ago. “We like to win and are not so excited about failure. But the culture of failure empowers your team to experiment. If you don’t, you’re not going to have creativity in the room. Experimentation includes failure, and organizations need to live with that. There is no digital product development that doesn’t have unexpected turbulences. But it also allows for agility.”

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