Yahoo's Marissa Mayer: 'It’s Totally OK to Fail'

Marissa Mayer, CEO of Yahoo!, at the TechCrunch Disrupt SF 2013 conference. Photograph by David Paul Morris/Bloomberg

You already know that to learn and work faster you’re supposed to fail more, fail faster, and fail forward. But how do you do that when bosses and market pressures make it so clear that failure is not an option?

That is one of the questions I put to 100 disruptive leaders—people who refuse to accept the status quo. For my latest book, I spent the last couple of years digging deep into the motivations, talents, and values of change agents—from chief executives to the geeks who are creating today’s biggest technological advances. Among their insights:

Dedicate yourself to continuous learning. Be willing to take heat for that. “It’s totally OK to fail. If what you’ve tried is working, throw more fuel on the fire. If not, pull back.” That’s Yahoo! CEO Marissa Mayer, a few months before she tackled unproductive telecommuting—and was loudly criticized for that move.

At the heart of everything Mayer does is a willingness to try new approaches. “I see everything as an experiment,” she says. “We’ll try anything once. Then, if something goes wrong, know how to learn from it.”

That’s the key. You don’t have to make big, even risk-filled moves, as Mayer continues to do. But you do have to be willing to try anything once and learn quickly if it doesn’t go as you had hoped.

Nobody is as smart as you’re expected to be. “We put a lot of stuff out there. We try, fail, and then adapt. Nobody is smart enough to say whether something new is going to work or not. We have to watch for what takes off and then adjust accordingly.” That’s Francoise Legoues, who heads up Innovation Initiatives for the chief information officer at IBM—focusing on bringing disruptive changes inside one of the world’s largest tech companies.

“My job,” says Legoues, “is to understand the technologies and uses of technologies where management will say, ‘No, this doesn’t apply to our business model,’ or, ‘No, this is too scary,’ and find a safe way to pilot it to see if it sticks. You need to find a way to try things, even if it looks counter to the current strategy or even if management doesn’t understand it.”

Piloting a project is a well-established approach to failing forward. And all piloted efforts need a pilot—someone who’s on point before there is buy-in. Being on point for pilot projects is one of the best ways for you to learn faster and learn from failures.

Iterate, iterate, iterate is a life mantra, not a business practice. The paradox of failing forward when bosses don’t make room for failure can be resolved only by putting your work and yourself out there long before you feel comfortable doing so. Making a daily mess of things is the new path to being a perfectionist.