Failure as a Leadership Strategy

Associations often trumpet their successes, but would they have more of them if they actively courted failure?

Growing up, I was routinely encouraged to “be like Mike“—there was no bigger symbol of success than Michael Jordan in the midst of the Chicago Bulls’ championship run in the early ’90s. An obvious replacement hasn’t emerged in recent years, though, but I think I can fix that. I’m here to recommend that you be like Jia Jiang.

Everybody has failures periodically. The people who are generally successful are the ones who bounce right back.

Jiang is a web entrepreneur who’s in the middle of a project he calls “100 Days of Rejection Therapy.” Videocamera in tow, Jiang approaches strangers and asks them for things they have no sensible motivation to give him. He asked a hotel security guard if he could borrow $100. (No.) He asked a software company CEO if he’d engage in a staring contest with him. (No.)  He asked a local TV station if he could do a live on-air weather report. (No.)

There’s a serious side to his prankishness: Jiang is courting all of these rejections as a way to get more comfortable hearing them. As the Rejection Therapy project continues, Jiang pays close attention to what he did wrong and what he could improve next time around. After he got stiff-armed by a pet-store groomer when he asked for a trim, he wrote about the value of humor in negotiation: “[R]ejection or not, humor lubricates the conversation for both parties. When you are engaged in a negotiation session or sales pitch, be open to laugh at other’s jokes.” A modest lesson, perhaps, but he’s giving himself a crash course in the kind of “soft” skills that CEOs are always told to cultivate. And he’s building some serious leadership muscle as well: “Everybody has failures periodically,” career coach Marty Nemko told Bloomberg Businessweek in a story about Jiang. “The people who are generally successful are the ones who bounce right back.”

Indeed, Jiang is bouncing back better these days: He’s been keeping a “Rejection Scorecard,” which, according to its most recent update, shows that he’s hearing “Yes” 38 percent of the time. And even if you dismiss all this as an attention-getting scheme, that in itself can be a smart strategy: If you don’t ask Tony Hsieh for a free ride on his private jet, you won’t get a free ride on his private jet.

Most for-profits aren’t as candid about their failures as Jiang, but in the past decade they’ve become more comfortable with it, if only because SEC rules, shareholder pressure, and viral complaints have forced corporations to open up and plead for forgiveness. Things are different at associations, where there’s arguably less of that outside pressure. Associations Now used to—tried to—run a regular feature called “Lessons From Failure,” in which executives opened up about their mistakes. It kicked off in March 2008 and wheezed to its end by December of that year; it’s just not something leaders want to discuss openly.

So, to paraphrase Bob Dylan, “Lessons From Failure” was no success at all. Of course, plenty of organizations conduct postmortems about projects that don’t work, and they also increasingly promote “fail fast” initiatives. But would the kind of candor and risk-taking that Jiang brings to his efforts prompt you to take more chances? What concerns hold your organization back, and how valid are those concerns?


(Phil Ashley/Lifesize/Thinkstock)

Mark Athitakis

By Mark Athitakis

Mark Athitakis, a contributing editor for Associations Now, has written on nonprofits, the arts, and leadership for a variety of publications. He is a coauthor of The Dumbest Moments in Business History and hopes you never qualify for the sequel. MORE

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