Embracing the Power of Awkward: Asking Good Questions at the Yahoo! Campus

I’ve joked for some time now that I’ve become an expert at creating a combination of connection and discomfort — but it’s becoming less of a joke when you see companies like Yahoo making that same combination a part of their essential mix.

I recently gave a talk for a small but important group of high-level Yahoo managers, who were gathered in Sunnyvale, CA to do whatever high-level IT managers do when they gather in Sunnyvale, CA. I don’t know — maybe Star Wars/Star Trek Venn Diagram Jeopardy? I wasn’t sure. But I was sure that I was feeling a little out over my skis.

Scene 1: Campus Comedy

The thing is, Yahoo has a campus and the word campus reminds me of college which reminds me of grades. And if test scores were a poker hand, amidst this team I was holding some loser cards and ready to bluff.

But I’m glad I didn’t. Because this is a story about the Power of Awkward, and how Yahoo is putting it to work for them.

So instead I marched awkwardly forward with my usual collection of stories, pokes, jokes, and improv games — highlighting the idea that when trust, teamwork, and connections are strong, faster re-dos of mistakes or mishaps are more likely to occur with less hand-wringing.

I finish my presentation, and they clap. In the moment it feels a little more golf-applause contemplative than "Wow, you just kicked butt!" enthusiastic. So I’m a little worried, but afterwards I discover that they seemed to like my unconventional methods.

Scene 2: Introducing ... the VP of Awkward

"Oh, hey," says Greg Sly, Yahoo's VP of Engineering. "Nice work." He’s the top Yahoo who found my shtick on the Internet and booked me for this gig. And no, I didn't ask if he found me on Google — although he would have liked that silly and yes, awkward question ... and here’s why.

Greg's next move is to reward me by introducing me to a kindred spirit. Let's call him Allen. Well, it’s Allen’s actual job at Yahoo to seek out awkward questions and uncomfortable issues, and then drag them out into the open.

Plus, Allen is highly skilled at what he does ... like a Jedi master. He's kind of an Obi-Awkward-Kenobi for the company. And he proceeded to hit me with a few of his own uncomfortable tips and thoughts on how I might better refine my next talk for an elite group of IT managers. I didn’t have the heart to tell him this was probably my only one. But his advice was keen, unfettered, and yes: helpful.

I came away admiring what Yahoo was attempting to do. It seems that during awkward or difficult transitions any thought-itch left unscratched can represent a missed opportunity to nip a problem in the bud, before it gets out of control. Or to lance a boil of resentment. Or to take advantage of a lightning-strike inspiration that leads to an important advance.

When we realize it’s our level of connection that allows for mistakes to be destigmatized and we open channels to dumb or awkward questions, we begin to see how valuable this fragile relationship between candor and trust truly is.

I can’t help but wonder if, during this fragile time we're going through as a country divided, we all couldn’t benefit a little from the Power of Awkward. In fact, maybe that’s what this moment is all about: A period to ask uncomfortable questions and be more open to the signals we often repress.

So thanks, Greg for introducing me to my long-lost kindred spirit of discomfort. Please give Allen a long awkward stare-down for me, will ya?