Distinguished Technical Evangelist

James Whittaker

written by

Jennifer Warnick

Lead Writer

How to change the way people think in four easy steps

It’s a Friday afternoon, and James Whittaker is sitting at Hi-Fi Brewing in Redmond. Laptop open, pint to the side, he’s working on his latest brainchild, a manuscript called “The Art of Stage Presence.”

After spending his career leading various deeply technical charges, Whittaker has spent the last year tucking his metaphorical soap box into countless overhead compartments as he travels the globe speaking about Microsoft. Stage presence, he said, is his super power.

“I’m convincing the world that Microsoft is a force to be reckoned with, that we do interesting work, that we’re thinking about the future, that we have great ideas,” Whittaker said. “I’ve spoken at all of the major developer conferences on every continent. Except Antarctica.”

Lou Reed’s “Walk on the Wild Side” begins playing overhead. “And I will totally teach penguins to code if you give me an opportunity,” he continues in his Kentuckian drawl.

“Anyone who has ever sat through a technology conference can confirm that brilliance is not always bestowed in equal measures with stage presence and public speaking skills,” Whittaker said. “See, there are four parts to every talk …”

The only time people will ever give you their attention – where you don’t have to earn it, they just give it to you – is the first 30 seconds of a presentation.”

Whittaker paces like a prize fighter as he waits for his session at the Seattle Interactive Conference to begin.

He’s been horribly sick for days, he explains wearily, and had to fill his veins with coffee and his head with Billy Idol in order to oust himself from bed. But head cold or no, the stage is Whittaker’s ring, and from the moment the lights dim, he’s bobbing, weaving, fighting to win the audience’s attention.

His industry experience and the countless hours he’s spent pondering how the future can be better (and how Microsoft can help make it so) will be distilled into a few moments on stage – Whittaker’s short window of opportunity to win minds and influence people. He begins without even introducing himself. “I’m going to talk about the future. Because, frankly, the present pisses me off.”

To steel himself for these high-energy presentations, it’s not unusual for Whittaker to spend weeks thinking, writing and developing even the smallest section of his well-polished speech. It’s also not unusual for him to drop and punch out a set of 50 push-ups back stage before he goes on.

When his opening is complete, all eyes are on him. No one appears to be idling on Facebook or sending emails – the audience is learning, laughing, tweeting putty in his hands.

Whittaker “is a fantastic presenter,” tweets Briana Saunders, a Seattle social media consultant from the audience. “Can we have the future of tech now please?”

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A future worth wanting - SIC 2013

At the Hi-Fi Brewery, I reminded him of this time he was deathly ill and still killed it.

“Thank you. You can put that in there if you’d like,” Whittaker says, chuckling and gesturing to my notes.

Whittaker can always be found wearing roughly the same ensemble: a driving cap, a soccer jersey or a band t-shirt, Puma sneakers and particularly fancy blue jeans. He has the lean look of someone who could short circuit a Fitbit in one afternoon. Even when he’s docked in Redmond between globetrotting speaking gigs, he’s still constantly on the move – hiking, jogging, visiting favorite breweries or going to live music or comedy shows.

His work habits are nomadic; he often totes his trusty, sticker-covered Sony Vaio laptop to local breweries to focus.

“In fact, the Hi-Fi is exactly 5.1 miles from my house,” he said. “I walk here, work for a little while, and walk home. It cancels the beer.”

“Every six minutes, include something of high interest. That’s the length of the average human attention span.”

“People connect with speakers who have passion – who are really in love with their subject. You inherit some of that love from them.”

Once Whittaker does get around to introducing himself, there’s plenty of material.

Whittaker was the first computer science graduate ever hired by the FBI to automate its caseloads. That was in 1986. It didn’t last long (not just because he was repeatedly written up for not wearing a tie).

“Working for the government was horrid. I have kind of an alternative personality, and it was very rigid,” he said.

He left the FBI (and Louisville, Kentucky, where he was born and raised) for the University of Tennessee, where he would earn his master’s degree, then his Ph.D and – graduating into an economic downturn – go to work for his professor’s startup.

“When the startup sold and he made millions of dollars and I made hardly anything, I realized that working for someone else’s startup is about the dumbest thing anybody could do,” Whittaker said.

Since then, Whittaker has shown an almost preternatural instinct for gravitating to a field of technology just as it was about to boom.

First, there was software testing. While he was teaching computer science at the Florida Institute of Technology, he wrote a series of bestselling books on how to break software code. Then he got into security. He created a computer security startup and eventually sold it to Raytheon, a major American defense contractor. In 2006, he decided to work for Microsoft.

James working at the brew-pub

“Working for a big company was the one thing I’d never done,” he said.

Whittaker eventually went to work as an engineering director at Google, leading teams working on Chrome, Google Maps and Google+.

“As a Google employee, the work is interesting, and there are all these cool toys and free food, but eventually you wake up and realize what you’re doing,” Whittaker said. “In a nutshell, Google’s business model is to attract as many users as they can by producing useful stuff, surveilling the hell out of them and then selling that information to advertisers so they can monetize it. At Google their product is literally their users. They hide it well.”

Whittaker decided to return to Microsoft after three years at Google. For months, he was asked one question repeatedly: “Why?”

Tired of answering individual inquires, Whittaker decided to write a post on his new blog to explain. In “Why I left Google,” Whittaker writes candidly about the complicated feelings involved with falling out of love with Google, and about his optimism for Microsoft’s potential. Though he assumed only a couple of hundred people would see it, the blog post garnered more than a million readers.

“To see it blow up was really, really surprising,” Whittaker said, shaking his head. “But you can never regret the truth, and everything I published was true.”

“Albert Einstein said, ‘Great spirits have always encountered violent opposition from mediocre minds.’ Quote powerful people. You can assume some of the power of those you quote.”

Whittaker is standing 12 floors above downtown Bellevue, Wash., explaining to a roomful of Bing engineers how sometimes it helps to practice public speaking while naked.

“Being vulnerable and flawed makes it harder to practice for a presentation,” he tells the Microsoft employees in his monthly “Art of Stage Presence” class. “But harder practice means the presentation will be stronger.”

Whittaker fills notebook after notebook on the inflections, gestures, props, delivery and mannerisms of people who he thinks are the world’s most compelling stage presences, from Martin Luther King to Carl Sagan and George Carlin to Amy Schumer. Good presenters take every chance they can to practice their message, he tells his students.

“I’m glad we talk to cars now, because before we did, people thought I was nuts. I’d pull up to a stop light, make eye contact with a woman in the next car, and give her the opening lines of my talk with the windows up,” he said, getting big laughs from the room.

Practice may make a presentation perfect, but authenticity is what helps it stick the landing. Part of Whittaker’s popularity and credibility with audiences also seems to come from his refusal to be anything but brutally honest. In a ketchup world, Whittaker is Sriracha hot sauce.

In a ketchup world, Whittaker is Sriracha hot sauce.

“I don’t have many filters. It can be a problem,” Whittaker said, with a chuckle. “But I think Kentucky is like that. If people take offense, they take offense immediately and to your face, and you talk about it, and you get over it. I’m very direct, and I do much better in cultures where directness is cherished.”

“I do quite well in Europe,” he added. “I don’t think I’ve ever pissed off a European.”

That honest streak means he will talk openly about his frustrations with Microsoft, like that the company sometimes moves more slowly than he’d like, or that it’s tough to navigate the tension between progress and the legacy that must be observed because “customers depend on us for the stuff we did last year and the decade before and the decade before.”

“But I still believe we’re the company who’s capable of moving the needle furthest,” he said.

James speaking

The needle he’s talking about is a future where technology, and therefore knowledge and information, comes directly to humans rather than vice versa. It’s what much of his presentation centers around, the idea that instead of having direct access to the world’s information, people have to go through a browser, or a search engine or an app to access it.

“We are in this hunter-gatherer mode in technology, and it sucks. Why should you have to go to a browser, and then to a search engine, to find something you’re looking for? Why have we granted browsers this special function? Not anymore. We need a different sort of world. I want to take everything that’s on the web, and in the app store, and I want to bring it to where you are. And where are you? You’re on email, Facebook, SMS. You’re on Skype or Twitter. Those are your homes, and I want to bring all the functionality of the web to your home.”

The future Whittaker wants is one that not only brings information directly to him, but one in which his closest technological companions make inferences about how to help him, whether it’s offering to find tickets for an “Of Monsters and Men” concert or helping to book a hotel for a trip to Hawaii. He wants his Windows Phone and his Xbox One to have a conversation and plan things around him, something like:

Xbox One: OMG, “Game of Thrones” is on, where is James – he’s gonna want to watch this! I’ll record it. Phone, please tell James it’s on.

Windows Phone: Oh totally, Xbox One. James is out jogging right now, but I’ll let him know you recorded it.

“We want to take the damn web by the collar and say, ‘No, we’re not coming to you, you’re coming to us in Outlook or Skype or Twitter. No more wandering around the web,’” Whittaker said.

We want to take the damn web by the collar and say, ‘No, we’re not coming to you, you’re coming to us in Outlook or Skype or Twitter.’ No more wandering around the web.

Whittaker is working at Microsoft because he believes that it’s the one company that can deliver on this idea, this “future worth having.”

“Avoid long and tiresome summaries.”

As successful as his career has been, Whittaker said there are tens of thousands of people who can out-code, out-project manage, and out-test him.

“If I have a super power Microsoft can take advantage of, it’s my stage presence,” he said. “With what you produce, you can change the way people work and play. But with the power of words, you can change the way people think. That’s powerful.”

One stage at a time, Whittaker will continue to help change the way people think about Microsoft. It’s also exciting, he said, to see Microsoft in the midst of changing the way it thinks about itself.

“What made Microsoft successful wasn’t thinking about competitors, or market share, but thinking about changing the world,” Whittaker said. “We’re starting to think about changing the world again. It’s the one attitude that I think will get us to where we need to be, and once again make us the most relevant software company in the world.”

“If we don’t change the world, someone else will.”

Photos by Brian Smale / © Microsoft