Digital Daredevils - exploring uncharted territory with a bold new squad of Microsoft early adopters

How can a company like Microsoft keep up with rapid and continuous digital development cycles? Send in the Elite—the Microsoft Elite, that is—a collective of the company’s most enthusiastic early adopters. Elite members line up for the opportunity to be the first to use, love, and break the company’s newest technology and to compete for the ultimate prize:
The Most Interesting Leather Jacket in the World.

By J.S. Warnick

Stop. Turn back. Here be dragons.

Back when the world was flat, cartographers drew ferocious-looking mythical creatures to warn sailors away from unexplored territory. While every age has its map monsters, every age also has a few intrepid explorers who fear complacency more than The Great Unknown.

One of the largest gatherings of damn-the-monsters types at Microsoft is in the Elite program, where employees volunteer to be the first to use, push, love, crash, and ultimately improve untested new technology.

The Microsoft Elite program was created to play matchmaker between the company’s more digitally adventurous souls and its engineers, who are eager to have their newest creations used and abused (and, yes, sometimes even broken) to help get them ready for customers. Early adopters help uncover shortcomings in early builds and give product teams valuable feedback and data.

“It’s been built into our DNA at Microsoft almost from the beginning, using employees as our earliest adopters,” said Diana McCarty, a Microsoft IT program manager who created the Elite program nearly three years ago. “We have such a breadth of technology and rapid pace of development now because of the digital transformation that the timelines are shorter for feedback, yet feedback has become more critical than ever before these things are released to the wild.”

Employees at Microsoft have access to all the digital spoils that come with working for one of the world’s largest technology companies. They have access to a smooth, productive ride on virtually risk-free versions of the latest and greatest hardware and software. So why would someone choose instead to be part of a scouting party setting out ahead of the crowd to explore and map new territory?

“These aren’t your typical information workers,” said Steve Reay, a principal product manager with Microsoft IT who helps manage deployment of Office 365 across the company. “You don’t join Elite because you want a safe, stable experience. Elite is for the tech equivalent of freerunners—curious, competitive, adventurous people.”

Elite is more than just a test track in today’s rapid, continuous product development cycle. Elite is a competition.

The Leaderboard

"It’s The Final Countdooooown.”

As the annual Microsoft Elite competition enters its final weeks, you can practically hear the synthesizer riffs of the (in)famous eighties power anthem echoing through the hallways.

As Microsoft employees rush to download, try, and report on as many new technologies as they can before the year-long annual contest ends, they rack up participation points. As their scores go up, up, up, the names on the worldwide leaderboard shuffle, and new frontrunners emerge. It’s not unlike the futuristic New York Times bestseller “ Ready Player One,” in which uber-geeks from all over the world compete in a massive digital contest (although the version in the book is rife with 80s pop culture references ranging from “Pac-Man” to “Blade Runner” to “Monty Python”) in pursuit of power and fortune.

The power and fortune to be won, in this case, is The Most Interesting Leather Jacket in the World, a sleek symbol of swagger and prestige that indicates you are one of the company’s (dare we say the world’s?) top early adopters.

"It would make quite the impact statement in meetings with my boss..."

Newcomer Arianna Tehrani, a premiere field engineer in Dallas, is currently ranked ninth in her region. A recent college graduate, she learned about the Elite program at a presentation for new hires a couple of years ago, and was very interested in being among the first to get her hands on new technology. When the speaker modeled the Elite leather jacket, she was sold.

“You could almost smell the leather,” Tehrani said, laughing. “It’s a cool jacket. It was nice to see it in person—to actually know it’s real.”

She paused, thoughtfully. “It would make quite the impact statement in meetings with my boss…”

Tehrani is a natural, which as McCarty sees it is one of the three main types of people who join Elite. They are:

  1. THE NATURALS.
    These people are driven by a zest to not only get their hands on the latest technology before anyone, but to provide insight that could potentially influence the products. Also, they may have disassembled at least one toaster, hair dryer, or television in their youth.
  2. THE LOYALISTS.
    These people are customer-obsessed and have pride in Microsoft and their job, and want to feel an emotional or intellectual connection to work being done across the company.
  3. THE COMPETITORS.
    These people are motivated by points, badges, stickers, kudos, and the quest for a sweet leather jacket that will make them look like an extra in “Top Gun.”

McCarty classifies herself mostly as the second type.

“I consider myself living proof that you don’t have to have deep technical knowledge or skills to participate,” McCarty said. “I’m a communications person. I do it because I care about our technology and the experiences our employees and customers have.”

In recent months, Channing Heffney, a 19-year Microsoft veteran but a newcomer to the Elite leaderboard, catapulted seemingly out of nowhere to take the No. 1 spot in his region. He’s a release manager, which means his customer obsession and his natural obsession to try new technology serve him well both in his job as well as in Elite.

“I really am obsessed,” Heffney said. “I used to work hard to find ways to get my hands on the latest stuff—to play around with it so I would have an idea of what’s coming. It’s nice to have a way to do that consistently, and with a line of feedback to engineering so we can help make the product better.”

When he first joined Elite, it was a kid-in-the-candy-store situation. He tried everything, but didn’t always take time to log his points. Eventually, he realized he was doing himself and the product teams a disservice by not offering formal feedback. He sat down one Saturday morning and filled out a large stack of surveys to give feedback on the many products he’d tried.

“I didn’t even realize that what I was doing was shooting me to the top of the leaderboard,” Heffney said. “I said, ‘Oh! Wait a minute, this is getting serious.’ Ever since then, I’ve continued to log my points. It’s not so much for the numbers, but the sheer fact that if I say I’m going to help, I want to actually help.”

Meet the Adventurers

Meet the Adventurers

Channing Heffney
"The Leaderboard Lion"

Home base: Redmond, Washington. Super strength: My focus and determination. Cape color: Red. Travel goals: Another galaxy to explore new worlds. Most desired super power: Teleportation.
Animal form: Lion. Most prized possession: Independence. Adventure philosophy: Is so adventurous in life and online he needs a theme song. “You’ve got to take those chances in the things you do so you can be the Indiana Jones of software, but also of life.”

Sergey Shantyr
"The Master"

Home base: Moscow, Russia. Super strength: Curiosity. Cape color: Moss green. Travel goals: Iceland to see White Walkers, Antarctica to chill with penguins, Pluto to be sure it is really not a planet. Most desired super power: Omnipotence. Or Doctor Who’s TARDIS. Or at least his sonic screwdriver.
Animal form: An elephant. Most prized possession: Two Elite jackets. Adventure philosophy: Strong wanderlust. “You take your left turn, and your right turn, and what do you see? What new things can you learn? I like that in the digital world as well.”

Arianna Tehrani
"The Hotshot"

Home base: Dallas, Texas. Super strength: Observant and aware of my surroundings. Cape color: Slate blue. Travel goals: A tropical island with no connection to cable or internet. Or Australia. Most desired super power: Invisibility, but also to freeze time for a few minutes.
Animal form: Definitely a cat, because I love them so much!  However, I took a Harry Potter quiz and was assigned a snake. I must have run through the questions too quickly. Most prized possession: Family. Adventure philosophy: She’s a fearless digital adventurer but in real life won’t even ride a roller coaster.

Two-time winner Sergey Shantyr, who works as a senior field IT manager for Microsoft Russia, is one of only two people in the company to win back-to-back leather jackets. This year, he’s tried to hit the brakes a bit to give someone else a chance to win, with mixed results—he’s still ranked No. 6 in his region.

“It’s not about winning, really,” Shantyr said.

He paused, and chuckled. “I know many winners always say that, but it’s really not. It’s about the whole experience that you’re getting by helping test new products and speaking to developers who are eager to get your feedback on their products.”

Shantyr is rather new to Microsoft—he came from Citibank a little over two years ago, right about the time the Elite program was created.

“The whole concept of being an early adopter was new for me. With some testing, you try something and then go back to your safe environment,” he said. “I could not grasp the idea that your primary work machine could be used for such exercises because every new product you install, it’s always like rolling the dice. Will it land smoothly? Will it bring you any new fun, or any new features?”

Shantyr was amazed that in the Elite program, there’s no safe retreat—no line between test-driving and real life.

“I think it’s really exciting that you’re not seeing the edge where the testing is ending,” Shantyr said. “It’s all around you, really.”

These three competitors, all from different spots on the globe and all with unique reasons for joining Elite, have one thing in common. It’s a truth they share with many of their fellow competitors as well as IRL explorers like Lewis and Clark, Ernest Shackleton, Nellie Bly, Edmund Hillary, Neil Armstrong, and Amelia Earhart. That truth: Whether you’re circumnavigating the earth in a hot air balloon, kicking up moon dust, or test-driving new tech, the most interesting things start to happen once you step outside your comfort zone.

Leaderboard

Rank 01 02 03 04 05 06 07 08 09
Name CHANH SSHANTYR RDECKARD ARTEH KFLYNN WWATTS ERIPLEY KDALLAS STEKOU
Score 39925 36025 28349 10650 9787 8955 7323 6934 6753

The Birth of Dogfood

In the old days (translation into tech years: several years ago), customers could count on being able to buy a disc containing the latest version of their favorite software on an Olympic Games cadence—about every two years. Now that we’re all citizens of the cloud traveling at the speed of digital, that cadence has changed drastically. But whether the development cycle is two years or two months, one facet of it has remained the same for decades: Microsoft employees are the first customers of the company’s own products.

The Elite program was only created three years ago, but the practice of early adoption is so baked into the company’s priorities it earned its own pet name more than 30 years ago: eating your own dogfood.

What does early adoption have to do with dogfood, of all things? It’s a bit of Microsoft lore that predates the birth of some of the company’s current employees.

Dogfood

How did a random joke about dogfood in a 1988 email exchange become a tech-industry buzzword to last three decades?

Read the story on our blog >

The term made its debut at Microsoft as the tongue-in-cheek subject line of a 1988 email exchange: “Eating our own dog food,” which was presumably a reference to Alpo advertisements in the 1970s and 80s in which celebrity spokesman Lorne Greene claimed the dog food was so good he fed it to his own dogs. The widely-forwarded email encouraged employees to beat up on the company’s technology to unearth any shortcomings before it went to customers, and “dogfooding” became a pet name for the ages. Nearly 30 years later, dogfooding is still widely used, both at Microsoft and in the tech industry.

Some have tried to replace dog food with more pleasing analogies (ice cream) or more straight forward descriptions (early adoption). Regardless of the love-hate relationship for the nickname, the point remains: Microsoft employees have always been ready and willing to be the first ones to the party, a willingness that has come to play a crucial role in the ever-quickening product development process. When products are used by thousands of Microsoft employees around the world before a public release, it also sends a “we’re all in” message to customers outside the company, McCarty said.

In 2009, Robert Van Winkle oversaw deploying Windows 7 to all the employees at Microsoft. Van Winkle, a Microsoft IT principal program manager, built up a deployment program, ran the program, shut it all down, and still had a couple of years to spare before the next version of Windows ramped up.

“Things have changed so much,” Van Winkle said. “And with moving to more continuous updates, things will probably only continue to speed up.”

A brief look at Microsoft Elite: The Mixtape, Vol. 1

A specially curated mixtape of 1980s hits to help explain the Microsoft Elite program, where enthusiastic employees line up to be the first to use, crash, and ultimately improve the newest technology.

Private Eyes

Hall & Oates

Microsoft IT calls itself the company’s first and best customer, and it’s true. IT helps deploy Microsoft products to tens of thousands of users inside the company before the technology ever goes external.

Wild, Wild West

The Escape Club

The ever-increasing volume of new technology Microsoft is creating (not to mention the velocity at which it’s being released to market) means early validation and feedback are crucial to product success.

Take on me

a-ha

Microsoft IT created the Microsoft Elite program so the company would have a squad of engaged, enthusiastic early adopters to help product groups get their (fast-moving) creations ready for customers.

Hit Me With Your Best Shot

Pat Benatar

Intrepid employees can sign up for Microsoft Elite and be the first to try everything from productivity software to games. Elite members download the Elite app, where they can download and use new technology and compete to be one of the company’s top early adopters.

What’s On Your Mind (Pure Energy)

Information Society

Employees energetically use, push, love, crash, and ultimately improve the new products before they are released to customers, but the real magic comes from the feedback they provide to product groups, often in the form of telemetry and surveys.

Sunglasses at Night

Cory Hart

The more products an Elite member tries, and the more feedback they provide, the more points they earn. The more points they earn, the higher they move on the Elite leaderboard toward the ultimate annual prize: The Most Interesting Leather Jacket in the World.

Sweet Dreams (Are Made of This)

Eurythmics

In three years, Microsoft Elite has amassed 26,500 members. The program has a thriving social community (including the most active private Yammer group in the company) and it plays a crucial role in helping product groups meet release deadlines by driving early deployments, gathering user feedback, and influencing product direction.

The Best

Tina Turner

Early adopters are the best. Maybe you’d like to create an Elite group in your space? Check out this IT Showcase article for more information on benefits and best practices.

Track 0 / 8

Brent Barnett, a program manager on Van Winkle’s team, said they are constantly looking for ways to reduce deployment costs and operationalize efficiencies. As product updates came faster and faster, people in IT were simultaneously trying to think of ways to unify and improve dogfooding programs.

Before Elite, individual product programs would search for groups of early adopters for each release. Dogfooding was focused on a single product, which meant lots and lots of emails, events, contests, and giveaways trying to solicit participants.

Everyone agreed there had to be a better way. McCarty was thinking about this conundrum on her way home one day while listening to talk radio, and the hosts were interviewing a restaurant owner. The man owned a two-floor restaurant, and talked about how he was losing money because no one ever wanted to sit on the lower level. He decided to hang a velvet rope across the stairs and a sign that said, “VIP only.” Waiters told customers, “I’m sorry, you can’t sit downstairs, it’s reservation only.”

“Listening to that, something clicked. I realized it’s the shift we needed to make, from asking people to join all the time to providing an exclusive opportunity people wanted to join because it was the place to be.”

McCarty mapped out an idea for a central, gamified “Elite” program designed to “flip early adoption on its head.”

“I pitched it hoping Microsoft IT leadership would think it was cool and hand it to a program manager,” McCarty said. “I was a little caught off guard when they said, ‘That’s a great idea, go do that.’”

Nearly three years later, Microsoft Elite has 26,500 participants all over the globe. Membership includes everyone from vendors to executives and represents a range of cultural and geographic backgrounds. All come from a variety of computing environments, which is helpful for testing. And they’re fired up—Elite also boasts the most active Yammer group at Microsoft.

Initially, the features and programs Elite members got to try were largely rooted in traditional Microsoft IT and enterprise offerings like Windows and Office 365. Word spread, and eventually groups from all over the company started submitting things—phone apps, consumer products, even gaming and entertainment experiences from Xbox (Elite members even got to test drive Age of Empires II).

“We realized very quickly this was a much bigger need than the traditional tech offerings supported by Microsoft IT,” McCarty said. “This was a One Microsoft need, and we wanted to make sure Elite was available to all of Microsoft.”

The flurry of interest from across the company brings with it the program’s main risk: member fatigue.

“There are more and more products, and some of it’s really fun, like Windows 10 or Bing Translator, and other stuff is really technical,” Reay said. “Something exciting people have never seen is always going to get more interest than a new Power BI that does three more widget things.”

"You can’t throw rubbish at them. They’re not shy about honest, even harsh, feedback."

Another challenge for the Elite program is for product owners to know when to send something to early adopters. They don’t want to wait too long, but also can’t send something too early. Reay said it’s important to carefully consider whether an offering is stable enough or worthy of members’ time.

“You can’t throw rubbish at them,” Reay said. “They are not shy about honest, and even harsh, feedback. They’ll come back and say it’s rubbish. You absolutely have to be respectful of people’s productivity and time.”

The Elite program and its legion of intrepid digital adventurers has come to play a crucial role in product development at Microsoft.

“Some engineering teams, like Office 365, are shipping new features every single month, and Elite has become a critical section of that pipeline,” Reay said.

From the point of view of Reay and other program managers across the company, if there is a product, feature, tool, or app worth testing, they now have a quick and streamlined way to reach a significant audience of potential users.

“Elite doesn’t eliminate all the hitches,” Van Winkle said. “What it does do is help us validate a lot of the problems that could be there. It’s a really good early listening system for what’s working, what’s not working, and what’s downright broken so we can address those things quickly.”

Elite is decidedly not Redmond-centric; the size and diversity of its membership is another major benefit. It includes a surprisingly wide range of roles in the company, from HR and legal to marketing and technical sales (many see benefits in their day jobs from getting an early look at upcoming tech).

Reay said the self-election part of Elite is essential.

“Elite has been a welcome addition because it’s given teams like mine a direct channel to passionate product validators—people who want to use the latest tech, but who are also vocal,” Reay said. “Instead of going to 50,000 people, you’re going to a much smaller audience, but getting a high ratio of focused and thoughtful feedback.”

Risk, Meet Reward

For thousands of Microsoft Elites, there is no actual edge to the leading edge—no line between safety and free climbing. As Shantyr said, it’s all around them.

Does this way of living follow them outside of the digital realm? When they log out of their work computers, are Elite members all jumping off mountains in wingsuits or kayaking over waterfalls? Yes and no.

Tehrani, as a kid, had such a knack for technology that her parents would put her on the phone with software support if something broke. She’s more digitally adventurous than most, but in real life she is one of the most risk-averse people she knows. She can’t even do roller coasters.

“I went on one in high school and it was awful,” she said. “I didn’t want the reputation of being the backpack holder, so I got on. I hated it, but I did it.”

Instead, she prefers hanging out with her dogs, reading, playing Candy Crush, and doing those escape room games with her boyfriend. They’re all the rage in Dallas.

“My boyfriend teases me that I have ‘analysis paralysis.’ Everything I do is calculated in terms of pros and cons,” she said. “Maybe that’s why I love trying new software. Even if my computer is bricked, there’s always a way to fix it, and I get to figure that out. And when I do, it’s incredibly rewarding. I guess there’s a small group of us who think things like that are fun, and not a hassle.”

Heffney said the spirit of exploration definitely transcends both his personal and professional life. A whitewater rafter, astronomy enthusiast, and avid hiker, it’s not unusual for him to wake up well before sunrise to head to the mountains before work.

“I always try the most difficult trail on the mountain first, because if I can do that, it means the others will be easier,” he said. “It’s all about trying things and experiencing and evaluating. You’ve got to take those chances in the things that you do so you can be the Indiana Jones of software, but also of life.”

And Shantyr. Even before he earned two Elite leather jackets, one of his favorite things is getting lost, on purpose, in an unknown city. Last year he had a 20-hour layover in Chicago, and decided to wander the city. He found the second-tallest building in the city (“that was fine”) and then recalled something he’d heard about deep-dish pizza.

“I started wandering around trying to find some, and I actually found the one where it was invented,” he said. “I was on the subway, in a rush to catch my plane, and realized I still hadn’t seen the Willis Tower, the tallest building in Chicago. So, I got off the subway and ran like hell to have a peek. I went to the top. It almost caused me to not catch my flight, but it was worth it.”

Life, as well as dogfooding, is a journey—not a destination.

“You take your left turn, and your right turn, and what do you see? What new things can you learn? I like that in the digital world as well,” Shantyr said.

Sometimes those turns take Shantyr and others like him into rough seas, or dangerously close to dragons. And when they do, these explorers tip their hats and sail on past.

“I like to explore by fate,” Shantyr said, “not just by guide.”