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Chris Capossela, chief marketing officer for Microsoft. (Microsoft Photo)

About six years into his career at Microsoft, one of Chris Capossela’s colleagues suggested that he apply for a very unusual gig: speech writer for then-CEO Bill Gates. His friend figured it would provide him with some great stories.

“It sounded like a crazy, exciting, weird job,” Capossela said. He went for it, and got the position. “It was fantastic.”

Capossela worked in the role for more than two years, starting in 1997. Now chief marketing officer for Microsoft, he’s not dishing any gossip about his time alongside Gates, traveling internationally, attending meetings and dining with the Microsoft founder.

But he does have a lasting admiration.

“He did a lot less holding court than I thought he would, and did a lot more asking questions and learning,” Capossela said. And Gates was surprisingly patient with him. “He was very good at teaching me. He took the time to explain why we did something. I felt like I could ask any question and he would take the time to answer it.”

The role also provided a big-picture look at the wide range of projects and initiatives being tackled by the software — and now cloud — giant.

Capossela traces his own passion for technology to when he was a kid growing up in Boston. He used dBASE for DOS on an IBM PC to build a reservation system for his family’s Italian restaurant. Then after earning a bachelor’s degree in economics from Harvard University, he went directly to Microsoft and has spent 26 years at the Redmond-based company. In his current role, Capossela runs marketing for Microsoft’s consumer and commercial businesses, leading its Worldwide Marketing and Consumer Business team.

He has seen Microsoft evolve and change over the decades, and is fired up to work with CEO Satya Nadella, who took the post from Steve Ballmer four years ago.

“The energy in the company is far higher than what it was a bunch of years ago,” Capossela said. In the past, high morale came from the release of cool new products. Now he says it’s driven by something broader: the empathetic, inclusive culture and mission that Nadella has worked to instill.

“For the newer employees and younger employees, it really resonates with them,” he said. “It’s what they want the company to be.”

That doesn’t mean that a kinder, gentler Microsoft is a less competitive, less innovative corporation, he added.

“Empathy shouldn’t be confused with a lack of desire or a lack of ambition or a lack of urgency,” Capossela said.

Microsoft has been shifting its business focus as well, reorganizing the company’s engineering divisions and putting more resources behind the company’s cloud and artificial intelligence groups. In April, the company reported that its revenue was up 16 percent over the previous year.

“It’s just a blast being part of this transformation,” Capossela said.

Microsoft Chief Marketing Officer Chris Capossela speaks at Microsoft Envision (GeekWire Photo)

Capossela has toyed occasionally with the idea of leaving Microsoft to explore the startup experience, but that time isn’t now, he said. If he left, he mused, it would have to be for a totally different pursuit. A return to the restaurant biz, perhaps?

“That would be a real left turn that I could see having a debate over,” Capossela said, though not entirely seriously. His two daughters, however, would love to see the family open a restaurant and Capossela said his wife is a terrific cook. The girls have Celiac disease, which makes them allergic to gluten, and each has a different nut allergy, so maybe a gluten- and nut-free bakery meets Italian restaurant?

“Now you’re in the realm of possibilities,” Capossela said.

We caught up with Capossela for this Working Geek, a regular GeekWire feature. Continue reading for his answers to our questionnaire.

Current location: Seat 12A on a flight returning from the Xbox briefing at the E3 conference in Los Angeles. The team shared new games, new studios joining the Xbox family and new ways to bring the best gaming experiences to fans of Xbox. When I’m not traveling, I live in Seattle and work in Redmond.

Computer types: All kinds. I work very closely with our Surface team so I use all the Surface devices with Surface Studio being my very favorite for long uninterrupted use. I also work closely with our key OEM (original equipment manufacturer) partners so I’m a big fan of the Dell XPS and HP Spectre laptops. I also love my Falcon Northwest gaming rig that I use to play PC games when I have the time. Dell has a great All in One that I love as a shared family device.

Chris Capossela’s workspace in Redmond. (Microsoft Photo)

Mobile devices: Google Pixel with either Apple AirPods or Bose earbuds. Microsoft Launcher has made the Android UI much better for me personally with easy access to my contacts and calendar.

Favorite apps, cloud services and software tools: Outlook Mobile gets a ton of use on my phone and is probably what I’d miss the most if I couldn’t use it. Microsoft Teams and OneNote have both become go-to apps across every device I use to get to all my stuff and collaborate with co-workers. Power BI dashboards on my phone and laptop make it easy for me to see how we’re doing on sales, engagement and campaign metrics. Audible is my favorite entertainment app. LinkedIn’s news feed is fantastic.

Describe your workspace. Why does it work for you? I have two sections to my office: one section for working with a single 28 inch all-in-one and an awesome old-school Realforce keyboard, and one section with a couch and chair for more casual conversations. I spend the majority of my time outside my office, either meeting with customers, partners or employees around the world or around our campus. I need very little space to be productive — just a great laptop and a decent network connection and I’m good to go.

Your best advice for managing everyday work and life? Make your life predictable by planning your year out in advance. Rather than letting the calendar control you, you need to control the calendar. Plan your travel out as far as you can. Create a regular rhythm of meetings that you can schedule way out in advance. Figure out what events/conferences you need to go to and book them early. Same for board meetings. Figure out who you want to meet with on a regular basis and get them booked. I also make sure to reserve time for family like taking kids to school or picking them up at the end of the day, etc. Some things will change during the year but a lot will stick and this gives you the ability to see the highs and lows of your year and make plans accordingly.

Among his roles during 26 years at Microsoft, Chris Capossela worked as speech writer for former CEO Bill Gates. (Photo courtesy of Chris Capossela)

Your preferred social network? How do you use it for business/work? No surprise here but LinkedIn is head and shoulders above Facebook, Twitter, etc. for quality of engagement and lack of trolls. I use it to learn about customers I’m meeting with, prospective candidates I’m interviewing for jobs, and as a way to make connections. I also love the news feed. Xbox Live is the other social network I use — but not for work!

Current number of unanswered emails in your inbox? 30. Four unread and 26 read.

Number of appointments/meetings on your calendar this week? 35 to 40

How do you run meetings? Depends on the goal of the meeting. If it’s for professional development and collective learning then I optimize for shared discussions, very few slides, more of the Socratic method. If it’s for making a key decision then it’s more structured with each person getting a chance to state their opinion, followed by some debate, followed by a decision.

Part of Chris Capossela’s office has a couch and chair for less formal meetings. (Microsoft Photo)

Everyday work uniform? Dark jeans, dark sneakers, button up shirt with an optional sport jacket or sweater for customer meetings.

How do you make time for family? See my answer on how to manage work/life. It’s all about planning ahead and creating predictability. Weekends are family time. I try to only miss dinner at home a maximum of one night a week if I’m not traveling. These scheduling rules help in saying no to the many work things that I could possibly do.

Best stress reliever? How do you unplug? Long walks after dinner with the dog and Pilates two to four times a week.

What are you listening to? Lots of great books on Audible, mostly focused on topics around inclusion. “Just Mercy” by Bryan Stevenson was a recent favorite as well as “So You Want To Talk About Race” by Ijeoma Oluo, who lives in Seattle.

Daily reads? Favorite sites and newsletters? New York Times, Techmeme, Hacker News, TheSkimm and of course GeekWire. I’m a tennis fan so lots of sites that cover the daily stories on the pro tennis tour.

Book on your nightstand (or e-reader)? “Factfulness” by Hans Rosling

Night owl or early riser? In this stage of my life, I’m an early riser up by 5:45 a.m. and asleep by 11 p.m or midnight.

Where do you get your best ideas? The shower and long walks.

Whose work style would you want to learn more about or emulate? Bill Gates because he reads voraciously about an incredible range of topics and he’s great at carving out time to think.

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