Leaving & Loving Microsoft

New Microsoft is pretty awesome. Surprise!

“Windows for Workgroups,” I said to an IT instructor in 1994. “Why crash one computer when you can crash six?” 15 years old and I already had a reputation as an outspoken Microsoft-basher.

I read a bunch of books in the 90's about Microsoft’s rise and came away believing that Bill Gates’ Microsoft wasn’t just breaking every law the DOJ accused them of, they were unethical businessmen as well. When it came time to jump from DOS to something more modern, I chose the Mac. As a result, I’ve never owned a Windows PC.

When Google famously said that their unofficial policy was “Don’t be evil”, everyone in my generation of computer geeks knew exactly who they were referring to. Microsoft was more than merely “dominant” back then, in some people’s opinion their presence and practices were holding the industry back. I believed this about Old Microsoft, and I still do.

But I’ve been working at New Microsoft for three years, and I have enjoyed, respected, even loved many aspects of it. Here are some things I learned:

There’s Design and There’s Design

Any designer can redesign something and post a graphic on tumblr. But it’s professional-grade software designers that can take a concept, work with a team of devs, testers, PMs, marketers, etc and still be proud of what comes out the other end. 90% of the work, if not more, happens outside Photoshop.

It feels like most designers on the web talk a lot about “beautiful pixels” and “perfection” as they post screenshots of their clean, elegant v1 app. But that’s like a skier that can only perform on fresh powder with no one else around.

On the other hand, high-level software design that affects millions of people is like navigating an over-crowded double black diamond. Covered in ice. At night. It’s a whole other experience, and not everyone can do it.

Microsoft Designers Are Amazing

I’ve been really impressed by the quality of the designers at Microsoft. I was lucky to learn a lot from some pretty phenomenal people, and this is not my first time at the rodeo. These designers don’t just perform in some pretty crazy circumstances, (see above), I believe they saved Microsoft.

In Redmond, it feels as if design has finally earned a seat at the table … and it wasn’t handed to them without a fight. Culture shifts this large are uncommon in corporations and it’s a testament to the design-minded leaders at Microsoft that it happened at all. It wasn’t Ballmer’s doing. It certainly wasn’t Sinofsky’s. (They’re both gone; I only wish they had left earlier.)

Ideas Are Easy, Help Us Execute

Before my first day at Microsoft, I filled a sketchbook with crazy ideas and concepts for Windows Phone. Some of them were really far out. Then I came into the studio and almost every one of them had been thought of already. Whoa. Awesome.

And it gets better — a significant number of them had been prototyped, tested, and explored, which led to really deep insights that you just don’t get from sketching and dreaming. I was amazed. The Windows Phone design studio (and Microsoft at large) isn’t lacking for great ideas. That was very encouraging to see.

Post-Defensive

Microsoft bought me a Mac. iPhones and Android devices are all over the place. People use Google products without getting in trouble, as some might assume. The company was far less defensive than I was expecting.

In fact, Microsoft is so aware of competitive products that I often wasn’t even the most knowledgable person about them. I’m not used to someone knowing more about Apple’s products/strategy/business plans than I am, but it happened at Microsoft frequently.

The executives carry iOS, Android, and Windows products and they are very aware of where Microsoft faces an experience gap. Witnessing these insights firsthand gave me a lot of confidence in Microsoft’s ability to catch up in some key areas.

A Grown-Up Company

The benefits, work/life balance, and fairness afforded its employees are pretty impressive. I could tell from my first day that the company genuinely wanted its (full time) workers to be healthy and happy. We still work really hard, like everyone in software, but there’s more balance than I expected. There’s a maturity here that benefits the long term viability of the company.

(Also our charitable giving is bonkers. This is a company that really does care about making the world a better place, and it reflects in the actions of its employees.)

Out With the Old

I wasn’t a fan of Ballmer. I’m not even a fan of Bill Gates when it comes to product vision or his belief in stack ranking. (though he’s one of the best people in the world thanks to the work of the Gates Foundation — that’s indisputable.)

But the last three years have been fascinating to see from the front lines. No more stack ranking! A realization that we need to be great on iOS and Android! A new CEO that everyone thinks very highly of! (I sure do) Old guard Microsoft leaders who were holding the company back and are being shown the door! Genuine (and newfound) respect for the value of design!

Things aren’t perfect, and Microsoft has some huge, well-understood challenges ahead of it. But the desire to improve, and move beyond the old world, is tangible and exciting.

So Much Opportunity

Once you’re a full-time employee, it’s not particularly hard to move to other teams. You’ll often meet Microsoft employees who have (for example) been on Xbox, then Office, then Windows, over to some secret project, maybe they left Microsoft for a few years, then maybe they came back to Xbox again. There’s so much work to be done that it can feel like a buffet of teams and fun design challenges to choose from. It’s pretty great.

And Yet

So why am I leaving? I got a new design head via the re-org and we don’t see eye to eye on team building and culture. It’s his call to make, but I didn’t think my style could be effective under his leadership. No big deal.

So I went to the buffet to see what other fun opportunities are available in Redmond. I spent a few weeks chatting with various teams, and in the end I found an interesting opportunity outside the company. (It came down to one great offer inside Microsft and one outside, and I almost had to flip a coin!)

So I’m headed out, but I may be back someday. I don’t like Old Microsoft, but over the last several years I got to see what New Microsoft is becoming. And I may be more surprised than anyone, but I can say it’s looking pretty great.