Career Advice from Gary Flake, Director of Live Labs at Microsoft

Gary Flake joined Microsoft as a technical fellow in 2005 and promptly founded Live Labs, which is focused on creating innovative Internet applications such as Photosynth. Prior to Microsoft, he founded and ran Yahoo! Research Labs and worked as the chief scientist at Overture.

1. If someone wanted to land a job at your company today, how would you recommend he or she do it?


There are three traits that will serve anyone wanting any role at any company, not just ours: systems thinking, passion, and clear communication. Systems thinking is a way of looking at the world that allows you to see how many small pieces come together to make a more complex whole. System thinkers see the hidden interconnections that bind together the parts and know how to make the best use of ambiguity and uncertainty as a result.

Passion isn’t just about liking what you do. It’s also about focus, determination, and obsessing over quality. Yes, you want a job, but do you want a mission? Having this sort of enthusiasm is essential because it will get you through difficult challenges more than almost any other trait.

Clear communication brings everything together. If systems thinking is about the higher-level patterns, and passion is about the details, then clear communication is the means by which the first two traits come into alignment. You need to be a clear communicator as an individual contributor, an executive, and everything in between.

2. What is the best piece of career advice you’ve ever been given?

I was once involved in a difficult strategy discussion that presented the following dilemma: we had an urgent need for something to change, but the timing of the change was outside of our control. Many people, when faced with this situation, can become paralyzed, fail to see the other things that they can control, and therefore fail. In the context of this discussion, Steve Ballmer recounted a story that he had read in James Stockdale’s biography, which I’ll do my best to paraphrase:

As a prisoner of war Stockdale had to endure every form of discomfort imaginable, and many of his compatriots understandably broke down under the pressure, losing the will to fight or even live. Stockdale was asked how he managed to endure when so many could not. Stockdale had noted that anyone who broke under captivity did so because they either thought that rescue should have come already (leading to disappointment) or that it would never come (leading to despair). Instead, Stockdale chose to believe the opposite of both: that rescue would not come tomorrow but that it would come someday, and in so doing he freed himself of a burden that could only do damage. Once he recognized and accepted that the timing was out of his control, he was free to focus on what he could control.


As I recall, Steve apologized for the comparison because what Stockdale faced was clearly at a different scale than our puny problems, but he still made a compelling analogy with our own situation: we don’t know when it will happen, but it will happen, so do what we can in the interim and don’t fret. It’s such a simple idea, but I’ve personally found this concept extremely useful and liberating. I’ve also shared this advice and story many times since then (thanks Steve!).

3. If you were job hunting in this economy, where would you look?

One word: Plastics. Just joking. I loved “The Graduate.”

One word: Data. Right now, we have the ability to effectively instrument vast portions of products, businesses, industries, and even society. It’s scary but it’s also a tremendous opportunity because the insights for making improvements — instead of taking years to discern and incorporate — can be discovered and used almost in real-time. We have only scratched the surface, and the potential impact really is unbounded because the value discovered with data can often be multiplied a billion-fold because of scale.

In times like these, it is natural for there to be a lot of belt tightening across the board, with traditional growth areas like software, technology, and the internet naturally cooling down a bit. But efficiency — in all things — is needed now more than at any other time, and it is our ability to process data — data into information, information into knowledge, and knowledge into wisdom — that will shape our world in profound and wonderful ways. When everyone has had a chance to step back and rethink their priorities, the essential nature of data, data analysis, and data mining will be more greatly appreciated.


About the author

Chuck Salter is a senior editor at Fast Company and a longtime award-winning feature writer for the magazine. In addition to his print, online and video stories, he performs live reported narratives at various conferences, and he edited the Fast Company anthologies Breakthrough Leadership, Hacking Hollywood, and #Unplug