Leon Wong: from Microsoft to Google and back


The ‘Softie in question: Leon Wong

Title: Principal Development Manager, Online Services Division (Bing)

Leon Wong is a man in demand. Throughout his career, he has performed at the top of his field: first at Microsoft, then at Google and now back at Microsoft again. His co-workers – and even his VP – regard Leon as a true rockstar engineer capable of feats unattainable by mere mortals.

But why would such a talent leave a company for a competitor only to return to the original company again? And what does Leon’s story teach us about what the two companies have to offer? 

Leon is now back at Microsoft, but he still enjoys a positive relationship with Google and his former colleagues. As such, he is uniquely suited to give us a balanced perspective into working at the two companies.

We sat down with Leon at his office at the Bing headquarters in Bellevue, Washington, to get the inside scoop.

Leon, could you start by telling us where you went to school and how you started your career in technology?

I’m originally from Toronto. My father is a physics professor and he always wanted me to go to the best: to MIT and I did. I received my BS and MS in Artificial Intelligence there started a PhD too, but left to work for a professor’s “decision support” company called Ascent Technology. Eventually, I took a second stab at a PhD at Stanford, but left to join the ‘90s dot com boom with some MIT classmates.

“Leaving school to join in on the ‘90s dot com boom” is often the beginning of a tragic story. But, we have a feeling that things went better for you.

We created a company called Flash Communications. It was arguably the first instant messaging service specifically for enterprise clients. We were bought by Microsoft and I came out to Redmond as part of the Exchange Group.

Did you always work for Exchange?

I held a variety of roles: I was a development lead then manager for Real-Time Communications which encompassed IM, audio, video, etc. I was later a Research Software Engineer in the Speech Technology Group in Microsoft Research and then worked on Version 1.0 of MSN Search back before it was Bing. Those were the days when it was still just a little group that fit around a single table.

When and why did you make the decision to go to Google?

I went to Google as part of the AdSense Group in 2006. At the time, Google had an impressive lead in technology for building online services. I was also interested in its culture of innovation and its reputation for having a great work environment.

What struck you the most in terms of career differences between the two companies?

Google’s organization is very flat, which is nice if you’re a frontline engineer, but if you want to move up to become a manager, it’s not ideal. Their managers can have 20-40 reports or more and it’s just a lower touch role. Decision-making is very much left in the hands of the individuals.

At Microsoft, the manager is part of a small team and is integral to the product design process. This helps to get things done in a swift, organized fashion.

Google may get the reputation as the brash innovator, but Microsoft is really good at focused execution and paying close attention to customer feedback. The structure of each company plays to their relative strengths.

Do these structural differences extend beyond the management role?

Well, Google is a very egalitarian company, but that can lead to difficulty in reaching consensus when there are large numbers of stakeholders with different opinions. People can be idealistic to a fault and strive to find a consensus that may not actually exist.

Microsoft, on the other hand, is more top-down and hierarchical. That may be a turnoff to some – like engineers who are accustomed to a high degree of independence – but that structure creates an ability to make hard decisions and make them quickly.

The fact that work at Microsoft adheres to a process also guarantees that you’ll be recognized for your hard work and accomplishments.

Why did you decide to leave Google?

I was at the Pacific Northwest Google offices and these satellite offices can get a bit small for senior tech talent. The biggest and most important projects are based in Mountain View, so it can be harder to have as much impact in a satellite office.

I hit a point where I felt like I could be doing more important things and was lagging relative to the folks down in Mountain View. I found myself at a crossroads, so I had to go to Mountain View or leave Google.

My family and I wanted to stay in the area, so there was, quite simply, a lot more opportunity at Microsoft.

What were some of the other reasons that you decided to come back to Microsoft and not go to, say, a different technology company?

Microsoft’s greatest strength is its breadth of opportunities. The company pretty much covers the entire software industry and it’s a very good company for making lateral career moves. Your good reputation from one group is likely to help you hit the ground running in a new role in a new group.

Tell us about your current role.

I lead a team at Bing. We figure out “whole page relevance” for Bing searches. That determines how images, video, ads, links and all render on the page to minimize the amount of work it takes for users to find the most relevant results

Again, there’s just so much opportunity here and so many areas to grow your career. Bing has gone from maybe twelve to a thousand people. We’ve come a long way since we could all fit around that single table.


Want to work with Leon? View jobs like his here!

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