Looking back: First year at Microsoft

One year at Microsoft, wow. After moving across the country last summer, I have met some incredible people, traveled a lot (16 trips in 12 months), and had a great time getting to know a new city. As it is with any major life change, I have grown in ways I could have never predicted. Here are a few stories from the past year that helped me learn and grow:

Don’t be afraid to be bold

At the University Innovation Fellows meet-up last March, I was leading a fireside chat with Peter Sims, an author, entrepreneur, and friend. During the interview, he began talking about GoldieBlox, a company working “to disrupt the pink aisle and inspire the future generation of female engineer”. Instantly, Nada, a young lady in the front row, became ecstatic; a huge smile burst onto her face and she began waving her arms in excitement.

I quickly wondered what is going on… Maybe she wants to ask a question? Maybe she works for GoldieBlox? Perhaps i’ll let her talk? then I stepped off stage and gave her the microphone, in front of more than 350 people, not having any idea what she was going to say. It was the greatest thing that could have ever happened.

Nada shares he love for GoldieBlox on stage at the University Innovation Fellows meetup.

Nada jumped up on stage and immediately began describing how important GoldieBlox’s mission was to her, so much so that she switched majors because she was so passionate about bringing girls into STEM.

She described how she had applied to GoldieBlox with no luck.

What happened next was too good to be scripted. Peter offered to introduce Nada to Debbie Sterling, the CEO of GoldieBlox. The room went nuts and it felt like Nada had just won the lottery.

I think about this chain of events often. Why did I give her the microphone? I’ll never know, but what I do know, taking the risk to invite her on stage was the best decision I could have made. I’ve always been a fan of “Ask for forgiveness, not permission” but never witnessed how important it really is until Nada jumped on stage. Don’t forget to be bold.

Find a way to kill good projects

“Killing projects is a normal part of doing business because it means we can go faster and take on ideas that are more promising” — Astro Teller

In the past few years, MOOC’s (Massive Open Online Course) have exploded as the tools for education have become radically democratized. As a side project, I began working with Udacity to explore the possibility of students from the University Innovation Fellows (a Stanford d.school program) creating a 4 week MOOC hosted on Udacity. The idea: bring the change-making strategies UIF’s have used to create change at universities across the nation to anyone across the world. The course “Design Thinking for Change Makers”, would focus on getting students out into the world creating change in any group they were passionate about. Over the course of a month, we created a prototype of the course including a 4-minute trailer, course syllabus and potential students to lead the modules.

The introduction to a prototype course we created to illustrate the possibilities of students leading a design thinking course hosted on Udacity to spread change making strategies across the world.

At the end of the day, we collectively agreed that while we could likely reach tens of thousands of people, the course did not fit Udacity’s core mission and would dilute the courses already being offered. I haven’t looked back since stopping this project and the freedom has given me the ability to explore even more incredible opportunities. The biggest blocker to doing cool shit is working on ordinary projects. If what you’re working on today isn’t the best thing you’ve ever done, stop doing it.

Be conscious of artificial red tape

“The regulatory systems in place disincentive innovation. It’s intense to fight the red tape.” — Travis Kalanick

At any time across Microsoft, there are 30 to 50 of what we call “Snacky Apps” or small, startup-like teams that are working on small applications independent from our core business, such as Microsoft Pix or Microsoft Hub. The goal of these applications is to quickly test hypothesis or prototype new technical tools without impacting regular business. During the past year, i’ve worked with many of these teams to catalyze their development and help the teams scale applications to millions of users as quickly as possible. Recently, I was working with a team that had the ambitious goal to scale their user base more than 10x in 3 months. The plan was to make their application global ready (aka translate their application to languages other then english) with the goal to launch in more than 60 countries. Everything was set and ready to go until one afternoon I got an email saying they were blocked on vice president approval for $55. What? You’re kidding me? A team working for a company that makes more than $80B in revenue per year was blocked on $55? Like seriously, I’ll just walk to the ATM and grab you $55…

This was my first introduction into artificial red tape, the annoying processes that feel like a waste of time but never change “because its always been that way”. In this case, the only applications that had ever been translated were apps like Word, Excel and PowerPoint that impact billions of people around the world. Never before had a team this small gone through this process. Luckily for me, my team helped me identify this artificial red tape and now we have a process for small teams to utilize this process for free.

Surround yourself with incredible people

“Whatever vocation you decide on, track down the best people in the world at doing it and surround yourself with them.” — Scott Weiss

You’ve heard this many times before but I had always missed a huge piece. I try to follow “The Law of 33%” from Tai Lopez. Your mentorship should be split into 3 parts: 1/3 of people you mentor, 1/3 of people who you work with on a daily basis and (the most important yet most often missed) 1/3 of people who are 10x better than you. In the past year, I have found some 10x mentors such as Sebastian Thrun (founder of Google[x] and Udacity), Lawrence Ripsher (General Manager at Microsoft; formerly CEO of Kikker), and Frederik Pferdt (Chief Innovation Evangelist at Google). Each has taught me something different such as “Whether your launch in 5 days or one year, the quality will be about the same” (Sebastian) or “Solve the problems you have” (Lawrence). Don’t be afraid to ask friends for introductions or cold-email people you admire.

Sebastian Thrun and I discuss driverless cars, the future of education and his life as an Uber driver during a fireside chat at the University Innovation Fellows meetup hosted at the Stanford d.school.

While i’ve learned a ton during the past year, the learning never stops. I have no idea what the next year has in store for me, but regardless, I can’t wait!

Thanks, Ryan