Trending: Blue Origin, ULA and Northrop Grumman weigh in on multibillion-dollar SpaceX rocket lawsuit

Guest Commentary: The last few months have not been great for Microsoft. First, the Surface turned out to be a flop. Then, Ballmer resigned without a successor in sight and admitted he missed the boat with smartphones. And two weeks ago, he held a company meeting where he bawled that Microsoft was still the best company in the world. He must have left his flight suit and “Mission Accomplished” banner backstage.

Microsoft CEO Steve Ballmer at his final company meeting

There’s always been a steady stream of talent leaving Microsoft, but after recent events, we’re certain to see more of an exodus. Picture this. You’re a young and ambitious Microsoft employee who joined out of college a few years ago. Some of your friends from school run startups, and every once in a while you see Facebook posts about them getting funded, getting their hundred-thousandth user, or maybe even exiting. Many of your other friends work at small companies where they enjoy huge scope and very little politics. They get to take advantage of the latest technology stacks and give back to open-source along the way. You read articles about quitting your job and starting your own company. You begin to wonder if the race to climb from level 59 to 65 is really the one worth winning.

Luckily, it’s never too late to get out and find a more fulfilling role, especially in today’s startup-rich landscape. Here are a few tips I’ve gleaned from my own experience and that of my friends on how to leave Microsoft and join the startup scene.

The first thing to do is to ask yourself what you really want. Starting a company may seem like the glamorous path but it’s a huge leap. If you are passionate about solving a big problem, have found an amazing cofounder and are willing to live without a safety net then please don’t wait for anyone’s permission. Just go for it. If that’s not quite the case then joining a startup (ideally early-stage & fast-growing) will undoubtedly give you the crucial experience necessary to build your own business someday.

Like all great experiences, joining a startup is risky. Life at Microsoft may be slow and full of politics, but it’s simple. Your annual review tells you how you’re doing, and there are mentors who can steer your career because they’ve seen every path through the organization. However, join a startup and you’ll work with little guidance and be measured on hard results – users and revenue. Your company might run out of cash five months after you join. And the way Microsoft is doing right now, you may not be able to go back to it. If you’re not willing to take this risk, you might be better off making the switch to Google or Amazon.

borispullIf you’re still set on the startup path, get a resume together. Make every point in it as concrete as possible. Don’t write that you “contributed” to a part of the Visual Studio code base, write exactly what you built and why it was important. More importantly, make sure to wipe all references to your Microsoft review scores. Outside of Microsoft, mentioning these things will only bring you pain. When you have a first draft, get your friends at startups to review it, and take their feedback seriously. You’ll often discover that their expectations for interviewing and hiring are quite different from what you’ve seen.

As you’re working on your resume, start putting together an online portfolio. The technical interview is dying, which is not something Microsoft and other major players have adapted to yet. Many startups won’t even screen a developer or designer who doesn’t have a portfolio of projects they can talk about, so if you’re a dev, make sure you have some good work on GitHub. At the very least, find a way to show your creativity and talent. Put your designs on Dribbble, write on a blog, or post a video of yourself giving a talk. Having side projects shows that you can’t help making things, even when you’re not paid to. This passion for creation is the cultural fuel of all startups.

If you’re an engineer, there’s another, more practical reason to have a presence on GitHub. It shows that you’re adept with more than just Microsoft technology. For example, if you’re thinking about data science, you should be versed in Hadoop, NOSQL, and MapReduce. It’s a turn-off for companies to meet you only to find out you’ve never left the Microsoft C# bubble.

Once you have a reviewed resume, material in your portfolio, and you’ve brushed up on the state of the art, it’s time to turn into a networking animal. Everyone knows a warm intro is worth 100 cold applications, so tell your friends and old colleagues that you’re on the market. You should even tell your friends of friends because weak ties score the most jobs. You want to be the person that someone says this about: “I know a really good engineer annoyed with Microsoft, and he’s looking around.”

Beyond your direct network, there’s a great way to connect with startups: get to know investors in the area. They are always open to networking (it’s a huge part of their job after all) and act as de-facto headhunters for their portfolio companies. It doesn’t hurt to cold-contact people at companies, but make sure you sound like you have something to offer. Generic sounding ‘I came across your jobs page’ emails go directly into spam. Instead, get on Google, figure out what the company’s biggest challenge is for the next six months, and suggest three ways to overcome it.

As you start to talk to acquaintances, investors, and interviewers outside your circle of friends, you should watch out for some of the biases you’ve probably picked up at Microsoft. Here are some things to keep in mind:

  • Never mention your review scores.
  • Know what job you want. It goes without saying that no one wants to hear that you just want to leave Microsoft.
  • If you’re a PM, be very concrete about what you’ve done. There’s a tendency to think that PMs at Microsoft don’t do anything useful.
  • Show that you’re eager to contribute, not manage. Managing may have been the end game at Microsoft, but it’s not at a startup.

Finally, be vision-driven instead of constraint-driven when discussing an idea or product. It’s a common stereotype that a Microsoft engineer’s first reaction to a new idea it to poke holes in it. Startups don’t operate on this type of thinking. They have bold, even crazy, visions and find ways to realize them. Think SpaceX.

It can take a few months to find the right job, but eventually you’ll find a company you like. You’ll discover that compensation at a startup is considerably different and you should learn how to negotiate offers effectively (hint: know about “shares outstanding”). When you finally accept an offer, pour yourself a drink, look forward to the adventure to come, and smile as you think about never having to eat in those soulless Redmond cafeterias again.

One more thing. When you give notice, do it gracefully. Be honest about why you’re leaving but also positive. Chewing out your coworkers in the exit interview won’t do you any good. Your relationships at Microsoft will likely come in handy. You might get a note from your manager a few months after you leave asking if he can ditch Microsoft, too.

borisBoris Jabes is the CEO of Meldium, a Y Combinator-backed portal designed for teams to securely access their web apps. He worked as a PM and Lead at Microsoft for seven years. 

Editor’s Note: Want more advice on joining the startup world? Get your tickets for GeekWire Startup Day, Oct. 25. Early bird rates end Friday.

Like what you're reading? Subscribe to GeekWire's free newsletters to catch every headline


Job Listings on GeekWork

Find more jobs on GeekWork. Employers, post a job here.