20 Years: Lessons from a Microsoft vet

A cat on a fire-breathing unicorn flying the Microsoft flag

HR tells me it’s officially been 20 years since I started at Microsoft. The thing that first comes to mind to be grateful for is that this anniversary hits while I’m in Scotland during a pandemic. If I’d still been in the States, Microsoft tradition would require that I purchase 20 pounds of M&Ms to sit outside my office door. My holiday weight gain is quite enough as is, thanks.

One of my favorite photos of one of my favorite teams. That’s me with the blond fro. It’s a long story.

I’ve taken a few mins during the new year break to reflect and muster up some practical advice from lessons learned:

  • A good manager is worth following. Especially when I was getting started, I lucked into a fantastic manager that gave me room to grow, encouragement to follow my passions, and most importantly, trust. I followed him through two org moves, and that consistency helped me build a solid foundation for the rest of my 20 years. Thank you, Gerry.
  • Mentors are critical during key career decisions. About 7 years ago, I started a mentor relationship with a senior leader that gave me the space to explore radical directions. Long story short, her advice led me to leave Microsoft. I’m sure that wasn’t the intention, but she supported the conversation, and it was a great decision leading to massive growth. I ended up returning 2 years later, but I don’t regret that “break” and all the lessons learned from stepping away to something very different.
  • Culture is a game-changer. There were great things about the Ballmer era (I joined just before Gates handed over the keys). However, the “know it all” culture and an evaluation system that pitted team members against each other created some pretty toxic interactions. Much has been written about the change in culture since Satya stepped in, and I can tell you it’s not hype. It’s fundamentally a different company since 2014, and in a very good way.
The way things USED to be.

  • Know your risk tolerance. For me, the big-corporation “tax” that you pay in extra process and more complex politics is a reasonable price, assuming the rest of the culture is positive. See previous point. That break outside of Microsoft taught me, among many other things, that always being on the hunt for your next customer to keep the company afloat isn’t the kind of stress that I thrive on. It may be thrilling and motivating for you, but not for me.
  • Be clear about the value of your role to the COMPANY. I was tempted to take on my current role several times, as it was ideal for ME. However, I didn’t see that the COMPANY saw the value in the role as it changed its place in the org structure several times. Not once, but twice, the role was effectively eliminated. I can’t imagine the stress that would’ve put me through if I’d jumped too early. The role is well-situated and valued now, so I’ve joined and couldn’t feel more secure in the value we’re providing both to me and the company.
  • Find your “sweet spot” with tech, and own it. We all work in a tech company now, so this applies to most anyone reading: our roles all sit somewhere on a spectrum from “people-focused” to “tech-focused.” Know that no matter where you sit, you’ll have to master both. Know your strengths and where you get energy. The more you know about the side that isn’t your strength, the more indispensable an asset you become.
  • Don’t get too comfy with that sweet spot. It moves.

I’ve had four main phases of my Microsoft career: first at corporate HQ in Learning Products, Web Properties (e.g. MSDN), Internal Social Enterprise (Yammer), and now in the field with Customer Success. Many thanks to the amazing managers that helped me navigate within and between those adventures: Gerry Lang, Jeff Gelfuso, Christian Finn, John Martin, Yuri Alkin, Alfredo Mendez, Jeff Ramos, Christian Wylde, Scott Weiskopf, Rob Jones, Matt Kitson, and Paul Doe. (Looking at that list… it’s about time I had a female manager!)

My first project: the Win NT to 2000 MCSE course materials

Here’s some random memories to provide a little “color” to those lessons:

  • Massive, opulent parties in the 00’s. Yes, they were a bit irresponsible by today’s standards, but they sure were fun at the time.
  • Building a 200-page XML schema in the same year (2001) that I learned what “XML” was. The name of that project? Corona. 😒
  • Getting a heads up by my kind manager (who will remain nameless) that our team was going to be cut in the weeks ahead. A shock to the system, of course, but it gave me the warning I needed to land what became one of the most important job-changes in my career. Forever grateful for a manager willing to put people ahead of process.
  • This life-changing moment: Microsoft to Acquire Yammer (archive.org)
  • Being interviewed by the founder of Yammer (Adam Pisoni) as the pre-show warm up to Satya’s first company-wide broadcast from his inaugural roadtrip.
Screenshot of my 5 min of fame on stage before Satya
  • That one dinner at Nobu in Vegas. If you were there, you know what I mean. Oof.
  • Being grilled by lawyers when Microsoft was caught up in a potential lawsuit over the naming of the Xbox console. And that’s all I can say about that. 🙄
  • Meeting the Customer Success team in Yammer after their acquisition and realizing that role was to be my future. Then waiting for 6 years to actually get the role!
  • Coaching Arianna Huffington on how to take questions from our internal social platform during an industry event we hosted.
  • Experiences in Beijing, Sydney, Nice, and so many other places that were only possible because of a generous, global company.
  • And countless meaningful conversations and relationships with the smartest people I know: my fellow Microsofties.
Still flying the flag, 20 years later.

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