Reflections on 5 years at Microsoft

It's July 9, 2018. I'm a new resident of Dallas, and it's the first time I've ever lived outside of Florida. In fact, only a few weeks ago, my mom and I packed my two dogs into my aging but loyal Mazda SUV and drove from the east coast of Florida to the middle of Texas. Compared to Gainesville--the college town where I'd lived for the past 13 years--Dallas is a dizzying maze of the tallest highway overpasses I'd ever seen. It was exhilarating, this new life I was starting.

And July 9 is the most exciting day yet in my new city. I'm starting my first day at Microsoft, my dream company--no, my moonshot company! As I enter the lobby doors of the Las Colinas campus for the second time, I'm engulfed in a stream of other recent grads (though I'm a bit older having been recruited out of grad school) eagerly lining up to sign HR forms and finally receive our blue badges.

Getting to Microsoft

The first time I strode through these doors was for my final-round interview. It had felt like a dream, probably because I'd slept for only 4 hours the night before.

See, I almost didn't get invited. After my initial phone interview with Microsoft, I didn't hear back for over a month. I contacted my recruiter, only to learn that all the spots for final-round interviews were filled, and it was unlikely I'd get a spot. I was devastated. I thought my phone interview had gone so well, and my academic record was stellar. But the college-recruiting process is its own crazy haze of suits, resumes, and elevator pitches, so it's easy to get lost in the shuffle.

But on December 7, 2017, sitting at my computer desk in Gainesville, procrastinating on my final-exam programming project, I finally got the call: someone had dropped out of Interview Day, and my recruiter was offering me their spot. The downside: the interview was tomorrow...in Dallas...over 900 miles away. Oh, and I needed to prepare a presentation on a technical topic as part of the interview. And that programming project? Yeah, it was also due tomorrow -- I had planned to spend all of the December 8 due date completing it.

Frantic, I say yes, because you don't say no to Microsoft. I booked a flight out of Gainesville for 7:00 am the next day, and as I dug my heels into my programming project, my partner at the time pulled together some basic slides and bullet points on a budding implementation of the blockchain: Cryptokitties. I worked well into the night, turned in my project, recruited a friend to watch my dogs, threw my suit and some pajamas into a suitcase, and arrived just in time to catch my plane out of the tiny Gainesville Regional Airport. Onboard, I finalized my presentation and worked on the talk track, and by 2:00 pm, I was sharing a long conference table with other Microsoft hopefuls, waiting for my turn to interview.

What made it all worth it was seeing one of my interviewers write "SMART" across the top of my resume in big block letters as we chatted.

That, and also earning the label of "that Cryptokitties girl."

So as I stood in the lobby 7 months later with the rest of Microsoft's newest class of graduates, I was grateful but in disbelief that I'd made it, knowing that I almost hadn't.

My first role: Premier Field Engineer (July 2018 to February 2021)

My first role at Microsoft was Premier Field Engineer (which was later retitled to Customer Engineer and recently retitled again to Cloud Solution Architect). Having never held a technical position in my previous jobs, being called an engineer felt so rewarding. Here I was, someone who knew things!

Except I didn't know anything yet.

Microsoft is a goliath compared to the companies I'd worked for in the past. HR devoted 2 weeks to teaching us about the company, its policies, the basics of our roles, and that Paul Allen is in fact not Bill Gates' dad.

And then we spent another 8 weeks studying our assigned technologies (mine was SharePoint/OneDrive), learning how to present to customers, and internalizing how to humbly say, "No, but I'll find out," when customers inevitably stumped us (a skill I still use to this day). It was a whirlwind of a time, and even after a year, I still felt like I'd barely scratched the surface.

It was during this time that I realized that my role was to evangelize and teach others about Microsoft products. It wasn't to help build those products, though I did spend a lot of time relaying customer feedback to product teams. If I wanted to make new things, I had to work in Engineering, not the field. Working on Microsoft's SharePoint/OneDrive Engineering team became my dream.

But transitioning to a role in "corporate" from the field isn't easy. And it's even harder if you want to work for a capstone product like SharePoint.

The field-based skill set doesn't always align with Engineering job descriptions. Though I had deep technical expertise in SharePoint and tons of experience working with customers of all sizes at all stages of their adoptions, I didn't have the desire or the technical chops to go into software engineering, and I didn't have the "2 years managing a technical product through the entire product lifecycle" that nearly all entry-level Program Manager (PM) jobs regurgitated as the first bullet point under the Requirements section of the job description. I spent the end of 2019 and all of 2020 trying to transition to a PM role. Despite trying to spin my experience to fit the PM skill set, I failed, and I ended 2020 feeling so defeated.

So I decided to pivot. Microsoft has hundreds of Content Developer (CD) roles that sit within the Engineering org. These roles require technical knowledge but also the ability to write and break down complex ideas into digestible concepts. With my BA in English and my MS in Information Systems, it seemed like the perfect role to help me bridge the gap to Engineering. Besides, I just needed a foot in the door; I could figure out how to get a PM role later.

My second role: Content Developer (February 2021 to September 2023)

On February 16, 2021, I started my first day as a CD. It felt like starting over. Because Microsoft is so big, each org truly is its own business. There were new hierarchies to understand, new rules of engagement, new standards, and a new culture. I had no idea one company could yield such disparate experiences.

In my role as a CD, I helped run Microsoft's documentation contributor guides--the guides that teach our internal writers and our external contributors how to write like a Microsoft-y and how to use the tools required to create content.

I remember feeling amazed at the luxury of time my team seemed to have. They had time to wax philosophic when deciding what to do next. In the field, everything is go, go, go! Deliver what the customer wants! Figure out the answer as fast as you can! But here, things moved much more slowly and deliberately. It took me a while to adjust to the pace and trust that my performance wasn't measured on how fast I could deliver something.

Eventually, I grew more confident in my role and more comfortable with my manager(s) (yes, all three that I had during my 2.5 years as a CD). With each reorg (and there were three), I prodded them to change my title from CD to PM. I didn't feel like CD reflected the actual work I was doing, plus I feared how going longer and longer without having PM on my resume might affect my future career opportunities within the PM space--a space that was starting to feel increasingly exclusive and, honestly, a little gatekeep-y.

When I requested changes, I heard "we have to make sure it's what the business needs" and "help me make the business case." These roadblocks taught me the valuable lesson of how to think from the company's perspective, not just my own. And in having these discussions, my managers learned what I wanted to do and found me opportunities to do it. One of my managers even loaned me to another team to help project manage a large-scale hiring initiative, my efforts on which earned me an org-wide award and a promotion.

So when our most recent reorg occurred a few months ago, it was time to bring up my title-change proposition once more. With this reorg, my team had been split up, with some staying on the Skilling Content team but most of us moving to the Skilling Partnerships team. My role changed too: I was working on building a new experience for external contributors, not writing content or working heavily on contributor guides anymore. Of all the times I'd brought up a title change in the past, now seemed the most apropos to make the case.

This time, my manager agreed: it was time to change my title.

My third role: Technical Program Manager (September 2023 to present)

After some behind-the-scenes HR wizardry, my manager sent me a screenshot in September that made my heart jump:

Finally, I'd achieved the goal I'd made 5 years prior: to be a PM in Engineering building stuff!

So what am I building? I don't work on a Microsoft product in the traditional sense. Rather, my team is working on building community among the experts and learners who love Microsoft Learn. We have a lot of work to do in this space, and I'm excited to do it. I spend my time thinking up ideas and then working with my team to make them happen. I get to be creative and technical. My work so far has been designing and publishing the new Microsoft Learn Contributor Home and our new Microsoft Learn Community Leader pages.

While I'm feeling a bit of imposter syndrome holding the title of technical PM, I'm excited to really dig my heels into this role and glean as much as I can from the immensely talented PMs on my community team.

And who knows...maybe one day I'll be talking to customers about SharePoint, but this time from the product team's perspective!

What I've Learned

Here are some platitudes to summarize what helped me along the way:

• Speak up. No one cares about your career as much as you do. If you don't tell people what you want to do, they can't help you. They won't recall your name when opportunities come up that they need to fill. Advocacy for your career begins with you.
• Be patient. Applying for new jobs takes time; it's its own part-time job. And waiting for company structures to change to grab a new opportunity also takes time. Nothing worth doing happens overnight.
• Trust your gut and trust your mentors. Don't be lured by opportunity just because it's handed to you. A career is built on smart, strategic moves, not hasty decisions made to escape a less desirable situation.

Personal Reflections

This article might have you believe that I've been laser-focused on only my career. On the contrary, these 5 years have been some of the most volatile in my personal life too. I'd be doing a disservice to my Microsoft adventure if I didn't add this context:

• I moved to Texas, the first time ever living away from my family.

• I got divorced.
• I made some incredible friends my first year who are still my friends today.
• I started rock climbing, something that started as a hobby with my new coworkers in Dallas and grew into an identity and community for me in Seattle.
• I met my current spouse on Bumble, moved to Washington with him, and then eloped during the pandemic.
• Those same two dogs who drove across the country with me passed away within a year of each other during the pandemic. But my heart had more space, so we adopted a rescue (Gumbo) from Louisiana shortly after.
• We became parents to a sweet little girl.

The end

So that's it! What a ride! I still can't believe I've worked here 5 years -- the longest tenure I've ever had at any employer.

If you've made it this far, thank you. Your interest in my life is humbling. Check back in 2028 for my next 5-year update. :)

And I couldn't end this piece without a special thanks to the friends, coaches, mentors, and managers who believed in me and helped me achieve this goal. And, of course, thanks to my husband, Daniel Revier , and his unending support.

Oh, and that programming project? I got an A.