Windows of Opportunity: My First 5 Years at Microsoft

Never get so busy making a living that you forget to make a life.

DOLLY PARTON

Coming into the new year, I was feeling a little bit burnt out from both life and work. I was working a lot, going out a lot, staying up pretty late. I was doing A LOT and not giving myself enough time to rest and recharge in between work, life, and friendly festivities. The intention was to rest up over the holidays when I flew back to Canada, but that didn’t happen—I got caught up with work and in catching up with friends and family whom I’ve missed (too many nights when I was up till 5am 😪).

January was my month of respite—intentionally meant to reset, recharge, and recover.

It didn’t really hit me until the day of that it actually marked a mini milestone in my career… 5 years since I’ve graduated university. 5 years at one of the coolest companies out there 🟥 🟩 🟦 🟨

5 years ago, I was actually at one of my lowest points in life 🥲

January 2020 started out exciting enough. I had just come back from 6 months of studying abroad in Singapore for my last semester. I had 2 weeks to pack my bags, move from Calgary to Toronto, and start a brand-new life and career as a Sales Operations Program Manager at Microsoft Canada.

My dad helped me settle in and buy a car… and then I was on my own! I was finally a free adult!

The novelty of living on my own kept things interesting in the beginning. I had a wonderful manager and an awesome onboarding buddy that pushed me to develop my personal brand as a newbie. Then the weeks went by… and I started to dread finishing a good day’s work in the office only to come back to an empty home that lacked the rambunctious energy of my rowdy family… I was starting to feel homesick.

And then, the COVID-19 pandemic took the world by storm.

What started off as living the dream in a new city quickly became a nightmare of uncertainty. People were dying. People were freaking out. I was just learning how to survive on my own (barely). And now, I had to learn how to survive in a freaking pandemic—away from my family on the other side of the country?!?!

The Ontario government then announced a city-wide lockdown while I was living in a basement suite—my only window into the world was literally one where I had to drag my dining chair from the kitchen and stand on it just to look out onto my landlord’s backyard. It was beyond lonely and depressing—and there were so many nights when I cried in bed, questioning whether this career opportunity was worth the unexpected emptiness that I was feeling. I missed my family and friends back home. I missed meeting new people and socializing. I missed walking into a Walmart or T&T Supermarket to grab groceries without fearing for my life.

*Alright… enough of the dramatic recollection of my first months into post-university life… I think you get the picture 😅*

Despite everything, I was still very lucky! Microsoft Canada soon announced that we’d be working from home for the next 2 weeks. That timeline stretched on indefinitely and I saw a window of opportunity to go back to Calgary and work remotely.

I will never forget what it was like to travel during peak pandemic pandemonium—walking through an eerily empty airport to board an even emptier plane with only 6 passengers—all of us flying in fear of reaping respiratory repercussions 😷

After 4 hours of crossing my fingers and toes in WestJet premium economy, I was finally home 🏠

Career changes and conversations in challenging times 💭

Now that I was back in the comfort of my own family home—annoying but loving parents lecturing me, annoying but funny brother bugging me, annoying but cute dog barking for no reason—I was ready to make an impact in my career 😎 From earning several Microsoft certifications to taking a High Performance Mindset course, I was immersing myself in professional development.

As an extrovert, it was tough to adjust to remote work. Still, I saw it as an opportunity to network virtually by setting up coffee chats and lunches with people around the world nearly every day. In my first year at Microsoft, I had over 100 coffee chats with those from my Aspire new grad community all the way to an Executive Vice President!

These conversations opened up many windows of opportunity and inspiration. I picked people’s brains. I heard about interesting career paths. I learned about different parts of the company. It was a lot of fun.

Early into my Microsoft Canada career, I knew that I wanted to work at our HQ and see how our company operated at a global level. When I shared this ambition with others, many told me to be patient and get around 5 years of experience before thinking about it, since it was not easy. I heeded their advice while keeping my eyes and mind open—especially because I had one Aspire friend who succeeded in transitioning over to a corporate role after just 6 months at Microsoft! He believed I could do it too, and so I had to believe in myself (fun fact: we still hang out to this day and reminisce about how much has changed since we were new grads back in 2020 😊)

In the latter half of 2020, I started getting a lot more serious about figuring out what was next for me, mainly because I was backfilling for a teammate who was on maternity leave (which is usually 12 months in Canada). Despite reassurances throughout the year, I had been anxious about my future at the company once my colleague returned from maternity leave because there was no clear next step. As we got closer to the 1-year mark, my manager mentioned that my teammate was extending her maternity leave to 18 months—so I had a bit of extra time to breathe!

Still, I knew the clock was ticking…

I continued talking to people, learning more about myself and what I wanted, and building my personal brand as an ambitious yet curious changemaker who delivered results in a positive and impactful way. As we continued having career conversations, my manager mentioned that she could secure an additional headcount to keep me on the team once my colleague returned from maternity leave.

This was great news! Yet, I felt this “itch” to try something new because I knew that sales operations wasn’t necessarily my passion… Fortunately, I had an awesome manager who was supportive of me exploring new roles as an early-in-career. While I started applying for a handful of jobs to test out the waters, she even helped put in a good word with other managers. *insert moment of appreciation for managers who genuinely want you to succeed even if it means moving on to something different 🙏🏼*

As summer of ’21 rolled around, I had applied for about a dozen roles that centered around storytelling, which was an area that I wanted to explore. I was very intentional about not wasting my time spam applying to everything under the sun so that I would have a high conversion rate between applying for a job and getting an interview.

It came down to 3 different roles:

  • Technical Sales Specialist for Power Platform, Microsoft Canada which I applied for because I wanted to go into sales.
  • Marketing Operations Manager, Microsoft Canada where the hiring manager reached out to me thanks to my manager’s referral.
  • Communications Manager, Microsoft HQ which I applied to on a whim and didn’t expect anything from because the job was a lot more senior and based in the U.S.

I did not end up getting an offer for the Technical Specialist role 🥲 but I was pretty close to getting the Marketing Operations Manager role because the hiring manager had implied that it was coming. I was excited about this role because I would be gaining people management experience and having my own team of direct reports.

I was also surprised that I got invited to the “Comms Super Hiring Day” for the corporate role because I didn’t have any formal comms experience and I had actually submitted my application quite late in the game, so the recruiter had to try and squeeze me into the schedule. Once I made it in last minute, I had a handful of days to prepare my career walking deck for 3 back-to-back interviews with 3 different hiring managers.

For weeks throughout the summer, I agonized in anticipation of a formal job offer. Verbal assurances did little to ease my anxiety because I believe that things aren’t really “official” until you have it in writing.

And then, while I was working remotely in my family kitchen one fine September day, I finally received one!!!

My glassy, glasses-covered eyes glossed over the offer letter for the Communications Manager role—I still remember calling out my brother’s name in equal parts delight and disbelief. I was thrilled that I’d finally landed a job—one that involved storytelling, was based in the U.S., and came with a double promotion, nonetheless 🙌🏼

Then, my delightful disbelief wore off… daunting dread soon taking its place as I realized my dilemma: I had no idea how I would bring this up to my current manager and the Marketing Operations hiring manager. On one hand, I was so grateful to both managers for investing their time and energy into helping me secure the role. On the other hand, I knew that I’d always wanted to work at the HQ… and was finally given the chance!

Thankfully, I had some tremendous mentors who helped me think through how to bring this up in a tactful manner without burning any bridges—which was my biggest concern. I did not want to come across as an ungrateful candidate who was leading them on and wasting their time. Mustering up some mental courage from my mentors, I set up a call with both managers and talked them through my turning-point trepidations. Although surprised, both seemed sensible and supportive about my decision to seize the Seattle opportunity. Phew!!!

Starting a new season of life in Seattle 🌦️

Although Seattle was geographically closer to Calgary than Toronto, it was still challenging to move to the neighbouring country of Murica 🇺🇸 Even as a Canadian, I experienced quite a bit of culture shock while encountering some pleasant surprises along the way in my first months. The stressful and overwhelming work visa and relocation logistics probably resulted in some hair loss, but I am super grateful that Microsoft provided me with hands-on support as part of my relocation package.

I was also incredibly lucky to have a kind and wonderful manager who gave me a lot of support during this stressful time. I recall a point when I was stressing over buying a car with the supply chain crisis, and my manager secured extra budget to extend my car rental term as part of my relocation package 🙏🏼 *insert another moment of appreciation for managers who go out of their way to look out for their people*

Aside from the stressful logistics, settling into Seattle felt like a second chance. We were coming out of the pandemic, and it was actually OK to go out and meet people. While I did face the foe of figuring out personal finances in America, I did not really face the Seattle Freeze that some people warned me about and have been extremely lucky to have met some kind, inspiring, and fun friends (one of them is now my roommate and she’s awesome).

I enjoyed exploring the Microsoft campus and community, feeling grateful for so many cool opportunities like meeting Dr. Michael Gervais and Kara Swisher, going to NYC for the International Association of Business Communications World Conference, learning more about the art and science of PR and Communications (which was quite different from sales operations), and embracing my extracurricular activities as an Employee Creator at Microsoft Build, Aspire Leadership Council Member, and Career Development Lead of the Asians in Marketing ERG.

Microsoft as a platform for personal passion and paying it forward 🌱

One of the best things was that I felt empowered to continue pursuing my passion around career development and empowering others along the way. Microsoft became a platform for me to pay it forward and share unique learnings, experiences, and insights with the world.

For example, I learned about the concept of a “Career Walking Deck” when I first joined Microsoft Canada and quickly saw it as a powerful job hunting and networking tool. I did a lot of personal research by talking to managers and peers about it and then I wrote a series of blog posts to help others get started. Then one day, a reader pointed out that my blog was ranked #1 on Google and Bing for “career walking decks” which was pretty cool!

I’ve also been invited to speak to nearly 8,000 people at events and conferences across North America, which helped me work on my fear of public speaking. I typically delivered workshops around personal branding and career walking decks, and digital networking through programs like Microsoft Discovery for high school students, Microsoft Explore for university students, Microsoft Aspire for new grads, Microsoft LEAP for retired NFL players and transitioning professionals, and Microsoft Software & Systems Academy for retired veterans!

Learning to love myself and leaning into the unexpected ✨

When I first started working at Microsoft HQ, it felt like “I’d made it”—I finally made my Asian parents proud (though I still felt huge imposter syndrome at times) 😅

Living in Seattle, I quickly realized that working at Microsoft, Google, or Amazon made you pretty average and that took me by surprise as someone who hailed from cow town Calgary where oil & gas was the dominant industry. As I looked around me, I met people who were much younger, way more ambitious and successful, and seemed to be way further ahead in their lives and careers. It was quite inspiring, but I also felt hints of envy as I sometimes got caught up in the game of comparison. As proud as I was of how far I’d gotten in my life and career, it sometimes felt like not enough 🥲

Immersing myself in therapy, mindfulness, and self-care has definitely helped me process my anxious thoughts and feelings a lot better. Adopting an attitude of gratitude and growth mindset have also helped me ground myself in times of uncertainty. And of course, giving it forward to others is where I feel a lot of abundance and fulfilment (e.g. I run Resume Rescue by asking people to make donations to charity instead of paying me)!

One of the more recent surprises in my career was being tapped for an opportunity to join the Office of the CEO.

Back in my role as a Communications Manager, my managers took a bet on me and empowered me to be the youngest/most junior person (from what I was told) in the company to run the customer and partner storytelling workstream for our quarterly Microsoft Earnings moments. This meant leading a virtual team of 100+ marketing and communications stakeholders around the world and partnering with the Office of the CEO & Office of the Chief Commercial Officer on the quarterly earnings scripts and pre-earnings blogs—a workstream that was traditionally managed by Senior Communications Managers who had extra hands-on support. Feeling empowered to try new things, I figured out how to optimize the process with tools like Power Automate so that it was possible to run on my own!

While taking on this behemoth of a workstream was one of the most challenging and highest pressure times of my career so far, I am grateful for the unique opportunity to meet some of the most senior leaders and stakeholders across the company and go behind-the-scenes of several earnings moments at one of the biggest publicly traded companies out there 📈 For 7 quarters, I did my best to show up, engage, and deliver what I needed to with a positive, can-do attitude! Along the way, I found a wise and well-respected mentor who always kept it real with me and looked out for me—it’s thanks to him believing in me that I ended up in the Office of the CEO!

These days in my new-ish role as a CEO Communications Manager, I’ve been adapting to a new level of intensity and pressure. Some days, I still feel like an imposter alongside my supportive yet hardcore teammates, but it is quite stimulating to be in such a central, fast-paced part of the company where time really is of the essence.

I am also honing more advanced technical skills by learning how to use and build AI copilots and agents to optimize our existing processes. From figuring out how to troubleshoot code with PMs and Devs to taking a prompt engineering course online, it’s been new and interesting to say the least!

Along with that, I am finding a new balance between work and life so that I can continue to grow my passions for empowering others in their careers… while staying fit and healthy… while having a fun social life with friends… while making time to do chores and other adulting things… while finding time to rest and relax… while continuing to invest in myself… while making time to travel and explore the word… while well—EXISTING!!!

Sometimes it gets exhausting, but I know that I am extremely privileged to be where I am in the world and in life. That’s why I am here—sharing my learnings and experiences in hopes of paying it forward with thanks to all my mentors, managers, sponsors, leaders, and teammates who have invested their valuable time and energy into my growth and development 🙏🏼

There’s so much more that I can say about the past 5 years at Microsoft and soooo many more people that I can thank—though I do try to do that personally ☺️—but I’ve probably hit a word limit by now because I don’t think I’ve ever written anything this lengthy that wasn’t an academic essay. If you’ve made it this far, you deserve a 19-course omakase experience with an OG sushi chef from Japan 🍣

Windows of Wisdom 🖼️

Here’s my TLDR learnings in case you got distracted while reading this lengthy blog post 😅

  1. No one makes it on their own. Find your people and community. Show up and open yourself to meeting new people. When you’re feeling stuck or uncertain, talk to mentors that you respect for advice and perspective.
  2. You grow the most when you lean into to new, ambiguous, and unexpected challenges and opportunities. Some of these you seek out, others come to you serendipitously. Proceed with cautious optimism!
  3. A career walking deck is a must-have job hunting and networking tool (I personally swear by this because I haven’t even shared my resume for the past 2 jobs I’ve had!)
  4. Practicing gratitude and journaling are great ways to ease anxiety. Take care of your mental health and make time for self-care before you burn out!
  5. You add the most value when you can make life easier for yourself and others. Always look for ways to give back time and energy without compromising excellence.
  6. Your passion gives you purpose, and you are so much more than your job title. Explore new interests and dive into what gives you energy and excitement outside of work. Give to others and pay it forward.

Thank you so much for taking the time to read my first post of the year and I hope we can stay connected 🤝

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