2020: A Year of Career Failure

In January 2020, I set a goal for myself: Transition to a program/product manager role at Microsoft within 6 months.

It seemed easy enough to do. Microsoft has hundreds of PM jobs listed on any given day. I'm a high achiever who had 1.5 years of customer-facing experience at Microsoft at the time. And I had the drive and desire to make it happen.

Don't get me wrong; I love what I do today. I'm a Customer Engineer, and I spend my days talking to some of our largest enterprise customers about their Microsoft 365 journeys. I get to learn about their company structure, technical architecture, and pain points, and then I get to help them transform their business, technology, and processes using Microsoft tools. It's invigorating, challenging, and something different every day.

But I want to do more than just talk about Microsoft tools. I want to be on the teams that build them. I'm so intrigued by the process of speaking to customers, understanding their needs, and then actually helping to build or improve features to address those needs.

So I set a goal for myself and started working towards it:

• I scheduled 30-minute meetings with other early-in-career colleagues who had started in my org and transitioned to PM roles in Engineering. To try to learn from their experience and success, I filled these conversations with questions on how they discovered their PM role, what they did every day, and what strategies worked for them in making the leap. Through the two initial conversations I scheduled, I met others like me and ended up speaking with five early-in-career PMs.
• I set aside time every week to search for jobs. I tried not to be too picky, and also tried to keep in mind that I don't have to meet every single job requirement to be worthy of applying. I was humbled by the job descriptions I read too. Even PM jobs that started at levels lower than mine required more experience than I had. Perusing job descriptions did nothing to help my imposter syndrome!
• For the jobs I really, really loved, I emailed the hiring manager directly, introducing myself and requesting 30 minutes of their time to discuss the role. Most managers responded immediately and were open to talking. And even when we determined I wasn't the right fit for the role, I found these conversations invaluable. I learned how to sell myself. I learned what hiring managers look for, and I grew my network just a little bit more. Most importantly, I received constructive feedback on my work experience.

To sum up the outcomes of nine conversations with managers: "I love how driven and hardworking you are, but I need someone with more experience in <insert very niche topic>."

By August, not only had I not met my goal, I was also so tired of hearing that I'm almost a perfect fit but I just don't have this one specific bit of knowledge. I became discouraged because I know myself, and I know I can learn to do anything rather quickly. In fact, that's all I want to do is learn!

• I'm the woman who worked full-time while earning her MS in Information Systems. I opted for the notoriously difficult (and scarcely enrolled) Programming track, having never written a real line of code in my life. I took the heavily avoided Accounting and Finance business electives because I knew they'd be a challenge, having never seen a balance sheet nor valued a stock before. And in all of those experiences, I finished top of my class: I graduated with a 4.0 and earned the accolade of Most Outstanding Graduate Student.
• I'm the woman who took a construction administration job at an engineering firm, having only a BA in English, and transformed and standardized its processes. I also wrote the company's manual on construction contract administration and then developed a course to teach Professional Engineers these skills.
• I'm the woman who took a program coordinator job in an IT department at a university and assisted with a enterprise-wide SharePoint deployment, having never done in-depth IT work before.

So perhaps you can understand my frustration: If I have the basic task-related skills required to do the job and a history of learning quickly, why don't hiring managers want to give me the chance and trust that I'll figure it out along the way?

And I think the answer here is obvious: They don't have to. For every candidate like me, there are 10 other over-qualified applicants. And COVID certainly didn't help my lack of competitiveness, with so many highly qualified workers finding themselves out of jobs.

As my motivation waned, I realized I needed a boost, and that boost could only come from within. I sat down with a notebook and pen and wrote:

And below that, I listed my goals for my next role:

1. Learn something new, expand technical knowledge, further professional development.
2. Be on a great team (good WLB, high performing, teamwork).
3. Have opportunities to work with customers.
4. Have opportunities to work on the products we actually build.

For whatever reason, this exercise helped me approach my job search with a new focus and vigor.

Then, at the end of August, a breakthrough! I found the perfect job for me on the SharePoint/OneDrive team. It was a customer-facing role, a sort of halfway point between what I do in the field and what the product groups build. And the hiring team was specifically looking for someone with field experience. Without a second thought, I applied and emailed the hiring manager.

In speaking with the hiring manager the following week, our conversation went well, and I felt even more excited about the role, but I was left with the feedback I'd heard too many times: "We like you, but we need someone with more experience." Still, the hiring manager graciously introduced me to two other members of the team, and those introductions led to some really great conversations.

To complicate matters, a colleague applied for the job too. And as much as I didn't want to admit it, that person was a much more qualified candidate, and so I shouldn't have been surprised when they inevitably got the job.

I can't begin to describe the mix of emotions that made up my September. I fluctuated between the highs of excitement and hope and the lows of frustration, sadness, and despair. I'd been working at this goal all year. It's hard to admit, but a part of me felt entitled to this job, like all of my efforts meant I had earned it, regardless of qualifications.

But in the end, it's just business. No one is entitled to anything.

So where did I end up this year? I didn't achieve my career goal, but my efforts still led to some really great outcomes:

• I was given the opportunity to start leading a team of Customer Engineers. My job has shifted from being a technical resource to leading a team of technical resources and having more oversight and interaction with the greater customer account teams. This means more executive visibility and opportunity for impact. It also means an opportunity to develop as a leader, which has already presented me with new and interesting challenges.
• I learned a lot about networking. I always thought networking was this scary, nebulous task, but really, it's about getting to know people. As it turns out, most people want to help and are eager to connect you with others who want to help too.
• I got to practice talking about and promoting myself again, something I haven't done since interviewing for full-time jobs during grad school in the fall of 2017.
• I learned so much about Microsoft's organizational structure and roles. Microsoft is a huge company, and getting to speak to hiring managers from so many orgs and role types helped me understand the company and further define where I want to end up.
• I became a bit more desensitized to rejection while also hearing great feedback about what I do well and where I can improve to be more competitive.

Of course, it still stings to be ending this post without a real outcome. I'm deeply disappointed that, of the 37 jobs I applied for (at Microsoft alone), I ended up with only a handful of informal conversations and never made it to a formal interview process. Not only did I fail, I failed hard.

But in all failure, there is opportunity, and hopefully with continued hard work and a little more experience, 2021 will tell a story of accomplishment!

(Do you have a strategy or tidbit to help me grow as a PM without PM experience? DM me or leave a comment below!)