Discernment for a Big Career Move

About a year ago, in July 2021, I’d been leading my group at Twitter, Infrastructure Automation, for three years as a director. We’d formed new teams for managing both on-prem and public cloud infrastructure, tripled our size, promoted amazing and diverse individuals, delivered on board-reviewed initiatives and were involved in acquisitions and contracts worth anywhere from tens of millions to hundreds of millions of dollars. But coming up on six years at Twitter, I was on the brink of a big change.

How did I get here?

I reflected back to the moment when I first took on my role in infrastructure. The space was new to me as an engineer with experience in enterprise software and full stack web development. The opportunity to deepen my technical knowledge of distributed systems at scale was compelling, and my boss and team gave me space and support to go on the learning journey (I’m forever grateful for this). Our focus was both within and adjacent to SRE (site reliability engineering), which is its own discipline apart from SWE (software engineering) but with significant overlap. I wasn’t sure if I was committed to SRE for the rest of my career, but I mentally committed myself to at least two years with the new org.

Three years in, after surviving outages,  pandemic peak traffic levels, and remote working conditions, it was past time to reevaluate. Had I learned what I came to learn about infrastructure? Did I want to go deeper? Or was it time to zoom back out, broaden, and put the narrative pieces of my career together in a new way? In addition to leading my group, I was involved in hiring, training, and promotion process improvements across engineering; I mentored several individuals outside my group as well as outside the company; and I’d also taken on driving a platform engineering workstream. I seemed to have more bandwidth to give.

Pause to evaluate and eliminate options

In August 2021, I took 4 weeks off to take our son on college tours and spend time reflecting – a time I called my “mini-sabbatical”. I thought about the options available at Twitter to take on more responsibility and scope. I thought about what it would take to be promoted to the next level. I made a big list of every career move I’d ever considered, listed the pros and cons of each, and then grouped them into three categories:

  • Under real consideration
  • Future possibilities, fringy or a little further out
  • Discarded for now

This step was key: I needed to eliminate those pesky but impractical ideas that randomly floated through my brain so I could focus on the real options. I also wanted to think 5-10 years out, and dropped ideas that wouldn’t come to fruition within 10 years.

I also looked back at my life goals. In January 2019, I set the following as one of three possibilities for my 3+ year career goal: “VP of Eng at a company with a powerful mission and a tight-knit team.”

I came back from my mini-sabbatical with a more clear idea about what I wanted at Twitter. Staying in my existing role could be nice in terms of work/life balance and would allow me to be present for my son’s last year at home. But the fact is, I’m ambitious, I’m always seeking to work myself out of a job to elevate those coming up behind me, and I’m an insatiable learner. Plateauing is not something I have been able to do for very long. With most in my cohort of fellow directors taking on more, people I mentored being promoted to my level or higher, and a decreasing sense of technical learning and development, it was becoming clear I needed more.

Asking for what I wanted

I spoke confidentially with a few executives to see what opportunities might be coming up for a bigger role, and I asked my boss to move my promotion process forward. I also started engaging with external opportunities for the first time since I joined the company. I remember telling my executive coach that I expected any of these options to take about a year to materialize. Taking on more responsibility in September 2022 would also coincide with my youngest going off to college. Wouldn’t that be tidy?

Forming the narrative arc

“I’m looking for something bigger” is not a compelling narrative to engage people to help you find the best new role. It’s too vague. As I reflected on the skills I could bring to a new role and where I wanted to go, the following criteria emerged:

  1. Draw on my engineering experience across front end, back end, and infrastructure to own end-to-end technology decision-making for a line of business
  2. Move closer to users, product development, and design, something I had missed since my days at WIRED and my earlier days at Twitter
  3. Combine my two largely separate efforts in 1) driving technical projects (at the group level) and 2) driving people processes like hiring, training and promotion (at the engineering-wide level) into one coherent role – either with a much larger group, executive-level autonomy, or both
  4. Contribute to a purpose I care about at a company with a culture that matches my values

With these in hand, I had my answer to “what are you looking for?” as well as the answer to why I was not interested in most of the opportunities coming to me organically. Most recruiters ping you to do more of what you are doing today (in this case, SRE, DevOps, Developer Productivity), and the above criteria required me to pivot to something bigger and broader (owning engineering for a line of products and applications). It also gave me a chance to share the narrative arc of my career: I worked backend on enterprise software and implementations; I then did full stack web development with both back-end and front-end migrations and redesigns; I then worked in infrastructure; and now I’m ready to put all the pieces together to own engineering end-to-end for a business domain.

Evaluating opportunities and prepping for interviews

A friend who was also looking for a new role posted a question to our women’s networking group, Hipower:

“Does anyone have a good decision matrix for helping to evaluate a possible career opportunity? Assigning weights to each attribute that makes up a desirable role… looking for some structure that has helped any of you.”

Several women responded on the thread (as they always do, this network is amazing), and from the many suggestions, I made myself a spreadsheet and shared it with the thread.

Engaging with my first external opportunity was challenging for many reasons. It was hard to juggle the interview schedule with a family and full time job. It was with a company whose interview process is notoriously difficult. While I had interviewed over 300 people for roles at Twitter, I hadn’t been on the other side of the interview table in six years. Luckily, I had peer mentors who helped me rehearse. Not gonna lie – it wound up being an emotional roller coaster to go all the way through that final round into negotiation. It didn’t turn out to be the right opportunity, but I was given specific interview feedback that helped me improve. It forced me to figure out what I really wanted, clarify my career narrative, prepare all my key examples, know my go-to frameworks, and tighten my storytelling. I used everything I prepared for the rest of the opportunities I considered.

Some examples I prepared included:

  • Detailed technical architectures (front end/mobile, backend, machine learning integration, infrastructure)
  • Dealing with conflict
  • Entrepreneurial experiences
  • Meaningful feedback I received and incorporated
  • Diversity actions I took
  • Times I had to disagree and commit
  • Organizational changes I made
  • How I evaluate technical tradeoffs
  • Articulating a technical vision
  • Managing stakeholders

New kinds of wisdom

A few months later, I encountered a role with a company I’ve been subconsciously keeping an eye on for a long time. The more I learned, the more excited I became. The effective/efficient/execution-minded driver in me was ready to seal the deal and jump to this solution. But since my mini-sabbatical, in addition to the career journey, I’d been on a parallel journey to process the life changes related to my kids going off to college and “empty nesting.” This journey has centered on developing new kinds of wisdom – not just head knowledge, but other forms of intuition and knowing. As just one example, during my year as a new fellow with ALF (American Leadership Forum), we were recently introduced to Theory U. Instead of zooming across the top of the U from problem to solution, you instead spend much more time going deep into the problem space, which causes you to consider many more possibilities and access deeper kinds of wisdom. With this in mind, I forced myself to interview with several more companies before making my final decision. In the end, I participated in final interviews with six companies. I did ultimately accept that role I was originally excited about, but when I did, I had significantly more clarity about why it was indeed the right next step. And the spreadsheet data I collected confirmed it.

On that spreadsheet, I included my existing role at Twitter. A year before, I had looked at the scores and understood it would be rare for any company to score as high for me as Twitter did. But interestingly, some of my scores for Twitter decreased over the course of my discernment process.

Surprising changes

When we think about staying where we are, we make some assumptions that the conditions around us will stay the same, too. I knew that over a year, the people and orgs around me could change, so my decisions shouldn’t be dependent on those factors. What I didn’t expect was that there would be significant changes to our people processes that were problematic for my values. And I certainly didn’t expect a hostile takeover!

While these changes were not the reason I ultimately decided to leave Twitter for a new role, they certainly helped me gain the clarity to know that this was the right time for me to make a change.

So what’s next?

We’re in the process of moving our son in at college, and then I’m starting my new role on September 12th. It’s the opportunity I dared to imagine and then manifested over three years ago, and even the timing is working for our family. Which goes to show: manifesting your dreams by writing them down, and even daring to ask for what you really, really want, is extremely powerful.

As for exactly what the role is… stay tuned! I’ll announce here and on LinkedIn in September. Thanks to my family, friends, coaches, peer mentors, and associates through my various networks who listened, provided wise council, asked tough questions, listened some more, relentlessly voiced their belief in my potential and constantly told me to reach higher. I share this story to pay it forward, in hopes that it helps others in their own career journeys.

Photo by Denys Nevozhai on Unsplash

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