How I became an Automattician Part 2

This is a continuation of How I became an Automattician Part 1.

Step 5: New year, new trials

My start to 2018 was tough. Heartland always launches into the new year with ambition and a robust workload, and this year was no exception. I didn’t receive definitive feedback on my skills test or whether I would move into the next interview phase with Automattic until January 30th.

I was asked about salary expectation at this point, which was tricky to answer. I had conducted some online research in anticipation of this question, but wasn’t satisfied with my conclusion. There simply aren’t comparable roles with published salaries, and I didn’t want to suggest anything out of the ordinary.  In the end, I was transparent about my research and expectations, and reemphasized that finding the right team fit was the most important factor to me. This may not have been the negotiation tactic leading businesspeople recommend, but I felt very reasonable and honest, and had no reason to think that Automattic would see it as anything else.

Which brings us to The Trial.

The Automattic Trial is the subject of many online posts and discussions (I found this HBR article particularly helpful early on). Here are some facts:

  • You’re brought on as a “Trial whatever job you applied for” and paid $25/hour. To my knowledge, this number does not change based on the job you’re applying for.
  • You immediately get access to the Automattic universe, which is infinite and flabbergasting.
  • You’re tasked with projects to work on that are accurate reflections of what you’d be doing if hired.
  • This is your chance to meet and get to know your potential future teammates.

I was officially offered a trial on February 13, 2018, and sent my contract back on February 15, 2018. I will always remember this week because I was miserable with the flu (which caused me to miss an important company meeting, a baby shower, and a visit to a close friend recovering from surgery, and which culminated in an expensive trip to the ER. Not that I’m still bitter or anything…) but still so thrilled to make it to this stage of the interview.

Step 5.1: All the work.

My time as a Trial Community Wrangler involved two distinct projects, each designed to test strategic thinking, research, writing and communication abilities, and ability to adapt. While Automattic does want a solid set of skills to begin with, they also look at a candidate’s growth while on trial. This might have been my saving grace, as my first project admittedly was not up to par.

In hindsight, I was frankly overwhelmed by how massive the Automattic engine is. First, it was a new communication style with some obviously talented people. Second, when Automattic says “Welcome to the Chaos“, they are not kidding around. There is serious thought behind a mountain of documentation and links to internal and external sources. Despite a couple check-ins with my project lead, I struggled to clearly understand what was being asked of me, got lost in all the resources, and ended up spending excess energy on lesser priorities.

The feedback provided on my first project was clear and direct, and while I appreciated the honesty and constructive criticism, I was frustrated with myself. Luckily, I was still assigned the second project, which allowed me to engage more directly with the WordPress community. I reflected on what went wrong with the first project, and launched myself into the second project with a stubborn determination to prove myself worthy. The beauty of it was that this wasn’t some personal quest to prove that I could get a job, but I had seen enough of Automattic and the WordPress community that I knew I wanted to be here, among creative, thoughtful, brilliant folks who work to democratize publishing.

There were three key changes that I conscientiously made going into my second project:

  • Relaxed and refocused. There was no way I would understand everything, so I honed in on what I had learned, identified key missing information relevant to my project, and prioritized accordingly.
  • More proactive outreach to everyone. I attended my first WordPress meetup. I doubled down on chatting with people for both my assigned projects, and I spent more time getting to know my team more broadly. This was very fun, and the gifs and witty comments had me grinning throughout the day.
  • The biggest change was my communication style. I was thoughtful when providing context for questions, shared what I understood, and aimed to be as clear as possible about what information I was seeking. I embraced both silly and strategic emojis as a way to channel feelings. As chat missed out on the nuances of a face to face conversation, this was a more effective, intentional way to communicate.

These adjustments led to a more successful project, and (I think) really saved my butt in the end. Moreover, all the time and effort spent on my trial provided a true glimpse of the company I wanted to work for, which was important, given my original hesitations around company culture and working remotely. It was reassuring to learn first-hand that Automattic’s ethos was aligned with my own.

On April 4, 2018, I received a surprise, bonus exercise which required some creative thinking. It was an activity I enjoyed, but poorly timed, as it was “due” the next morning during a scheduled chat. That particular day, I had a full day of work, an evening obligation, and I needed to pack for an international trip, so I was up into the wee hours of the morning. Dane unfortunately kept me company, as he was on-call and tackling some complex bug (he’s a very gifted developer/engineer). At 1:30 am on April 5, 2018, we joked that we would sleep very well on the flight to Taipei, scheduled to depart in 24 hours.

7:00 am that same day is the first time I see another Automattician over video chat. Most notably, I was asked for feedback about the trial, and yet again I leapt at the opportunity to have a transparent conversation. I shared what I liked (engaging with the team and WordPress community), what I didn’t (being patient with myself and with the interview process), and what I felt I could have done better (continuing to evolve my communication style). My comments were thoughtfully responded to, and we then discussed the surprise exercise and my work to date. At the end of our conversation, I was told that I would be recommended for hire, and that all that was left was to speak with HR. I got off of Zoom, ran into the other room where Dane was discreetly listening, and we both jumped for joy. We then shuttled ourselves off to work, and then to Taiwan.

Step 5.2: All the emotion, and the main reason for this series.

It would be an understatement to say that being a Trial Community Wrangler was tough. I put in approximately 20-25 extra hours a week, on top of my work at Heartland, which has always averaged about 45-55 hours a week. On top of that, we were traveling frequently, adjusting to married life, and dealing with some tougher family circumstances. I normally balance more laborious duties with exercise, social activities, and volunteer fun, but had to cut back on all three during my trial period. This did little for my emotional health, so as I had time, I fit in as many krav maga and yoga classes as possible. Friends were very kind in accepting my schedule and encouraged me to keep going.

Worst of all was the self doubt. As much as I am an extrovert and thrive on engaging with people, I am not immune to feeling inadequate, and I do worry about how I am perceived. I am used to in person interactions, so learning adapting to communication over Slack was an adjustment. If anything, the trial was preparation for being hired. During the trial, the lack of seeing another face led to a number of insecurities. I gave in to comparing myself to other hires, who had more experience with WordPress and were witty and interesting. I analyzed my resume and realized that never before had I felt more like an impostor just waiting to be found out and laughed at. In a particularly despondent, sarcastic moment, I even voiced to Dane: “I bet they all think I smell funny.”

By way of disclaimer, three additional, influencing factors include: 1. it had been over eight years since I had searched and interviewed for a job, 2. my personality seeks certainty, which job interviews tend to lack, and 3. I simply care deeply about my career, and this was a job I really wanted.

All the lows were balanced by highs. I loved interacting with the WordPress community to the point where I decided to participate in a WordPress Diversity Outreach group. I looked forward to “Otter Fridays”, when my Automattic team would share adorable gifs and memes of otters. Despite the additional stress, Dane and I had immense fun on our travels. I worked hard and was, at times, happy with what I produced. When I felt this way, I acknowledged that, even if the interview ended unsuccessfully, I could say that I gave it my all.

Simultaneously, my logical nature recognized that if I wasn’t up to par, Automattic wasn’t the type of company to string me along for “cheaper labor”, as some online opinions would have you believe. Many Automatticians took the time to answer my continual questions, to review my work and provide feedback, and to simply chat. I loved these interactions, and I realized that even if I didn’t get this job, I would always want to be a part of the WordPress community. The sense of belonging was palpable.

More than anything else, I relied on Dane. Despite his own demanding career, Dane picked up extra chores and reminded me to take breaks and stay healthy. At every turn, he shared that he believed I was stronger than any insecurity I felt. He understood when I wanted to be left alone, and he listened without judgement when I needed to share. It was taxing on both of us, yet he always had words of encouragement and a smile for me.  I’m selfishly happy that we made it through a tough period so soon after our wedding, and came out stronger for it.

Taiwan was lovely, by the way, as Dane got to meet my extended family. We also made a quick stop through Seoul and the DMZ, which I’d highly recommend visiting for the sake of history, culture, and delicious food.

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Step 6: Final chat and saying YES!

I had my final conversation with HR after we returned to Seattle. It was very straightforward, covering basic confirmations of expectations and final salary negotiation, and I was elated when presented with an official offer. It was one of the easiest affirmatives I’ve ever given, second only to Dane’s proposal almost two years ago.

Heartland Send Off
That’s right, I got a lasso and a cowgirl hat in preparation for being a Community Wrangler

Leaving Heartland was also an emotional experience. I had been with this company for over eight years, and built some particularly strong relationships with my colleagues and project partners. I had been honest with my coworkers about where I wanted my career to go, however, so this move wasn’t a particular surprise to anyone. They sent me off in wrangler style.

So there you have it. My “How I became an Automattician” story is mercurial one, but one that I am immediately grateful for as a personal and professional growth experience. I wouldn’t take anything back.

My advice to you, should you want it and solely based on my experience, is to be patient with the process. The interview process is a long one, but there is clear reason for it, and know that there are phenomenal coworkers and cohesive culture at the end. During those patient moments, think about if/how your style aligns with Automattic. It’s not going to be a match for everyone, but if it is a match for you, that’s amazing.

I joined Automattic as a Community Wrangler sponsored to work on the WordPress project on June 11, 2018. Even then, the first three weeks were spent on a whirlwind support rotation, so I’ve only been with my team for two full weeks. As such, I’m don’t feel it would be possible to give an objective view on what it is like to work on the WordPress project full time just yet (rest assured I am appropriately starry-eyed at this point), but I do feel that what I experienced during my trial was an accurate reflection of what it means to be an Automattician, and that everything I loved from my trial is amplified now that I am full time. I have very high hopes for the future.

2 thoughts on “How I became an Automattician Part 2”

  1. What an experience you’ve had. And a wonderful learning curve for me! Companies and employment are changing to meet the needs of the 21st century. How fun to be on the cutting edge, Angela. And, how fun for me to get to know you this way. I’m so proud of you!

    1. Thanks, Kimberly! You are so sweet 🙂 The conundrum is that one can never quite be on the cutting edge because the cutting edge is always changing! All we can do is to keep learning and growing as best we can.

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