My biggest leadership failure (so far)

Or that time I hid in a boat to run away from my responsibilities

In 2018, I felt on top of the world. I had just been promoted off of a string of highly impactful projects. I was proud of how hard I pushed myself and how I’d earned the trust of those I worked with.

Less than a year later, I found myself hiding from my team in a wooden boat tucked away on the top floor of the office. My newest project had just doubled in size for the third time that month as “solve Brexit” was added to the growing list of expectations. All progress ground to a halt, three new teams were added as highly opinionated stakeholders, and my PM left the project — transferring his responsibilities to me.

I felt lost. It wasn’t the growth that worried me, it was how ineffective I suddenly felt. For the first time, the harder I worked, the more people got involved, and the slower things moved. I felt the pressure of failing my teammates, who I had confidently convinced to bet a year of their career on me.

I just needed a moment — alone, in a boat — to bang my head against the technical design to see if I could shake out any answers for why nothing I tried was working.

Definitely one of my top 5 cozy working spots in the office though

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As a freshly minted “Software engineer II”, I was eager to immediately prove myself as “Senior”. But wow was I staggeringly unequipped.

It wasn’t even clear to me what the problem was. The engineering had been designed, proven out, and successfully rolled out to half of our countries. Since then, our 3-step country rollout grew to over a dozen steps including a handoff to an external third party company.

We went from launching 3 countries a week to a country a month. My job was no longer to write code but to drop uninvited into meetings and beg teams to unblock whatever step we were stuck on that day.

After sputtering for months, the project eventually wound down and I took it pretty hard. This was my project, my fault, my failure.

Boxing Wizard

In hindsight, it’s clear what happened — I was blindly playing the role of “Staff engineer”.

My entire career up to that point I had trained to be a boxer. I went to boxing school, took classes on all the boxing punches, and won boxing championships and boxing accolades. Then one day I had unknowingly signed up for a wizarding league without having heard of magic before. I felt lost because all of my experience was suddenly irrelevant, and I couldn’t bring myself to abandon the tools that had brought me success so far.

What had I needed to hear in that moment on the boat? I needed to know that this job is different and that almost none of the tools I’d used so far would be the right one here.

The technical design wasn’t the problem — I had failed to advocate for clear leadership sponsorship. Honestly, I didn’t know what leadership sponsorship was at the time, which is kind of the theme here. The lessons that had gotten me success so far were the wrong ones for this job. Briefly:

• Communication — I had strong individual relationships. What was needed was for teams to believe that this project’s success was also their success, not the individual’s.

• Technical design — I had a strong technical perspective backed by investigation and early success. What was needed here was flexibility so that teams were invested, understood the problem space, and expressed their priorities through design contributions.

• Ownership — I was constantly rewarded for taking on as much as possible and working hard to pay it off. What was needed here was escalation of the gaps. When our PM left, that should have been a gap that I filled only temporarily and with a clear long term plan in mind.

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It’s been 4 years since that project wound down and I’m finding myself about a year into tech leading a different kind of project again. This time I want to be ready. I intend for this newsletter to be a journal to keep me honest and help me synthesize my thoughts, readings, and mistakes.

Feel free to follow along and who knows, maybe by the end of 2025 or so I’ll find myself confidently navigating the world of Staff engineering 🧙‍♂️