Becoming CTO of a small startup

June 20, 2022

#94 – June 20, 2022

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Supporting a global remote company in hypergrowth is no easy feat and the playbook is different from traditional IT work. In this article by Teleport, learn about some of the IT philosophies that enable employees to keep their agility despite working very asynchronously around the world.

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In every software engineer’s life comes a time when they need to decide if they want to pursue a career in engineering or switch to management. There are pros and cons to both of those choices, and it all depends on what your character is like, what you want out of life, and how well you can manage work-life balance.

Planning timelines have been getting shorter and shorter across every industry over the last couple decades. Companies that used to make ten-year plans now make five-year plans. Companies that used to make five-year plans now make three-year plans.

Most teams struggle with removing operational friction because they concentrate on surface-level reactionary fixes (usually bandied as tech debt removal) instead of addressing the fundamental causes of inefficiency.

We have been interviewing and hiring a pile of engineering directors at Honeycomb lately. In so doing, I’ve had some fascinating conversations with engineering managers who have been trying unsuccessfully to make the leap to director.

Three months into my first Big Tech gig I was talking to a mentor about the overhead involved with the way the organisation worked. Meetings for standups, tech huddles, refinements, retros and product reviews; Processes such as limiting work in progress, desk checks, spikes, stories, and tasks. Coming from a startup we delivered high quality software without all of that labelled process. The mentor lent me his copy of Extreme Programming by Kent Beck, and that book gave me a framework to develop my own philosophy on software delivery and engineering practices. Since then I’ve followed Beck’s writings and talks.

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