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April 26, 2026 30 mins

Most technical leaders assume the path to executive is paved with more technical excellence. It isn't. At a certain level, the ceiling stops being technical and starts being about business fluency, and that ceiling is invisible until you've hit it.

In this episode, Kevin walks through the shift that CTOs, VPs, and directors need to make to actually lead at the executive level, and why the skills that got them there are the ones they have to partially unlearn. He shares a framework he calls the four moves of business fluency (translate, trade off, commit, compound) and the four contexts where technical leaders either build this skill or fail to: P&L, sales and customer work, fundraising and investor relations, and strategy.

This one is for senior engineering leaders eyeing an executive seat, current CTOs who want to stop being read as specialists at their own exec table, and anyone whose career has started to feel capped despite shipping well.

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