Modern Tech Leadership

Steve wrote this one as a documentarian rather than an inventor: the first sentence disclaims credit for all of it, since the system belongs mostly to Grab CTOs Theo Vassilakis and Mark Porter. What follows is the closest thing in the archive to an actual company operations manual, and the pleasure is in the strange specifics — the recommendation to top every policy document with a three-minute video, because asking busy millennials for "those extra seven minutes of reading" would prove unduly onerous, or the aside crowning Confluence "perhaps the last tech stack that still incorporates the powerful 1996 AltaVista search engine."

Read against Steve's note above, that three-minute-video joke curdles: a system already sugar-coating itself for people who wouldn't read it was forecasting its own cause of death. Near the end, a leadership debate about adding video editing and courting internal followers hands Steve an uncomfortable realization about what modern leadership is turning into. And he mentions, almost in passing, that he wakes a few times a night to check work notifications and is fine with it — then in the very next paragraph warns that everyone else in the org needs real downtime or they'll burn out in a hurry. The essay never squares those two sentences, and that's the one spot where the whole cheerful system looks expensive.