Most successful executives are filled with self doubt and humility
Jim Collins research highlights that top-performing executives often struggle with self-doubt and lead with humility. This counterintuitive finding challenges the image of the ego-driven leader and marks a key characteristic of enduring company success.
I map scepticism and humility into four ways of deciding, from testing carefully like a scientist to acting confidently under uncertainty. Each mode helps in some situations and harms in others.
I’ve returned from my Diwali break and wanted to highlight the posthumous release of Douglas Adams' book, A Salmon of Doubt. The collection features unfinished writings and essays recovered from his computer after his death.
I highlight an experiment by the Annals of Improbable Research involving mailing various unusual items. While two-thirds reached their destination, I doubt the Indian postal service would be as successful with such a test.
AI can generate plausible personality critiques, but a more useful workflow is to demand evidence and then have multiple models rate the strength of that evidence.
Letting LLMs talk to each other creates surprisingly rich emergent behavior, from witty fictional banter to unsettling philosophical dialogues and useful synthetic interview formats.