A founder friend recently confessed to me that he spends more time now ‘chatting’ with his AI assistant than with his exec team. Scheduling, roadmaps, even some hiring — the assistant drafts his playbook by default. At first, he thought he was delegating low-value work. But quietly, the balance started to shift: strategic questions, customer insights, even team conflict resolution — AI had a seat at the table.

It’s uncomfortable to admit how quickly decision-making can migrate from gut and experience to algorithms and models. Most leaders still imagine that only routine tasks are at risk. But as the boundary blurs, what exactly will ‘leadership’ mean when AI offers ideas with more context, fewer biases, and infinite energy?

The challenge isn’t just learning new tools. It’s evolving a new kind of presence: less about being the expert with all the answers, more about curating questions, connecting judgment to context, and weaving meaning when the map keeps changing.

If you’re still leading like it’s 2019, you’ll be outmaneuvered not by AI itself, but by those who leverage it as a superpartner.

A shift is already underway: Leadership that thrives isn’t threatened by smart algorithms — it thrives in dialogue with them. I think the future belongs to those who can interrogate, not just instruct, their new digital “colleagues.” Read More