The Leadership Reckoning Room with Stefani Okamoto
In this special follow‑up episode, Stefani sits back downwith Simon Curran to go deeper into one of the most urgent leadership questions of our time: What does it actually take to redesign an organization for an AI‑enabled future? Simon opens up about the core problem that sparked ROKT’sbold restructuring, the assumptions he had to release, and the unexpected lessons that surfaced once the new design was in motion. Together, they explore the growing “fewer managers” trend—what Simon chose to reduce, what he fiercely protected, and why the manager role is evolving but far from obsolete. They dig into the real influence of AI tools and agents onroles, layers, and spans of control; what’s working inside the new structure; and where the friction still lives. Simon shares how he prepared leaders for the shift, what they had to unlearn, and the cultural ripples that followed—both the breakthroughs and the risks. For leaders staring down the same complexity—AIacceleration, org design upheaval, and the rising bar for human‑centered leadership—Simon offers one clear piece of advice to start with. This is a candid, practical, future‑facing conversationabout the work of redesigning not just an org chart, but the way people lead, collaborate, and create value in a new era.
8 episodios
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