Why Leadership Teams Fail To Change (And How To Fix It)

30 Jan 2026 · 58 min
58:16

In this interview Dom Monkhouse talks with Gerry Toombs, founder of Clearvision, investor, and creator of Agentimize/AgendaWise, about how AI is reshaping leadership and management. Toombs explains that AI will not replace most leadership roles but will expose under‑performers and make leaders far more efficient by automating routine reporting and decision‑support tasks. He introduces Agentimize’s three‑part approach – educating leadership teams, enabling the business with AI tools, and embedding AI agents alongside CEOs, CFOs and other executives. The conversation covers the need to shrink bloated leadership teams, the generational shift toward younger, more tech‑savvy leaders, and the future of managers overseeing hybrid human‑AI teams. Toombs shares concrete examples, such as AI‑driven planning‑application generation and customer‑service agents that revealed poor documentation. He discusses the importance of delegating low‑value work to AI, building trust using Patrick Lencioni’s Five Dysfunctions framework, and implementing a “tour of duty” employment model to retain A‑players. The interview also delves into Clearvision’s growth, its acquisition, the founder’s transition out of the business, challenges scaling in the US, and the cultural achievements that earned the company a spot in the Times 100 Best Employers. Finally, Toombs reflects on the books that shaped his thinking, the balance between innovation and BAU, and his belief that AI will change everything, though human adaptation will be slow.

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