HeyJaredLeadership, Rewritten
The playbook is broken. I write about what comes next for leaders navigating complexity and collapse.
- Indexed issues, last 90 days
- 8
- Latest publication
- Sep 17, 2026
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- Earliest in this view
- Jul 17, 2026
Latest issues
We Know How to Worry About AI That Fails (opens the original)
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Over the past year, a growing proportion of my client work has involved developing people to lead in organisations increasingly shaped by AI. That has sent me fairly deep into the research on what AI is doing to work, organisations and leadership, and into a literature that seems capable of expanding faster than anybody can reasonably read it.A particular thank you here to Professor Fernando Suarez, who has been extraordinarily generous in connecting me with some of the best AI research being pr
The Organisation Behind the Business Case (opens the original)
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Over the past week, I published three stories about Maya and AI.In the first, her organisation discovered that a collection of individually useful AI agents could produce a remarkably incoherent customer experience. In the second, a professional-services firm became much faster at producing sophisticated work and quietly shifted a growing assurance burden onto its most experienced people. In the third, an executive team built an unusually good AI-supported decision environment and then had to co
The Architecture of Judgement: Maya Gets Exactly the Answer She Asked For (opens the original)
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AI-supported decision environments can give leaders faster access to evidence, stronger organisational memory and much clearer comparisons between competing options. They can also influence executive judgement before any recommendation is made. Every curated environment privileges particular sources, definitions, prompts, assumptions and forms of evidence, shaping what becomes easy to see and what remains outside the frame. As shared AI environments improve, teams may converge more quickly aroun
The Architecture of Expertise: Maya Notices the Experts Have Stopped Going Home (opens the original)
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Generative AI can dramatically increase the speed and apparent quality of professional work. More proposals can be written, more research completed and more sophisticated analysis produced by less experienced employees. That gain creates a second-order problem. The volume of plausible work can grow much faster than the supply of experienced judgement required to verify it, creating new assurance burdens for experts and senior leaders. At the same time, automating routine professional work can re
The Architecture of Agency: Maya and the Employees Nobody Hired (opens the original)
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AI agents allow organisations to automate increasingly consequential forms of action across sales, service, finance and operations. Each agent may work exactly as intended within its own domain, while their combined behaviour produces confusion, contradiction and customer harm at enterprise level. The deeper problem is one of organisational design. Agency is being distributed across machines, functions and workflows while accountability remains concentrated in human roles that may have limited v
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