AI as a Historically Significant Capability: Why Boards Should Reassess Organization Design Before They “Implement AI”
Organizations have always been shaped—sometimes quietly, sometimes violently—by the constraints of their era. When capital intensity demanded scale, firms built functional hierarchies. When markets expanded geographically, organizations aligned around regions. When product lines proliferated, divisional business units emerged to restore focus and accountability. When knowledge work and motivation became central, matrix structures and team-based operating models rose to promin
Richard Diamond
Jan 265 min read
The Friction of Change - Two Operating Systems
Why progress resists us at every stage, and what it really takes to make improvement last Maypopgrove.com is for people who see what is broken, imagine what could be better, and feel compelled to act. Builders, reformers, innovators, organizers, leaders, teachers, founders, investors, policymakers, and quiet custodians—anyone trying to turn “we should” into “we did” in a world that is, at once, astonishingly opportunity-rich and stubbornly resistant to lasting improvement.
Richard Diamond
Jan 95 min read
Making Progress in the Real World
Preamble This essay is written for the agents of change —the people who see what is broken, imagine what could be better, and feel compelled to act. It is for builders, reformers, innovators, organizers, leaders, teachers, founders, investors, policymakers, and quiet custodians—anyone trying to turn “we should” into “we did” in a world that is, at once, astonishingly opportunity-rich and stubbornly resistant to lasting improvement. We live in a time of immense capability. Too
Richard Diamond
Jan 711 min read
Why AI Demands an AI Digital Asset System (ADAS)
Beyond Code: Why AI Demands an AI Digital Asset System (ADAS) How change and project leaders must reinvent delivery and governance for the age of AI agents For decades, project and change leaders have rallied teams around a familiar center of gravity: “The code is the product. Documentation supports it.” In the world of AI agents, that assumption quietly breaks. An AI agent doesn’t just run on code. It runs on digital assets : prompts, policies, data scopes, tools, and guardr
Richard Diamond
Dec 11, 20256 min read
Thinking about "Semi-autonomous" AI
For decades, “computing” meant something very specific: we told machines exactly what to do, step by step, and they did it—fast, consistently, and without ever coloring outside the lines. Today, with AI, we’re crossing into something very different: systems that don’t just execute instructions, but interpret situations, choose among options, and act with a degree of initiative. That in-between space is what many people now call semi-autonomous AI. It’s not a robot overlord
Richard Diamond
Dec 10, 20255 min read
From Automation to Agency: Why 2026 Will Break Your Project Playbook
From Automation to Agency: Why 2026 Will Break Your Project Playbook Perspective from a CIO with 40+ years in the chair In more than four decades in technology leadership, I’ve ridden every major wave: mainframes, client–server, ERP, internet, cloud, mobile, analytics, and now AI. Each one forced us to adjust how we run projects. Agentic AI — systems of semi-autonomous agents that can perceive, decide, and act — is different. Beginning in 2026, many of your “digital transfor
Richard Diamond
Dec 7, 20256 min read