AI Is Not Agile 2.0: What PMs Must Rethink About Software Delivery
Agile solved the right problem for a world where implementation was expensive. AI has changed that world. For more than two decades, agile has been the dominant operating philosophy of software delivery. It was not merely a methodology — in many enterprises it became the language of legitimacy. Teams signaled modernity through sprints, standups, backlogs, and iterative release cycles. To question agile was to invite skepticism about one's grasp of modern development. That cre
Richard Diamond
Mar 264 min read
Dignity, Strategy, Technology: Three Axes Every Change Leader Navigates
Every change decision sits in the tension between dignity, strategy, and technology. Leaders who read all three axes navigate change well. Leaders who ignore one — usually dignity — produce initiatives that are technically sound and humanly inadequate.
Jennifer Diamond
Mar 55 min read
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
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