

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
Jun 14 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 266 min read


Running the Machine: What Operational Thinking Actually Looks Like in a Project
Project managers aren't CEOs — they're operators. Thinking like a COO shifts the focus from owning the mission to designing the engine that delivers it with resilience and respect.
Jennifer Diamond
Jul 24, 20255 min read


Redefining Project Quality: From Compliance to Excellence in Change Leadership
True excellence in change leadership uses quality metrics to demonstrate excellence at every stage of the change process.
Maypop Learning
Nov 10, 20245 min read


The Regenerative PM: Leave Everything Better Than You Found It
Regenerative project management isn't a methodology — it's a stance. It's the choice to treat every project as an opportunity to strengthen people, systems, and organizations, not just deliver an outcome.
Jennifer Diamond
Jun 1, 20233 min read


Why I Built Maypop Grove
Maypop Grove was built for people carrying meaningful work through complexity — people who need practical tools, honest language, and a steadier way to move from intention to impact.
Jennifer Diamond
Jul 1, 20222 min read




