

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


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 266 min read


When the Scope Won't Sit Still: Designing Work That Stays Designed
When scope drifts quietly, projects lose integrity before anyone raises a flag. Four stress-test lenses help change leaders design work that holds up under real-world pressure.
Jennifer Diamond
Jun 12, 20254 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


Check, Apply, and Lead: A Practical Framework for Lifelong Learning in Leadership
The Check–Apply–Lead framework helps practitioners turn learning into judgment, application, and shared practice — with useful off-ramps when something does not add value.
Maypop Learning
Oct 14, 20244 min read


The Power of Stakeholder-Obsessed Communication in Project Success
A stakeholder-obsessed communication approach can transform your project by building trust, aligning goals, and ensuring project success.
Maypop Learning
Feb 11, 20243 min read


The Consulting Mindset: Landing and Thriving as an Independent Consultant
Success relies on a true mix of skills, mindset, and practical strategies to thrive as an independent consultant.
Maypop Learning
Jan 28, 20243 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


15 Truths: A Practitioner's Credo for Change Leaders
After 30 years of leading change across more than 50 organizations, here are the 15 truths I keep coming back to. Not rules. Not a methodology. A credo — the things I remind myself of before I walk into the room.
Jennifer Diamond
Aug 1, 20223 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




