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
No More Secret Rulebooks: What AI Will Expose About Your Culture
No More Secret Rulebooks: What AI Will Expose About Your Culture Why serious AI projects force change leaders to confront the gap between stated values and real behavior—and how to turn that into an advantage. Quick Video If you lead change, you’ve always had to navigate two versions of your organization: The one in the slide decks, values statements, and town halls. And the one people quietly describe over coffee: “Here’s how things really work.” Until now, those two versio
Richard Diamond
Dec 4, 20256 min read
Raising AI: Why It’s More Like Having a Baby Than Building a House
Why AI Is More Like Having a Baby Than Building a House Missteps and hallucinations are natural growing pains, not a verdict on the technology. Most of the public conversation about AI still sounds like a construction meeting. We talk about “building a model,” “deploying a system,” “rolling out a solution.” We expect that, after some testing and debugging, the system will do what it’s supposed to do, just like a new building is expected to stand straight, keep the rain out, a
Richard Diamond
Dec 2, 20256 min read
Organizational Charts for Reality
Modernizing an Industrial-Revolution Artifact for Mid-21st-Century Enterprises—Without Breaking the Org Chart Abstract Organization charts were designed for an industrial-era reality where work was primarily human labor, information moved slowly, and control depended on hierarchical supervision. Mid-21st-century enterprises operate as socio-technical systems: outcomes are produced by humans working through core platforms (ERP, CRM, PLM, MES, CMS, workflow, data platforms) and
Richard Diamond
Oct 15, 20256 min read
Following up on the Death and Life of the Green Building Movement
This post captures an action plan following "the Death and Life of the Green Building Movement" summit from SoRD September 20, 2025. Let's get to work.
Jennifer Diamond
Oct 8, 202513 min read
LF25 Part 2 of 3 - Why Are We Still Having This Conversation?
Still trying to “make the case” for sustainability? Maybe it’s not a messaging problem—it’s a resistance system. A sharp, honest look at why good leaders keep repeating themselves and how to move forward with clarity.
Jennifer Diamond
May 14, 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
Leveraging the Plan-Do-Check-Act Cycle for Continuous Improvement
The PDCA cycle offers a reliable, iterative approach to achieving proactive quality management and iterative learning in project workflows.
Maypop Learning
Oct 6, 20242 min read
Kaizen for Continuous Improvement: Making Small Changes for Big Wins
A kaizen approach can enhance efficiency, boost morale, and drive team success with small, consistent changes that add up over time.
Maypop Learning
Sep 22, 20243 min read
Collaborative Planning with the RACI Matrix: Building Ownership and Accountability
The RACI Matrix helps teams define roles together, enhances ownership, boosts accountability, and improves team cohesion.
Maypop Learning
Aug 4, 20244 min read
Strategic Goal-Setting with Tuckman’s Model for Team Performance
Use Tuckman’s stages of team development, Forming, Storming, Norming, and Performing, to set and achieve team goals effectively.
Maypop Learning
Jul 28, 20243 min read
The Five Dysfunctions of a Team: Breaking Down the Barriers to Success
Spot and tackle common issues using Patrick Lencioni’s Five Dysfunctions of a Team model, and turn dysfunctions into growth opportunities.
Maypop Learning
Jul 14, 20244 min read
Embracing Change with the ADKAR Model: A Roadmap for Successful Transitions
Change can be challenging, but the ADKAR model provides a clear path to guide teams through it.
Maypop Learning
May 19, 20243 min read
Mapping the 5 Ws for Stakeholder Engagement in Change Projects
Engaging stakeholders effectively is crucial for successful change projects. Use the 5 Ws—Who, What, When, Where, Why—to ensure buy-in.
Maypop Learning
May 5, 20243 min read
Embracing a Hybrid Approach in Project Management: The Best of Agile, Waterfall, and Stage-Gate
A hybrid approach combines the flexibility of Agile with the structure of Waterfall and the control of Stage-Gate.
Maypop Learning
Apr 28, 20244 min read