Food for Agile Thought #502: Cultural AI Adoption, Discovery not Creation, Product Model Pilot Teams, Self-Organization as a Concept
Also: Sunk Costs, AI Enshittification, ‘Big Picture’ Loop, Building Faster
Hello everyone!
Welcome to the 502nd edition of the Food for Agile Thought newsletter, shared with 40,607 peers.
This week, we learn how Shopify scaled reflexive AI from memo to a movement of cultural AI adoption by empowering teams and centralizing tooling. Andrew Bosworth reframes innovation as discovering natural user behavior rather than inventing features, and Marty Cagan underscores the strategic use of pilot teams to reduce risk in product model shifts. Tim O’Reilly warns of AI’s descent into enshittification, while Mike Cohn champions structured autonomy for self-organizing teams.
Next, Andrew Ng outlines how speed, agentic workflows, and coding fluency fuel GenAI success. Sayash Kapoor and Arvind Narayanan warn that AI may accelerate junk science without structural reform, and John Cutler critiques leadership’s addiction to oversimplification. Additionally, Calvin French-Owen provides an inside view of OpenAI’s relentless pace, and Seth Godin reframes sunk costs as optional, rather than obligations.
Lastly, Catherine Connors explores storytelling as a leadership tool to build shared culture and ownership. Maarten Dalmijn cautions against outsourcing understanding to AI-generated user stories, and Addy Osmani advocates for context engineering over prompt tinkering to ensure reliable AI performance. Finally, Assaf Elovic and Harrison Chase introduce the CAIR framework, revealing that user confidence, not technical brilliance, drives AI product success.
🛑 2 Days Left — The AI-Enhanced Advanced Product Backlog Management Course Version 2 at $99
While many Product Owners spend sizable chunks of their time defending Product Backlog decisions, top-performing teams use systematic alignment processes to turn stakeholders into allies and backlogs into strategic assets.
This intensive course delivers the exact frameworks and AI-enhanced workflows that save successful Product Owners 5–10 hours weekly while improving stakeholder trust.
What’s Included:
✅ Self-paced video modules with practical exercises
✅ Launch week live Q&A sessions with Stefan
✅ Custom GPTs for Product Owner workflows
✅ Complete anti-patterns diagnostic toolkit
✅ Community access
✅ Lifetime access to all course updates and materials
✅ Certificate of completion.
👉 Please note: The course will only be available for sign-up until July 22, 2025!
🎓 Join Your Peers Now: Learn How to Master the Most Important Artifact for any Successful Agile Practitioner!
Did you miss the previous Food for Agile Thought issue 501?
🏆 The Tip of the Week
(via First Round Capital): From Memo to Movement: Shopify’s Cultural Adoption of AI
The article details how Shopify transformed reflexive AI use from memo to movement by aligning leadership, removing access barriers, and centralizing tooling, enabling teams across functions to automate workflows, challenge assumptions, and redesign how work and decisions happen.
Source: First Round Capital: From Memo to Movement: Shopify’s Cultural Adoption of AI
🎯 Product
Andrew Bosworth: Product Innovation is Discovery not Creation
Andrew Bosworth argues that product innovation is less about invention and more about discovering how people naturally engage with tools, much like filmmakers uncovered storytelling techniques by observing audience response.
Source: Product Innovation is Discovery not Creation
Author: Andrew Bosworth
📺 Andrew Ng (via Y Combinator): Building Faster with AI
Andrew Ng shares lessons from building AI startups, emphasizing the importance of execution speed, concrete ideas, agentic workflows, rapid prototyping, and coding literacy as keys to thriving in the fast-evolving GenAI landscape.
Source: Y Combinator: 📺 Building Faster with AI
Author: Andrew Ng
Marty Cagan (via Silicon Valley Product Group): The Politics of Pilot Teams
Marty Cagan highlights why pilot teams are essential to successful product model transformations, showing how carefully scoped problems, hand-picked talent, and targeted coaching build credibility, reduce risk, and accelerate organizational learning.
Source: Silicon Valley Product Group: The Politics of Pilot Teams
Author: Marty Cagan
John Cutler: The Wicked ‘Big Picture’ Loop
John Cutler describes a familiar leadership loop where the demand for simplified “big picture” views gradually disconnects from reality, triggering distrust, fire drills, and backchanneling, until a crisis resets the cycle.
Source: The Wicked ‘Big Picture’ Loop
Author: John Cutler
🧠 Artificial Intelligence
Tim O’Reilly (via O’Reilly Media): Where Is AI on the Enshittification Curve?
Tim O’Reilly explores how AI’s impact on jobs and value creation depends on where companies are in the innovation cycle, warning that many are already entering the extractive phase of enshittification.
Source: O’Reilly Media: Where Is AI on the Enshittification Curve?
Author: Tim O’Reilly
Sayash Kapoor and Arvind Narayanan: Could AI slow science?
Sayash Kapoor and Arvind Narayanan argue that AI could actually slow scientific progress by accelerating paper production without improving human understanding, reinforcing flawed incentives, and entrenching outdated theories, unless institutions rethink how science is evaluated and rewarded.
Source: Could AI slow science?
Authors: Sayash Kapoor and Arvind Narayanan
Calvin French-Owen: Reflections on OpenAI
Calvin French-Owen reflects on a fast-paced year at OpenAI, describing a culture of bottom-up experimentation, high-impact collaboration, and ambition that’s pushing technical and organizational boundaries at breakneck speed.
Source: Reflections on OpenAI
Author: Calvin French-Owen
Sean Goedecke: How I use LLMs to learn new subjects
Sean Goedecke explains how LLMs can be powerful learning tools when used interactively, not passively, emphasizing collaboration, caution around hallucinations, and the value of asking follow-up or Socratic questions.
Source: How I use LLMs to learn new subjects
Author: Sean Goedecke
🖥 💯 🇬🇧 AI for Agile BootCamp Cohort #2 — September 15 — October 6, 2025
The job market’s shifting. Agile roles are under pressure. AI tools are everywhere. But here’s the truth: the Agile pros who learn how to work with AI, not against it, will be the ones leading the next wave of high-impact teams.
So, become the professional recruiters call first for “AI‑powered Agile.” Be among the first to master practical AI applications for Scrum Masters, Agile Coaches, Product Owners, Product Managers, and Project Managers.
Tickets also include lifetime access to the corresponding online course, once it is published. The class is in English. 🇬🇧
Learn more: 🖥 🇬🇧 AI for Agile BootCamp Cohort #2 — September 15 — October 6, 2025.
Customer Voice: “The AI for Agilists course is an absolute essential for anyone working in the field! If you want to keep up with the organizations and teams you support, this course will equip you with not only knowledge of how to leverage AI for your work as an Agilist but will also give you endless tips & tricks to get better results and outcomes. I thoroughly enjoyed the course content, structure, and activities. Working in teams to apply what we learned was the best part, as it led to great insights for how I could apply what I was learning. After the first day on the course, I already walked away with many things I could apply at work. I highly recommend this course to anyone looking to better understand AI in general, but more specifically, how to leverage AI for Agility.” (Lauren Tuffs, Change Leader | Business Agility.)
➿ Agile & Leadership
Mike Cohn: Understanding and Leading Self-Organizing Teams
Mike Cohn explains how self-organizing teams thrive when leaders provide clarity, remove obstacles, and foster autonomy, enabling innovation, resilience, and faster decision-making without abandoning structure or accountability.
Source: Understanding and Leading Self-Organizing Teams
Author: Mike Cohn
Seth Godin: Sunk costs and the framework for forward motion
Seth Godin reminds us that sunk costs are gifts from our past selves, but we are free to decline them when they no longer serve our present direction or goals.
Source: Sunk costs and the framework for forward motion
Author: Seth Godin
📺 (via IDEO U): 5 Storytelling Techniques for Leaders Who Want to Shape Culture
Catherine Connors shares five storytelling techniques for leaders, emphasizing co-creation, play, and empathy as key elements in shaping culture, sparking collective ownership, and inviting everyone to become part of the narrative.
Source: IDEO U: 📺 5 Storytelling Techniques for Leaders Who Want to Shape Culture
📯 The Advanced Product Backlog Management Course v2 with AI
The Advanced Product Backlog Management Course with AI is available on July 15th, 2025, at $99with free lifetime access to all updates. It cuts through AI hype to address real product management challenges.
Instead of treating AI as a silver bullet, it examines how Generative AI and LLMs genuinely improve Product Backlog management versus when they’re expensive distractions. It uses the practical HealthXYZ startup scenario to distinguish value-adding AI applications from organizational theater, perfect for teams ready to confront uncomfortable truths about their current backlog dysfunction.
📺 Watch the ‘The Advanced Product Backlog Management Course v2 with AI’ video now!
🎓 Join Your Peers Now: Learn How to Master the Most Important Artifact for any Successful Agile Practitioner!
🛠 Concepts, Practices, Tools & Measuring
Addy Osmani: Context Engineering: Bringing Engineering Discipline to Prompts
Addy Osmani introduces context engineering as the discipline of constructing complete input environments, including data, instructions, and tools, so AI systems perform reliably by moving beyond clever prompts to structured system-level design.
Source: Context Engineering: Bringing Engineering Discipline to Prompts
Author: Addy Osmani
Maarten Dalmijn: If You’re Using AI to Generate Requirements or User Stories: You’re Completely Missing the Point
Maarten Dalmijn argues that using AI to generate user stories misses the point: requirements are not about writing faster, but about achieving a shared understanding through collaboration, problem framing, and genuine team involvement.
Source: If You’re Using AI to Generate Requirements or User Stories: You’re Completely Missing the Point
Author: Maarten Dalmijn
Assaf Elovic and Harrison Chase (via Medium): The Hidden Metric That Determines AI Product Success
Assaf Elovic and Harrison Chase introduce CAIR, a practical framework for measuring user confidence in AI products, showing that thoughtful product design often outweighs technical excellence in driving adoption and success.
Source: Medium: The Hidden Metric That Determines AI Product Success
Authors: Assaf Elovic and Harrison Chase
📅 Training Classes, Meetups & Events 2025
Upcoming classes and events:
🖥 💯 🇩🇪 September 2–3 — Live Virtual Class: Professional Scrum Product Owner Training (PSPO I; German)
🖥 💯 🇬🇧 SOLD OUT: September 4–25 — Live Virtual Cohort: AI for Agile BootCamp Cohort (English)
🖥 💯 🇬🇧 September 15–October 6 — Live Virtual Cohort: AI for Agile BootCamp Cohort (English)
🖥 🇬🇧 September 23–24 — Live Virtual Class: Professional Scrum Master — Advanced Training (PSM II; English)
🖥 💯 🇬🇧 October 1–November 12 — Live Virtual Cohort: AI for Agile BootCamp Cohort (English)
🖥 🇬🇧 October — Live Virtual Class: Professional Scrum Product Owner AI-Essentials Schulung mit PSPO-AIE-Zertifikat (English)
👉 See all upcoming classes here
🗞️ Last Week’s Food for Agile Thought Edition
📺 Join 6,000-plus Agile Peers on YouTube
Now available on the Age-of-Product YouTube channel:
Hands-on Agile #68: How to Analyze Unstructured Team Interview Data with AI.
Hands-on Agile 2025: The 5 Obstacles to Empowered Teams — Maarten Dalmijn
Hands-on Agile 2025: The Top Reasons Why a Product Strategy Fails — Roman Pichler
Hands-on Agile 2025: Taylorism-Lean-Agile-Product Mindset — Jonathan Odo
Hands-on Agile Extra: How Elon Musk Would Run YOUR Business mit Joe Justice
🎓 Do You Want to Read More Like This?
Also:
📅 Join 6,000-plus peers of the Hands-on Agile Meetup group
🐦 Follow me on Twitter and subscribe to my blog, Age of Product
💬 Alternatively, join 20,000-plus peers of the Slack team “Hands-on Agile” for free.