Category: Our posts by Stefan Wolpers

TL; DR: Cultural AI Adoption — Food for Agile Thought #502

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 introduces the CAIR framework, revealing that user confidence, not technical brilliance, drives AI product success.

TL; DR: Passive AI Use — Food for Agile Thought #501

Welcome to the 501st edition of the Food for Agile Thought newsletter, shared with 40,598 peers. This week, Ethan Mollick warns that passive AI use can dull creativity and critical thinking, while Johanna Rothman emphasizes that product development’s core lies in collaborative learning and flow, not code typing. David Pereira interviews PostHog’s James Hawkins on scaling through engineer autonomy and minimal control. Seth Godin explores AI’s historical parallels, and Cedric Chin distills practical insights from Jobs to be Done interviews for product strategy.

Next, Teresa Torres and Hope Gurion unpack resistance patterns in product operating model pilots and offer ways to build shared clarity. Aakash Gupta interviews Tanguy Crusson on Atlassian’s AI-powered discovery. Maarten Dalmijn critiques budgeting myths, Louis Columbus details Walmart’s scalable AI platform, and Daniel Lereya shares how Monday.com’s AI Month fostered a culture of bold, decentralized innovation at scale.

Lastly, Grant Harvey dissects Grok 4’s impressive yet troubling launch, and Elvis Saravia reframes prompt engineering as context design for LLMs. Chuck Whitten and team call for AI-led business reinvention beyond tech. Megan Saker maps product documentation’s lifecycle value, and Gregor Ojstersek, with Laura Tacho, offers a framework to measure AI’s real impact on engineering teams.

TL; DR: 5C Strategy Framework — Food for Agile Thought #500

Welcome to the 500th edition of the Food for Agile Thought newsletter, shared with 40,612 peers. This week, Maarten Dalmijn highlights how companies often confuse comfort with strategy and offers the 5C strategy framework to foster genuine strategic thinking. Janna Bastow warns against “enshittification,” the slow death of products driven by misaligned incentives. David Pereira reframes “fail fast” as harmful, advocating for deliberate learning, while McKinsey and Thomas Claburn scrutinize the prerequisites and limits of generative and agentic AI in delivering real business value.

Next, Mike Goitein critiques the obsession with shipping speed, showing how Linear wins by polishing for quality. Richard Mironov reminds product leaders to defend user value and team integrity. Additionally, insights from MIT Sloan’s CIO Symposium reveal that leadership-induced AI failures occur when vision and human factors are ignored. Vaidheeswaran Archana warns of looming LLM cost hikes, and Andy Cleff calls for proactive, trust-based team health strategies.

Lastly, Annie Peshkam and David Dubois stress the importance of shared unlearning for progress. David Burkus urges transparent adaptability, and John Cutler rethinks value hierarchies. Finally, Brian Rain clarifies the true essence of Kanban by pointing to its “theater version,” and Diegovz introduces the RAAEE framework for tracking meaningful product impact beyond vanity metrics.