Stefan Wolpers

Food for Agile Thought #516: Sabotaging AI, Feature Flags for Discovery, AI Slop Field Guide, Upskilling Teams

by Stefan Wolpers | 2025-10-24 News

TL; DR: Sabotaging AI — Food for Agile Thought #516

Welcome to the 516th edition of the Food for Agile Thought newsletter, shared with 40,359 peers. This week, Jenn Spykerman addresses unknowingly sabotaging AI according to a 1944 manual, masquerading endless committees, perfectionism, and cautious delays as good governance. Leah Tharin challenges claims that LLMs can stand in for real customer insight, warning that dashboards can fuel strategy theater, while John Cutler connects prioritization to strategic leverage and power dynamics. Jing Hu reframes AI failure stats as early-stage noise, and Duncan Brown warns that AI favors the visible over the messy, human glue that makes effective teams work.

Next, Chetan Kapoor shows how eBay uses feature flags as discovery tools to validate demand early and surface usability issues. Kyle Poyar critiques popular SaaS pricing models and shares fixes that avoid complete overhauls. Ethan Mollick maps the current AI landscape with practical guidance on tools, tiers, and tactics. At the same time, Zvi Mowshowitz highlights key takeaways from Karpathy’s AGI views, and James Shore reframes engineering accountability through product bets instead of features and deadlines.

Lastly, Anthropic’s Claude receives “skills” as modular guides for specialized tasks, now open-sourced on GitHub. One author explores how great teams grow through targeted support and bold delegation, and Jeff Sauro and Jim Lewis dissect NPS claims, separating useful signals from misleading noise. Charlie Guo calls out the creeping signs of AI-generated content and its cost to authenticity. Finally, Karen Dahut presents Google Skills, a vast new learning platform for AI and tech upskilling.

Food for Agile Thought #516: Sabotaging AI, Feature Flags for Discovery, AI Slop Field Guide, Upskilling Teams — Age-of-Product.com

The Dangerous Middle: Agile Roles That AI Will Erode First

by Stefan Wolpers | 2025-10-19 News

TL; DR: Dangerous Middle and the Future of Scrum Masters and Agile Coaches

Peter Yang, a renowned product leader, argues that AI will split product roles into two groups: Generalists who can prototype end-to-end with AI, and specialists in the top 5% of their fields. Everyone else in the dangerous middle risks being squeezed.

How does this apply to agile practitioners: Scrum Masters, Product Owners, Agile Coaches, and transformation leads? It does, with important nuances.

The Dangerous Middle: Peter Yang's Product Role Framework Reveals About the Future of Agile Practitioners — Age-of-Product.com

Food for Agile Thought #515: Poor Decisions by Managers, LLMs Getting Dumber, POM Explained, AI Zombie Projects

by Stefan Wolpers | 2025-10-17 News

TL; DR: Poor Decisions by Managers — Food for Agile Thought #515

Welcome to the 515th edition of the Food for Agile Thought newsletter, shared with 40,381 peers. This week, Henrik Mårtensson explores six decision-making traps managers fall into and how to overcome poor decisions with candor and deliberate practice. Janna Bastow highlights how skipping feasibility checks sabotages product delivery, offering lightweight tactics for trust and clarity in the AI era. Also, Teresa Torres and Petra Wille explore how product leaders shape their legacy through their impact, values, and reflection. Meanwhile, Jacob Poushter and team find AI anxiety outweighs optimism, and Maarten Dalmijn warns how process bloat kills team ownership.

Next, Melissa Suzuno outlines how product operating models shift focus from outputs to outcomes, scaling through pilot teams and leadership support. Roger Snyder addresses the tension between PM and PO, emphasizing the importance of alignment on purpose, ownership, and cadence, while Charlie Guo examines LLM performance drift, providing mitigation strategies. Barry O’Reilly lists 21 signs your AI project might be undead, and Martin Eriksson warns that empowerment fails without a strategic context and a deliberate shift in leadership stance.

Lastly, Pawel Brodzinski warns that autonomous AI agents lack the trust needed for broad adoption without transparency and alignment. Jens Meyer critiques veto-heavy cultures and calls for genuine accountability, where saying yes means accepting the outcome. Also, Emily Webber shares tips on selecting meaningful icebreakers that promote safety and connection, and Steve Blank defends science as the engine of innovation. Finally, Matt Kamelman stresses that smart AI starts with context, not just more data.

Food for Agile Thought #515: Poor Decisions by Managers, LLMs Getting Dumber, POM Explained, AI Zombie Projects — Age-of-Product.com

Earn Your Free AI 4 Agile Certificate — Test-Drive the Questions

by Stefan Wolpers | 2025-10-15 Agile and Scrum

TL; DR: Test-Drive the Questions of the AI 4 Agile Assessment

Help me QA the questions for the AI 4 Agile Certificate by taking three short practice quizzes on the intersection of AI and Agile. In return, pass 2 out of 3 and get a free shot at the real AI 4 Agile Certification (40 questions, 45 minutes). The top performer of this small competition also receives the full AI 4 Agile online course.

Your feedback on the questions matters tremendously and helps shape a better curriculum for all practitioners.

Earn Your Free AI 4 Agile Certificate — Test-Drive the Questions — Age-of-Product.com

Mastering AI as Agile Practitioners — The AI 4 Agile Course Is Out!

by Stefan Wolpers | 2025-10-12 Agile and ScrumAgile Transition

TL; DR: Mastering AI 4 Agile with the Best Self-Paced Online Course

The Mastering AI with the AI 4 Agile Online Course launches this week, and I am proud that I avoided another delay. Scope creep happened despite my supposed expertise in preventing exactly that. The course expanded from a simple prompt collection to over 8 hours of video, custom GPTs, and materials that I’ll apparently continue to update indefinitely, as I’m still not satisfied that it’s comprehensive enough. (Also, the field is advancing so rapidly.)

At least the $129 lifetime access means you will benefit from my urge to fight my imposter syndrome with perfectionism and from my inability to call a project “done.” I guess we are in for the long term. 🙂

🎓 🛒 The AI 4 Agile Online Course Is Available — Join Now at $ 129 until October 20, 2025: AI 4 Agile — Master AI Integration for Agile Practitioners.

Food for Agile Thought #514: State of AI Report 2025, Stakeholder Management, What Breaks Product Decisions, 25 Years of XP

by Stefan Wolpers | 2025-10-10 News

TL; DR: State of AI Report 2025 — Food for Agile Thought #514

Welcome to the 514th edition of the Food for Agile Thought newsletter, shared with 40,403 peers. This week, Nathan Benaich’s State of AI Report 2025 highlights advancements in reasoning, China’s momentum, massive compute, sharper geopolitics, and a pragmatic shift toward reliability and governance. Jenny Wanger offers a hands-on way to surface implicit strategy through learner-mode interviews, drafting, and iterative feedback, while John Cutler tackles product-centricity in non-digital firms, urging a networked operating model that links funding, intent, collaboration, architecture, and outcomes. Nino Paoli notes Citi’s prompt training push while warning that real impact needs ongoing upskilling and integration. Additionally, Maarten Dalmijn highlights trust as the actual bottleneck that must be addressed before AI can effectively amplify execution.

Next, Roman Pichler sharpens stakeholder management with a power-interest focus, trust building, early involvement, and NVC for real conflict resolution. David Pereira draws out Ryan Singer on keeping six-week bets lean through framing, alignment, and timely founder input, while David Shapiro challenges “AI pilot failure” myths, focusing on integration and governance issues. Then, Sangeet Paul Choudary shifts AI agent talk to coordination and standards, and Dave Rooney marks 25 years of XP, calling for TDD, pairing, CD, and lean flow.

Lastly, Casey Newton probes OpenAI’s platform push, weighing integrations against privacy, incentives, and trust. Teresa Torres urges teams to own interview synthesis, then use AI to spot cross-patterns without losing empathy or skill. Sean Goedecke demonstrates that staff engineers can influence politics by aligning momentum and delivering visible wins, and Shane Hastie and Marcos Arribas share culture-at-scale practices from autonomy to right-sized quality. Finally, Anton Zaides advocates ruthless meeting hygiene to protect deep engineering flow.