TL; DR: Challenging Assumptions — Food for Agile Thought #459
Welcome to the 459th edition of the Food for Agile Thought newsletter, shared with 42,779 peers. This week, John Cutler suggests structuring organizations to become comfortable with challenging assumptions and thrive amid changing conditions, while Simon Powers examines culture’s impact on individuals and Agile’s decline. Bob Galen emphasizes the shift from rigid frameworks to flexible, context-driven agile patterns, Ted Neward highlights common ‘manager antipatterns’ in leadership, and Gustavo Razzetti stresses intellectual humility to prevent doubling down on poor decisions.
Next, Melissa Suzuno highlights how Botify’s transition to product-trio-supported enhanced collaboration and decision-making, while Todd Lankford offers a 5-step guide for teams to prioritize user needs over excessive planning. Stephanie Leue shares her approach to building high-performing teams, and Vlad Loktev, interviewed by Lenny Rachitski, discusses leadership insights from his decade at Airbnb, emphasizing chaos, impact, and balance in product development.
Lastly, Jacob Bennett shares his structured approach to work estimation for better outcomes, and Roman Pichler introduces product strategy discovery to minimize failure risk. Also, Pim de Morree critiques hierarchical team structures, advocating for more collaborative models, and Chris Stone presents the ‘Days Since Last’ metric for driving team accountability. Finally, Paul Graham reflects on the importance of a ‘founder mode’ approach to scaling companies, challenging conventional management wisdom.
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🏆 The Tip of the Week: Challenging Assumptions
: Boundary of Safely Challenged Assumptions
John Cutler explores the challenges of managing assumptions and legitimacy in software development, suggesting that organizations should be structured to adapt and thrive when conditions change, rather than relying on idealized models.
I have a theory. The idealized view is simultaneously: a) Very effective when the stars align—“ perfect execution of an ideal system.” b) Surprisingly fragile when things “go wrong” (you lose legitimacy, accumulate chronic issues, the business landscape changes, etc.)
🍋 Lemon of the Week
➿ Agile & Leadership
: State vs Step Change – The individual inside culture
Simon Powers explores how culture impacts the individual and how understanding these influences can help protect against negative effects, enhance personal well-being, and foster significant cultural change. He also points to the possible reason for Agile’s decline.
: Coaching Frameworks or Patterns
Bob Galen discusses the shift from rigid frameworks to more flexible pattern-based approaches in agile, emphasizing the need for experienced practitioners and context-driven solutions for sustainable and effective agility.
: Manager Antipatterns
Ted Neward highlights common ‘manager antipatterns,’ where companies repeatedly make mistakes in leadership roles, offering insights into identifying and addressing these dysfunctional management styles to improve team effectiveness.
: When Leaders Double Down on Bad Decisions
Gustavo Razzetti explores why leaders often double down on bad decisions, emphasizing the importance of intellectual humility, self-awareness, and adopting a learning mindset to avoid costly mistakes.
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🎯 Product
: Product in Practice: How Botify Broke Down Silos and Moved to Product Trios
Melissa Suzuno shares how Botify successfully broke down silos by transitioning to product trios, fostering collaboration and improved decision-making, and creating a more user-focused and efficient product development process.
(via Medium): The Real Reasons Why Most Product Teams Struggle to Delight Users
Todd Lankford explains that product teams often fail by focusing too much on planning rather than user needs, offering a 5-step guide to prioritize learning, adaptability, and user engagement.
: 🎙 How to Build High Performing Product Teams: Lessons from 15+ Years in Product with Stephanie Leue
In this podcast with Aakash Gupta, Stephanie Leue shares insights from her 15+ years in product management. She focuses on building high-performing teams by fostering trust, leveraging frameworks, and aligning around solving real user problems.
and : 🎙 Airbnb’s Vlad Loktev on embracing chaos, inquiry over advocacy, poking the bear, and ‘impact, impact, impact’
Lenny Rachitski interviews Vlad Loktev, who shares insights from his ten years at Airbnb. They discuss leadership, the importance of embracing chaos, prioritizing impact, and balancing speed with quality in product development and company culture.
📯 From Transparency to the Perils of Oversharing
While transparency is often touted as essential in Agile, too much can have negative consequences. Oversharing can lead to micromanagement, misinterpretation, and loss of trust within the team. Examples include excessive scrutiny during Daily Scrums, misreading progress metrics, and creating a blame culture that erodes psychological safety.
Strategic opacity may sometimes be necessary to protect the team’s autonomy and maintain a healthy dynamic. Be transparent, but not at the expense of the team’s independence and well-being.
Learn more: From Transparency to the Perils of Oversharing.
🛠 Concepts, Tools & Measuring
(via Medium): How to estimate work like a senior software engineer
Jacob Bennett shares his structured approach to work estimation, emphasizing understanding requirements, breaking tasks into components, identifying risks, and iterating estimates based on new insights for better project outcomes.
: Product Strategy Discovery
Roman Pichler introduces product strategy discovery as a systematic approach to minimize the risk of failure and maximize product success by developing an effective, well-aligned product strategy.
(via Corporate Rebels): Hierarchy in Teams: Why It Often Does More Harm Than Good
Pim de Morree argues that hierarchical team structures often harm performance, fostering conflict and reducing coordination, and advocates for flatter, more collaborative structures to unlock teams’ full potential.
: Have you heard of DSL metrics: The Simple Metric Most Teams Don't Know About?
Chris Stone introduces the ‘Days Since Last’ (DSL) metric, a simple visual tool for reminding teams of essential behaviors, driving accountability, and focusing on desired outcomes by tracking time since key events.
🎶 Encore
: Founder Mode
Paul Graham reflects on how conventional wisdom about scaling companies can mislead founders, advocating for a ‘founder mode’ approach, which emphasizes direct involvement and challenges traditional management practices
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📺 Join 6,000-plus Agile Peers on Youtube
Now available on the Age-of-Product Youtube channel to improve learning, for example, about Challenging Assumptions:
- Hands-on Agile 62: From Backlog Manager to Product Manager with David Pereira.
- Hands-on Agile 61: Toyota Kata Coaching for Agile Teams & Transformations with Fortune Buchholtz.
- Hands-on Agile 59: Tackling Fake Agility with Johanna Rothman.
- Hands-on Agile 57: Humble Planning with Maarten Dalmijn.
- Hands-on Agile 53: An Agile Coaches Guide to Storytelling with Bob Galen.
- Hands-on Agile EXTRA: How Elon Musk Would Run YOUR Business with Joe Justice.
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Help your team to learn about Challenging Assumptions by pointing them to the free Scrum Anti-Patterns Guide: