/John Cutler

Yes, Or... tl;dr: John calls out the counterpoints to wisdom often cited in common phrases we hear: (1) "Be customer-obsessed.” (2) Teams need clear objectives!” (3) "Think big. Start Small.” (4) "You can’t improve what you don’t measure." (5) "Focus on outcomes, not outputs."

featured in #562


Where More Effective Product Teams Spend More (and Less) Time tl;dr: “When trying to understand where a team or company is at, one of the first things I do is talk to people about how they spend their time and energy. Words like empowered, feature factory, and outcome-oriented are squishy and can mean a million things. Behaviors don't lie. There are only so many hours in a week, and we have finite energy to do thoughtful work.” John shares where teams that are further along their product journey spend time. 

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How Capable Leaders Navigate Uncertainty And Ambiguity tl;dr: “What do leaders who are skilled at navigating complexity know how to do? What do they do differently? What would you observe if a leader had these skills?” The authors asked these questions, and answered them using general behaviors they’ve observed first. These include: (1) Accepting they are part of the problem and have contributed to the current situation. (2) Encourage new interaction patterns and not simply remove individuals. (3) Patient divergence by resisting the urge to converge on a path forward prematurely. 

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The Ultimate Guide To Developer Counter-Productivity tl;dr: John highlights 20+ specific areas where developers often lose productivity, including: (1) Reactive, unplanned work. (2) Context switching and startup costs. (3) Non-value-adding admin & compliance work. (5) Ineffective planning. (6) Dependency management overhead. (7) Ineffective meetings and communication. (8) Redundant manager briefing & orientation. (9) Consensus seeking and decision-making drag. (10) Ineffective collaboration arrangements. And more.

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From Assumption To Next Step tl;dr: John discusses how to go from risky assumption to next steps using a single phrase. “One of the significant challenges was what to do with all of the discomfort and anxiety-inducing assumptions. Teams understood the theory — why it might benefit them to surface assumptions, designate “operating assumptions”, prioritize risky assumptions, and make plans to reduce uncertainty where it counts.”

featured in #408


A Problem vs The Problem tl;dr: “Most conversations about problems, and causes, are negotiations — negotiations about identity, reputation, controlling the narrative, and spheres of influence and control. People look for the "definition" they can live with and process. Deciding how much to constrain the collection of root causes — from one cause to a whole graph of related causes — is as much a political decision as a factual or solution-oriented one.”

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First Focus. Then Simplify tl;dr: "Imagine two people - Person A acknowledges the complex problem, and focuses. Person B doesn’t see the complex problem, and simplifies." Both approaches may seem very similar at first glance. "Focus looks like simplification. Simplification looks like focus." But when things go wrong, as they tend to do, Person B will make bad decisions. They’ll pick bad strategies and tactics and spread the lack of context awareness to their team. 

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Why Most Strategies Lack Clarity tl;dr: "The unlock, I think, is realizing that you can confidently communicate a coherent strategy that also acknowledges uncertainty. You know what you know. You assume what you assume. You believe what you believe." John explains that the reason this tends not to happen is we fear showing that we lack clarity, and lean towards displaying certainty. 

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A Conversation With Shreyas Doshi & John Cutler tl;dr: "We cover topics like leadership, becoming a better listener, the role of middle management, career and self identity, stubbornness, calendar theater, and treating your dashboards as products."

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Mandate Levels tl;dr: John came up with nine "levels" of work, "ranging from very specific, to very general." calling them Mandate Levels, "to capture the idea of a sphere of authority and autonomy." He discusses how they operate here.

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