“John Cutler”

What differentiates the highest-performing product teams

TBM 429: How To Thrive At Work When You Think Too Much

John Cutler introduces an intended-but-unwritten book about thriving at work when you think too much, framing his years of TBM posts as already containing the material. He describes a recent breakthrough that clarified…

TBM 433: The Border Collie Faustian Bargain

John Cutler's essay uses the image of a border collie, a dog bred to be intensely focused and productive, to examine the trade-offs organizations make when they optimize hard for a single drive or output. The argument…

TBM 440: The Problem With Putting People in Boxes

John Cutler questions the usefulness of personality and strength tests in the workplace. He notes they make for entertaining conversation and can feel uncannily accurate, but seldom improve everyday collaboration. He…

TBM 432: Bundling & Unbundling Capabilities (and AI)

John Cutler reflects on his early product career, when a single product manager bundled research, analysis, design sketching, requirements writing, release coordination, support, and even coding into one role. He notes…

TBM 437: AI and the Recontextualization Tax

John Cutler argues that AI tools can reduce the cost of gathering and reusing context, which he calls a 'recontextualization tax' that teams pay whenever knowledge has to be re-explained across people, documents, and…

TBM 441: AI, the Loss of Positive Friction, and What to Do About It

John Cutler argues that AI tools remove not only wasteful friction but also 'positive friction': the productive struggle, debate, and slow sense-making that builds shared understanding and sound judgment in product…

TBM 442: 10 Career Traps (Thoughtful People Fall Into)

John Cutler outlines ten career traps that thoughtful people, including capable product and tech professionals, tend to fall into. The core argument is that good intentions and strong work ethic can quietly steer…

TBM 424: Why We Help (And How To Stay Helpful)

John Cutler reflects on the pull many product people feel to help and improve things, and on how that impulse can turn into exhaustion if left unchecked. He frames the desire to help as a real gift that helps people…

TBM 436: Tension-Based Prioritization (A Non-Framework)

John Cutler argues that teams often prioritize better when they pay attention to the underlying tensions they observe and act on daily, rather than focusing mainly on the specific items being prioritized. Those items…

TBM 431: The Denominator That Matters

John Cutler argues that organizations measuring AI success often fixate on the wrong denominator, counting outputs or usage rather than the outcomes that actually matter. The piece is framed around a simple model for…

TBM 426: The Trouble With Mirrors

John Cutler examines the difference between using mirrors and practicing mirroring, two ways of reflecting back what teams and people do. He describes how his own thinking about this distinction has evolved over the…

TBM 435: 20 Unfiltered Operating Takes

John Cutler, writing in response to a friend who wanted his unpolished, opinionated view, presents a set of candid operating takes for product and team leaders. The piece's premise is that leaders often hedge or present…

TBM 427: The Bottleneck Strike Again!

John Cutler critiques the recurring pattern of slides that wrap AI into old SDLC diagrams with logos, claiming the 'bottleneck has moved' and that the answer is settled, even as new methods appear weekly. The essay…

TBM 428: Yes, Robot. Yes, Boss?

John Cutler reflects on the growing role of AI in product and team work, framing it as something that can play several supporting roles: a scribe that captures notes, a thought partner that challenges ideas, a tool that…

TBM 434: How Maps Can Hide Problems

John Cutler argues that visual maps of product work, such as value streams, dependency diagrams, or process flows, can create a false sense of clarity and hide real problems. When the underlying system is incoherent, a…

TBM 437: Tokens, Hours, Points, and Other Curious Proxies

John Cutler examines the sudden enthusiasm for measuring "return on tokens" as AI usage grows inside companies. He argues that vendors and executives eager for clean numbers are reaching for yet another proxy, much like…

TBM 439: Day At The Gig...

John Cutler, writing in his newsletter The Beautiful Mess, reflects on starting a new job and the intensive effort of learning how the product, workflows, history, people, and artifacts all fit together. Rather than…

TBM 443: The Standard Setter

John Cutler introduces a leadership archetype he calls 'The Standard-Setter', a manager who is skilled at advancing their own career while misreading pressure as motivation. The core belief is that everyone has another…