John Cutler
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Articles by John Cutler
TBM 451: What We Learn to Notice and Ignore
We’ve all probably experienced something like this. At a company meeting, a leader makes statements like “We put customers first” and “Our people are our greatest asset.” Some people in the audience immediately start comparing those statements with the company’s actual incentives, decisions, and everyday behaviors. They’re connecting the dots across different contexts. They notice where things don’t add up and perhaps feel increasingly uncomfortable with the contradictions.
TBM 450: The Loss of Positive Friction
A constraint can be “enabling” and “limiting” at the same time. For example, I’m working with a home contractor who takes his time. It is frustrating because I really need this job done. But there’s a side benefit. On a couple of occasions, being forced to look at the plans for a bit, consider the cost, and walk impatiently around the house thinking about how we live has inspired objectively better decisions about what we want (and need).
TBM 449: Game Design, Consulting, and the Engagement as Product
I'm currently knee-deep in the overlap between the product operating model, platform product management, consulting, and service design. It's a blast. This post is about using game design concepts to design better consulting engagements. Everyone, including your customers, loves a good game. Even if you’re not in consulting or don’t offer a service, you might find some of this content interesting. It touches on what happens when you treat your whole company as a product.
TBM 448: The Software Factory as Identity Defense (and Reinvention)
“Software factory” is a kind of identity defense (and branding). And there’s a historical precedent here. I’ve been pondering the almost Dionysian fervor surrounding all these new “factories” people are building. The sheer exhilaration, obsessive energy, and unmistakable pride people seem to take in building systems that build things. Imagine your whole profession of “building” has shifted. Things that underpinned your identity are no longer considered valuable.
TBM 447: Why We Sabotage Our Careers
Still from False Confidence (2019). Choreography by Sean Lew. Performed by Sean Lew and Kaycee Rice. Cinematography by Jon Hernandez. Music by Noah Kahan. I’ve been isolating in bed with COVID for the last week, with way too much time on my hands to think, watch YouTube, and revisit old favorites, including Sean Lew and Kaycee Rice’s incredible dance to Noah Kahan’s False Confidence.
TBM 446: Halos, Vibes, Causality, and Identity
Life gets easier when you stop getting pulled into debates over people’s implicit causal claims and start recognizing that many of these conversations are really about values, identity, and worldview. Yours/ours included. This is difficult because those beliefs can be hurtful, dismissive, or diminishing. And you may have very good reasons to believe the causal claims are wrong. But recognizing what’s happening doesn’t mean agreeing, abandoning rigor, or letting harmful claims go unchallenged.
TBM 445: The Feature Factory: A 10-Year Retrospective
10 years ago I wrote a post on Medium about Feature Factories that literally changed my life. Funny story: I was trying to get a Medium researcher to understand something. I wrote the post in a couple minutes to “prove” that the punchier, more hard-hitting, more judgmental, and more “oh, I’ve seen that before” a post was, the more traffic it would get.
TBM 444: What a Workplace Can’t Promise
In other posts, I’ve written about the distinction between “the work” and “the workplace.” I want to dig a little more into what makes workplaces unique. It is not naïve to seek autonomy, mastery, and purpose at work. Given how much of our lives we spend working, it would be strange not to. The seductive mistake, however, is to assume that companies function like families, guilds, unions, friendships, expeditions, sports teams, congregations, neighborhoods, or communities.
TBM 443: The Standard Setter
May I present to you: The Standard-Setter. The Standard-Setter’s superpower is failing upward while confusing pressure with motivation. They believe everyone has another gear, and that their job is to force people into it. The Standard-Setter operates from a simple belief: that by merely telling you to “make the impossible possible,” and by “setting extremely high standards,” they can somehow magically make you more effective. But they often have no idea what they’re actually talking about.
TBM 442: 10 Career Traps (Thoughtful People Fall Into)
In this post, I’m going to share ten career traps thoughtful people often find themselves ensnared in. I’ve found myself in every one of these traps over the years, so I speak from experience. I’ve also watched some of the most thoughtful (and experienced) people I know fall into them, even when they “knew better.” Or perhaps partly because they knew better. As sports coaches sometimes say, we go where we’re looking. Every trap below begins with a strength or virtue. Curiosity. Empathy. Courage.
TBM 441: AI, the Loss of Positive Friction, and What to Do About It
Customer call → synthesize insights → decide what to do about it → do it → ship it → measure impact Pre-AI, this would involve 1) reading/reviewing a call transcript and your notes, 2) synthesizing that into a set of takeaways either in a document or presented somehow, 3) considering a set of options by talking about those options, writing about them, and narrowing those down to some tangible actions/investments, 4) taking those actions (e.g., building something) using whatever collaborating...
TBM 440: The Problem With Putting People in Boxes
Personality and “strength” tests at work have never sat right with me. Sure, they became fodder for some fun discussions and had that occasional “wow, how right!” horoscope vibe. But they rarely seemed to help with day-to-day work, and they never replaced the hard work of truly getting to know people, including how they interact with others and how different contexts bring out different versions of them.
TBM 439: Day At The Gig...
I recently started a new job, which means I’m spending a lot of my time trying to figure out how everything works: the product, the workflows, the history, the people, the artifacts, and all the context that everyone else has accumulated over time. So instead of trying to turn that experience into a neat argument, I thought I’d just write down what one of those days actually feels like. 8:30. Kid-school tornado is over. Second cup of coffee.
TBM 438: The Myth of Workplace Consensus
Have you ever felt like a complete weirdo in your company? Like there are only a handful of people who “get you”? Or have you gone to a conference and gotten a little confused because suddenly it seems like you have a lot more in common with everyone? Then you return to work, and somehow the weirdness comes back. You may be less alone than you think.
TBM 437: AI and the Recontextualization Tax
Here’s an area where I am optimistic about AI (for now, at least). So many companies flatten things to meet the needs of the person with 1) the most power, 2) the lowest appetite for detail/seeing real-world complexity, and/or 3) the least amount of time to actually work through details and nuance. For good (and less good) reasons, a CEO says, “This is too in the weeds.
TBM 438: The Right But Early Club
Life update! New job! Big shift! More here if you are curious. And more to come… I can’t get this out of my head. I was doing book research recently, and I learned about a “secret” group inside a company called the Right But Early Club.
TBM 437: Transition Week (And Some Fun Links)
A transition week with back to school and some other (soon to be shared) exciting news. To tide folks over until next week… I was active on Twitter for a long time. I likely met many of you during that time. I recently collected 50 threads and 500 tweets (many with images) in this simple viewer. Check it out for a blast from ye olde Twitter. I also made this strategy prompts activity for teams hoping to get good strategy conversations going. Give it a try with your team! Let me know how it went.
TBM 437: Tokens, Hours, Points, and Other Curious Proxies
Everyone is talking about “return on tokens.” Vendors love it (as long as the news is good). Companies that had long since given up on any sort of value architecture or on understanding the ROI of product work are suddenly chomping at the bit. Which makes sense: they haven’t been able to lay off enough people to cover their token budgets while still hitting their promises to the board.
TBM 436: Tension-Based Prioritization (A Non-Framework)
I’ve come to believe that teams can prioritize much more effectively by focusing less on the specific things they’re prioritizing (which will naturally be important, and will naturally get attention) and more on the tensions they’re observing and acting out day after day. The tensions point the way to the real decisions. Most of what we call prioritization is forging agreeable narratives. It resolves very little and produces very little real commitment.
TBM 435: 20 Unfiltered Operating Takes
I had a friend reach out recently for advice. He said something funny/telling. “Half the time I don’t know what you really think. I have to figure out how my team works. What is your actual, opinionated advice?” So here it is: advice for a friend on how to operate. Raw. Not “polished John”. I wanted to send a huge thank you to my paid subscribers. They don’t get anything in return but still support the newsletter. Until recently I didn’t have a way to do a one-off tip. But now I do.
TBM 434: How Maps Can Hide Problems
If what you are mapping is incoherent, don’t fall in love with the map (or your personal ability to navigate with it). Use it to refactor what you see. Here’s why. When strategy, structure, technology, and incentives are coherent, an organization can leave a great deal implicit. A team and its mission become reliable shorthand for its goals, ownership, work, funding, and intended path to impact. These are technically distinct structures.
TBM 433: The Border Collie Faustian Bargain
(I have a question at the end, if you get there) Picture a company annual kickoff. Leaders are sharing a strategy that is objectively not a strategy. Not just by a purist’s standards, but assume for a moment that the experienced people in the room all know it isn’t a strategy. So we have: The less experienced people in the room who are happy that someone seems to have a plan. They’re not skilled enough to know what a strategy is. If it sounds somewhat coherent to them, they’ll be excited.
TBM 432: Bundling & Unbundling Capabilities (and AI)
Early in my product career, I wore many hats. I conducted research, analyzed data, sketched interfaces and wireframes, wrote requirements, coordinated releases, answered support questions, and even, shudder, wrote some code. Some of that was empowering. Some of it was amateur hour. But it was all bundled into the loose idea of “product management.” Over time, those capabilities separated into dedicated roles and disciplines.
Mammina - Film (2026)
LA TRAMA DI MAMMINA Mammina, film diretto da Rob Savage, racconta la storia di un a bambina di solo otto anni che conosce bene il terrore. Nella nuova casa in cui si è appena trasferita con la sua famiglia c'è qualcosa che non la lascia mai sola: un'entità oscura che lei chiama "L'Altra Mamma". Apparentemente premurosa, questa creatura inquietante cerca di insinuarsi nella mente e nel cuore della bambina, spingendola verso persecuzioni sempre più sinistre.
TBM 431: The Denominator That Matters
Here’s a simple model for thinking about AI success in organizations. \(\text{Success} = \frac{\text{Machine Understanding} \times \text{Problem Understanding} \times \text{Practice Evolution}}{\text{Social Contract}}\) How AI actually works. The inputs and outputs. The failure modes. You don’t need an expert-level sense of the math, but you need a viable mental model of how the technology and what it is doing. Understanding the costs (based on a very incomplete current sense of the costs).
TBM 430: Incubate, Compound, Refinance, Liquidate
Last week, things got super heavy with a post about identity, thriving, and figuring out how to navigate the workplace (when you love your work). For this week, to keep my own energy balanced, I needed to stick with something much lighter. Diagrams! Metaphors! But given AI craziness…it is probably worth reviewing. tl;dr: AI does not eliminate complexity, coupling, coordination, uncertainty, or decay. But it can change the cost, speed, and feasibility of responding to them.
TBM 429: How To Thrive At Work When You Think Too Much
This post is important. It is the introduction for a book that’ll I’ll probably never publish. Why? I already have! I’ve written it across countless TBM posts (multiple books worth), but have had trouble getting to the crux of it. Over the weekend I had a breakthrough. It has been sitting under my nose with posts like 20 Things I’ve Learned as a Systems (Over) Thinker and How (And Why) We Help. It was yelling out from this LinkedIn post that has 1400 reactions and counting. But the insight was elusive.
TBM 428: Yes, Robot. Yes, Boss?
AI can be your scribe, your thought partner, data-stitcher, or your counselor. And AI can be your consigliere, your spin doctor, or your propagandist. Team superpowers. Or Orwellian Ministry of Truth. If a behavior is blocked by poor signal visibility, high workflow friction, missing scaffolding, weak shared representations, or limited procedural fluency, AI can help.
TBM 427: The Bottleneck Strike Again!
My goodness. If I see another slide with a 2005-era SDLC diagram sprinkled with little AI logos and a bunch of words suggesting “the bottleneck has moved” or that this has all been figured out, when in reality every week there’s something new like Loop Engineering, or _____________.
TBM 426: The Trouble With Mirrors
There’s a difference between mirrors and mirroring. Over the years I’ve come to see that difference, and I wanted to share how my thinking has shifted. Earlier in my career, I was smitten by the idea that if teams could “just” visualize how they work, embrace transparency, etc., then almost any team could improve. This is similar to the “if we could just talk it out” belief, or the “if we could just hear each other out” (or consider other perspectives, etc. etc.) belief.
TBM 425: AI and Agency
So you want your team to figure out how to use AI for the benefit of your company? Then stop stripping them of the agency to do it. AI is posing all of us hard questions about agency, worth, and identity. But the far bigger problem is how we’re talking about it, mandating it, and wielding it. You see leaders blabbering on about everything they're doing to drive adoption, while trampling the most basic elements of human nature: agency, trust, and dignity.
TBM 424: Why We Help (And How To Stay Helpful)
A quick ask: I’m doing positioning research for the product I manage, and I have a goal of running 50 short sessions over the next couple weeks. It’s 30 minutes. I’ll share a short presentation/demo, then spend the rest of the time on feedback and questions. I’d really appreciate the help, especially if you work in product operations, program management, or working on an “AI operating model” transformation.
AI Won’t Save the Kingdoms We Built
This post is about the people who built the fiefdoms now looking to AI to save them from the fiefdoms, and why that will only work if we are honest about what those fiefdoms were built to avoid in the first place. Unfiltered Saturday morning coffee writing engaged. The people who built the fiefdoms are now complaining about the fiefdoms That is the part I can’t stop thinking about.
TBM 423: Why Defining Teams Is So Hard
Hint: It’s not some magic skill. This post is for anyone who has tried to answer “What is a team?” and been caught between three things: confusion at why such a simple question was so hard, a gut feeling that if people could just describe reality honestly things would get so much better, and the deflating experience of watching that honesty get met with resistance. Why is it so easy to describe how an organization actually works, and so hard to say it out loud?
TBM 422: Exception, Presence, Delegation
Side note, I have a live talk up on YouTube that I’m proud of called Single Player to Multiplayer: AI, Context, and Collaboration if watching/listening is more your thing. Like a lot of leaders and practitioners I talk to, I’m trying to wrap my head around what I see happening in companies right now. The fatigue is real, the pressure is coming from many directions, and it’s impacting people in often very different ways.
TBM 421: Minimally Viable Consistency (Part 3)
Almost ten years ago, Arlo Belshee used a line that stuck with me: “Org design is basically about solving the puzzle of what must be consistent, and what you’re willing to lose to keep it consistent.” I've written about consistency, and minimally viable consistency, before (Part 1, Part 2). In this post I want to explore what I've been calling sharp consistency,flexible consistency, and legible variety. You work with all three in your quest to find minimally viable consistency.
TBM 420: The AI Playbook Puzzle
I’ll be hosting a small TBM pop-up meetup next week in San Francisco (financial district) on Wednesday, May 6th. Let me know if you’re interested. I might be able to find a sponsor. The theme: multi-player mode AI. Everyone wants tactical advice on “how to AI.” But I keep arriving at the same conclusion. We already know a lot, but struggle to explain it in the new context. We don’t know a lot, but aren’t willing to sit with that uncertainty. And the biggest threat is identity threat.
You ask a hard question in a meeting and someone hears negativity. You name a risk and you’re a pessimist. You push on a plan because you think the team can handle it, and people wonder why you’re not on board. Or maybe you’re on the other side. You’re trying to keep the team moving. You’re holding the group together through uncertainty. And then someone starts poking holes, surfacing risks, pulling the conversation into the weeds. You think: we were aligned. Why are you making this harder?
Learn to Spot Scams Launches Comprehensive Digital Security Platform to Combat Rising Online Fraud and Identity Theft
With online fraud reaching epidemic levels — costing Americans billions of dollars annually — Learn to Spot Scams is stepping up to for digital protection. We built this platform because the digital threats is upon us.
TBM 418: Campfires, Trails, and Quests
I guess I’m putting together an AI series of sorts. This is #7. Hope, Context, and Control Seeing Everything, Understanding Nothing (The Context Trap) Institutionalized Overload (Now With AI) Legibility and Legitimacy Before You Fire All Your Glue People Because of AI Simple-player to Mutliplayer: Context Through Collaboration At the day job, I’m deep in the question of how AI can help teams do more effective work, hence all the thinking below.
TBM 417: Before You Fire All Your Glue People Because of AI
(Sometimes I get excited by a topic and write more than once a week. This is a topic I am very passionate about.) The hardest part of figuring out how to use AI at work is that our heuristics are right often enough to feel reliable, and wrong often enough to cause real damage. We develop mental models for where AI fits. Those models work in some contexts. Then we carry them into contexts where they don’t work, and because the logic sounds the same, we don’t notice the difference until it’s too late.
TBM 416: Investment Stewardship (As Habit)
I made this little skill if anyone is up for giving it a try. It is based on some prior posts including TBM 320: From Fluffy Concepts to Concrete Outcomes & Behaviors. I’d love your feedback. Every company eventually asks the question: “What are we getting from our engineering investment?” And it almost always goes sideways. There’s finger-pointing. There’s fear. There’s weird math that nobody believes. People retreat to flow metrics because the real question is terrifying.
Demand Mix, Shaping, and AI as (Dys)function Multiplier
I’ll be chatting with Birkan Icacan from Enterpret today (Thursday, April 9, 9:00 AM - 9:45 AM PDT) about “Why Product Teams Struggle Despite More Customer Feedback”. Should be fun! The topic actually (loosely) relates to today’s post. I have also been working lately on a new playbook. Beware…it is about words, so not everyone’s cup of tea. Orgs spend a lot of time talking about dependencies, intake, predictability, “discovery,” capacity, and so on.
TBM 414: Legibility and Legitimacy
There is a big difference between legibility and legitimacy. The terms sound related, and they do share a lineage, but they diverge in meaning. Legibility derives from legere, meaning “to read” or “to gather,” referring to what can be seen, interpreted, and made understandable. Legitimacy, by contrast, derives from lex (legis), meaning “law,” and refers to what is considered lawful, justified, and worthy of acceptance.
TBM 413: In That Space Is Our Power
One thing I’ve noticed (and experienced firsthand) is that when change agents advocate for a better way of working, there’s a moment that feels extremely unfair. The burden of proof is all on you. You’re tiptoeing through nonviolent communication, channeling your utmost curiosity, trying to connect, trying to not rock the boat, and still somehow ending up in the position of having to prove that what you’re seeing and feeling is even real. Suddenly, you’re on the witness stand.
TBM 412: Institutionalized Overload (Now With AI)
(I’ll be playing a bit of TBM catchup over the next couple days. Apologies for the gap in posting.) We’ve gotten so acclimated to organizational overload, endless work in progress, and constant unplanned demands that it has become the norm. It is clearly too much for any person, but people adapt. Their defense mechanisms kick in, and over time that overloaded state just becomes what work feels like. When I look at how people are using AI, I see the same pattern.
TBM 411: Messy Docs As Helpful Pattern
Existing stuff, now more accessible! Check out the POM Starter Pack and OS Discovery playbook, now in non-Gdoc form. In my day-to-day work (at Dotwork), I hear about all the real-world exceptions, “things that work,” “things that never work” (but we keep trying), and everything in between. I’m a big fan of saying, “Can you show me?” on discovery calls. A slide, agenda, doc, dashboard, screen, etc., combined with the person talking about the “thing”, is worth a million abstract summaries.
TBM 410: Dancing With Problems
Read this quote: We’ve got to make the app easier to use! If you’ve been doing product for a while, you probably cringed. It’s not specific. It has no diagnostic value whatsoever. It could apply to almost any product in the world. There’s no hint at what outcomes or impacts might be possible as a result of making the app easier to use. Another quote: Users take too long to create an initiative. Better? Not really. Is speed actually the goal?
TBM 409: Minimally Viable Consistency (Part 2)
Help needed! I have to do some discovery for the PM day job with enterprises that sell non-digital products (consumer, cars, toys, media, etc.) and have 1000+ people across product, engineering, design, data, etc. Specifically I am looking to chat with people working at companies in the middle of some sort of “product operating model” transformation. And AI, of course. Because that’s everyone it seems.
TBM 408: Basic Links
(I used to do more of these visual build posts. I miss them! If you want the messy/heavy posts, check out last week’s post on context emerging from interactions.) A back to basics post… Yet, not so basic… When you ship something, you’re not delivering an outcome. You’re delivering the potential of an outcome and starting a chain of effects that unfold over weeks, months, and years. You’re committing the organization to a new state that may or may not produce the results you want.
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