John Cutler
@johncutle.fish
I like the beautiful mess of product development.| newsletter: https://cutlefish.substack.com
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. cutlefish.substack.com/p/tbm-434-ho...
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).
cutlefish.substack.com
Other bets never prove much value at all. When the team keeps building anyway, the product moves right w/o moving up, turning a cheap experiment into an expensive obligation: the build trap. Liquidation is not necessarily failure. Refusing to liquidate is... cutlefish.substack.com/p/tbm-430-in...
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).
cutlefish.substack.com
If you love what you do and want to keep doing it, you’ll need to figure out how to detach from using the workplace as a proving ground for your worth. cutlefish.substack.com/p/tbm-429-ho...
TBM 429: How To Thrive At Work When You Think Too Much
This post is important.
cutlefish.substack.com
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. cutlefish.substack.com/p/tbm-428-ye...
TBM 428: Yes, Robot. Yes, Boss?
AI can be your scribe, your thought partner, data-stitcher, or your counselor.
cutlefish.substack.com
The language sounds like “this is for your growth,” but the structure (and any halfway sensible reading between the lines) says “this is for our Q3 goals.” They’re co-opting a personal journey for organizational benefit and calling it empowerment. substack.com/home/post/p-...
TBM 425: AI and Agency
So you want your team to figure out how to use AI for the benefit of your company?
substack.com
And once you are pulled in, you are more likely to escalate the situation. You may push harder, read resistance less generously, over-identify with the pain, reach too quickly for a practice, turn disappointment into anger, cutlefish.substack.com/p/tbm-424-wh...
TBM 424: Why We Help (And How To Stay Helpful)
I have been thinking a lot about self-care, especially for people who find themselves pulled into helping people and making things better. The desire to help can be a gift. It can make you notice pain...
cutlefish.substack.com
Some of the same people who benefited from riding the ZIRP wave to safer places of leadership are now waxing, not very poetically, about flattening orgs, 10x engineers, getting into the details, reducing bureaucracy, and getting closer to the work. cutlefish.substack.com/p/ai-wont-sa...
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...
cutlefish.substack.com
"The founder stays involved because the context lives in their head. The team never develops that context because the founder is always there. The founder concludes they must remain involved. " cutlefish.substack.com/p/tbm-422-ex...
TBM 422: Exception, Presence, Delegation
It has driven me to some “back to basics” thinking. One model I’ve been playing with lately is the triad of Exception, Presence, and Delegation. The ideas aren’t new, but it has sparked some good conv...
cutlefish.substack.com
So four buckets: bad ideas AI makes worse, good ideas AI can supercharge, genuinely new things we haven’t imagined yet, and the meta-skill of reading context that ties it all together. cutlefish.substack.com/p/tbm-420-th...
TBM 420: The AI Playbook Puzzle
...and the journey of self-awareness we are all going through
cutlefish.substack.com
But humans aren’t ants. We have more to convene about than which path to take. The trails are the traces we leave for each other: context pointers, shared docs, evolving principles. The quests are the purposeful work we do together cutlefish.substack.com/p/tbm-418-ca...
TBM 418: Campfires, Trails, and Quests
I guess I’m putting together an AI series of sorts.
cutlefish.substack.com
And I want to make a passionate plea: before your organization goes off and fires all of its “glue people” on the assumption that AI can pick up what they were doing, please stop and think about what those people were actually doing. cutlefish.substack.com/p/tbm-417-be...
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.
cutlefish.substack.com
change lenses and actions... give it a go! github.com/johnpcutler/...
GitHub - johnpcutler/change-lenses-and-actions: A seven-step behavior diagnosis framework for organizational change, built on COM-B, BCW, BCTs, and original diagnostic lenses.
A seven-step behavior diagnosis framework for organizational change, built on COM-B, BCW, BCTs, and original diagnostic lenses. - johnpcutler/change-lenses-and-actions
github.com
Legitimacy, by contrast, determines whether that control is accepted as justified. cutlefish.substack.com/p/tbm-414-le...
TBM 414: Legibility and Legitimacy
There is a big difference between legibility and legitimacy.
cutlefish.substack.com
I built my dream talk prep "app" ... with all the dumb quirks I like
"Links to everything and anything, and those links go everywhere (Miro, dashboards, Jira tickets, other docs, call recordings, etc.). The pool of artifacts is ever-expanding" cutlefish.substack.com/p/tbm-411-me...
TBM 411: Messy Docs As Helpful Pattern
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, “...
cutlefish.substack.com
The work of product leadership isn’t simply defining the problem and handing it to the team. It’s creating the conditions where people can engage with the situation from multiple elevations and perspectives. cutlefish.substack.com/p/tbm-410-da...
TBM 410: Dancing With Problems
But I’d reframe it slightly. The work of product leadership isn’t simply defining the problem and handing it to the team. It’s creating the conditions where people can engage with the situation from m...
cutlefish.substack.com
In AI discourse, “context” is increasingly framed as the new source of truth. It’s a familiar and seductive idea that if only enough information can be assembled and surfaced, clarity and control will follow. cutlefish.substack.com/p/tbm-406-se...
TBM 406: Seeing Everything, Understanding Nothing (The Context Trap)
AI is supercharging legacy leadership assumptions about context and control.
cutlefish.substack.com
Techno-authoritarian thinkers elevate centralized, algorithmic control above humanistic complexity. People who bought into these areas (with their wallets and political donations) are on product podcasts talking about how great everything is. cutlefish.substack.com/p/tbm-405-ho...
TBM 405: Hope, Context, and Control
This essay is about hope, fear, AI, and the tension between control and collective sensemaking.
cutlefish.substack.com
We want to believe, in our bones, that if we could just understand where all the energy and time is going, it would unlock newfound confidence and certainty. But as with many seductive things, the truth invariably feels just out of reach. cutlefish.substack.com/p/tbm-403-th...
TBM 403: The Seduction (And Folly) Of Rollups, Points, and (Most) Time Tracking
I made a simple tool to help make sense of a new team, group, or company: https://johnpcutler.github.io/team-association/ .
cutlefish.substack.com
Below, I take a journey across companies at different stages of evolution. I explore the competing mental models, what is important, and how perceptions shift. It is not an attempt at a linear model or a maturity model, but rather a narrative device. cutlefish.substack.com/p/tbm-402-th...
TBM 402: The Real-World Journey to Value and Product-Centricity
A story in five acts...
cutlefish.substack.com
A few years ago, I read an article from @johncutle.fish and @tomdkerwin.bsky.social on how leaders navigate uncertainty and ambiguity. It inspired me to write my answers down to a new section of questions every few years. This is part two! It's been fun to look back and see my thinking mature
Observations of Leadership (Part Two) | Hazel Weakly
Hey again! Welcome back to part two of me reflecting on the past few quarters and writing down my answers to John Cutler and Tom Kerwin’s questions on how...
hazelweakly.me
With a vineyard, any rebalancing of the vineyard portfolio involves multi-year, largely irreversible changes to the land, vines, labor model, and production cycle. www.linkedin.com/pulse/spm-me...
SPM Meets Product-Centricity
I was in a discussion recently about Strategic Portfolio Management (SPM), and I asked what turned out to be a surprisingly uncomfortable question: if the people responsible for strategic portfolio ma...
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