I have no idea what this ... but it was fun!
johnpcutler.github.io/rightwords/i...

TBM 414: Legibility and Legitimacy There is a big difference between legibility and legitimacy.

Legitimacy, by contrast, determines whether that control is accepted as justified.

cutlefish.substack.com/p/tbm-414-le...

Yes

I built my dream talk prep "app" ... with all the dumb quirks I like

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, “...

"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 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...

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...

I'm so sick of things being dead. And quiet (but not).

TBM 408: Basic Links (I used to do more of these visual build posts.

cutlefish.substack.com/p/tbm-408-ba...

TBM 407: The Three Juggling Acts (Strategic, Lazy, and Survival) Here’s a simple model I’ve been using lately to discuss strategy and focus.

Three kinds of juggling...

cutlefish.substack.com/p/tbm-407-th...

TBM 406: Seeing Everything, Understanding Nothing (The Context Trap) AI is supercharging legacy leadership assumptions about context and control.

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...

"context engineering"

TBM 405: Hope, Context, and Control This essay is about hope, fear, AI, and the tension between control and collective sensemaking.

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 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/ .

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 402: The Real-World Journey to Value and Product-Centricity A story in five acts...

​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...

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...

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

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...

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...

TBM 399: 10 Prioritization Traps Happy 2026, and thank you for reading the newsletter!

Burning Down the House

Too Much Time on My Hands

Everybody Wants to Rule the World

Just Enough Is Never Enough

Running on Empty

Dreamer

Slow Ride

Someday Never Comes

The Logical Song

Takin’ Care of Business

cutlefish.substack.com/p/tbm-399-10...

Will try to make it

TBM 397: The Initiative Shape Activity (And a Favor to Ask) Nearing the big 400!

Need a bit of help to improve this, and maybe this is helpful as is!

cutlefish.substack.com/p/tbm-397-th...

TBM 396: So You Want To Define “The Problem”? I created this graphic a couple weeks ago.

The layers are not steps toward a single, correct explanation. They are ways of seeing the situation from different angles, adding context and constraints. The goal here is not to fully explain the situation, but to act more thoughtfully within it.

cutlefish.substack.com/p/tbm-396-so...

TBM 395: Words! Damned Words! It’s all bets, opportunities, and BAU until someone loses their job.

It’s all bets, opportunities, and BAU until someone loses their job.

cutlefish.substack.com/p/tbm-395-wo...

As a facilitator, I always like to run a quick confidence straw poll on items once you've taken a first pass at urgency, value, and duration: johnpcutler.github.io/prioritizer/...

Mobile ... ugh. My enemy

I made a little prioritization tool

johnpcutler.github.io/prioritizer/...

100% ... it is cool to watch people grapple with three types of collaboration relationships between teams, rotating / changing / contextually applied

I'm still in the "free-styling and figuring it out" phase ! Lets chat though. Getting closer to some of the classes of relationships

TBM 393: Why Labeling Relationships Is So Important So much becomes clear when you actually label the relationships between things. It’s something I do every day, and I do it very naturally. But it is not something everyone does naturally.

The basic idea is this. So much becomes clear when you actually label the relationships between things. It’s something I do every day, and I do it very naturally. But it is not something everyone does naturally.

cutlefish.substack.com/p/tbm-393-wh...

I'm getting out of tech and starting an accessory company

Why (How and When) Tools Matter YouTube video by The Beautiful Mess-John Cutler

How and why tools matter...

youtube.com/watch?v=qcAH4x0e4XM&feature=youtu.be

"...people kept asking me what solutions I had in mind. I finally cracked, put my head down, turned off the filters, & just gave them what they asked for. Suddenly, that was “just what we needed.”"

To me, that's a key reason why lots of ppl love the idea of PMs delivering vibe-coded prototypes.