John Cutler
@johncutle.fish
I like the beautiful mess of product development.| newsletter: https://cutlefish.substack.com
Reposted by John Cutler
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
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
January 6, 2026 at 12:04 AM
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
This is part two! It's been fun to look back and see my thinking mature
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...
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...
www.linkedin.com
January 6, 2026 at 6:41 PM
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...
www.linkedin.com/pulse/spm-me...
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...
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...
TBM 399: 10 Prioritization Traps
Happy 2026, and thank you for reading the newsletter!
cutlefish.substack.com
January 2, 2026 at 12:10 AM
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...
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...
Need a bit of help to improve this, and maybe this is helpful as is!
cutlefish.substack.com/p/tbm-397-th...
cutlefish.substack.com/p/tbm-397-th...
TBM 397: The Initiative Shape Activity (And a Favor to Ask)
Nearing the big 400!
cutlefish.substack.com
December 21, 2025 at 9:07 PM
Need a bit of help to improve this, and maybe this is helpful as is!
cutlefish.substack.com/p/tbm-397-th...
cutlefish.substack.com/p/tbm-397-th...
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...
cutlefish.substack.com/p/tbm-396-so...
TBM 396: So You Want To Define “The Problem”?
I created this graphic a couple weeks ago.
cutlefish.substack.com
December 18, 2025 at 4:19 PM
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...
cutlefish.substack.com/p/tbm-396-so...
It’s all bets, opportunities, and BAU until someone loses their job.
cutlefish.substack.com/p/tbm-395-wo...
cutlefish.substack.com/p/tbm-395-wo...
TBM 395: Words! Damned Words!
It’s all bets, opportunities, and BAU until someone loses their job.
cutlefish.substack.com
December 14, 2025 at 5:53 AM
It’s all bets, opportunities, and BAU until someone loses their job.
cutlefish.substack.com/p/tbm-395-wo...
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/...
December 13, 2025 at 7:50 AM
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
December 11, 2025 at 8:03 PM
Mobile ... ugh. My enemy
100% ... it is cool to watch people grapple with three types of collaboration relationships between teams, rotating / changing / contextually applied
December 7, 2025 at 7:20 PM
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
December 7, 2025 at 6:49 PM
I'm still in the "free-styling and figuring it out" phase ! Lets chat though. Getting closer to some of the classes of relationships
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...
cutlefish.substack.com/p/tbm-393-wh...
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.
cutlefish.substack.com
December 7, 2025 at 6:22 PM
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...
cutlefish.substack.com/p/tbm-393-wh...
I'm getting out of tech and starting an accessory company
December 7, 2025 at 12:21 PM
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
youtube.com
December 1, 2025 at 3:39 AM
Reposted by John Cutler
"...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.
To me, that's a key reason why lots of ppl love the idea of PMs delivering vibe-coded prototypes.
November 28, 2025 at 6:33 AM
"...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.
To me, that's a key reason why lots of ppl love the idea of PMs delivering vibe-coded prototypes.
The challenge with anything this nuanced is that some people lack the experience to understand it. For example, many people perceive product management’s role as running a functional feature factory, and nothing more.
www.linkedin.com/pulse/functi...
www.linkedin.com/pulse/functi...
"Functional" Feature Factories Explained
In the past, I have used the term “functional feature factory” to describe a somewhat nebulous concept. The basic idea I was trying to convey was twofold: There’s a middle ground of product-centricity...
www.linkedin.com
November 28, 2025 at 10:43 PM
The challenge with anything this nuanced is that some people lack the experience to understand it. For example, many people perceive product management’s role as running a functional feature factory, and nothing more.
www.linkedin.com/pulse/functi...
www.linkedin.com/pulse/functi...
TL; DR, if you keep tilting at windmills around empowerment, autonomy, being “problem first”, or any of these broad industry memes, you are probably missing (a big part of) the actual challenge and opportunity in your company.
cutlefish.substack.com/p/tbm-391-yo...
cutlefish.substack.com/p/tbm-391-yo...
TBM 391: You’re Not Misaligned. You’re Thinking Differently.
I’ve been thinking a lot about why some people are wired for concrete solution-thinking while others naturally gravitate toward more abstract, problem-focused, or strategy-level thinking.
cutlefish.substack.com
November 27, 2025 at 8:01 PM
TL; DR, if you keep tilting at windmills around empowerment, autonomy, being “problem first”, or any of these broad industry memes, you are probably missing (a big part of) the actual challenge and opportunity in your company.
cutlefish.substack.com/p/tbm-391-yo...
cutlefish.substack.com/p/tbm-391-yo...
"I’ve had people swear up and down that governance framework X explicitly requires projects and programs, or that you can’t “do governance” using durable objects like capabilities, products, value streams, and so on.
It just ain’t so."
cutlefish.substack.com/p/tbm-390-go...
It just ain’t so."
cutlefish.substack.com/p/tbm-390-go...
TBM 390: Governance by Principle, Not by Template
"My company has a highly detailed process involving project codes and program codes, tracking time, highly detailed (and premature) estimates, and lots of very precise reporting with dollar figures do...
cutlefish.substack.com
November 23, 2025 at 5:16 PM
"I’ve had people swear up and down that governance framework X explicitly requires projects and programs, or that you can’t “do governance” using durable objects like capabilities, products, value streams, and so on.
It just ain’t so."
cutlefish.substack.com/p/tbm-390-go...
It just ain’t so."
cutlefish.substack.com/p/tbm-390-go...
Reductionism can be wrong, but actionable.
Complexity can be right, but paralyzing.
cutlefish.substack.com/p/tbm-389-ov...
Complexity can be right, but paralyzing.
cutlefish.substack.com/p/tbm-389-ov...
TBM 389: Overthinker!
From a young age, being accused of “overcomplicating” or “overthinking” things felt like a dismissal of who I was.
cutlefish.substack.com
November 16, 2025 at 11:20 AM
Reductionism can be wrong, but actionable.
Complexity can be right, but paralyzing.
cutlefish.substack.com/p/tbm-389-ov...
Complexity can be right, but paralyzing.
cutlefish.substack.com/p/tbm-389-ov...
Some people are comfortable wading into the mess; other people, less so. Some people are fine dancing between the various lenses; for other people, they have a violent, knee-jerk reaction to anything “complicated”.
cutlefish.substack.com/p/tbm-387-le...
cutlefish.substack.com/p/tbm-387-le...
TBM 387: Lenses
I see a lot of diagrams in Miro. And one thing that fascinates me is how fluid and expressive people can be when they are untethered from the task of creating a “simple slide.” It highlights one of th...
cutlefish.substack.com
November 12, 2025 at 7:02 PM
Some people are comfortable wading into the mess; other people, less so. Some people are fine dancing between the various lenses; for other people, they have a violent, knee-jerk reaction to anything “complicated”.
cutlefish.substack.com/p/tbm-387-le...
cutlefish.substack.com/p/tbm-387-le...
straightforward D3. I really like kumu though, so I'd probably like to put it there (it is backed by D3, but has nice features)
November 9, 2025 at 5:22 AM
straightforward D3. I really like kumu though, so I'd probably like to put it there (it is backed by D3, but has nice features)