John Cutler

Santa Barbara

Blogger at Medium

Writer at The Beautiful Mess

I like the beautiful mess of product development.| newsletter: https://t.co/tCLvCkCdiS

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Articles

TBM 361: Context, Collaboration, Intent, and Investment

3 weeks ago | cutlefish.substack.com | John Cutler

I've often struggled with distinctions like "strategy vs. execution" and "problem vs. solution." Here's a basic framework I use with Dotwork customers to tease out the different entities and signifiers they use as part of their operating system. The basic distinction is: Context, Intent, Collaboration, and Investment. Here's how it works:Context describes perspectives on what is. Examples include jobs-to-be-done maps, customer insights, capability trees, KPI trees, service directories, and customers.
TBM 359: Process Person

1 month ago | cutlefish.substack.com | John Cutler

I admit it. I’m a process person, in that I’ve intentionally designed processes throughout my career. Some of those have been baked into external products, and others have been internal. Reflecting on my career, I remember many situations where I implemented bad processes. Most of the time, this was due to a lack of experience or contextual awareness. One situation early on stands out. I was creating a template for a team. I did a lot of research and dutifully added different sections and instructions.
TBM 358: The Genius of SVPG

1 month ago | cutlefish.substack.com | John Cutler

This post begun with a quick thought shared on LinkedIn (200+ comments):No one gets fired for recommending "Transformed"What is a book you could share internally that could get you fired? If you have a moment, I’d love you to chime in!Transformed by Marty Cagan, Lea Hickman, Chris Jones, Christian Idiodi, and John Moore has been a big part of day-to-day lately. This may have seemed like a critique, but it wasn’t at all. Let me explain.
TBM 357: Perspectives on Change and Improvement

1 month ago | cutlefish.substack.com | John Cutler

Ah the weekend! Time for some introspection…I am continuously fascinated by how people think about problems and improvement in their companies. This fascination applies internally as well. I've noticed how my perspectives have changed over the years—sometimes without me noticing, and often with some internal rationalization where I justify my past views. While some perspectives are definitely "wrong" in context, you can usually identify strengths and weaknesses in all of them.
TBM 356: Product Party Modes

1 month ago | cutlefish.substack.com | John Cutler

For some context, I’m back in the product management game as Head of Product at Dotwork. Apologies for the delay in posting — it can be hard to juggle the day job and writing! We’re definitely in the controlled chaos stage as we onboard new customers. A simple post for this week. I’m constantly reminded of how product teams don’t function like widget factories.
TBM 355: Who Should Care?

1 month ago | cutlefish.substack.com | John Cutler

Some % of product leaders and product managers could care less about how their company works. If something gets in their way, they care—they'll have no shortage of critique and ideas—but once the immediate problem disappears, they'll return to doing their thing. This is a feature, not a bug, even at a leadership level. I'll always remember a great VP of Product telling me:Look, I could care less about annual planning. All I want is my number because the rest will change.
TBM 353: Conversation Quality and Scale

2 months ago | cutlefish.substack.com | John Cutler

If you enjoy my newsletter, and want to help me out somehow, please take a couple minutes to fill out this quick survey on meetings/rituals at your company. TBM posts are now searchable all in one place. This is an experiment. What do you think? I used AI to extract 270 specific behaviors and 180 rituals mentioned by ~10 guests of the podcast. Check it out!I've been on a kick recently about conversations and interactions.
TBM 352: Funding, Planning, and Context

2 months ago | cutlefish.substack.com | John Cutler

If you like my newsletter and are interested in finding a way to support my writing, please consider becoming a paid subscriber. This post is all about planning, funding, and context. My main thesis is as follows:In a lot of early-stage startups and companies experiencing rapid growth, there is basically only one context. Any variation is consumed by inertia and the “one thing”. But as these companies grow and mature, it becomes increasingly untenable to treat everything the same way.
TBM 351: The 4 Prioritization Jobs (And Why It Matters)

2 months ago | cutlefish.substack.com | John Cutler

After all these years, I finally put something into words about prioritization. The key insight was that humans jam four primary jobs into the prioritization discussion. These jobs are related—but they're distinct enough that conflating them really gets in the way of effective collaboration around prioritization. In my experience, when people talk about prioritization, they're typically talking about one of the following:They're trying to minimize context switching.
TBM 350: Connecting Dots

2 months ago | cutlefish.substack.com | John Cutler

As the title of my newsletter suggests, I'm obsessed with the mess of product development. Over the last couple of weeks, I've spent a lot of time with operations leaders trying to bring some order to that mess. They show me mad-scientist Miro boards, sprawling spreadsheets, Jira dashboards, and carefully written docs. And they ask questions like:What should we put into our various systems? Why does no one ever like the roadmaps we show?