The Beautiful Mess

In 2020, I aim to focus on writing more intentionally and frequently about the intricacies of cross-functional product development. While Twitter offers quick engagement and Medium was a straightforward platform (though I felt overwhelmed by my over 400 posts), Cutle.fish gave me more control but lacked the instant feedback I craved. This year, I want to take on a new challenge. I'll commit to writing a weekly post—likely on the shorter side—about my passion: the wonderful chaos of cross-functional product development. This topic goes beyond just product management, design, or any single area; it encompasses the entire complex process.

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Articles

TBM 357: Perspectives on Change and Improvement

5 days 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 week 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?

2 weeks 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

3 weeks 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

3 weeks 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)

1 month 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

1 month 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?
TBM 349: A "Product Transformation" North Star

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

What % of product teams in your company can operate fairly independently while having a clear line of impact from their day-to-day work to what matters for customers and the company? What %:Have a set of actionable inputs that act as leading indicators for their sustained success—and that they've shown an ability to "move" based on their work? Can you interact with real customers without much red tape and process overhead?
TBM 348: Shared Understanding At Scale

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

Information overload, lossy models, telephone games, the lure of loops, pretty-but-mostly-worthless-cascades, and the quest for the one roadmap view to rule them all. This week's post is all about the models we use and how information moves around (or doesn't move around) in an organization. Here's an overview. It's like 5 short posts in one longer post. Cascade FlatteningStop over-engineering goal trees. Focus on the layers you actually engage with.
TBM 347: "Why Don't Our Leaders Care About How We Work?"

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

I received this great question recently:John, many of your posts are about taking a thoughtful and intentional approach when designing your company's operating system. I very much appreciated TBM 336: Product OS Design Tips and Principles. But at my company, no one thinks this way. It is all seen as a process, and everyone hates it unless they can benefit directly. Why is this the case? Is what you are talking about only possible in rare cases?