John Cutler

TBM 271: Diagnosing Your Company's Strategy Problem In this post, I want to give you a way to diagnose what is going on. Too many people default to a simplistic explanation like, "We just need a strategy." Well, yes, that helps, but it is critical to d...

Many companies end up losing because they stubbornly hold on to a view of their context, their game, and their "old" way of aligning from 5-10 years ago.

cutlefish.substack.com/p/tbm-271-di...

TBM 370: Dependencies Aren't Your Problem Thought experiment.

Visualizing dependencies is not enough. Instead, you need a visualization that shows each team’s competing priorities, highlights the value gap between those priorities, and measures the drag caused by multitasking.

cutlefish.substack.com/p/tbm-370-de...

TBM 369: Sources Of Truth Most 'source of truth' problems in product development aren't really about the source of truth at all.

"Most 'source of truth' problems in product development aren't really about the source of truth at all. They assume that everyone wants the truth, that they can agree on what truth they're seeking, and that they're willing to put in the work to forge coherence"
cutlefish.substack.com/p/tbm-369-so...

TBM 368: Goals Take Practice Once or twice a week, I run into teams struggling with OKRs. To me, OKRs are goals. And you know what? Goals are hard. Setting good goals and reflecting/pivoting based on your progress is a mix of ski...

Hard things take practice. Do we expect to get good at something by practicing it once a quarter?

cutlefish.substack.com/p/tbm-368-go...

Forget vibe coding. Enter vibe leadership.

Funny how we force engineers to write ADRs for every trade‑off, yet billion‑dollar strategic bets live in hallway whispers and fluffy slide decks.

What if we treated business decisions like architecture? Context, options, trade‑offs, metrics, all in a repo, version‑controlled and reviewed?

If a leadership team is unwilling to sit with reality and explore what is happening, or creates an environment that is unfriendly or unsafe to do so, then you will never "get clear."

cutlefish.substack.com/p/tbm-367-th...

TBM 366: Empowered For Delivery, But... There's an emphasis on team independence and autonomy, but also fairly traditional ideas about the role of the manager (as gatekeeper, filter, escalation resolver, etc.). In many ways, these ideas are...

But when it comes to feedback, concerns, "pulling the andon cord", or questioning the current strategy, front-line team members are expected to route everything up the official chain. Boundary-spanning is great for delivery, but not for dissent.

cutlefish.substack.com/p/tbm-366-em...

"Teams are being asked to jump headfirst into AI efforts, innovate, and respond to a generational shift in the technology landscape. It is like asking a race car driver to drive the race of their life while in fuel-efficiency mode."

www.dotwork.com/post/thrivin...

How Operations Can Prepare for Continuous Transformation Operations leaders face constant change, shifting realities, and persistent challenges. Success depends on balancing order and chaos, adapting systems, and enabling momentum—knowing there’s never a fi...

Official Narrative: “We are a PLG company now.”
Sales Reality: “We still make our number through sales-led enterprise deals. PLG is a distraction.”
Product Reality: “We’re building self-serve features but don’t control pricing, packaging, or onboarding.”

www.dotwork.com/post/how-ope...

ya think ;)

A critique of a recent Cagan post that I think deserves some counterpoint. cutlefish.substack.com/p/a-cagan-cr...

The product advice landscape has gotten to the point where you need battle second order gaslighting ... basically defending yourself against the peddlers offering you ways to defend yourself (while make you feel shitty about yourself)

YouTube video by The Beautiful Mess-John Cutler The Limits of Cascades and Value Hierarchies

An initiative is an initiative...right?

www.youtube.com/watch?v=aOFa...

Whatever it is .... it is sad.

It could be if it reinforced individual queues

TBM 364: Three Team Vibes I was reflecting recently on how stark the differences between teams can be and how often you can pick up on those differences within seconds just by asking someone how things are going. You can feel ...

I was reflecting recently on how stark the differences between teams can be and how often you can pick up on those differences within seconds. You can feel it. The words they use are different. The way they describe their work tells you almost everything.

cutlefish.substack.com/p/tbm-364-th...

Juggling this dichotomy is a huge challenge right now for managers/leaders, etc. www.dotwork.com/post/thrivin...

The heroic change narrative narrative is one of many... helpful, but incomplete.

After a couple years in stealth model working with amazing design partners/launch partners, we're "open for business". It is a blast (and scary as hell) to be back in a product role, and heading it up to boot. www.dotwork.com

unless you are curious about opinions?

TBM 363: Is Matt A Loser? It was far easier to rationalize a layer of inexperienced managers than to face the fact that the strategy was scattered and shifts in the technology landscape threatened the core business model. "It ...

Is there objectively such a thing as low-hanging fruit? In Matt's mind, everything could be more effective if leadership could "just." But maybe that is an illusion. Maybe the ppl with more power in the org are getting exactly what they need and want.

cutlefish.substack.com/p/tbm-363-is...

I think this is actually very much based on the context section. Answer those questions, and you define this in context.

I've been collecting some "work object" patterns from our design partners in this document. As with all things, this is part "art" and part logical modeling. It boils down to what you want/need to improve in your company. Comments appreciated! docs.google.com/document/d/1...

Thanks for checking it out Jason!

thank you!

TBM 362: How (And Why) We Help While it's easy to dismiss the standard consulting approach as formulaic or unlikely to spark deep systemic change, I believe it is also what makes it politically viable, repeatable, and relatively lo...

"Internally, I wrestled with questions of meaning, responsibility, and what I believed. Externally, it often looked like contradiction or even self-sabotage. Working through this has been a work in progress."

cutlefish.substack.com/p/tbm-362-ho...

101 ops discovery questions with some examples to spark ideas.

johnpcutler.github.io/dotquestions...

TBM 358: The Genius of SVPG Between 60-80% of all large enterprises I speak to have brought in Marty Cagan and/or SVPG at one point in the last couple of years. That is an outstanding achievement for the SVPG mission. The positi...

"Transformed lets the leader stay the hero of the change story, & challenges the org w/o directly threatening the leader's self-image. Change is often about creating conditions where people can negotiate with their self-identity and still find a path forward."

cutlefish.substack.com/p/tbm-358-th...

TBM 356: Product Party Modes I’m constantly reminded of how product teams don’t function like widget factories. It’s so tempting to imagine your “capacity” as being a function of the number of developers on your team, and to rati...

But maybe you’re in a mode with one person Spellcasting, another Chipping, while others are Questing, and maybe someone is Trailblazing. You’re doing more at once, but the shapes of your actions are a lot more complementary.

cutlefish.substack.com/p/tbm-356-pr...