Many systems and complexity-informed thinkers become bogged down in selling complexity, uncertainty, systems thinking, and the like. Meanwhile, most people in an organization are looking for a solution and path forward, not a lecture about “the system”. cutlefish.substack.com/p/tbm-380-bu...

I thought the reply was a joke.... but I don't think it was.

I'll be doing a little show-and-tell / workshop on visualizing your company operating system (free). Would love to see folks. zoom.us/meeting/regi...

I'll be doing a little show-and-tell / workshop on visualizing your company operating system (free). Would love to see folks. zoom.us/meeting/regi...

"And the truth is, it's always about a buzzword. Whatever buzzword catches on becomes the obsession, and that's all people talk about for a couple of years until the next buzzword takes over and the cycle starts again." cutlefish.substack.com/p/tbm-376-wh...

My mom, a DC resident, is terrified. Childhood memories of growing up during the German occupation of Greece are hard memories to shake.

Mandate Levels Day 9/30 sharing my favorite doodles and drawings.

WIP it Real Good Day 8/30 sharing my favorite doodles and drawings.

Strategy is as much about when you do things as it is about what you do. Strategy is heavily concerned with timing and the impact of timing on leverage (urgency). cutlefish.substack.com/p/tbm-374-pr...

Should vs. Can Day 7/30 sharing my favorite doodles and drawings.

Just... Day 6/30 sharing my favorite doodles and drawings.

Do This. Not This. Or ... Day 5/30 sharing my favorite doodles and drawings.

The area between oversimplification and inaction Day 4/30 sharing my favorite doodles and drawings.

Journey to Product Teams Day 3/30 sharing my favorite doodles and drawings.

It is easy to nod along with the idea of less premature convergence, but in practice it often gets mistaken for waffling or an inability to be bold. The real skill is knowing when a decision truly needs to be made and when it should wait. cutlefish.substack.com/p/tbm-273-wh...

The Way of Ways Day 2/30 sharing my favorite doodles and drawings.

Trust Day 1/30 sharing my favorite doodles and drawings.

For the scale-up, the highest leverage thing you can do is to figure out a model for linking these new product-forward ways of working to your current business challenge, and essentially a new “model” for investment. cutlefish.substack.com/p/two-pom-tr...

Where are the areas of overlap in what they want, even if the language they use makes them sound opposed? cutlefish.substack.com/p/tbm-272-th...

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...

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...

"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...

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...

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...

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...

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)

An initiative is an initiative...right? www.youtube.com/watch?v=aOFa...

Whatever it is .... it is sad.

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

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'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...

"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...

"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...

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...

Even when a team chooses a framework thoughtfully, people may still disagree about what they’re trying to accomplish. Are they trying to teach skills? Create shared language? Bootstrap a team? Ensure quality? cutlefish.substack.com/p/tbm-354-th...

I haven't been able to stop laughing since this happened to me this evening. It is hilarious on a couple levels.

How funding mental models vary with context cutlefish.substack.com/p/tbm-352-fu...

Experimenting with Obsidian Publish 350+ posts with a reasonabe search

It’s not easy seeing yourself on a billboard. But I’ve been up all day and night taking calls on the rescue line.

Are you trying to improve flow, make better tradeoffs, push for more strategic alignment, or clarify what's supported and what isn't? cutlefish.substack.com/p/tbm-351-th...

Exploring the dots ... yet again cutlefish.substack.com/p/tbm-350-co...