The Beautiful Mess Podcast

John Cutler
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Dec 1, 2025 • 7min

TBM 392: When (And How) Tools Matter

A video post!The Miro board used in the video can be accessed here:https://miro.com/app/board/uXjVJi6NCs8=/?share_link_id=616280785572(PS: Miro, I’d love another sweatshirt!)This framework explains why tools help in some situations and fail in others by grounding everything in the current state of a behavior. Every important behavior in an organization sits somewhere on a spectrum: it might be purely aspirational, weakly practiced, inconsistent, friction-heavy, fully stable, actively suppressed, or not even clearly defined. Each of these states is held back by different blockers—lack of clarity, lack of skills, lack of time, workflow friction, political risk, or social norms—and each requires a different kind of support. Using a behavior-design lens like COM-B, the idea becomes simple: tools only work when they address the real blocker. Sometimes their job is to scaffold early steps and turn aspiration into practice. Sometimes it is to remove operational drag from a behavior that already exists. Sometimes it is to create shared visibility and reduce political friction. Tools matter, but how they matter depends entirely on the behavioral context they are dropped into.Show Notes (AI Generated) The Core QuestionWhen do tools matter, and how do they matter?Answer: It depends entirely on the current state of the behavior you want to see.The Seven Behavior StatesA. Normal States* Aspirational / Not RealizedOnly talked about. No real practice.* Weakly RealizedPeople agree it matters and occasionally try it, but it gets displaced by urgency and habit.* Partially Realized / InconsistentHappens in pockets. Conflicting interpretations. Local successes that have not scaled.* Mostly Realized but Friction-FilledBehavior is accepted and happening, but it is painful due to workflow friction, manual effort, tool constraints, or time pressure.* Fully Realized / StableConsistent, predictable, routinized. Embedded norms. Change feels risky.Special States* Actively SuppressedCounter-behaviors, incentives, or power dynamics prevent the behavior.* Contested / UndefinedNo shared understanding of what the behavior even is or how it should show up.COM-B EssentialsA behavior emerges when people have:* Capability* Psychological: knowledge, mental models, clarity* Physical: skills, practice* Opportunity* Physical: time, tools, workflow space* Social: norms, permission, cues, legitimacy* Motivation* Reflective: beliefs, intentions, identity, political risk* Automatic: habits, impulses, shortcutsTools can influence any of these.How Tools Help Depends on the Behavior StateIf the behavior is…Aspirational / Not RealizedPrimary tool role:Turn aspiration into a repeatable practice.Strategies:* Provide structure and scaffolding* Make early steps easy* Visualize desired state* Reinforce identity and intentWeakly RealizedPrimary tool role:Lower activation energy and make it harder to forget or skip.Blockers:* Not enough time* Habit competition* Too many steps* Short-term urgency wins over long-term valueStrategies:* Reduce steps* Support self-regulation* Nudge and cue the behavior* Make it easy to startPartially Realized / InconsistentPrimary tool role:Create a shared frame without forcing uniformity.Strategies:* Clarify purpose* Help reconcile or visualize different interpretations* Provide minimally viable standardizationMostly Realized but Friction-FilledPrimary tool role:Remove operational drag.Blockers:* Workflow friction* Manual coordination* Confusing handoffs* Tool gapsStrategies:* Standardize routines* Streamline workflows* Make bottlenecks visible* Automate repetitive workFully Realized / StablePrimary tool role:Preserve what works while reducing risk and effort.Blockers:* Risk aversion* Fear of destabilizing the ritual* Manual grind that no one wants to mess withStrategies:* Automate low-value steps* De-risk changes* Protect institutional knowledgeContested / UndefinedPrimary tool role:Clarify, name, and frame the behavior.Strategies:* Make interpretations explicit* Help teams converge on a definition* Reveal misalignmentActively SuppressedPrimary tool role:Shift legitimacy, visibility, and power dynamics.Strategies:* Provide shared visibility* Depoliticize the behavior* Reinforce norms or incentives* Create social proofTool Change Vectors (How Tools Influence Behavior)Tools can work through different mechanisms depending on the blocker:Influencing Capability* Clarification* Instruction* Cognitive offloading* Guided workflows* ChecklistsInfluencing Opportunity* Automation* Better workflows* Reducing steps* Making time and spaceInfluencing Motivation* Social proof* Legitimacy* Identity cues* Reduced political risk* ReinforcementWhat This Means for AIAI’s role will differ depending on the behavior state:* In aspirational states: scaffold early steps, provide examples, generate clarity.* In friction-filled states: remove manual overhead, automate stitching, reduce coordination cost.* In stable states: protect quality, ensure consistency, prevent regressions.* In contested states: help surface meaning, definitions, and distinctions.AI is another lever in the COM-B system — not magic, but highly state-dependent.The Core InsightTools always matter, but they matter in different ways depending on:* Which behavior you’re trying to support* Where that behavior currently sits on the realization spectrum* What is actually blocking it (Capability, Opportunity, Motivation)Getting this right means choosing the right intervention instead of assuming tools “fix” or “don’t fix” things. Get full access to The Beautiful Mess at cutlefish.substack.com/subscribe
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Jun 30, 2025 • 15min

TBM 365: The Problem With Value Hierarchies (Video)

Explore the flaws in traditional hierarchical models used by organizations. The discussion reveals how these structures often limit feedback flow and obscure the true impact of initiatives. Emphasis is placed on the importance of insights from all levels rather than a strict top-down approach. The podcast also delves into how time-to-impact varies across tasks and advocates for recognizing small wins to foster a more dynamic organizational culture.
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12 snips
May 26, 2024 • 34min

Product Coaching with Petra Wille

Experienced product leader Petra Wille and Arne Kittler discuss coaching dynamics in product leadership, the importance of emotional regulation, navigating difficult conversations, balancing individual agency and environmental impact in product management, and exploring deep thinking for effective team guidance.
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May 19, 2024 • 18min

20 Things I've Learned as a Systems (Over) Thinker (Extended Commentary)

This podcast delves into the complexities of overthinking and problem-solving, emphasizing self-care and adapted communication styles. It discusses the power of co-conspirators in influence and the importance of celebrating wins. The episodes explore navigating change strategies within organizations and the significance of concise problem-solving approaches.
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4 snips
May 12, 2024 • 31min

Sociotechnical Maestros with Gene Kim

Gene Kim, author of influential DevOps books, discusses slowification, simplification, and amplification in organizational dynamics. Topics include moving a couch metaphor, data plumbing, company evolution challenges, empowerment, problem-solving styles, and organizational restructuring.
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Apr 28, 2024 • 27min

Software Development As Collective Learning With Hazel Weakly

Software developer and blogger Hazel Weakly discusses transitioning from individual to collaborative learning in software development. They cover topics such as emergence, systems, developer productivity, architecture, migrations, values, culture, and feedback. Hazel emphasizes the importance of continuous change and effective leadership in the industry.
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19 snips
Apr 20, 2024 • 30min

Octopus Careers & Throwaway Stickies with Chris Butler

Chris Butler, a staff product operations manager at GitHub, shares insights on being a change agent, introducing new work methods, and Google culture. He discusses community connections, design fiction, and shaping future narratives. Navigating internal and external idea expression, strategic rehearsal in community practice, and balancing organizational culture and decision-making are also explored.

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