TBM 423: Why Defining Teams Is So Hard

John Cutler from The Beautiful Mess · email · 2026-05-21 Reader 🖥️

Hierarchy & Org Charts Organizational Coherence Organizational Legibility Sociotechnical Architecture

Honestly describing how teams actually work in product-and-technology organizations is cognitively easy but politically expensive, because the gap between the legible aspirational org chart and the lived collaboration reality is sustained by asymmetric incentives (cheap for product to redefine, costly for engineering to absorb, invisible to design) rather than by any lack of skill or insight — so the real organizational competence is the willingness to hold both views at once and work with the gap.

practical · argumentative — An argumentative essay about organizational design, advancing the claim that the difficulty of defining teams is not a skill problem but a political/structural one. It uses observational evidence from workshops, references multiple authorities (Argyris, Larson, Simon, Brunsson, Dame), and ends with a prescriptive coda. The argument is diagnostic-prescriptive rather than narrative or expository.

Structure

Part	Role
Opening framing — undiscussables and the easy/hard asymmetry	States the central puzzle (describing reality is easy, saying it out loud is hard) and frames it via Argyris's 'undiscussables.' Establishes that the obstacle is political, not epistemic.
The frames in the room (product / design / technology / platform / collaboration)	Inventories the multiple co-existing 'views' of organizational design that practitioners can already articulate. Demonstrates the claim that the descriptive work is cognitively tractable.
The Tension Between Frames	Diagnoses the structural friction between product, design, and engineering views of team structure. Introduces architecture as a constraint (Larson, reverse Conway) and strategy instability as another.
The Pendulum	Historical pattern — orgs swing between 'everything is a product' and aggressive simplification, neither of which captures the actual coordination reality. Introduces the 'enterprise architecture trap' and the 'market-tecture trap.'
Triad Fractals	Critiques the fractal product-design-engineering triad model. The triad breaks at the management layer because incentives are not self-similar — engineering culture is a 'load-bearing wall' the product-centric model cannot absorb.
Why It Stays This Way	Spells out the asymmetric cost structure. Product pays low cost to redefine; tech absorbs operational pain; design has no structural power. Reframes resistance as rational, not character-flawed.
Pragmatic Change Aversion	Defends the resisters. Reframes 'change aversion' as earned skepticism from people with context. Introduces Brunsson's 'organized hypocrisy' as a functional theory of the aspirational/real gap.
So What? + Coda for change agents	Prescriptive close. Names the dual requirement (legible aspirational model AND honest account) and offers low-tech tooling (templates, spectrums). Coda reframes change agents' role from 'fix the incoherence' to 'surf it' — find pockets of overlap.
Eight diagnostic questions	Operationalizes the post for the reader. Each question is a probe for the gap between described and actual.

Key terms

undiscussable Hierarchy & Org Charts
Borrowed from Chris Argyris — a fact visible to everyone in the room but tacitly off-limits to name, not because describing it requires expertise but because the act of describing threatens narratives, incentives, and power structures.
frame Hierarchy & Org Charts
A coherent partial view of organizational design (product, design, tech, platform, collaboration). Each frame is internally legitimate; the problem is that practitioners must hold several simultaneously and they don't reconcile.
team
Treated as a problematized object whose definition shifts depending on which frame is dominant; not a fixed unit but a contested mapping between product taxonomy, technical ownership, and collaboration reality.
coherence Organizational Coherence
The degree to which the product view and the technology org naturally align. Teams sit on a spectrum from high coherence to deep misalignment; achieving coherence is constrained by existing architecture, not just by intent.
reverse Conway maneuver Sociotechnical Architecture
Intentionally restructuring teams to match the architecture you want (rather than the architecture you have); Cutler grants it is 'compelling in theory' but argues most aspirational models underestimate the constraint of existing architecture.
organized hypocrisy Hierarchy & Org Charts
From Nils Brunsson — the productive (or destructive) gap between what an organization says it does and what it does. Cutler argues this gap may be functional when it's a North Star being incrementally closed and dysfunctional when it's permanent theater.
load-bearing wall
Metaphor for engineering culture — something that cannot be removed in service of an org-chart aesthetic without structural consequences (team cohesion loss, productivity loss, on-call breakdown).
organizational confession
Service boundaries (and by extension team boundaries) reveal historical power structures and accidents more than intentional design. Borrowed from an unnamed consulting group.
museum of boxes Hierarchy & Org Charts
Pejorative for enterprise architecture capability maps built in a vacuum that nobody uses operationally.
surfing the tension
The recommended posture for change agents — instead of trying to close the gap between the two org charts personally, find pockets where the maps overlap and a team has enough coherence to move.
asymmetric cost of being wrong
Implicit term for the geometry where product can propose structures cheaply (rename if wrong), engineering pays the operational cost (attrition, on-call fragmentation, reliability incidents), and design absorbs incoherence with no structural power.

Propositions

explicitThe skill required to describe how an organization actually works is low; the political cost of doing so is high.conf: high
explicitProduct, design, and technology hold structurally different views of team structure that do not reconcile cleanly, even in organizations that have ostensibly adopted cross-functional teams.conf: high
explicitArchitecture is a binding constraint on team structure that cannot be wished away by labelling exercises or org-chart rearrangement.conf: high
explicitThe fractal triad model (product/design/engineering at every level) breaks at the management layer because incentive structures are not self-similar.conf: high
explicitProduct management can propose taxonomies at low personal cost because the headcount, on-call, and operational accountability sit in engineering.conf: high
explicitDesign occupies the structurally worst position — sees the seams across product boundaries but has no budget authority or structural home to act on what it sees.conf: high
explicitResistance to honest descriptions of team reality is rational rather than character-flawed — it reflects earned skepticism from people who carry historical context.conf: high
explicitdevelopedThe gap between aspirational and actual org models may be functional, not pathological — Brunsson's 'organized hypocrisy' lets contradictory stakeholders be satisfied simultaneously.conf: high
refines ←What 60 Years of Data Reveals About How Men and Women Experience Leadership · p7 — That proposition holds the aspirational/actual org-model gap 'may be functional, not pathological' (Brunsson's organized hypocrisy satisfying contradictory stakeholders). This doc refines that by exhibiting a domain — gender and promotion — where the same formal/informal gap is dysfunctional and self-reinforcing: proclaiming meritocracy loudly (the aspirational layer) causally worsens the underground bias it claims to have solved.
explicitThe competence that distinguishes an effective organization is the willingness to hold both the aspirational and actual maps at once and do something with the delta.conf: high
explicitEngineering culture functions as a load-bearing wall in product organizations — dissolving it into a product-centric tent destroys team cohesion that retention alone cannot recover.conf: high
explicitRe-orgs that simplify the public taxonomy (e.g., 'we now have three products') frequently make the underlying coordination reality harder to discuss, not simpler to execute.conf: high
explicitBoth the enterprise architecture community ('museum of boxes') and the product framework community ('market-tecture') fail in symmetric ways when they treat their categories as mutually exclusive and collectively exhaustive.conf: high
explicitDomain-driven design boundaries are discovered, not invented, and rarely match existing org charts; over time strategic shifts make even discovered boundaries unstable.conf: high
explicitEvery team carries sediments of past re-orgs, strategies, and leaders, and that history is rarely documented; the people who carried it have moved on.conf: high
explicitChange agents who internalize the tension burn out; the healthier posture is to surf the tension by finding pockets of overlap where the system is ready to move.conf: high
explicitOrganizations need a legible aspirational model and an honest account simultaneously; most struggle to hold both.conf: high
explicitThe visibility of the multiple org charts is not the bottleneck — people can already see them. The bottleneck is what the org will publicly admit.conf: high
implicitPower asymmetry between functions, not lack of insight, is the primary mechanism that keeps team definitions misaligned with reality.conf: high
implicitThe product function in many companies has been institutionally over-credentialed relative to its actual operational accountability.conf: medium
implicitReorganizations are often rituals of relabeling rather than instruments of changing how work flows.conf: high
implicitThere is no neutral position for describing teams — every description embeds assumptions about who matters, who is funded, and whose work is visible (a Simon-flavored claim that 'preferred futures' carry hidden politics).conf: high
implicitThe 'team' has become a unit of accounting (headcount, budget, on-call) more than a unit of meaningful work, which is why the descriptive question is so politically charged.conf: medium
implicitAI tooling, despite Cutler's recent focus on it elsewhere, does not appear in this post — implying that organizational design pathologies have an etiology and time-scale independent of the AI wave.conf: medium

Arguments

The misalignment between described and actual teams persists because of asymmetric incentives, not lack of skill. strength: high

Explicit premises:

Describing reality is cognitively easy — workshops with psychological safety reliably surface the multiple frames.
Product can propose structures at low personal cost (renaming is cheap); tech absorbs the operational consequences (on-call fragmentation, attrition, reliability incidents); design has no structural power to push back.
Engineering managers face incentives (headcount-as-promotion-eligibility, uptime accountability, career-ladder ownership) that make honest description risky.
Architecture pays off over years while product strategy shifts quarterly — eng leaders rationally resist reorganizing around something likely to change.

Implicit premises:

Behavior in organizations follows incentive geometry more reliably than it follows stated values.
Cost asymmetry between functions is itself a power relation, even if no one names it that way.
Rational actors will not volunteer information whose surfacing imposes asymmetric cost on them.

Inferences:

Therefore, attempting to fix the misalignment by raising the skill/insight level (workshops, taxonomies, frameworks) will fail because the bottleneck is elsewhere — in the incentive structure.
Therefore, frameworks that treat the gap as a 'maturity' problem misdiagnose it as a learning problem when it is a political-economy problem.

Engineering culture is a load-bearing wall in product organizations and cannot be dissolved into a product-centric model without significant productivity loss. strength: high

Explicit premises:

Engineering managers actually manage people, run on-call rotations, hire, mentor, build team culture.
Product orgs do not do team culture as well as they believe; many PMs are solo operators.
Larson: disassembling a high-performing team causes productivity loss even if members are fully retained.

Implicit premises:

Team culture is a property of stable management+membership configurations, not a property of the work itself.
Product-centric models implicitly under-resource the relational work that produces team coherence.
Productivity has a non-linear relationship to team stability — small disruptions cause large losses.

Inferences:

Therefore, the popular 'product is everyone' tent reorganization is not just an aesthetic preference but a structurally costly choice.
Therefore, the CTO running a parallel goal hierarchy is responding rationally to pressures (reliability, performance, debt) that the product model doesn't absorb.

The gap between aspirational and actual org models is not inherently pathological — its valence depends on whether leadership treats it as a closing distance or as a convenient fiction. strength: high

Explicit premises:

Brunsson's 'organized hypocrisy' shows that gaps between rhetoric and practice can satisfy contradictory stakeholders.
Aspirational models keep executives, boards, and customers happy.
Real models let practitioners get work done.
Gaps become dysfunctional when permanent and disbelieved.

Implicit premises:

Some duality between aspiration and reality is structurally unavoidable in organizations with multiple stakeholder groups.
It is leadership's responsibility (not the front line's) to differentiate North-Star gap from theatrical gap.
The act of distinguishing functional from dysfunctional gaps is itself a leadership competence that few leaders practice.

Inferences:

Therefore, demanding that organizations close all gaps between aspirational and actual is naive and possibly destructive.
Therefore, change agents should evaluate the gap's trajectory, not its existence.

Change agents should surf the tension between maps rather than try to close it themselves. strength: medium

Explicit premises:

The incoherence isn't yours to fix alone, and it may not be fixable in the way you imagine.
There are pockets where the two org charts happen to overlap and a team has enough coherence to move.
The tension is where the system is most ready to shift, if someone is paying attention.

Implicit premises:

Change agents have a finite capacity for absorbing systemic incoherence before they burn out.
Organizational change is opportunistic, not architectonic — it follows where the system has slack, not where the slide deck says it should.
Personal sustainability of the change agent is a precondition for sustained change.

Inferences:

Therefore, the change agent's job is reconnaissance and timing, not heroic transformation.
Therefore, organizations that punish change agents for finding overlap pockets (rather than executing the global aspirational map) are destroying their own change capacity.

Simplifying the public taxonomy ('we have three products') often increases — not decreases — the organization's incoherence. strength: high

Explicit premises:

Simplification obscures the collaboration reality for the purpose of legibility.
Each 'product' may actually require coordination across many teams and architectural layers.
Simplification 'makes it harder to talk about what's actually happening.'

Implicit premises:

The legibility of an org map and its operational truthfulness are inversely correlated past a certain threshold.
What gets named gets managed; what gets unnamed becomes invisible work.
Discussability is a property of the map, not of the people — a map that has no language for X cannot host honest conversations about X.

Inferences:

Therefore, reducing the number of named entities in an org chart may be a deliberate maneuver to make certain conversations impossible.
Therefore, executive demands for 'simpler' org maps should be examined for what they are foreclosing.

Narratives

A workshop facilitator (Cutler) consistently finds that, when psychological safety is established, practitioners have no trouble articulating the multiple org-design frames — product, design, tech, platform, collaboration.
→ Supports the central asymmetry: the descriptive task is easy, the political task is hard. Empirical evidence from Cutler's own consulting practice.
A designer assigned to multiple teams sees a customer journey as one continuous experience, while product has carved it into three capability areas and engineering has split it across five services.
→ Concretizes the misalignment between frames as a lived experience for design — sets up design's structural powerlessness.
One PM needs coordination from a dozen teams to deliver what they see as a single capability; elsewhere, four PMs fight over a single team that owns a critical shared service at the intersection of multiple product areas.
→ Two symmetric pathologies that follow from the asymmetric cost geometry — illustrates 'product gets to describe the world; tech has to live in it.'
A team that looks puzzlingly structured today turns out to be the remnant of a 2019 platform bet that was half-funded and never fully unwound.
→ Hypothetical but archetypal — supports the claim that organizational history is load-bearing and rarely documented.
A manager whose team has been perpetually underfunded is suddenly told 'you are a platform' when realistically they are early in that journey; or a dependency-weary leader pushes back on yet another mapping exercise; or a director who has seen glossy narratives collapse 'knows how things go.'
→ Three vignettes that defend resisters as informed rather than change-averse. Reframes pushback as legitimate political content.
A CTO creates a parallel goal hierarchy with their own OKRs under the 'technology strategy' banner because the product-centric model doesn't absorb pressures around reliability, performance, and technical debt.
→ Concrete example that the structural asymmetry between functions can produce shadow management systems rather than alignment.
Cutler's own past Kanban work — dumping reality onto a board was theoretically easy, MUCH harder when the reality bumped up against narrative tension.
→ First-person witness to the central asymmetry. Builds authority for the diagnostic claim.

Questions addressed

✅ Why is it so easy to describe how an organization actually works, and so hard to say it out loud?
Because describing reality threatens existing narratives, incentives, and power structures (Argyris's undiscussables). The skill is low; the political cost is high.
✅ What sustains the gap between described and actual teams?
Asymmetric costs across product/design/engineering: product pays low cost to redefine, engineering absorbs operational pain, design has no structural power.
✅ Is the gap between aspirational and actual org models always pathological?
No. Brunsson's 'organized hypocrisy' shows it can be functional when leadership treats it as a closing distance; it becomes dysfunctional when it's permanent theater.
✅ What should change agents do?
Don't internalize the tension; surf it. Find pockets of overlap where teams have coherence to move.
✅ Should organizations adopt the fractal P/D/E triad model at every level?
No — it breaks at the management layer because incentives are not self-similar.
✅ What is the role of architecture in determining team structure?
Architecture is a binding constraint; you can't 'flip a switch' to rearchitect; the reverse Conway maneuver is compelling but underestimated by aspirational models.
⭕ How does a change agent distinguish a 'pocket of overlap' worth investing in from a temporary opening that will close?
Open — Cutler advises surfing but doesn't supply diagnostic criteria.
⭕ When does the gap between aspirational and actual cross from functional North Star into dysfunctional theater?
Open — Cutler names the question but provides no threshold or signal.
⭕ What does honest leadership at the C-suite level actually look like in this geometry — not just 'hold both views' but what decisions follow from that?
Open — Cutler prescribes for change agents in the middle, not for leaders at the top.
⭕ If the cost asymmetry is the mechanism, can it be rebalanced (e.g., by changing how product is accountable)?
Open — Cutler diagnoses the asymmetry but never asks whether product accountability itself should change.
⭕ What is the role of customer experience — design's view — when design has no structural power?
Open — design is described as occupying the worst position, but Cutler doesn't propose how to repair it.
⭕ Is the dual-map requirement (aspirational + actual) compatible with public reporting (investors, boards, regulators) that demands a single legible version?
Open — Cutler treats the gap as an internal organizational property without addressing external legibility pressures.

Gaps

incompleteCutler's prescription ('surf the tension', 'find pockets') leaves the change agent without a diagnostic for distinguishing a real pocket of opportunity from a temporary opening that will close, or from a trap that consumes effort without producing change. The post advises a posture but not a method.
Read next: Donella Meadows' 'Places to Intervene in a System' (leverage points hierarchy) supplies the missing taxonomy of where intervention has high leverage. Fearless Change (Manns & Rising) — which Kjetil's persona shows he highlights heavily — supplies pattern-level guidance for what to do once a pocket is identified.
incompleteThe post diagnoses the asymmetric cost geometry but never asks whether the asymmetry could itself be redesigned. Could product be held accountable for operational consequences? Could design have budget authority? Cutler treats the geometry as a given and prescribes only how to live within it.
Read next: Allen Holub's #NoAccountability work and the broader DRI (Directly Responsible Individual) literature — which Kjetil already engages with — would supply the missing accountability-redesign frame. Henrik Kniberg's writing on Spotify-era squad accountability is another natural extension.
incompleteThe post is silent on AI tooling, despite Cutler's recent series on AI and organizational design. This is a striking absence — if AI is changing how work is coordinated (skills, agents, asynchronous artifacts), does it also change the cost asymmetry that this post identifies as the root cause?
Read next: Re-read TBM 412 (institutionalized overload + AI) and TBM 418 (campfires, trails, quests) against this post. Test whether AI-mediated artifacts could shift the cost asymmetry — does cheap AI-generated documentation make tech's 'I have to live with it' position cheaper or more expensive?
uninformedCutler invokes Brunsson's 'organized hypocrisy' as a positive frame but does not engage with Brunsson's own caveats about when the gap becomes self-reinforcing (when the aspirational model is used to deflect accountability for the real model). The post borrows the lens but not the warning.
Read next: Brunsson, 'The Organization of Hypocrisy' (1989/2002) — the original argument is more pessimistic than Cutler's borrowing suggests. Worth reading directly.
closed byTBM 433: The Border Collie Faustian Bargain — That gap flagged Cutler's uncritical borrowing of Brunsson's 'organized hypocrisy' without its caveat about self-reinforcement. TBM 433 directly supplies that missing engagement: the four-step creep (rewrite, explain, defend, correct) is a worked mechanism for exactly how an aspirational gap turns self-reinforcing -- each step converts a former critic of the gap into one of its maintainers.
incompleteThe post barely engages with what 'aspirational' actually looks like — there is no example of a North-Star map that is being incrementally closed versus one that is permanent theater. Without exemplars, the distinction is rhetorical rather than operational.
Read next: Team Topologies (Skelton & Pais) — their stream-aligned/platform/enabling/complicated-subsystem taxonomy is the closest thing to an operational aspirational map; useful to read it through Cutler's lens to see whether it survives the 'permanent theater' test.
illogicalCutler argues both (a) describing reality is cognitively easy and (b) organizational history is load-bearing and rarely documented. If the historical context is missing, then describing reality is not actually easy — it is partial in ways the workshop participants cannot fully see. The post does not reconcile these two claims.
Read next: Engage with Edgar Schein on organizational culture as historically embedded — the surface-level description that workshops surface may be necessary but not sufficient, and the post understates how much remains invisible even after the political cost has been paid.
incompleteThe C-suite is named (via Dame's quote — 'cross-functional with complete oversight') but never analyzed as itself a structural location with its own incentive geometry. If the fractal breaks at middle management, what is the corresponding pathology at the top?
Read next: Henry Mintzberg on structure in fives; Russ Ackoff on idealized design — both supply tools for analyzing the C-suite as an organizational location rather than a moral category. Camille Fournier on engineering leadership ladders is closer to home.

TBM 423: Why Defining Teams Is So Hard

Structure

Key terms

Propositions

Arguments

Narratives

Questions addressed

Gaps

Related documents