TBM 423: Why Defining Teams Is So Hard

John Cutler · rss · 2026-05-21 source ↗ Reader 🖥️

Hierarchy & Org Charts Organizational Coherence Organizational Legibility Sociotechnical Architecture

Defining teams in product/tech orgs is hard not because the analytic skill is rare, but because honestly naming the gap between the aspirational org chart and how work actually flows threatens existing power, incentives, and narratives — so the work is political and emotional, not technical, and the goal should be to hold both views at once and act on the gap rather than collapse it.

practical · mixed — Mostly argumentative-expository with a practical thrust. Cutler diagnoses why team definitions in product/tech orgs are hard, then prescribes a posture (hold both views; surf the tension; be honest). The closing 'So What?' and the 'change agents' note make the practical orientation explicit.

Structure

Part	Role
Opening framing: 'undiscussables' (Argyris) and the four frames (product, design, technology/platform, collaboration)	Sets the diagnostic frame and the central claim that skill is low but political cost is high
'The Tension Between Frames' — product vs. design vs. technology mental models; designers stretched across teams; PMs competing for capacity or fighting over shared services; architecture as constraint	Evidence and mechanism for why frames diverge in practice
'The Pendulum' — historical swing between 'everything is a product' and 'we have only three products'; both obscure reality; DDD note that bounded contexts are discovered; organizational history as sediment	Historical/structural evidence that simplification in either direction fails
'Triad Fractals' — fractal product/design/eng triads break at the management layer because incentives are not self-similar; engineering culture is load-bearing	Argument against a popular org-design pattern; introduces the asymmetry of incentives
'Why It Stays This Way' — flattening systems, Simon on design, asymmetric costs across product/tech/design, engineering manager incentives	Causal explanation of persistence; the core mechanism section
'Pragmatic Change Aversion' — resistance is earned skepticism, not bad faith; Brunsson's organized hypocrisy as functional gap	Reframes resistance and introduces a normative test (functional gap vs. permanent theater)
'So What?' and the note for change agents — hold both views, surf the tension, find pockets of coherence	Practical conclusion and stance
Eight diagnostic questions	Operationalization — turns the diagnosis into a self-assessment tool

Key terms

Undiscussables Hierarchy & Org Charts
Things everyone in the room can see but that are tacitly off-limits to name because describing them threatens narratives, incentives, or power structures (borrowed from Chris Argyris).
Frames Hierarchy & Org Charts
Distinct mental models for organizing work: product-centric, design (journeys), technology (architecture/services), platform, and collaboration (who actually talks to whom). All coexist in the same org.
Coherence (and misalignment) Organizational Coherence
The degree to which the product view and the technology org naturally line up. A spectrum, not a binary; most teams sit somewhere between high coherence and deep misalignment.
Reverse Conway maneuver Sociotechnical Architecture
Intentionally restructuring teams to match the architecture you want (rather than letting architecture mirror existing teams). Compelling but constrained by the architecture you actually have.
Fractal triads
The pattern of product/design/engineering triads mirrored at every level of the org. Cutler argues the self-similarity breaks at the manager layer because incentives diverge.
Organized hypocrisy Hierarchy & Org Charts
Borrowed from Nils Brunsson: organizations may need a gap between stated and actual practice to satisfy contradictory stakeholder demands. Can be functional (North Star) or dysfunctional (permanent theater).
Pragmatic change aversion
Resistance from people with earned context — the underfunded manager, the dependency-weary leader, the burned director — that looks like politics but is rational reaction to past organizational behavior.
Service boundaries as 'organizational confessions'
Quoted approvingly: the lines between services reveal historical power structures and accidents more than intentional design.
Surfing the tension
The change agent's posture: don't try to eliminate the gap personally; find pockets of coherence and leaders honest enough to work with reality, and move there.
Engineering culture as load-bearing wall
Engineering managers do team building, on-call, hiring, mentoring, career paths — work that 'product-is-everyone' models tend to dissolve at real cost.

Propositions

explicitThe skill required to describe how an organization actually works is low; the political cost of saying it out loud is high.conf: high
explicitProduct, design, and technology hold different and partly incompatible mental models of team structure even in nominally cross-functional orgs.conf: high
explicit⚡ disputed & corroboratedArchitecture is a hard constraint on how fast teams can be realigned; the reverse Conway maneuver underestimates this.conf: high
supports ←Beyond Autonomous Teams in Software Product Development · p11 — Both treat architectural/value coupling as a hard constraint on team structure that org-design ideology (autonomous teams / reverse Conway) can understate.
contradicts ←Team Topologies: Organizing Business and Technology Teams for Fast Flow · p2 — This book treats the reverse Conway maneuver as a workable design lever; TBM #423 argues directly that architecture is a hard constraint which the maneuver underestimates — a genuine tension, not just emphasis difference.
explicitCalling everything a product (2010s) and now calling almost nothing a product are both forms of obscuring reality.conf: high
explicitThe fractal triad model (product/design/eng mirrored at every level) breaks down at the management layer because product, tech, and design managers face structurally different incentives.conf: high
explicitEngineering culture is load-bearing; absorbing engineering into a 'product is everyone' model damages team cohesion and productivity.conf: high
explicitProduct can describe the world cheaply; technology has to live in it, so the cost of being wrong is asymmetric.conf: high
explicitDesign has the worst structural position: matrixed, budget-less, sees the seams but has no power to push back.conf: high
explicitEngineering managers rationally resist re-orgs because product strategy shifts quarterly while architecture pays off over years.conf: high
explicitResistance to honest description is often earned skepticism from informed practitioners, not bad-faith politics.conf: high
explicitA gap between aspirational and actual organizational models can be functional (a North Star) or dysfunctional (permanent theater); the test is whether leadership treats it as something to close or as a convenient fiction.conf: high
explicitChange agents should not try to close the gap personally; they should find pockets of coherence and work there.conf: high
implicitdevelopedMost organizational systems (org charts, taxonomies, planning tools) are structurally incapable of holding more than one frame at a time; they flatten multi-frame reality into a single canonical view.conf: high
extends ←TBM 434: How Maps Can Hide Problems · p3 — Restates and extends Cutler's own earlier claim that 'most organizational systems... are structurally incapable of holding more than one frame at a time' by supplying the map-layers metaphor and the coherent/incoherent framing that makes the mechanism concrete.
implicitDesigners are systemically more accurate observers of how customer-facing work actually flows than either product or engineering, because they sit across the seams.conf: medium
implicitdevelopedHonesty in organizational description is a moral/political act, not an analytical one — and the analytical framings on offer (capability maps, journey maps, DDD) become traps when used to substitute for that act.conf: high
extends ←TBM 434: How Maps Can Hide Problems · p6 — Same mechanism as Cutler's earlier claim that analytical framings (capability maps, journey maps, DDD) 'become traps when used to substitute for' the honest, political act of description — this piece generalizes that trap to any coping tool (translators, fixers, forums), not just analytical maps.
explicitOrg structures encode the unwritten history of past strategic decisions; people who could explain why a team is shaped as it is have often left, so the rationale is unrecoverable.conf: high
explicitDomains themselves are non-stationary; DDD risks freezing a point-in-time semantics of a still-emerging domain.conf: high
explicitThe PM/engineer ratio (~1:8-12) plus the lack of PM headcount accountability means PMs can propose org structures whose costs they don't bear.conf: high
implicitPower in product/tech orgs flows along the line of who absorbs operational pain when a mapping is bad — and that is engineering.conf: medium
implicitcorroboratedA reorganization that changes reporting lines without changing how work flows is, by Cutler's standard, not a real reorganization.conf: high
supports ←Software Development As Collective Learning With Hazel Weakly · p5 — The same underlying critique -- that a visible, career-rewarded structural change (a reorg; a stack migration) can leave how work actually flows unchanged -- applied to architecture-level migrations here and to org-chart reorganizations there; both are from John Cutler, extending his own standard across time.

Arguments

Misalignment between product and technology team structures is structural and predictable, not the result of poor leadership or organizational immaturity. strength: high

Explicit premises:

Product, design, and technology each have legitimate but partly incompatible frames.
Architecture constrains how quickly teams can be restructured.
Product strategy changes faster than architecture pays off.
Managers in product, tech, and design face structurally different incentives (headcount, reliability, matrixing, career ladders).

Implicit premises:

Incentive structures dominate stated intent in shaping behavior.
There is no available reorganization that satisfies all frames simultaneously without slack/resource that orgs typically don't have.

Inferences:

Therefore, prescriptive org-design frameworks that ignore this asymmetry will systematically fail in execution, even when adopted in good faith.

Resistance from experienced managers and directors to 'just describing reality' is often legitimate and informed, not pathological politics. strength: high

Explicit premises:

The underfunded manager told 'you are a platform' knows the leadership assumptions are unrealistic.
The dependency-weary leader has already tried explaining and been ignored.
The director has seen glossy narratives collapse before.

Implicit premises:

Leadership behavior is path-dependent: past glossing-over creates rational future skepticism.
The cost of speaking truth in these orgs is borne disproportionately by the speaker (career, role).

Inferences:

Change agents who frame resistance as 'change aversion' or 'politics' will misdiagnose the system and lose trust.

Engineering culture should not be dissolved into a product-centric 'product is everyone' model. strength: high

Explicit premises:

Engineering managers do the practical team-building work: hiring, on-call, mentoring, career paths.
PMs are largely solo operators and don't build team cohesion at the same depth.
Larson: disassembling a high-performing team causes a significant productivity loss even when members are retained.

Implicit premises:

Team cohesion is a separate value from product alignment and is not substitutable by it.
The aesthetic appeal of a clean org chart ('product is everyone') has currency with executives in a way that the operational cost of dismantling teams does not.

Inferences:

Org models that look elegant on paper but require absorbing engineering's team-building function should be presumed to underweight the cost they impose.

Orgs should aim to hold two views simultaneously (aspirational and actual) and treat the gap as something to incrementally close, not erase or pretend away. strength: medium

Explicit premises:

Both views are necessary: legibility for executives/customers, honest mapping for practitioners.
Brunsson's organized hypocrisy: the gap can be functional if it's a North Star, dysfunctional if it's permanent theater.
Most current systems flatten reality into one view.

Implicit premises:

Leaders can in fact change their relationship to the gap by intent, even if they cannot eliminate it.
Tools and rituals (templates, spectrums, plain-language dimensions) are sufficient if the will exists; the binding constraint is courage, not method.

Inferences:

Any tool/framework whose purchase is 'solve the gap' is overselling; tools that help describe and live with the gap are more honest and more useful.

Change agents in misaligned orgs should 'surf' the tension rather than try to fix it personally. strength: medium

Explicit premises:

The incoherence is structural and won't be fixed by one person.
There are pockets of local coherence: teams that happen to align, leaders who are honest.
The tension is where the system is most ready to shift.

Implicit premises:

The cost of trying to fix the whole system personally (burnout, role loss) outweighs the marginal change one person can produce.
Local coherence can be cultivated even when global coherence cannot.

Inferences:

An effective change agent's career strategy in such orgs is to develop a 'pocket-finding' skill: detect where reality and aspiration overlap and concentrate effort there.

Narratives

The Kanban-board anecdote: in Cutler's earlier work, dumping reality onto a board was theoretically trivial but politically charged when it bumped up against the org's preferred narrative.
→ Concretizes the central claim that the skill barrier is low and the courage barrier is high. Establishes Cutler's personal experience as evidentiary backing.
The PM-on-a-slide vignette: one PM 'draws a box on a slide and calls it their product' which actually requires a dozen engineering teams to deliver — while elsewhere, four PMs fight over a single team owning a shared service.
→ Illustrates the asymmetric cost of misnaming, and grounds the abstract 'frames disagree' claim in a recognizable pattern.
The 2019 platform bet: a puzzlingly-structured team turns out to be the remnant of a half-funded platform initiative that was never fully unwound.
→ Supports the proposition that organizational history is sediment that explains otherwise irrational team structures, and that the rationale is often lost.
The CTO's parallel goal system: a CTO under reliability/performance/tech-debt pressure builds a parallel OKR hierarchy alongside the official product-centric one, so everyone reports into two goal trees.
→ Evidences both 'tech rationally builds shadow structures' and 'the product-centric model doesn't absorb tech leadership's accountabilities'. Also a concrete example of organized hypocrisy in action.
The David Dame observation: 'The C-suite is cross-functional with complete oversight. The team is cross-functional with limited sight outside the teams. The middle management continues to be functional.'
→ Compresses the fractal-breaks-at-the-middle argument into one quotable line.
The 'McKinsey' aside: outside consultants who pronounce 'these are your real products' weren't there for the years the company was running a well-oiled feature factory accumulating org/tech debt.
→ Supports the proposition that current team shapes are path-dependent and that frameworks parachuted in without history are illegitimate.

Questions addressed

✅ Why is it so hard to define what a team is in a product/tech organization?
Because honestly describing teams forces a confrontation with mismatched frames, sedimented history, and asymmetric incentives across product/design/tech, and that confrontation threatens existing power and narratives.
✅ Why does honest description of org reality get resisted?
Because resistors have earned skepticism from past leadership behavior; because the costs of being wrong are asymmetric across roles; and because organized hypocrisy is sometimes functional.
✅ What should change agents do about it?
Don't internalize the tension; surf it; find pockets of local coherence; treat the gap as the opportunity rather than the enemy.
✅ When is the aspirational/actual gap functional vs. dysfunctional?
Functional when leadership treats it as a North Star and incrementally closes it; dysfunctional when it's permanent theater no one believes or acts on.
⭕ How should orgs hold two views at once in their systems and rituals?
Cutler asserts that orgs need to but offers only the lightweight prescription of templates/spectrums/plain-language dimensions, without describing how the formal systems (planning, budgeting, OKRs, headcount allocation) could carry two views simultaneously.
⭕ How is the courage/trust barrier actually lowered?
Cutler names it as the binding constraint but treats it as a precondition rather than something the essay knows how to develop. The conditions under which honesty becomes safe are gestured at (psychological safety in workshops) but not theorized.
⭕ What would a planning/budgeting system look like that natively encodes coherence as a spectrum rather than a binary?
Not addressed; this is an open design problem implicit in the analysis.
⭕ Whose 'preferred future' gets designed, and whose reality gets erased in the gap-closing process?
Cutler raises this Simon/design-theory question explicitly but does not answer it; he names that these questions 'are usually left implicit' but his own essay also leaves them implicit.

Gaps

incompleteThe essay names courage/trust as the binding constraint but does not theorize how it is produced. What organizational conditions, leadership behaviors, or institutional commitments actually lower the political cost of honest description? Cutler mentions 'psychological safety in workshops' in passing but doesn't extend it to the org level.
Read next: Amy Edmondson on psychological safety at the team and org level; Patrick Lencioni on vulnerability; potentially Kim Scott on radical candor — but also more structural treatments like Argyris/Schön on double-loop learning that connect the act of 'naming undiscussables' to organizational learning capacity.
closed byIs Your Organizational Culture Too Nice? — Names concrete leadership mechanisms — CEO-first structured peer feedback and redesigned review/governance-meeting agendas — that lower the political cost of honest description, directly answering that gap's question of what organizational conditions actually produce the courage/trust Cutler names but doesn't theorize.
incompleteCutler's prescription is essentially individual ('surf the tension', 'find pockets'). He gestures at — but does not develop — what institutional design would look like for an organization that natively holds two views. The flattening tendency of org systems is named but not redesigned.
Read next: Stafford Beer's Viable System Model and Espejo on organizational cybernetics (which explicitly model multiple recursive views of the same system); Wardley mapping for multi-frame strategy; Niels Pflaeging's beta-codex / 'org physics' (cells vs. functions). Also Cutler's own earlier writing on 'operating systems' for product orgs.
incompletePower and political economy are named but not modeled. Who actually has standing to call an undiscussable? When does the act of naming protect the speaker (e.g., a senior leader with capital) and when does it ruin them (the director who 'knows how things go')? The essay treats these as moods rather than as predictable functions of organizational position.
Read next: Jeffrey Pfeffer on power in organizations; Mary Parker Follett on integrative conflict; Argyris on defensive routines (Cutler cites Argyris on undiscussables but doesn't engage the full theory). Also Henry Mintzberg's typology of power configurations.
closed byTBM 433: The Border Collie Faustian Bargain — That gap asked who has standing to call an undiscussable, and when naming it protects versus ruins the speaker. TBM 433 supplies a concrete answer at the individual level: the Coherence Checker's own risk calculus (would speaking help, embarrass someone, derail the meeting, damage standing, or mark her as difficult) plus the recalled consequence of having tried before ('told to be more of a team player') gives exactly the cost-benefit texture that gap found missing from a purely structural treatment.
incompleteDesign is positioned as the 'truth-telling' frame because designers see the seams, but design's own blind spots and the cost of giving design more structural power are not examined. The essay grants design moral authority without scrutinizing it.
Read next: Jared Spool and Don Norman critiques of design's overreach; service design literature on the limits of journey-mapping; Tony Ulwick / jobs-to-be-done as a competitor frame that disputes design's own narrative.
incompleteThe essay focuses on the product/design/tech axis inside a single org. It does not address how this dynamic changes in regulated, public-sector, or critical-infrastructure orgs where 'teams' are also legal/audit/governance entities — a context particularly relevant to Norwegian public-sector tech (NAV, Entur, public services).
Read next: Pia Andrews / GovTech writing on public-sector team design; Mark Schwartz ('A Seat at the Table', 'War and Peace and IT') on bureaucracy and IT leadership; Mariana Mazzucato on mission-led public organizations. For the Nordic context: Skatteetaten/NAV/Entur case studies on team topologies in regulated environments.
incompleteThe 'pendulum' framing is descriptively useful but normatively underspecified. Cutler observes the swing between 'everything is a product' and 'three products only' but doesn't propose what the stable middle looks like — what's the unit of organization that resists both inflation and deflation of the product label?
Read next: Team Topologies (Skelton & Pais) explicitly types teams (stream-aligned, platform, enabling, complicated-subsystem) as a possible answer; Sriram Narayan on agile organization design; Marty Cagan's 'empowered product teams' framing as a competitor.
incompleteThe 'organized hypocrisy' frame is borrowed but not pressure-tested. When is a publicly stated aspiration actually load-bearing (it constrains future decisions; it can be used as leverage) and when is it inert? Cutler's 'is leadership treating the gap as something to close or as a convenient fiction' is a binary test where reality is likely a spectrum with measurable indicators.
Read next: Brunsson's original 'Organization of Hypocrisy' and 'Mechanisms of Hope'; March & Olsen on logics of appropriateness; Pfeffer & Sutton 'The Knowing-Doing Gap'.
closed byTBM 433: The Border Collie Faustian Bargain — That gap asked when a stated aspiration is load-bearing versus a convenient fiction, and whether leadership is treating a gap as something to close or as permanent theater. TBM 433 pressure-tests this by tracing what happens to the person managing the gap rather than to leadership: the gap becomes 'convenient fiction' precisely at the moment someone (the newly-Fox Border Collie) starts being paid, in influence, to keep it convenient -- reframing the leadership-level question as a question about who benefits from the gap staying open.
incompleteAI/agent-assisted development is conspicuously absent from an essay published in 2025/2026 about how teams are defined. If a meaningful share of engineering work is mediated by agents, the definition of 'team', headcount-as-cost, and the engineering manager's role all shift. Cutler doesn't touch this, though it is plausibly the next pendulum swing.
Read next: DORA AI capabilities report; Kent Beck on AI-assisted design ('Tidy First?' series); Addy Osmani / Steve Yegge on agentic engineering; Cutler's own TBM pieces on institutional overload and AI (TBM 412).

TBM 423: Why Defining Teams Is So Hard

Structure

Key terms

Propositions

Arguments

Narratives

Questions addressed

Gaps

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