Beyond Planning Series - Article 1: The Great Unraveling
Updated: Aug 25
Prologue
I come to strategy from several directions. For thirty years, I have worked across product, strategy, and organizational design, collaborating with organizations large and small. Interwoven with that work has been a lifelong obsession with music theory, composition, and jazz. What once seemed like separate pursuits have become, to borrow Douglas Hofstadter’s phrase, an eternal golden braid: different ways of understanding how people create coherence together when the next move cannot be fully known in advance.
Good strategy and good jazz confront the same fundamental challenge: how to create coherent action over time in the presence of uncertainty. Both require structure without rigidity and freedom without chaos. Both work within constraints while remaining open to emergence. Both depend as much on listening and response as on anticipation and design. And both live or die in performance—not through the brilliance of the score alone, but through the quality of the collective improvisation that brings it to life.
Jazz therefore serves here as more than a metaphor. It is both a system and a language. As a system, it organizes multiple voices around a shared form without requiring those voices to become identical. As a language, it makes possible call and response, variation and quotation, tension and release, dissonance, silence, and surprise. It allows individual expression to strengthen collective coherence rather than threaten it.
When we study how jazz musicians hold a structure while transforming it, how they listen across difference, how they respond to what is emerging in the room, and how they recover when the music moves somewhere no one anticipated, we are studying many of the same dynamics that determine whether strategy succeeds or fails. Whether a leadership team can merely administer a plan or create a living course of action together.
This opening essay begins where the old promise of strategic planning starts to unravel. It examines what happens when plans become substitutes for judgment, when analysis is mistaken for strategy, and when organizations become more committed to preserving the score than hearing the music changing around them.
From there, the Beyond Planning series follows a larger movement: rupture → emergence → collective intelligence → uncertainty → temporal capability → transition → regeneration. Together, these essays ask what strategy becomes once the plan relinquishes its claim to be the strategy—and how organizations might recover the perception, discipline, imagination, and collective capacity required to act coherently in a world that will not hold still.
A companion playlist runs alongside the series. It is not background music, but a parallel line of argument: another way of hearing what the prose is trying to say.
How strategic planning lost the future
"I had a dream, which was not all a dream.
The bright sun was extinguish’d, and the stars
Did wander darkling in the eternal space,
Rayless, and pathless, and the icy earth
Swung blind and blackening in the moonless air;
Morn came and went, and came, and brought no day,
And men forgot their passions in the dread
Of this their desolation…
Lord Byron, “Darkness” (1816), lines 1–8
Prelude · The room remains lit after the city has gone dark
Edward Hopper’s Nighthawks has lived rent free in my head for more than a decade. I encountered it in 2013 at the Whitney’s old Madison Avenue building, before the museum moved downtown. The exhibition, Hopper Drawing, placed the finished painting in conversation with the sketches through which Hopper had worked his way toward it. Those drawings were a revelation. They made visible the labor beneath an image that feels as though it had simply been found: the diner’s acute angle, the sweep of glass, the figures held together beneath electric light, and the dark city pressing in around them.[1]
The finished painting remains uncannily ordered. The counter is clean. The coffee urns shine. Every object appears to be in its proper place. Yet the order of the room does not relieve the unease. It intensifies it.
I do not take this as a claim about Hopper’s intention. It is an image of how strategic planning now feels to me. Inside the glass, the organization is illuminated by targets, forecasts, initiatives, road maps, and performance measures. The future has been converted into rows and columns. Outside, the world remains dark, moving, and unavailable to the instruments that make the interior feel secure. The glass allows us to see that another reality exists. It offers no guarantee that the room can respond to it.
For much of the twentieth century, this illuminated interior was a remarkable achievement. Planning helped large organizations coordinate capital, technology, labor, and ambition across long periods of time. It gave executives a common language for investment and gave operating units a basis for committing resources. It remains indispensable wherever sequencing, budgeting, and coordination matter. The unraveling begins when this useful discipline is mistaken for strategy itself.
That distinction sits at the center of this series. Planning organizes commitments within a world we can describe with reasonable confidence. Strategy creates a way of acting when consequential parts of the world remain contested, uncertain, or still in formation. A plan seeks coherence through specification. Strategy seeks coherence through choice, learning, and adaptation. Organizations need both. Trouble begins when the first is used to evade the demands of the second.
I come to this question from a few directions. Thirty years of work in product, strategy, and organizational design have taken me through organizations large and small. Music came earlier and never stopped, through theory, composition, performance, and a lifetime of listening to jazz. The two practices share a deep concern: how to create coherent action over time when no participant possesses the whole truth and no score can fully anticipate what will happen next.
Jazz gives me a language for the organizational capacities that planning leaves underdeveloped. Musicians work inside form while listening for what the form is becoming. They carry memory, technique, and intention into a performance that cannot be repeated. They make individual choices whose meaning depends on the choices of others. They know when to state an idea, when to leave space, when to support, and when to disturb. Their discipline appears as freedom because it has been absorbed deeply enough to become responsive.
The Beyond Planning series follows that logic across seven movements. We begin with rupture, the failure of planning to contain the future. We turn next to emergence, and to the patterns that become visible when the score no longer governs the performance. From there we examine collective intelligence, the living system through which many partial perceptions can become coherent action. We then enter uncertainty, where judgment must operate before proof is available, and temporal capability, where timing, pacing, sequence, and duration become materials of strategy. The final movements concern transition, the work of moving between systems, and regeneration, the capacity to renew what strategy has too often treated as expendable.
This opening essay will not resolve those later questions. Its purpose is to establish why they have become unavoidable. What has unraveled is the belief that planning can produce strategy, that strategy can be separated from action, and that analysis can remove the uncertainty inherent in consequential choice.
I · When planning became strategy
There was a time when strategic planning made persuasive sense. Postwar corporations grew across products, regions, and technologies. Capital-intensive businesses required long horizons. Markets appeared more bounded, industry structures more durable, and product life cycles slow enough to support extended forecasting. The boardroom could imagine itself as a concert hall, with executives conducting an orchestra of divisions and functions.
Everyone had a part. The plan supplied the score.
Igor Ansoff’s Corporate Strategy, published in 1965, helped codify this analytical settlement.[1] Strategy could be decomposed into decisions about products, markets, growth, and diversification. Formal methods promised to bring order to complexity. Forecasts established the future environment, analysis identified the best position within it, and programs translated that position into action. The promise was simple and seductive: if the process were sufficiently rigorous, the strategy would follow.
This promise solved a genuine problem. Large organizations cannot coordinate through inspiration alone. They must allocate capital, build facilities, develop people, negotiate dependencies, and make commitments that bind one part of the enterprise to another. Planning created a disciplined arena in which those commitments could be compared and reconciled. It made assumptions discussable and gave a temporal structure to collective work.
Over time, however, the apparatus acquired authority beyond its competence. A practice designed to support strategic judgment began to impersonate it. The language of planning and the language of strategy collapsed into each other. A strategic plan became a document, strategy became a cycle, and the quality of thinking was inferred from the polish and internal consistency of the output.
The underlying model separated conception from action. Senior leaders formulated. The organization implemented. Analysts gathered facts, planners assembled options, executives chose among them, and operators delivered the result. Knowledge was expected to travel upward in a clean form and decisions downward with their meaning intact. This hierarchy looked efficient because it removed the mess of discovery from the official account.
Reality was always less obedient. Markets were made through interaction rather than merely observed from above. Technologies changed the terms of competition while forecasts were still being approved. Customers used products in ways their creators had not intended. Frontline employees encountered information that could not be reduced to a dashboard without losing much of its significance. Strategy often appeared retrospectively as a pattern in action, even when the organization described it prospectively as a plan.
The planning system responded by adding detail. More analysis promised to reduce uncertainty. More targets promised to strengthen accountability. More milestones promised to protect execution. The interior of Hopper’s diner became brighter while the city outside continued to change.
How a method became an institution
Strategic planning did not acquire its influence through an intellectual argument alone. It became embedded in the institutional machinery of the corporation. Annual budgets, capital requests, board calendars, executive compensation, investor communication, and performance management converged around the same cycle. The plan became a place where many legitimate demands met: financial control, operational coordination, managerial accountability, and a public narrative about the future.
That convergence made planning difficult to question. A method can be revised when it fails. An institution defends itself through all the activities that depend on it. If the strategy process determines budgets, status, and promises to the board, disagreement with the plan is easily interpreted as a threat to coordination. The organization begins to select for people who can navigate the process, speak its language, and produce the evidence it recognizes.
The document then does more than describe a course of action. It creates a temporary political settlement. Growth aspirations are reconciled with capital constraints. Functions secure their initiatives. Business units preserve optionality. Senior leaders distribute disappointment carefully enough to maintain coalition. The resulting plan can be internally coherent because its real achievement is agreement among powerful participants. Whether that agreement constitutes an intelligent response to the external world is a separate question.
This helps explain the curious mixture of intensity and resignation surrounding annual planning. The process consumes enormous attention. Leaders debate assumptions, defend numbers, and negotiate priorities. Yet many participants know that a portion of the result is ceremonial. Forecasts will change, initiatives will accumulate, and exceptional decisions will be made outside the cycle. The official system remains because it performs governance work even when its strategic claims are weak.
The difficulty is that governance and discovery have different requirements. Governance seeks comparability, consistency, authorization, and control. Discovery seeks anomaly, variation, experimentation, and the freedom to change the question. Force both through one process and governance usually wins. It has deadlines, owners, templates, and consequences. Discovery arrives as an interruption.
This is also why adding a workshop on innovation rarely changes the strategic system. The workshop may generate excellent possibilities. Those possibilities return to capital criteria, operating metrics, and review forums designed for the known business. The organization celebrates divergent thinking at the edge and requires convergent justification at the center. New ideas learn to disguise themselves as familiar ones.
The great unraveling is therefore institutional as well as intellectual. It concerns the calendar, incentives, roles, and rituals through which planning became the operating system of managerial attention. A different understanding of strategy must eventually alter those arrangements. For now, it is enough to see that no conceptual correction can survive if the surrounding institution continues to reward the old category error.
Kodak and the knowledge that could not become action
Kodak carried the promise and failure of strategic planning through disruption inside the same company. In 1975, Kodak engineer Steven Sasson built the first self-contained digital camera. The company did not lack awareness of digital imaging. It possessed technical knowledge, capable people, patents, market access, and time. Its difficulty was more intimate: the new technology dissolved the economic logic that made the existing enterprise successful.
I understand this story differently because I once lived, in a very small way, inside Kodak’s business model. In 1990 I was an undergraduate at Occidental College in Los Angeles, carrying my father’s old Nikon. I loved photography. The economics of film created a constraint I felt directly. Darkroom equipment could be purchased once and used for years, and most schools already had it. Paper and chemicals were different. A student who wanted to shoot constantly, experiment, fail, and learn could consume an alarming quantity of both.
So I took a job at the college newspaper, The Occidental. The pay was terrible, perhaps a hundred dollars a week. What the job gave me was access to the darkroom and, more valuable still, an effectively unlimited budget for chemicals and Kodak paper. I went through a great deal of Kodak paper.
That recurring consumption was the engine. Cameras brought photographers into the practice. Film, paper, developer, fixer, processing, and printing made the economics compound. Each photograph participated in a physical and chemical system of value. Digital imaging did more than offer a better camera. It removed most of the consumables from photography and shifted value toward sensors, software, storage, networks, displays, and sharing.
Kodak could see the technology and still remain captive to the business model. Research on the company’s response describes a culture and structure that struggled to translate technical recognition into a sufficiently rapid reorientation.[2] The organization faced a conflict that no forecast could settle. To embrace the emerging system meant accelerating the decline of the system that funded the company, rewarded its people, defined expertise, and made its identity coherent.
The familiar telling makes Kodak a parable of blindness. That interpretation is too comfortable. Blindness suggests the remedy was better sight. Kodak’s leaders did see much of what was coming. The harder problem was that knowledge had to pass through incentives, capital commitments, professional identities, channel relationships, measures of success, and a narrative about what kind of company Kodak was. By the time a signal reached the strategic plan, it had been translated into the language of the existing enterprise.
The plan could therefore acknowledge a digital future while protecting a film-centered present. Each choice made sense locally. The resulting pattern was ruinous. This is one of strategy’s recurring tragedies: an organization may possess the relevant facts and remain unable to organize itself around what those facts require.
They knew the notes. They could not swing.
The phrase matters because the failure was neither ignorance nor simple incompetence. Kodak had competence. It had resources and foresight. It lacked a way to make the transition while the old form was still generating cashflow. That question belongs later in this series. Here, Kodak establishes the rupture: the separation of knowing from doing, and of planning from the organizational conditions through which strategy becomes possible.
Jazz Interlude #1: Duke Ellington – "Diminuendo and Crescendo in Blue"
Listen to the 1956 Newport Jazz Festival performance. The arrangement was written and the orchestra knew the score. Paul Gonsalves rose for what was expected to be a brief tenor saxophone solo. Twenty-seven choruses later, the crowd had changed the event and the event had changed the band. Ellington let the solo continue. His authority appeared as restraint, as the capacity to recognize that the performance had discovered something the arrangement could not have specified.
The recording adds a second lesson. Gonsalves had played into the wrong microphone, so Columbia later combined festival material with studio re-recordings. For decades, many listeners encountered a carefully repaired document of a night remembered for its emergence. The performance was real, and so was the institutional impulse to restore coherence after the fact.
The record you are hearing is an edit, and so is your strategy narrative.
II · Strategy is a way of knowing
Analysis and synthesis do different work
A strategy is not discovered by arranging enough facts in the correct order. Facts are indispensable, but they do not announce which pattern matters, which possibility deserves commitment, or what an organization should risk in response. Analysis can divide a problem, test a claim, compare economics, and trace consequences. Strategy must do something different with that knowledge. It must compose a provisional whole.
This is the distinction Henry Mintzberg made with unusual clarity: “Strategic planning isn’t strategic thinking. One is analysis, and the other is synthesis.”[1] The sentence is not an argument against rigor. It is an argument about the limits of method. Evidence can reveal that customer behavior is changing. It cannot, by itself, determine whether the change is temporary or structural, whether it favors an adjacent move or a new business model, or whether the organization should defend its position, leave it, or redefine the field.
Strategic knowing therefore combines kinds of intelligence that organizations often separate. It uses hard data and embodied experience, historical pattern and imaginative conjecture, economic logic and social meaning. It draws on what can be measured without discarding what has not yet become measurable. The work is interpretive before it is programmatic. Someone, usually more than one someone, must connect fragments into a view of what may be happening and what the organization could become in relation to it.
The word synthesis can sound mysterious, as though strategy depends on an inspired individual seeing what others cannot. Sometimes insight does arrive with startling compression. More often it forms through a disciplined conversation: a weak signal from the field, a customer behavior that does not fit the segmentation, a technical possibility, an economic anomaly, a memory from another industry, a question that reorganizes the evidence. The strategic act is not merely noticing each element. It is creating a relationship among them that was not previously visible.
A useful strategy process must protect this movement from fragments to form. It should ask not only, What do we know? but also, What might these things mean together? What accepted category no longer holds? What becomes possible if we interpret the evidence differently? These are not softer substitutes for analysis. They are the questions that make analysis strategically consequential.
Knowing cannot be detached from the work
The quality of strategic judgment depends on where knowledge is allowed to originate. Formal planning favors information that travels cleanly: market shares, margins, forecasts, capacity figures, survey scores. The closer knowledge is to lived experience, the less obedient it becomes. A salesperson hears hesitation that has not reached the churn data. A service employee sees customers invent a use the product team never intended. An engineer understands that a technical limitation is about to become negotiable. A community experiences a cost that the operating model classifies as external.
Rich knowledge carries context, timing, emotion, tacit skill, and unresolved contradiction. By the time it has been abstracted for executive review, the detail that made it strategically interesting may have disappeared. Detachment does not remove perspective from the process. It grants authority to the perspectives that can survive formalization.
This is one reason planning fails most dramatically at moments of discontinuity. Prediction, detachment, and formalization begin to support one another. A forecast makes distance appear safe because the environment seems knowable. Distance makes the model appear objective because experience has been stripped from the account. Formalization gives uncertainty a precise-looking range. The plan becomes most internally coherent at the point where its contact with reality is most fragile.
Strategy forms closer to the work than the planning hierarchy usually admits. It appears when a local adaptation reveals a repeatable pattern, when an experiment changes the governing question, or when several partial observations can be heard together. The task of leadership is not to surrender judgment to every local perception. It is to build channels through which strategically important experience can reach the places where commitments are made without being flattened on the way.
Planning begins after insight, and returns to test it
Once a strategic direction has begun to form, analysis and planning become essential. They can expose contradictions, estimate consequences, identify dependencies, and reveal what the emerging logic would require. They can ask what must be true, which assumption carries the greatest consequence, what evidence has been ignored, and where the organization is already behaving as if another strategy were present.
Planning can then translate direction into commitments: budgets, capabilities, sequences, decision rights, thresholds, and programs. Mintzberg called this strategic programming, a useful phrase because it gives formal planning an exact and honorable role. Planning articulates and elaborates a strategy; it does not manufacture one. Its purpose is to broaden consideration before choice, to coordinate action after choice, and to keep the logic of the choice available for revision.
The planner’s posture changes accordingly. The planner is not the author of the future but a disciplined interrogator of the organization’s claims. What are we assuming about customers, competitors, technology, and ourselves? Where does the evidence disagree with the story? Which commitments would make this direction real? What would we stop? What would cause us to reconsider? The questions keep analysis in living contact with action.
Jazz Interlude 02 · Charles Mingus, “Haitian Fight Song”
Mingus begins alone. The bass states a line with enough force to establish identity, then the ensemble enters and gives the line a larger life. The composition does not disappear when the other musicians arrive. It becomes a field of relationship: written material, personal voice, political feeling, rhythmic pressure, and collective response remain distinct while making one performance.
That is the useful place of a plan. It gives the players something worth entering. It establishes enough form for difference to become meaningful. The music is completed through listening, conflict, repetition, and development.
A strategy should be strong enough to organize action and open enough to acquire intelligence from action.
III · The organization must become a listening system
Orthodoxy is built into the operating model
Even a strategy process that respects synthesis can hear only what the organization permits to become audible. In many enterprises, the people with the greatest investment in the existing model also hold the authority to judge which departures from it are credible. Gary Hamel’s compact diagnosis remains useful: “The bottleneck is at the top of the bottle.”[2]
The problem is not simply that senior leaders are conservative. They have been selected, educated, and rewarded for understanding the current business. They carry its history, relationships, and economic logic. Those are necessary forms of intelligence. They are also a concentrated exposure to the past. When mastery of the existing system becomes the principal credential for imagining the next one, unfamiliar possibilities must seek permission from the people whose status the familiar system created.
Orthodoxy rarely calls itself orthodoxy. It appears as maturity, focus, brand protection, operational realism, respect for the core, or insistence on evidence. Each term can express legitimate stewardship. Together they can become an immune system against novelty. A new possibility is required to demonstrate the confidence, data, and predictable return of an established business before it receives access to the experiments through which those qualities might be earned.
The annual strategy meeting can therefore contain serious debate while leaving the governing frame untouched. The participants share similar incentives. The evidence arrives in categories derived from the current portfolio. The conversation begins with the businesses the organization already owns and concludes by allocating resources among them. The future is invited into a room whose grammar permits it to speak only in the language of the past.
Distributed perception must reach commitment
Strategic intelligence is distributed unevenly across the organization. New employees notice conventions that veterans no longer see. People at the geographic or organizational edge encounter emerging behavior earlier. Technical specialists perceive changes before their commercial significance is clear. Frontline teams see where the official process is being repaired through unofficial practice. People poorly represented by the dominant model often recognize its exclusions first.
A more plural strategy process is therefore an epistemic requirement, not merely an inclusion initiative. The organization needs greater variety in what can be noticed, interpreted, and proposed. But wider voice is not enough. Suggestion portals, listening tours, innovation contests, and energetic workshops can collect imagination while leaving the structure of commitment unchanged. Participation becomes theatre when ideas have no protected access to attention, experimentation, sponsorship, or capital.
Strategic possibility must be able to acquire consequence. It needs a route into an experiment, a sponsor able to cross boundaries, and a forum in which evidence can alter senior judgment. Without those conditions, the organization teaches people that speaking is permitted and movement is not.
Resource allocation is where orthodoxy becomes material. Established businesses arrive with customers, data, cash flow, familiar measures, and leaders whose reputations are legible. Emerging possibilities arrive with assumptions, unfamiliar indicators, and less political capital. Apply identical criteria to both and the existing business wins through the design of the comparison. The outcome looks like neutral discipline because the preference has been embedded upstream.
A living strategy system uses asymmetric commitments. An early possibility may receive a small amount of protected capacity in exchange for explicit learning. Its first obligation is not to prove that it can scale but to reduce a consequential uncertainty. The established business, meanwhile, should not receive indefinite investment merely because its evidence is historical and abundant. It must show that continued commitment serves the future rather than extends the authority of the past.
Authority must remain capable of being changed
Distributed strategy does not mean that every idea is equally sound, every decision is collective, or accountability dissolves into participation. Listening widens the field of possibility; leadership must still integrate perspectives, make choices among incompatible claims, allocate resources, and accept responsibility for consequences.
The character of authority changes, however. It becomes less proprietary and more compositional. A leader does not need to originate every important idea. The leader must create the conditions in which important differences can surface, judge what deserves commitment, and explain the logic by which the field was narrowed. The legitimacy of the decision depends partly on whether the decision process was capable of being changed by what it heard.
This is the organizational discipline that Kodak lacked at the decisive moment. Digital imaging was not merely another technology to be evaluated. It challenged the film-centered organization’s authority to define photography, value, expertise, and economic performance. The signal existed. The invention existed. What failed was the system through which that knowledge might have reorganized commitment.
The lesson is more unsettling than the familiar warning to listen to outsiders. Every established enterprise develops guardians of what has worked. Strategy requires a designed passage by which people whose identities and prospects are less dependent on the existing answer can revise the question itself.
IV · Strategy is a disciplined wager
From controllable activity to consequential choice
Planning becomes especially seductive when leaders confront a future they cannot control. Initiatives, headcount, capital, schedules, and costs can be itemized and assigned. Customer preference, competitive response, technological maturation, and social permission cannot. The first set of variables produces the reassuring sensation of management. The second contains the actual wager on which value depends.
A strategic plan can therefore become a sophisticated form of anxiety management. It fills the future with activities while avoiding the choice that would give those activities meaning. Roger Martin names this the “comfort trap” and puts the underlying demand plainly: “True strategy is about placing bets and making hard choices.”[3] The purpose is not to glorify risk. It is to stop describing uncertainty as though it were an implementation detail.
A genuine strategy identifies a field in which the organization will act and a theory of how it will create distinctive value there. It establishes where to play and how to win, then aligns capabilities, management systems, and resources with that claim. The choices create exclusion. They reveal where the organization will not play, which attractive possibilities it will allow to pass, and what familiar work will no longer command priority.
That exclusion is one reason portfolios of initiatives are so common. A long list permits every constituency to remain represented. It can be financially reconciled without becoming strategically coherent. Costs are especially comforting because the organization can largely decide whether to incur them. Revenue is conferred by customers. A company can choose to reduce a budget; it cannot choose to be preferred. Cost discipline is necessary, but it cannot substitute for an external theory of value.
Capability language can create a similar refuge. Becoming excellent at innovation, data, service, agility, or artificial intelligence may support a strategy. It is not a strategy until the capability is joined to a particular customer, need, position, and logic of advantage. Otherwise the organization has converted what it knows how to improve into a reason not to choose.
Make the logic vulnerable to evidence
To call strategy a wager is not to celebrate intuition without accountability. A responsible wager makes its logic visible. It states what must be true about customers, economics, competition, technology, regulation, partners, and the organization’s own ability to act. It distinguishes assumptions that can be accepted provisionally from those that should be tested and from those so consequential that commitment should wait.
The choices must fit. An organization cannot credibly promise an intimate customer experience while designing every process for standardized volume. It cannot claim speed as an advantage while requiring decisions to climb several layers of approval. It cannot enter an ecosystem business while measuring value only inside the boundary of the firm. Strategy becomes legible in the coherence among its claims, capabilities, systems, and allocation of attention.
That coherence should make the strategy easier to challenge, not harder. If customers do not value the proposed difference, if the economics deteriorate at scale, if the required capability cannot be developed, or if a competitor changes the field, the governing logic needs revision. The organization can learn because it knows which belief the evidence bears upon. A plan containing dozens of initiatives often lacks this property. Every result can be explained by another moving part, leaving the central thesis protected from a decisive test.
Analysis is most valuable when directed toward doubt rather than reassurance. The question is not, How can we prove the plan? It is, Which uncertainty carries the greatest consequence, and what is the least costly action that would teach us something real about it? This converts uncertainty into structured inquiry without pretending to convert it into certainty.
Choice also has moral and political content. Strategy distributes opportunity, risk, attention, and sacrifice across customers, employees, partners, communities, and time horizons. The neutral language of initiatives can conceal those distributions. The language of choice makes them harder to evade. Strategic responsibility includes asking who benefits if the wager succeeds, who bears the loss if it fails, and whether those people had any meaningful presence in the reasoning.
Commitment without closure
The correction to overplanning is not perpetual openness. Organizations learn through commitment as well as observation. A choice mobilizes attention, develops capability, provokes response, and produces evidence that spectatorship cannot. Waiting for a pattern to become obvious can be another way of asking the future to remove the burden of judgment.
The necessary discipline is commitment without closure. Leaders make a consequential claim, organize enough resources to test and enact it, and remain capable of revision when the field answers. A strategic choice should be firm enough to generate information and provisional enough to be changed by that information.
Jazz holds this apparent contradiction in ordinary practice. A musician listens for the direction of the ensemble and still has to play a note. Endless receptivity becomes silence. Endless assertion becomes deafness. The phrase is a commitment: once sounded, it changes what the others hear and what can follow. It is also an invitation, incomplete until the ensemble responds.
Jazz Interlude 03 · Ornette Coleman, “Free Jazz”
The title tempts the casual listener to hear an absence of structure. The performance offers another reality: two quartets, sustained attention, instrumental roles, recurring materials, and a demanding social discipline. Freedom is carried by musicians whose choices remain answerable to the whole.
Organizations often alternate between two mistakes. They write the performance in advance, or they call every sound emergence. Coleman offers a stricter possibility. Freedom acquires meaning inside relationship, and relationship becomes audible through committed acts.
V · The grammar of living strategy
Form, voice, listening, and response
Strategy is a practice of composing coherent action under conditions of partial knowledge and unequal power. It requires synthesis because evidence does not organize itself. It requires distributed perception because no center can see the whole. It requires choice because possibilities do not become strategy until resources and consequences attach to them. It requires revision because the organization’s actions alter the field it is trying to understand.
Jazz gives these requirements more than a metaphor. It offers a working grammar. Form establishes identity, direction, boundary, and expectation. Voice allows a participant to contribute something irreducibly situated rather than merely reproduce the score. Listening makes each contribution responsive to what the system is becoming. Commitment gives a phrase consequence by placing it in time. Response receives that consequence, extends it, contests it, or redirects the performance.
None of these elements is sufficient alone. Form without voice produces compliance. Voice without listening produces collision. Listening without commitment produces drift. Commitment without response becomes command. Response without memory dissolves continuity. Coherence arises from their movement together.
This is why jazz is both a system and a language. As a system, it distributes attention and agency among interdependent participants. Each musician acts locally while remaining responsible to an emergent whole. The rhythm section, harmonic field, melodic material, venue, audience, and history create constraints that shape what can happen without fully determining it. As a language, jazz carries shared conventions through which difference becomes intelligible. A musician can quote, delay, substitute, reharmonize, leave space, or disturb the pulse because the others understand enough of the grammar to recognize the move and answer it.
Organizations also act through systems and languages. Their structures distribute authority; their measures direct attention; their routines establish tempo; their categories determine what can be said; their stories carry memory; their budgets make some phrases possible and silence others. A strategy process cannot become more adaptive merely by instructing people to improvise. The organizational grammar must allow signals to travel, differences to remain legible, commitments to be made, and responses to alter what happens next.
Coherence is composed, not imposed
Traditional planning locates coherence in the document. Goals align with initiatives, initiatives with measures, measures with budgets. This is useful, but it is a representation of coherence rather than coherence itself. Living coherence appears in the pattern of choices the organization can sustain and revise across time.
The distinction matters because uniformity can masquerade as alignment. Everyone can repeat the priorities while cross-unit dependencies remain unresolved. Measures can cascade while local teams conceal the adaptations required to meet them. A system facing a changing environment needs shared direction and meaningful variation, common language and the capacity to challenge what the language excludes.
In jazz, the musicians do not produce coherence by playing the same thing. They hold enough common form to make difference consequential. The drummer may displace the pulse without destroying time. The soloist may move outside the harmony while allowing the ensemble to hear the relation. The bassist may simplify when the texture becomes crowded. Coherence is continually composed through attention to what the whole requires now.
The organizational analogue is not consensus. It is coordinated difference. Teams need enough strategic clarity to make locally intelligent decisions and enough connection for those decisions to inform the larger system. Leaders need enough authority to resolve incompatible commitments and enough openness to recognize when an adaptation at the edge has discovered a better way. The strategy must travel as a logic, not merely as a set of instructions.
Planning as score, memory, and rehearsal
Formal planning still belongs inside this grammar. Research has found positive relationships between strategic planning and organizational performance, particularly when planning is adapted to context and connected to learning and implementation.[4] The evidence supports neither worship nor abolition. Planning creates value when it provides focus, coordination, preparation, shared assumptions, and institutional memory.
The score is useful because musicians cannot renegotiate every convention at every moment. It preserves decisions, communicates structure, and makes complex coordination possible. Rehearsal builds capability before the performance places it under pressure. A chart can remind the ensemble where the bridge begins or which figure returns. None of this confuses the chart with the music.
The phrase beyond planning therefore names an enlargement, not a rejection. We retain the score and place it within the performance. We retain analysis and place it within judgment. We retain commitments and place them within a system capable of learning. Planning becomes more valuable when it no longer has to pretend that describing the future is the same as creating a capacity to meet it.
VI · Strategy happens in action
Execution is not downstream
The most durable fiction in conventional planning is the clean handoff from formulation to execution. Leaders decide what should happen. The organization carries it out. If results disappoint, the strategy remains conceptually intact while implementation absorbs the blame.
This separation makes the plan difficult to falsify and the organization easy to accuse. People were insufficiently aligned, disciplined, focused, or accountable. The players failed; the score returns next year with revised targets.
Execution can certainly fail. Capabilities may be weak, priorities confused, dependencies unmanaged, or leadership inconsistent. The alibi begins when implementation is treated only as obedience and never as evidence. A strategy cannot be judged apart from the organization and environment through which it must become real. If the choice cannot be understood, enacted, or adapted by that system, the defect may sit in the strategy, the system, or the relationship between them.
The familiar call for alignment often aims at the wrong problem. Research by Donald Sull and his colleagues found that managers reported relatively strong vertical reliability and goal clarity, while cross-unit coordination and adaptability were much weaker.[5] Organizations can become highly aligned around a plan at the very moment they need to negotiate dependencies, preserve local judgment, and revise assumptions. Perfect alignment around a mistaken model accelerates failure.
Strategic coherence is not uniformity. A changing environment requires differences in perception, local experimentation, and channels through which disconfirming information can travel. The task is to align people around a governing intent and logic while preserving the capacity to detect when that logic no longer fits.
Read the commitments, not the declarations
An organization’s enacted strategy can be read in its allocation of money, people, attention, authority, and time. The official plan may emphasize innovation while capital approval protects the existing business. Leaders may celebrate customer intimacy while incentives reward product volume. A transformation may be declared urgent while the strongest people remain assigned elsewhere.
These inconsistencies are commonly described as execution gaps. They are more revealing than that. They are the strategy the organization is actually pursuing. Budgets and calendars are not downstream from strategy; they are among the media through which strategy becomes material. Decision rights, promotion criteria, meeting agendas, and measures tell people which claims carry consequence and which remain ceremonial.
This is why implementation cannot wait until thinking is finished. Action exposes hidden constraints, incompatible assumptions, political resistance, missing capability, and consequences that were invisible in abstraction. It also generates new possibilities. A local workaround may reveal a better operating model. A customer response may redefine the value proposition. A failed experiment may show that the original question was wrong. Action is part of strategic knowing.
A useful integrated standard appears in Richard Rumelt’s kernel of good strategy: diagnosis, a guiding policy, and coherent action belong to one logic.[6] The value of the formulation lies in the connection. Action should express the diagnosis and policy, while the results of action return information to both. If implementation repeatedly fails, leaders must investigate capability and coordination. They must also reopen what they believed about the challenge and the approach.
Learning without alibi
A useful strategy review therefore asks more than whether milestones were met. It asks what the pattern of action now reveals. Which assumptions have strengthened? Which have weakened? Where did the organization have to depart from the plan, and what intelligence did the departure contain? Which commitments remain coherent, which need revision, and which should end?
This does not make commitment disposable. Learning requires enough persistence for reality to answer. Nor does it make every deviation virtuous. Some variance is error, avoidance, or poor execution. The discipline lies in distinguishing among failure of effort, failure of capability, failure of coordination, and failure of the governing idea. A review system that presumes the idea is sound cannot learn strategically.
Jazz makes the point without abstraction. A chart can indicate melody, harmony, tempo, and form. It cannot specify the performance because the performance consists of responsive acts. The drummer’s placement changes the soloist’s options. The bassist can make a harmony feel settled or suspended. A phrase gains meaning from what preceded it and alters what can follow. Composition and performance remain distinct, but neither is complete without the other.
Jazz Interlude 04 · Miles Davis, “Pharaoh’s Dance”
Bitches Brew feels like an eruption captured in real time. It was also constructed through editing. Teo Macero cut, repeated, and assembled passages from the sessions into the released work. Improvisation generated material; editorial judgment shaped duration and form.
Keep both levels in view. The musicians could not have planned the final record in advance. The producer did not merely document whatever happened. Strategy needs generative action and retrospective composition, then another round of action informed by what the organization has heard.
VII · What planning is still for
From author to instrument
The critique becomes useful when it changes practice. Planning should retain the work it performs well and relinquish the authority it cannot justify.
Planning is well suited to translating strategic choices into coordinated commitments. It can identify dependencies, sequence investments, test capacity, establish thresholds, and expose contradictions among objectives. It can make assumptions visible and create regular occasions to examine whether they still hold. It can preserve institutional memory in organizations otherwise condemned to rediscover the same lessons.
Planning also supports preparedness. Scenario work, contingency design, reserves, options, and rehearsals can increase the range of conditions through which an organization remains viable. The objective is not to predict the one future that will occur. It is to notice which commitments are robust across several plausible futures and which depend on a fragile assumption.
Analysis remains indispensable. It should widen perception, discipline claims, and clarify consequences. It should help leaders understand unit economics, customer behavior, system dynamics, capability gaps, and competitive response. Its role is to make judgment more responsible, not to make judgment disappear.
Finally, planning can program strategy after real choices have been made. It can give form to commitments, convert intent into resource decisions, and establish the cadence through which progress and evidence are reviewed. The distinction from traditional planning is that revision is designed into the system. A review asks more than whether milestones were met. It asks what has been learned, which assumptions changed, what the current pattern of action reveals, and whether the strategy still deserves commitment.
This is planning after the fall: more modest in its claims, more intimate with action, and more valuable because it no longer has to pretend to create the future by describing it.
A practical test
The next time a strategic plan is presented, five questions can reveal whether it serves strategy or substitutes for it.
What consequential choice does this plan express? If every attractive priority remains included, the document may be a portfolio of aspirations rather than a strategy.
Which uncertainty cannot be removed before we act? If the plan contains only controllable variables, it may have avoided the external wager on which value depends.
Whose knowledge could overturn the governing diagnosis? If the answer contains only the people who wrote the plan, the process has probably confused authority with perception.
What evidence would cause us to revise or stop? If no plausible finding can alter the commitments, the plan is doctrine. If every result permits a pivot, there is no commitment to test.
Where do resources contradict the stated strategy? Budgets, calendars, incentives, and appointments disclose priorities with greater fidelity than language.
These questions do not create strategy. They clear away some of the structures that prevent it.
VIII · The first movement of a larger work
Rupture is a beginning
The collapse of planning’s authority can feel like a loss of discipline. Organizations know the old process is inadequate and continue performing it because no alternative has acquired equal legitimacy. The calendar remains. The templates remain. The forecasts become less credible and more elaborate. People learn to present uncertainty as a narrow range around a preferred answer.
Rupture is the moment when that performance can no longer contain experience. The city outside becomes too dark, too active, and too consequential to ignore. A plan misses a discontinuity. A local adaptation outperforms the approved model. A crisis reveals that the formal organization and the working organization are different systems. A younger technology, business model, or social expectation changes the terms faster than the planning cycle can absorb them.
The temptation is to replace the old certainty with a new method that promises certainty under another name. Agile planning, dynamic strategy, artificial intelligence, real-time dashboards, and continuous transformation can all be useful. Each can also become a brighter light inside the same diner if the underlying theory of strategy remains unchanged.
The alternative begins by developing capacities rather than installing a single process. Article 2 turns to emergence, asking how organizations recognize patterns while they are still becoming visible. Article 3 examines collective intelligence, and the conditions under which a living system can integrate distributed perception without erasing difference. Article 4 enters uncertainty, where leaders must remain capable of judgment amid ambiguity, conflict, and constraint. Article 5 treats time as material, examining pacing, sequence, rhythm, and the unequal clocks through which strategy moves. Articles 6 and 7 carry the argument through transition and regeneration, where the task becomes moving between systems and renewing the conditions on which durable value depends.
This sequence is cumulative. Emergence without collective intelligence remains anecdotal. Collective intelligence without negative capability collapses under anxiety. Judgment without temporal capability mistimes its interventions. Transition without regeneration reproduces the conditions that made transition necessary. The series moves from the failure of a governing model toward a richer practice of strategic life.
From score to living strategy
The jazz metaphor should not be pushed into a false opposition between classical music and improvisation. Orchestral performance also involves interpretation, timing, listening, and adjustment. Jazz itself depends on composition, memory, convention, and formidable technique. The useful contrast concerns where completeness is imagined to reside.
In the planning tradition, the strategy is treated as complete before action begins. Performance is successful to the extent that it reproduces intention. In a living strategy, intention establishes direction and constraint while action continues to generate knowledge. The strategy is expressed through an evolving pattern of choices whose coherence must be continually composed.
This demands more discipline, not less. Musicians can improvise together because they have studied form, trained perception, developed technique, and learned how to make space for one another. Organizations that wish to move beyond planning need an equivalent practice. They must learn how to notice weak signals, distribute authority without dissolving accountability, hold uncertainty without rushing to false certainty, and revise commitments without making commitment meaningless.
They must also learn to hear power. Which voices are amplified? Which risks are borne by people absent from the room? Which histories are treated as data and which are treated as noise? Collective improvisation is never socially neutral. The quality of the music depends on the conditions under which people can enter, challenge, support, and transform the shared form.
Jazz Interlude 05 · Max Roach and Abbey Lincoln, “Triptych: Prayer / Protest / Peace”
The work moves through states that cannot be reduced to a single mood or message. Lincoln’s voice and Roach’s percussion carry suffering, refusal, and the possibility of release. Structure does not domesticate the force of the material. It gives the force a passage through time.
This is the larger promise of strategy. Coherence does not require the suppression of rupture. It can arise through the disciplined transformation of rupture into attention, choice, and collective movement.
Coda · The courage to leave the light
Strategic planning offered a luminous room. It made complexity discussable and large-scale action possible. We should preserve those achievements. We should also recognize the boundary of the light.
Mintzberg shows why analysis cannot manufacture synthesis and why planning must return to a supporting role. Hamel shows how hierarchy and orthodoxy narrow the range of futures an organization is permitted to imagine. Martin shows why planning so easily becomes a refuge from choice, uncertainty, and the external test of value. Together they do more than dismantle a method. They reveal the capabilities that method allowed organizations to neglect.
The next practice of strategy will still use plans. It will use them as maps drawn by travelers, provisional records of terrain encountered and commitments made. It will value a plan’s capacity to orient action while expecting reality to revise the map. It will understand that the organization does not stand outside the system it seeks to navigate. Its actions alter the field, and the field answers.
Hopper’s figures remain inside the glass. The city is present as darkness, reflection, and unanswered possibility. For an organization, the task is not to extinguish the light or romanticize the street. It is to recover the ability to move between interior order and exterior reality, carrying enough structure to act and enough openness to be changed by what it finds.
The unraveling is therefore an invitation. Once the plan releases its claim to be the strategy, the work of strategy can begin.
My name is Ozymandias, King of Kings;
Look on my Works, ye Mighty, and despair!
Nothing beside remains. Round the decay
Of that colossal Wreck, boundless and bare
The lone and level sands stretch far away.
Percy Bysshe Shelley, “Ozymandias” (1818), lines 10–14
It is time to swing.
Next in the Series:
Article 2: Patterns in the Storm: Recognizing Emergent Signals
Listening Notes · A playlist for the unraveling
1. Duke Ellington - "Diminuendo and Crescendo in Blue" (1956, 14:39)
Album: Ellington at Newport
Lesson: Structure overwhelmed by emergence
2. Charles Mingus - "Haitian Fight Song" (1957, 12:10)
Album: The Clown
Lesson: Organized rage against systems
3. Ornette Coleman - "Free Jazz" (1961, 37:03)
Album: Free Jazz: A Collective Improvisation
Lesson: Complete abandonment of structure
4. Miles Davis - "Pharaoh's Dance" (1970, 20:05)
Album: Bitches Brew
Lesson: Categories dissolving
5. Cecil Taylor - "Enter Evening" (1966, 11:00)
Album: Unit Structures
Lesson: Percussion destroying harmony
6. Albert Ayler - "Ghosts" (1964, 10:03)
Album: Spiritual Unity
Lesson: Primitive return
7. John Coltrane - "Ascension" (1966, 40:23)
Album: Ascension
Lesson: Collective breakthrough
8. Sun Ra - "The Magic City" (1966, 27:44)
Album: The Magic City
Lesson: Alternative paradigms
Coda: Keith Jarrett - "Part I" from The Köln Concert (1975, 26:01)
Bridge: From chaos, new order emerges
References
Christensen, C.M. (1997). The Innovator's Dilemma: When New Technologies Cause Great Firms to Fail. Boston: Harvard Business School Press.
De Geus, A. (1988). Planning as Learning. Harvard Business Review, March-April, 70-74.
Hamel, G. (1996). Strategy as Revolution. Harvard Business Review, July-August, 69-82.
Martin, R.L. (2014). The Big Lie of Strategic Planning. Harvard Business Review, January-February, 78-84.
Meadows, D.H. (1999). Leverage Points: Places to Intervene in a System. Hartland, VT: The Sustainability Institute.
Mintzberg, H. (1987). Crafting Strategy. Harvard Business Review, July-August, 66-75.
Mintzberg, H. (1994). The Rise and Fall of Strategic Planning. New York: Free Press.
Pascale, R.T. (1984). Perspectives on Strategy: The Real Story Behind Honda's Success. California Management Review, 26(3), 47-72.
Rumelt, R.P. (2011). Good Strategy Bad Strategy: The Difference and Why It Matters. New York: Crown Business.
Senge, P.M. (1990). The Fifth Discipline: The Art and Practice of the Learning Organization. New York: Doubleday.
Sull, D., Homkes, R., & Sull, C. (2015). Why Strategy Execution Unravels—and What to Do About It. Harvard Business Review, March, 57-66.
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