Why Organizations Still Plan Like It Is 1965

Organizations keep planning as if certainty still exists, investing in elaborate forecasts and strategies based on the belief that the future can be controlled—despite mounting evidence that unpredictability now rules.

As the pace of change increases, many organizations still adhere to traditional planning tools, even as the ground shifts beneath them.

The Illusion of Detailed Planning

Traditional strategic planning operates on a seductive fiction: that organizations are machines, and futures are compositions to be written in advance. The corporation imagines itself as an orchestra, with leadership as the composer-conductor, writing every note, anticipating every dynamic shift, controlling every voice. The plan becomes a score, and in many cases, it is exhaustive and only prescriptive, total.

I have prepared many sales forecasts and instructed my sales teams to do the same. We were working long hours, mapping many data points and predicting what the next quarter would look like. We gave it to Marketing and the field sales force so they now had a plan and an in-depth structure to work with.

The problem is that most of the plans cannot be fully translated into daily sales negotiations.

This model of a detailed, structured plan assumes three conditions that no longer exist:

Stability of cause and effect. Strategic planning presumes that if we do X, Y will follow with reasonable predictability. It assumes linear causality in a world that has become a complex adaptive system, where small inputs produce disproportionate outputs, and where feedback loops create emergent behaviors no one designed.

Sufficient planning horizons. The industrial model was built for environments where change moved at the speed of capital investment—factories, supply chains, product cycles measured in years. Today, a “disruptive technology” can go from concept to market dominance in eighteen months. By the time your five-year plan reaches the implementation phase, the battlefield has relocated.

Centralized omniscience. The plan assumes that those at the top possess superior information and perspective. But in exponential environments, the front-line worker often sees the incoming wave before the executive—yet their observations are trapped beneath layers of implementation timelines and approval hierarchies, waiting for “the plan” to catch up.

The result? Organizations become more invested in defending rigid plans than in adapting to change. Rather than tools, plans turn into political shields. When reality upends these plans—and it always does—leaders must either confront their obsolescence or try, often destructively, to bend reality to fit. Most choose the latter, with severe consequences.

The Logic of Improvisation

A jazz group enters a performance with almost nothing: a key signature, a tempo, a chord progression, perhaps a melody to serve as a shared reference point. No one has written out what will happen. There is no score dictating the trumpeter’s note choices in measure 47, no instruction manual for how the drummer should respond when the pianist modulates unexpectedly.

What emerges is not chaos but a responsive order created in real time.

Minimal structure as maximum flexibility. The jazz ensemble agrees on just enough to coordinate—the “form” of the tune, the roles (who solos when), and the basic harmonic framework. These constraints are not limitations; they are enabling conditions. They provide just enough shared understanding that musicians can make independent decisions that still cohere. The structure doesn’t prescribe behavior; it makes collaboration possible without constant negotiation.

Distributed intelligence. In jazz, there is no single conductor orchestrating every moment. Leadership rotates. When the saxophonist takes a solo, they lead; the rhythm section supports. Then the roles reverse. Authority is situational, emerging from whoever has the clearest read on where the music needs to go right now. The ensemble continuously self-organizes around the most relevant information source in each moment.

Embracing error as information. When a jazz musician plays a “wrong” note, they don’t stop the performance to consult the plan. They lean into it—they repeat it, transform it, make it intentional, weave it into what comes next. Error isn’t failure; it’s unexpected data. The system treats surprises as opportunities for innovation rather than deviations requiring correction.

Retrospective sense-making. Jazz musicians don’t know in advance what their performance will sound like. They discover the shape of the music by playing it. Meaning emerges through action, not before it. They are constantly interpreting the recent past to inform the immediate future, operating in rapid feedback cycles that planning-based systems cannot match.

When I was a young teenager, I played the piano extensively and practised for hours every afternoon. I played in a small Jazz band and in a big band. Sometimes I just couldn't practise enough the Jazz pieces we had to play in many concerts, because the huge classical themes I had to practise were too much for me. But because I knew the basic rhythm, patterns, and rules of jazz harmony with all keys, I was able to improvise.

Improvisations and the ability not to stick rigidly to a plan are among the most important skills you need for every business project. The key takeaway: optimizing outcomes relies more on adaptability and responsiveness than on predicting or controlling every outcome in advance.

The Score You Cannot Define

Many corporate cultures discourage improvisation. Decades of reinforcing compliance and penalizing deviations have made adherence to “the plan” the norm.

Operating like a jazz ensemble requires more than adopting new vocabulary. It demands a philosophical reorientation around three principles:

Launch a direction, not a destination. Leadership’s job is not to write the score but to establish the “key” and “tempo”—the purpose, principles, and boundaries within which teams improvise. This is harder than it sounds, because it requires clarity about what matters (values, strategic intent) and humility about what cannot be known (the specific path forward). It means accepting that you cannot control outcomes, but only shape conditions.

Cultivate an organization that accepts deep listening. Jazz musicians survive uncertainty through radical attentiveness—they listen not just to what has been played, but to what wants to be played next, to the spaces between notes, to the emotional tenor of the room. Organizations must build equivalent capacities: frontline teams empowered to surface signals, cross-functional forums where weak data is taken seriously, and cultures where “I noticed something weird” is treated as valuable intelligence rather than noise.

Rotate your authority with a new context. The person who leads the Monday meeting may not be the person best positioned to lead the Friday decision. Jazz ensembles understand this instinctively—whoever has the clearest musical idea at any moment takes the lead. Corporations must develop similar fluidity, which requires both psychological safety (so people feel safe stepping forward and stepping back) and shared competence (so everyone can play multiple roles).

Improvisation demands abandoning the false comfort that someone knows and controls the outcome. Despite claims of agility, most organizations remain wedded to outdated leadership models predicated on prediction.

It terrifies us because it means admitting that the CEO does not, in fact, know where the company will be in five years. It means accepting that the frontline worker may understand the problem better than the strategy consultant. We need to build organizations where control is distributed, where plans are provisional, where authority flows to whoever holds the most relevant information in this moment, not whoever holds the highest title.

It means designing for a world where not knowing is the permanent condition, where the appropriate response to exponential change is not better forecasting but better sensing, not tighter planning but faster learning.

Most of all, it means confronting the possibility that our entire conception of leadership, as the capacity to envision and impose a predetermined future, has become obsolete.

In the end, we come back to the jazz ensemble: with only a few shared agreements and the courage to just start playing. What would your organization sound like if you gave it permission to improvise, and what do you fear so much that you might discover if you did?