Strategy in an Age of Radical Uncertainty: A Dialogue Report

In a thought-provoking dialogue hosted by Paul Barnett, founder of the Enlightened Enterprise Academy, included four leading thinkers in management, economics, systems science, and strategy came together to explore the relevance and future of strategic thinking in an era defined by complexity, unpredictability, and radical change. The conversation featured Henry Mintzberg, John Kay, Mike Jackson, and Andrew Firth, each bringing a unique perspective shaped by decades of experience and scholarship. Anchored around six core questions posed by Barnett, the dialogue offered a penetrating analysis of the challenges and opportunities of strategic practice in an age of radical uncertainty.

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1. What is radical uncertainty?

John Kay introduced the concept of Radical Uncertainty as developed in his book (co-authored with Mervyn King), defining it as the kind of uncertainty that cannot be reduced by gathering more data or assigning probabilities. Unlike risk, which is measurable, radical uncertainty involves unknown unknowns and the unpredictability of human behaviour.

He emphasized that many real-world problems, such as financial crises, pandemics, and political upheaval, are not just complex but truly unknowable in probabilistic terms. This challenges the traditional economic models that assume calculable risks and perfect information.

Henry Mintzberg added a social and political lens to the concept. For him, radical uncertainty is embodied in the erosion of democratic norms, the rise of populism, and growing inequality. He warned of a deepening imbalance between the economic and social spheres, where a dominant private sector is hollowing out both the public and civil sectors. This societal disequilibrium, he argued, generates uncertainty not just about markets but about the very fabric of collective decision-making.

Mike Jackson, drawing from systems theory, underscored the dual nature of uncertainty: ontological (inherent complexity of the world) and epistemological (limitations in our understanding). He referenced Nicholas Rescher’s work, suggesting that radical uncertainty emerges from both the messiness of the world and the diversity of worldviews.

Jackson emphasized that traditional approaches to decision-making often fail to accommodate the pluralistic nature of society and the systemic interdependencies that characterize modern problems.

Andrew Firth, offering a practitioner’s view informed by military strategy and business leadership, argued that radical uncertainty is a constant. For him, the real issue is not whether uncertainty can be removed but how to navigate it wisely. Drawing parallels with his experience in the Royal Navy and corporate turnarounds, Firth stressed the importance of cultivating strategic foresight, building flexible structures, and embracing continuous learning in the face of unknowability.

2. Do current strategic models work in a radically uncertain world?

The panel largely agreed that traditional strategic models fall short. Mintzberg was especially critical of strategic planning as it is commonly practiced. He argued that what organizations call strategy is often just extrapolated operational planning, which fails to account for real-world dynamics. True strategy, he insisted, emerges from action and synthesis, not detached analysis. He cited examples where strategic insights arose unexpectedly from frontline workers or spontaneous problem-solving, not from executive retreats or consulting frameworks.

Kay echoed this view, noting that most strategic statements are more about aspirations than plans grounded in reality. He argued that real strategy is always emergent and iterative, reflecting the fluid nature of the environments in which organizations operate. In his words, effective strategists operate more like gardeners than engineers, nurturing conditions for success rather than attempting to impose control.

Jackson critiqued the underlying assumptions of classical strategy: prediction, control, and optimization. He explained that these assumptions are rooted in a mechanistic worldview that no longer serves us. In contrast, systems thinking emphasizes adaptation, multiple perspectives, and relational dynamics. He underscored the limitations of linear logic and encouraged more holistic, integrative approaches that consider both hard data and soft insights.

Firth added that many strategic failures stem not from uncertainty itself but from poor methods and the illusion of control. He stressed the importance of designing strategy as an adaptive and relational process rather than a rigid framework. He shared anecdotes from defence and business contexts in which improvisational strategies outperformed well-laid but inflexible plans.

3. Why do strategies often fail?

Mintzberg was blunt: strategies often fail due to incompetence and a failure to synthesize diverse insights into coherent action. He also emphasized the dangers of imbalance, particularly the dominance of the private sector over both the public and plural (civil) sectors. Without systemic equilibrium, even the best strategy falters, he argued, because the institutional context becomes unstable and unjust.

Firth identified a gap between strategic design and strategic reality. He argued that many strategic frameworks are not equipped to deal with radical uncertainty because they lack mechanisms for continuous learning and adjustment. Strategic rigidity, he noted, is often mistaken for strength, when in fact it is a liability in dynamic contexts.

Jackson and Kay pointed to cognitive and structural limitations. Jackson highlighted the disconnect between complex realities and the simplified mental models used in strategy. Kay noted that overconfidence and the assumption of predictive accuracy often lead to flawed decision-making. Both emphasized the importance of humility and openness in the face of uncertainty.

Kay also suggested that strategic failures often come from an overreliance on best-case scenarios and an underappreciation of the role of contingency and narrative in shaping human behaviour. Rather than assuming rational actors and predictable outcomes, he called for strategies that are grounded in storytelling, metaphor, and evolving context.

4. Can systems thinking help us develop better strategies?

All four participants affirmed the value of systems thinking in strategy. Jackson provided a nuanced view of systems approaches, explaining that they have evolved beyond engineering-style optimization to include interpretive, emancipatory, and critical systems thinking. These newer approaches prioritize stakeholder engagement, pluralism, and reflective practice. Jackson argued for “systemic thinking for systemic practice,” a call to embrace complexity while remaining action-oriented.

Firth outlined three principles drawn from systems thinking that inform effective strategy:

1. Strategy must be dynamic and iterative.

2. Relationships, not just entities, must be the focus.

3. Multiple perspectives must be integrated.

He noted that strategy is ultimately a human-cantered endeavour, requiring empathy, dialogue, and the capacity to bridge divides. He suggested that strategic leadership is more about convening conversations than dictating directives.

Kay appreciated systems thinking for its capacity to embrace uncertainty without collapsing into chaos. He likened successful strategy to biological evolution: many attempts fail, but through variation and selection, effective adaptations emerge. Systems thinking, he noted, allows for modular, experimental approaches that reduce the cost of failure and accelerate learning.

Mintzberg valued systems thinking for its emphasis on synthesis and integration. He reiterated that real strategy comes from weaving together multiple strands of information and experience. He praised the capacity of systems thinking to foster resilience, not just efficiency, and to illuminate connections that are otherwise invisible.

5. Can we still develop strategy in this environment?

Despite their critiques, all panellists were optimistic about the potential for meaningful strategy, if reconceptualised. Kay pointed out that while many individual firms in the mobile tech sector failed, the system as a whole advanced. This underscores the importance of system-level thinking and the value of multiple experiments. He highlighted that strategic vitality lies not in avoiding failure but in failing intelligently and adapting accordingly.

Firth argued that strategy is more essential than ever in uncertain environments, provided it is treated as a flexible learning process. He emphasized the need to build strategic capabilities that are responsive and resilient. In his view, organizations should shift from “plan-and-execute” to “sense-and-respond.”

Mintzberg insisted that strategy must shift from being a top-down imposition to a bottom-up, emergent process grounded in real-world experience. He used the example of IKEA, whose flat-pack business model emerged from a practical problem encountered by an employee, not a boardroom plan. This example, he argued, reveals the importance of listening to those closest to the work.

Jackson noted that we must abandon the fantasy of control and embrace strategies that are open-ended, participatory, and ethical. He called for a new strategic paradigm cantered on dialogue, experimentation, and feedback rather than command and control.

6. How do we move forward?

Mintzberg called for a rebalancing of society: restoring strength to the public and civil sectors to counteract the dominance of capital. He proposed fostering pluralistic forms of governance and management that support social cohesion. He advocates for a stakeholder focused approach. In particular, he highlighted the need to revitalize civil society, the "plural sector," as a space for citizen engagement and collective learning.

Kay emphasized the importance of cultivating diversity in strategy, not just in demographics but in thought, approach, and experimentation. For him, the path forward involves making peace with uncertainty and focusing on evolutionary progress. He encouraged leaders to ask better questions and design systems that can learn faster than their environments change.

Jackson recommended adopting critical systems thinking as a guiding framework. This means being open to multiple worldviews, designing for learning, and embedding ethics into strategy. He argued that strategic renewal is inseparable from systemic reform.

Firth called for strategic leadership that is humble, curious, and relational. He argued that leaders must be comfortable with ambiguity and skilled in convening diverse voices. He concluded with a call for strategic literacy across society, not just in boardrooms but in communities, schools, and civic institutions.

Conclusion

This dialogue revealed both convergence and divergence among the participants, yet it was united by a shared commitment to rethink strategy for a radically uncertain world.

Key Points of Agreement:

• Radical uncertainty is real and irreducible; traditional strategic models are insufficient.

• Emergent, adaptive, and relational approaches are essential.

• Systems thinking, especially its interpretive and pluralistic forms, offers valuable tools that can help overcome some of the challenges strategy as a discipline has struggled with.

• Strategy must be dynamic and inclusive, integrating multiple viewpoints and grounded in lived experience.

Points of Divergence:

• Sources of failure: While Mintzberg emphasized incompetence and societal imbalance, others focused on structural and cognitive limitations.

• Solutions: Jackson leaned toward critical systems design, Kay toward evolutionary adaptation, Firth toward strategic design thinking, and Mintzberg toward societal rebalancing.

Ultimately, the conversation underscored that in a world of radical uncertainty, strategy is not about predicting the future but preparing to learn from it. It is less a blueprint and more a dialogue, a continuous act of sensemaking, synthesis, and adaptation. In this light, strategic thinking becomes not just a managerial task, but a civic and moral responsibility.

Insights from the Audience Q&A

The Q&A session following the main panel discussion on strategy and systems thinking unfolded as a rich, candid, and at times humorous dialogue between leading thinkers and an engaged audience. Chaired by Paul Barnett and moderated by Jase P., the session featured questions from participants and responses from panellists including Mike, John Kay, Henry Mintzberg, Andrew Firth, and others. Below is a synthesis of the core insights and highlights from the discussion, grouped by theme.

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1. The Role and Limits of Models in Systems Thinking

Question by Sally Bean, Response by Mike Jackson and John Kay

Sally Bean, quoting Checkland, asked about the utility of models in shifting mental frameworks within systems thinking. Mike Jackson emphasized the value of conceptual models as tools to aid reflection and decision-making. Unlike predictive models, conceptual models are designed to explore implications, test feasibility, and challenge groupthink (e.g. via “Red Team” alternatives).

John Kay added a critical distinction: models and scenarios are not predictive devices but tools for organizing thought. Drawing a contrast with the physical sciences, he warned against overreliance on economic models that mimic physics, stressing that business systems are socially constructed and responsive to beliefs, unlike planetary orbits.

“We don’t know the underlying equations… they change over time and are affected by beliefs—both true and false.” — John Kay

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2. Character vs. Strategy: Who Really Drives Change?

Question by Mary Crossan, Responses by Henry Mintzberg, John Kay, Andrew Firth

The debate on the “great man/woman” theory of leadership drew a lively exchange. Mintzberg used Elon Musk as a paradoxical case, nominating him as both the best (Tesla) and worst (Twitter) CEO, to illustrate how character can be both an asset and a liability, depending on context. Kay nuanced the point: while remarkable individuals shape organizations, the reverse is also true, organizations shape the outcome of character.

Andrew Firth brought the conversation back to strategy’s role in coherence and sustainability, cautioning against overreliance on charismatic individuals, whose energy may be unsustainable over time.

“We would still have electric cars without Musk. He didn’t invent the industry, unlike Ford with automobiles.” — Henry Mintzberg

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3. Overcoming Bureaucracy and Enabling Simplicity

Question by Eugen Oetringer, Responses by Henry Mintzberg, Andrew Firth

Eugen Oetringer raised a heartfelt question about why simple, impactful solutions often fail to penetrate bureaucratic systems. Mintzberg resonated deeply, noting his decades-long struggle to promote a simple idea: the need for a balanced three-sector society to counteract divisive two-party politics.

Andrew Firth attributed systemic resistance to a misplaced focus on internal metrics over external purpose. Organizations, he argued, must shift from performance for performance’s sake to outcomes aligned with purpose, a change that requires both leadership and cultural transformation.

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4. AI, Strategy, and Radical Uncertainty

Question by Claudio Lazo, Responses by Mike Jackson, John Kay, Andrew Firth

The panel was cautious, if not sceptical, about AI’s potential to resolve complex strategic dilemmas. Mike Jackson likened current AI optimism to Herbert Simon’s earlier belief in computers helping optimize decisions. However, he warned that AI may reinforce dominant interests rather than support pluralistic, value-driven decision-making.

John Kay noted that AI is powerful for well-specified problems, but most strategic and societal challenges are inherently ill-defined. Andrew Firth echoed this from a military lens: AI can assist with data and signals but cannot replace human contextual judgment, at least not yet.

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5. Universities and the Public Good

Question by John Pritchard | Responses by Mike Jackson and John Kay

Responding to concerns about academia’s declining contribution to the public good, Mike Jackson lamented the stranglehold of disciplinary silos and the retreat from transdisciplinary, real-world problem solving. Universities, he argued, often fail to engage with society because academic incentives reward insular publishing over public impact.

John Kay supported the call for reform but with his characteristic wit quipped that “Donald Trump is not the person to lead it,” despite ironically pushing the issue into public discourse.

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6. Serendipity vs. Strategy

Question by Chander Nagpal | Responses by Henry Mintzberg, Andrew Firth, Mike Jackson

Nagpal asked about the balance between serendipity and strategy, referencing IKEA’s famed flat-pack innovation and OpenAI’s rise after predecessors like Eliza. Mintzberg argued that serendipity isn't rare, but capitalising on it is. Entrepreneurs don’t get lucky; they know how to use luck.

Andrew Firth stressed the importance of creating organizational cultures that are attuned to weak signals and willing to act on them, even when they deviate from the current strategic path.

Mike added that most organizations penalize “sins of commission” (acting wrongly) but fail to recognize “sins of omission,” failing to act on opportunities.

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7. Leadership: Decision-Makers or Condition-Makers?

Observation by Geoff Marlow, Response by Andrew Firth

Geoff Marlow provocatively suggested that executives should not make decisions but create the conditions for good decisions. Andrew Firth agreed, adding that leadership is about enabling agility, delegating appropriately, and focusing on effect, not micromanagement. This insight echoed broader themes about avoiding over-centralization and fostering distributed intelligence.

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8. Final Thoughts: Strategy for Governments and PhDs

Questions by Bhavya Jakhu and Jane Graham, Responses by Henry Mintzberg, Mike Jackson, John Kay

• To PhD students, Mintzberg’s advice was to be bold, original, and independent. Don't serve your supervisor’s agenda, build your own.

• To governments, he was scathing: ten-year strategies are often a fig leaf for inaction. “Tell me what you're doing today,” he demanded, criticizing climate plans that vanish with electoral cycles.

Mike and John Kay discussed missions-based approaches (à la Mariana Mazzucato) as more promising. However, they warned that missions must remain focused on real outcomes, not become pretexts for growth agendas or political posturing. Both expressed concerns about the limits of Mazzucato’s thinking and the need for it to be questioned and developed further.

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Conclusion: Wisdom for Navigating Complexity

The Q&A underscored a shared conviction: strategy in an uncertain world is not about control or prediction, but about cultivating purpose, character, awareness, and judgment. Whether discussing AI, leadership, serendipity, or reform, panellists emphasized the need for adaptive thinking, humility, and cultural coherence, qualities as vital to systems as they are to societies.

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The Series To Follow

A SALON series, Strategy in an Age of Radical Uncertianty will begin in September / October this year as a collaboration between the Enlightened Enterprise Academy and Aperture Strategy. The issues raised in this first event will each be explored in greater depth in live online dialogues with other guest speaker. And we plan to run off-line retreats.

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The Recording

A recording of the whole event is available to paid subscribers to the Salon. Access can also be requested from the Enlightened Enterprise Academy: contact@enlightenedenterprise.ac