Chapter 10. Strategy for an Uncertain World

Marcus Guest
15 min readSep 5, 2022

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The problem isn’t that some people are playing checkers while others are playing chess; the problem is that we’re playing chess while others are playing weiqi.

Uncertainty sits at the heart of both Eastern and Western approaches to strategy. The Chinese tradition, from which Sun Tzu emerged, recognises that minor fluctuations in conditions can amplify into dramatic changes, meaning no two situations are ever identical and universal solutions are ineffective. In the West, Clausewitz identified ‘friction’, the accumulation of many unforeseen events that complicate even the simplest things, rendering analysis and predictions unreliable. While both traditions acknowledge uncertainty, they diverge in how they respond to it. These differences can be explained by looking at the strategic games that dominate in the East and the West.

Chess is the leading game of strategy in the West. “The purpose of the game is checkmate, to put the opposing king into a position where he cannot move without being destroyed. The vast majority of games end in total victory achieved by attrition or, more rarely, a dramatic, skilful manoeuvre. The only other possible outcome is a draw, meaning the abandonment of the hope for victory by both parties⁠[1]”. Chess reflects Clausewitzian strategic thinking — one seeks absolute domination by concentrating forces against the enemy’s ‘decisive point’.

Weiqi (Go) is the leading game of strategy in the East. Unlike chess, which is a “struggle for the centre of the board” with players seeking to eliminate their “opponent’s pieces in a series of head-on clashes”, weiqi “teaches the art of strategic encirclement”. A “talented weiqi player moves into ‘empty’ spaces on the board, gradually mitigating the strategic potential of his opponent’s pieces⁠[2]”. Weiqi reflects Sun Tzu’s strategic thinking — seeks relative advantage by cultivating superior potential that becomes impossible to counter.

In this final chapter of part one, we’re going to use the lenses of chess and weiqi to explore three key differences between the Eastern and Western approaches to strategy and how they apply to both warfare and business. These key differences are:

  1. Focusing on the internal vs external
  2. Focusing on singular vs multiple ‘wheres’
  3. Strategic ‘genius’ as nature vs nurture.

Difference 1: Internal vs External

“A chess mindset … focuses on what one can achieve given limited resources at the moment, whereas a Go player thinks about what he can bring to bear with additional resources⁠[3]”.

Clausewitz argued that ‘power determines everything in war’. This is reflected in chess as each piece has a clear hierarchy of power: the queen outranks the rooks, rooks outrank bishops, and so on down to the least powerful pieces, pawns. A game of chess starts with this power fully deployed, with all pieces on the board, before being gradually eroded through a battle of attrition, with less powerful pieces sacrificed in exchange for positional advantage. The player who retains power best, by keeping more pieces on the board or deploying them more effectively, gains a competitive advantage.

Fig.18: The Opening Situation In Chess

The accumulation of power became the focus of Western military strategy in the 19th century, especially following Prussia’s victories in the German wars of unification. However, Germany’s subsequent emergence as a major power triggered an arms race with Europe’s other established powers, most notably Britain, as each sought to build a superior military machine with which to dominate the other with. The ‘Great War’ that broke out in 1914 quickly descended into a bloody, attritional stalemate in the mud of the Western front, as mighty military machines, cursed by technological parity, were continually launched at the other’s ‘centre of gravity’ (the opposing military). Western leaders, mistaking indifference to lives of their soldiers for the determination they believed marked one out as a Clausewitzian genius, sacrificed their men, like pawns on a chessboard, on an industrial scale of killing never seen before. The senseless, multi-year destruction brought an entire continent to its knees and led some Western military strategists to find “fundamental faults [with this] costly and wasteful attrition style of warfare … and the strategic mindset ever since in the West⁠[4]”.

A notable critic of Clausewitzian military orthodoxy was T.E. Lawrence, a British liaison officer during the Arab revolt against the Ottoman empire, an ally of Germany’s during the ‘Great War’. The man who would become better known as ‘Lawrence of Arabia’ realised the smaller, irregular Arab forces couldn’t match the larger Ottoman army in conventional warfare. But where military orthodoxy provided little guidance, military history more than made up for this, with countless examples of smaller ‘Davids’ defeating mightier ‘Goliaths’: Julu (207BCE); Badr (624); Morgarten (1315); Agincourt (1415); Panipat (1526); and Lacolle Mills (1814). Numerically weaker forces triumphing over larger rivals continues to persist. Since 1900, larger forces have won only 60% of military engagements — only slightly better odds than tossing a coin⁠[5] — suggesting that power alone doesn’t determine everything in war.

While western military strategists continued to challenge Clausewitzian orthodoxy⁠[6], but his ideas spread further, shaping the Western approach to strategy in other fields. In the business world, leaders often believe that success comes from having an organisation that runs like a ‘well-oiled machine’, echoing Clausewitz’s belief that a ‘formidable military machine is the decisive factor’[⁠7]. This has led to a fixation on internal improvements; adopting the very latest technologies and “best practices” despite these being easily imitated by competitors. As a result, many businesses today are locked in an endless and costly ‘arms race’ of technology adoption and consultant-driven transformations that offer no lasting competitive advantage over their rivals.

In contrast to chess, where maximum power is deployed from the start, weiqi (Go) begins with an empty board. Each player has the same number of ‘stones’, which are all of equal value and can be deployed in a near-infinite number of ways. Whilst victory in chess comes from deploying one’s power better, dominating the centre of the board and exchanging weaker pieces for stronger ones, victory in weiqi comes from cultivating superior potential by connecting one’s stones to make the whole more than the sum of its parts. Multiple engagements across the entire board are undertaken simultaneously, which makes it difficult for the untrained eye to see who’s winning. But eventually, one player’s accumulated potential becomes irresistible, limiting the opponent’s options for making any further moves and forcing them to concede victory.

Fig.19: The Opening Situation In Weiqi (Go)

Weiqi reflects the Eastern belief that cultivating potential (shi) is key to success in competitive situations. As in the West, Eastern strategists stress the importance of adopting the latest technology, developing sound tactics, managing logistics impeccably and knowing how to engage the enemy in a ‘straight-forward’ way. Orthodox moves make leadership easier by developing the capabilities one needs to adapt to “shifting conditions and circumstances in a world where chance, uncertainty and ambiguity dominate[⁠8]”. However, they also warn that orthodox moves alone are insufficient to deliver victory because unexpected events and the unpredictable actions of rivals can undermine even the most ‘well-oiled machine’.

The Eastern approach to strategy therefore also emphasises unorthodox moves that, unleashed at the right time, surprise and confuse rivals, increasing the levels of uncertainty they must deal with and hindering their ability to adapt — creating a mismatch between you. Misdirection plays a key role in unorthodox moves: subtle feints — moves initiated but not completed — conceal one’s true intentions; whilst distorting signals — appearing weak when one is strong — lure rivals into making mistakes that create openings for decisive action that distracted rivals can’t anticipate nor counter effectively. This is why Lao Tzu, a contemporary of Sun Tzu, advised that ‘to win the empire’, one must:

“Govern the state by being straightforward;

Wage war by being crafty⁠[9]”.

The constant interplay between orthodox (cheng) and unorthodox (ch’i) moves symbolised by yin and yang in Chinese philosophy — enables one to remain indiscernible, or ‘shapeless’ and therefore difficult to attack. Cultivating potential from the conditions — identifying where the terrain favours you more, or the climate changes you can use beneficially — and unleashing it at the right moment, ‘like a torrent crashing down a gorge’, is how even weaker forces can vanquish the stronger.

Fig.20: Yin and Yang

However, one must be aware that successful unorthodox moves quickly become orthodoxy. Repeating past successes — re-fighting the last war or copying “best practices” — makes one predictable and easier for skilled opponents to counter. General Bonaparte, the archetypal Clausewitzian genius, famously⁠[10] combined orthodox moves (well-drilled formations) with unorthodox moves (unexpected operational thrusts) to out-manoeuvre European rivals. But, as Emperor Napoleon, his innovative unorthodox moves had become military orthodoxy. After victory over Napoleon at the battle of Waterloo the Duke of Wellington observed wryly that the French merely, “came on in the same old way, and we sent them back in the same old way[⁠11]”.

Difference 2: Singular vs. Multiple Wheres

“In Go, it is a war with multiple campaigns and battlefields. There is no one single focus on the board. A Go player must always keep the whole situation in mind⁠[12]”.

The Arab irregulars, advised by ‘Lawrence of Arabia’, launched lightening-fast attacks against the Ottomans across the vast expanse of the Arabian desert. Their deep knowledge of the terrain, coupled with their ability to cover huge distances at speed, enabled the Arabs to exploit conditions best and drive their enemy crazy with unorthodox moves: attacking at different points, huge distances apart, created the illusion of being a much larger force; partially destroying supply lines at various places, forcing them to be continually re-built, exhausted the Ottomans; and keeping the Ottoman troops guessing about where they would be attacked next increased their uncertainty and undermined their morale. The eventual success of the Arab Revolt — culminating in the capture of Damascus in November 1918 — was a clear rejection of Clausewitz’s principle that winning in war requires identifying and focusing on a singular ‘decisive point’.

Yet, the Western approach to strategy retains its singular focus, mirrored in chess, where “all the moves are geared toward checking the king … [meaning] naturally, chess players are single-minded⁠[13]”. This singular mindset is evident in the business world, where ‘annual strategic plans’ — focused on dragging the organisation forward to an idealised image of where it ‘should be’ in the future — have become an obsession, with bonuses and promotions tied to hitting key milestones along the way. Yet, rarely does reality unfold as predicted. Consider the many ‘strategic plans’ made for 2020 rendered irrelevant by COVID after just a few months. The long planning process prevents many organisations from adjusting their thinking quickly enough when shocks hit, leaving them a choice: abandon their expensive plan or ‘double down’ on it. Many choose the latter, making a virtue of ‘sticking to the plan’. But this is like a chess player deciding every move they’ll make before the game starts and then not adjusting even when their opponent makes an unanticipated move and the situation on the board unfolds in an unforeseen way. Single-mindedness limits strategic flexibility.

In contrast, weiqi eschews the single-mindedness of chess. As each stone is placed on the board, different situations wax and wane in importance. Focusing on one area, to the exclusion of others, limits the strategic awareness needed to win. Weiqi players therefore focus on multiple wheres — exploring opportunities and guarding against threats everywhere, simultaneously — reflecting the distrust Eastern strategists have for a singular focus that demands attention to the exclusion of all other options. This is why Honda entered the US market with ‘no strategy other than seeing if they could sell something’ — to retain the flexibility needed to adapt if the situation changed unexpectedly⁠[14]. Similarly, it’s why, when facing a crisis, Fujifilm pursued multiple wheres to play, whilst their Western counterpart focused on a single big bet that failed to pay off⁠[15]. In a fast-changing and unpredictable world, focusing on a singular where is a risk no strategist can afford to take.

Fig.21: Multiple Wheres In Play In Weiqi

Detailed plans provide a comforting sense of certainty, but in a complex world, where we don’t control all the variables — like the actions of rivals, new technologies emerging, or external shocks — certainty is an illusion. Both Sun Tzu and Clausewitz recognised this, but only Sun Tzu argued that one doesn’t need certainty to win; one simply needs to be less uncertain than rivals. One must increase awareness of the current situation — seeing conditions as they really are, anticipating how they’ll change and identify where options for action are — and unleash the potential one has accumulated at the right moment, which can’t be predicted before-hand. This is why a “prescribed plan and action are the last things a general should seek in warfare⁠[16]” or a leader in business. Plans encourage people to be ‘heads down’, focused on artificial targets conceived in ignorance, leaving them vulnerable to attack from more skilful rivals who can exploit their detachment from reality. “Nothing is more dangerous than becoming immobilised” by a rigid plan — a focus on a singular where that can “make conduct inflexible and prevent an actor from the variation from which all potential stems⁠[17]”.

Difference 3: Strategic Genius: Nature vs. Nurture

“As a prolonged and complex game, Go players focus on building or creating rather than chess players’ emphases on removal and destruction⁠[18]”.

Clausewitz’s influence in the West established strategy “an activity in its own right, separate from politics”[⁠19]. This distinction shaped the perception of strategy as an ‘art-form’, detached from the practicalities of implementation. Many western organisations have embraced this divide today, separating themselves into ‘thinkers’ (who make plans) and ‘doers’ (who implement plans), a split that feels natural for, after all, we “have heads with which to think and bodies with which to act”. This belief is now “so deeply rooted in the very philosophical basis of western society that it seems indisputable⁠[20]”.

This separation of ‘strategy creation’ from ‘execution’ has fuelled the rise of an “industry [of] management consultants, strategic planning staffs, and business school academics[⁠21]” that have grown up around modern businesses. Leaders often outsource their strategic thinking to them on complex challenges — such as adopting new technologies, entering new markets, or transforming the organisation. In an uncertain world, seeking the counsel of ‘strategic geniuses’ is seen as prudent, as they are believed to be capable of peering through the ‘fog’ and identifying the ‘decisive point’ to focus on, freeing leaders up to drive implementation.

When ‘strategic plans’ fail — as they often do when confronted with an unpredictable reality beyond their control⁠[22] — ‘thinkers’ blame ‘doers’ for poor execution⁠[23]. However, any plan that can be derailed by poor execution could not have been much of a plan to begin with — “thinkers” may direct efforts from above, but “doers” need to inform them of what is, or is not, possible — meaning “every failure of implementation is, by definition, also a failure of formulation⁠[24]”. Despite this, the ‘strategic geniuses’ usually escape scrutiny. In fact, the more often such plans fail, the easier it becomes for them to convince business leaders that it’s their ‘doers’ that are the problem and the organisation needs a (digital/cultural/agile) transformation to fix its ‘execution gap’ — a multi-year, high-cost engagement that is, of course, often led by the same consultants.

In the East, strategy was not seen as a separate activity, but integrated into the overall affairs of state, encompassing the political, diplomatic and logistical. Strategy was not just focused on achieving victory on (or off) the battlefield, but was also concerned with the aftermath of war as well. “In this broad framework, the art of war is, in essence, the process of diplomacy⁠[25]”. As a result, strategy in the East is a collective responsibility, an integral part of what everyone should be doing — success requires a ‘whole of board’ focus.

Where there is no division between strategy and execution — between ‘thinkers’ and ‘doers’ — people are expected to identify moves they should make (e.g. seizing opportunities, guarding against threats) but also develop the capabilities needed for making them. This is why Fujifilm’s CEO warned his people ‘not to rely on outside consultants’ as strategy cannot be outsourced to others, it must come from within⁠[26], with a simultaneous focus on what could be done and what can be done. This explains how Honda beat the British in the US — their team was able to learn more quickly and adapt more effectively to emerging opportunities and threats[⁠27].

The “ancient Chinese notion of genius [being teachable, is] at odds with Clausewitzian genius[⁠28]”. But Sun Tzu’s ‘Five Factors’⁠[29] — purpose, climate, terrain, commands and regulations — is a framework anyone can use to increase their awareness about the current situation and how to adapt to conditions more effectively. Awareness-adaptiveness are the mutually reinforcing capabilities one uses to cultivate superior potential that, unleashed at the right time, makes victory inevitable. Strategy is not a singular plan of action devised far from the battlefield by a ‘strategic genius’. It’s a series of ‘next-best’ moves made by those on the frontline, constantly responding to changing conditions. What appears to be a ‘strategic plan’ is a mirage of hindsight.

Strategy for an Uncertain World

Isiah Berlin⁠[30], the Russian-British theorist and historian, famously distinguished between hedgehogs and foxes. Hedgehogs, he suggested, focus on one grand idea, while foxes juggle many smaller ideas. Western strategists, influenced by Clausewitz, resemble hedgehogs: planners who seek to identify a single ‘decisive point’ and launch all their power at it, demonstrating the rugged determination to see it through. In contrast, Eastern strategists, influenced by the Chinese philosophical tradition Sun Tzu emerged from, are akin to foxes: opportunists who seek to learn how situations are evolving and, recognising they’re in a ‘democratic game’ where the actions of others shape conditions, forgo rigid plans in favour of active problem-solving (and problem-making for rivals) and adapting as they go.

Understanding the Eastern approach to strategy — awareness/adaptiveness, orthodox/unorthodox moves, and harnessing potential from conditions — is challenging for those more accustomed to Western thinking. Yet, for those willing to learn, the Art of War provides a framework for mastering strategy, which challenges the dominate belief in western businesses that ‘strategic genius’ is something we’re born with or not. Sun Tzu’s ‘Five Factors’ can help us democratise strategy, showing us how to cultivate potential from conditions and make moves that are as powerful as a river racing down a mountain, “capable of arriving [at the sea] at multiple and thus interchangeable outcomes[⁠31]” and impossible to resist.

The next part of this book explores how to apply these insights in the modern world of business.

1 On China. Kissinger (2011) p45

2 On China. Kissinger (2011) p47

3 Learning from the Stones: A Go Approach to Mastering China’s Strategic Concept, Shi. David Lai (2004) p.28

4 Science, Strategy and War: The Strategic Theory of John Boyd. Frans P.B. Osinga (2007) p.311

5 Military Power. Biddle, S. (2004) p63

6 We will explore the ideas of one of these, John Boyd, later in this book.

7 See chapter nine — The Western Approach to Strategy.

8 Science, Strategy and War: The Strategic Theory of John Boyd (Strategy and History). Frans P.B. Osinga (2007) p45

9 Tao Te Ching (chapter 57)

10 “Napoleon was said to have studies a French Jesuit’s translation of the Art of War” Strategy: A History. By Lawrence Freedman p.95

11 https://victorhanson.com/the-lessons-of-wellington/

12 Learning from the Stones: A Go Approach to Mastering China’s Strategic Concept, Shi. David Lai (2004) p.28

13 Learning from the Stones: A Go Approach to Mastering China’s Strategic Concept, Shi. David Lai (2004) p.28

14 See chapter six — Miscalculations, Mistakes and Serendipity.

15 See chapter five — Innovating Out of a Crisis.

16 Deciphering Sun Tzu. Derek M. C. Yuen (2014) p. 162

17 The Mind of War. Hammond p198 quoted in Deciphering Sun Tzu. Derek M. C. Yuen (2014) p. 89

18 Learning from the Stones: A Go Approach to Mastering China’s Strategic Concept, Shi. David Lai (2004) pp.28–9

19 On China. Kissinger (2011) p.48

20 Rise and Fall of Strategic Planning. Henry Mintzberg (1994) p406

21 The Honda Effect. R.Pascale. (1996) California Management Review, Vol 38, №4 p80

22 Hence, Mike Tyson’s now famous quote — “Everyone has a plan until they get punched in the face” — when he was asked in an interview leading up to a fight whether was concerned about his opponent’s strategy.

23 See the end of chapter one — Stop Making Strategic Plans for an example of this from Hewlett-Packard.

24 Rise and Fall of Strategic Planning. Henry Mintzberg (1994) p59

25 Learning from the Stones: A Go Approach to Mastering China’s Strategic Concept, Shi. David Lai (2004) p.3

26 See chapter five — Innovating Out of a Crisis.

27 See chapter seven — Time as a Strategic Weapon.

28 The idea of genius in Clausewitz and Sun Tzu. Lukas Milevski (2019)

https://www.tandfonline.com/doi/full/10.1080/01495933.2019.1573076

29 See chapter eight — The Eastern Approach to Strategy.

30 https://www.amazon.com/Hedgehog-Fox-Tolstoys-History-Second/dp/069115600X

31 Deciphering Sun Tzu. Derek M. C. Yuen. (2014) p. 82

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Marcus Guest
Marcus Guest

Written by Marcus Guest

Govern the state by being straightforward; And wage war by being crafty. — Laozi, Tao Te Ching marcus@powermaps.net PowerMaps.net

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