On Humility: Further Thoughts About Bad Strategy

Judging by the number of views and the degree of subsequent interest, the essay that appeared in the Summer 2023 edition of Military Strategy Magazine, “The Roots of Bad Strategy,” clearly struck a chord with readers. Evidently many felt that this was a subject that had yet to receive the necessary attention it deserved. The article identified a paradox in the contemporary discourse on strategy in the West, namely, that the grander the effort devoted to identifying the prerequisites of effective strategy, the worse the outcomes.

Over the past 25 years, repeated instances of policy failure and underperformance in military interventions from Afghanistan and Iraq to Libya and Syria (as well faltering Western support for Ukraine in its war against Russia), suggested a pattern of activity that needed interrogation. The greater the number of students, think-tanks, and centres of learning dedicated to expounding upon the principles of good strategy, the essay suggested, led only to the production of more bad strategy. The correlation appeared to exist almost as an iron law of unintended consequence.[i]

The article, which was intended only to be a first incision into a complex and understudied area, argued it was the over-determining influence of total war thinking on the Western psyche that accounts for much of this failure in recent years.[ii] It has rendered Western decision-making susceptible to disproportionate responses that lack prudence and considered judgement. This has resulted in outcomes where objectives were either unobtained or obtained at inordinately high cost. In each case, the results of Western military intervention have not left the world in a better condition. By this simple criteria, Western policies have been characterised by bad strategy.

The question that several readers had in reaction was, having stated the paradox, could bad strategy be remedied, or at least mitigated? It is a tough question. As most honest academics will confess, describing a problem is easy. Finding solutions is far more difficult. It is a question that also reinforces the paradox. In attempting to put forward remedies to bad strategy one risks compounding the iron law of bad strategy – the greater the highbrow attention to identifying good strategy leads only to more bad strategy.[iii] How to get out of this doom loop?

Escaping the paradox

The first requirement for escaping the paradox is the need for humility and self-reflection, commodities that do not necessarily exist in abundance within self-designated communities of strategy scholars and practitioners.[iv] The subsequent course of this article will therefore proceed in four stages. First, it will seek to offer a reflection upon the need for humility as the gateway to thinking better about strategy. Second, it will then use this reflection to inquire into one of the most fundamental – and again understudied – questions: what is, or should be, the object of strategic studies? Third, having addressed this question, the analysis will use this as a basis to ask how strategic effectiveness can be assessed, and how good and bad strategy can be differentiated? Finally, the essay will illustrate how several of the insights drawn from these questions can be further examined via a case study of contemporary wargaming.

The path to strategic humility

Any discussion about how strategic performance might be improved needs to begin from the recognition that any expectation of perfection or mastery over matters of higher national foreign or defence policy is unrealistic.[v] Policy implementation at this level is a hard task by almost any standard. In this domain myriad factors, ranging from the inherent uncertainty of the external (and internal) environment to competing bureaucratic imperatives and the scrabble for scarce resources, impede strategic art. They create ideal conditions in which human fallibilities can all too easily come to the fore. It therefore behoves anyone who seeks to critique policymaking to refrain from excessive judgmentalism by assuming that they could necessarily do much better.

Likewise, in seeking forms of redress for the inclinations that might lead to bad strategy, it is necessary to accept that it will be impossible over the short- or medium-term to dislodge ingrained and reflexive habits of mind, especially those that constitute the basis of victory in the Western imagination, as notions of total war undoubtedly do.[vi] A short essay of this nature is unlikely to change many minds in policy making circles (if indeed anyone in such circles even reads such essays). Still less are superficial recommendations for yet more workshops, short courses, and training sessions on how to ‘think strategically’ given by self-proclaimed strategy experts likely to improve the situation.

The first order requirement to chart a course towards better strategy, therefore, is to reject the fundamental erring, lack of humility, and closed thinking of much Western strategic theorising. Any suggestion that strategic insight comprises a form of ‘secret knowledge’, the preserve of a few experts who stand in Olympian detachment over everyone else, needs to be repudiated.

By contrast, this article advances the opposite view, arguing that everyone can strategise and that everyone does strategy, because the world essentially is a semi-cooperative place in which the interaction of opposing wills and the play of chance is customarily a universal, daily occurrence. Strategy is therefore ubiquitous and, as such, we can learn from anyone’s struggle in some ways. There is no such thing as masters of strategy, only those who have gained proficiency in specific struggles, whether we are talking about a chess master, a successful entrepreneur, or a military commander.[vii]

What is the object of strategic studies?

In this respect, there is only one viable path that intimates the prospect of achieving better strategic outcomes, which is an appreciation of the desirability for open conversation. A conversation on bad strategy, what may account for it, and in what ways it might be alleviated, cannot be based on predetermined conclusions. It does not, in fact, need to possess a conclusion at all. It requires only the understanding that no one person is in possession of the answers or a higher branch of knowledge. There are only infinitely debatable questions. And the first order question when opening a conversation on bad strategy is ‘what is the object of strategic studies?’

The three ifs

If the answer to the question is ‘teaching people how-to do-good strategy’ then we are probably mistaken, as it merely reinforces the iron law of bad strategy. Rather, the aim should be to illustrate why it is so hard to do good strategy, how ubiquitous and multifaceted strategy is, and why there is no one golden road to becoming good at it.

If, by studying the constraints and pitfalls in strategic practice through various lenses, a general consciousness can be developed that strategy is all about contexts, nuances and the agglomeration of individual stories and singularities about how people have thought about – or not thought about – achieving their aims in a proportionate manner, then we might contribute to a more informed strategic conversation.

If such a consciousness is to be cultivated, however, it will depend on bringing down numerous barriers that inhibit the conversation and reinforce the current gatekeeping of strategic studies. These barriers include the prevalent idea that strategy is primarily about ‘problem solving’ and military decision-making;[viii] that strategic expertise resides primarily within a few preeminent centres of defence and security studies;[ix] the closed-minded nature of some of the leading journals in the field;[x] and especially the sense that the primary role of strategic analysts should be to act as supporting counsellors to official narratives.[xi]

In that regard, a better conversation would be to encourage strategic studies to consider heterodox voices and be receptive to perspectives of different kinds of non-military practitioners (from industry for example), and from other academic fields such as economics, mathematics, psychology, philosophy, and neuroscience.[xii] The point is that a more open view on strategy should be welcomed. Strategic studies in our view, extends beyond simply the study of war. The study of war and military power only captures the most extreme segment of strategy. Paradoxically, restricting strategy to an ostensible focus on war is one reason why a lot of insights that could enlighten the study of war are missed by actively deterring heterodox voices from other academic fields from getting involved at all. The issue here is not about adapting or co-opting different voices into a conversation about strategy but truly welcoming them in the first place.

How to assess strategic prowess? Differentiating between good and bad

If all this sounds vague and aspirational, as it probably does, the easiest way to think about it is that good strategy is a plan that justifies its design in the first place. A bad one does not. If an actor has attained their goals in a sufficiently cost-effective way, howsoever defined, then we are entitled to argue that their design has been successful. They have demonstrated that, in this instance, their plan has been a ‘good’ strategy.

This results-orientated approach makes sense for most people and would not require further elaboration were it not for the highly contextual aspect that characterises strategic practice. We may play badly and win (ask any sports team). We may develop a sound and coherent plan and still fall short of our goals (ask any sales manager). Failure may arise from any number of sources: poor implementation, unsound assumptions, or just plain bad luck.

A results-orientated approach is not enough, not least because we lack the counterfactuals that make it possible to judge how good or bad the strategic thinking behind a course of events was. Judgement is therefore applied retrospectively. We only have an outcome. And we read good or bad strategy into the outcome.

An outcome, moreover, is subject to continuous re-evaluation over-time. Looking back, the appraisal of any strategy or set of decisions may differ vastly one, ten or fifty years later. An assessment of the situation in Afghanistan in the decade after Western military intervention that swiftly removed the Taliban from power in late 2001,[xiii] for example, would be radically different to one after two-decades of futile nation-building in 2021.[xiv] Likewise, the utility of Western support for Ukraine in its war against Russia and the prospects for success on the battlefield in 2022 are thrown into sharp relief in 2024,[xv] as the war drags on and the much-heralded Ukrainian counter-offensive during the summer of 2023 petered out.[xvi]

Tactics rewards consistency, strategy rewards judgement

Evaluating the success or failure of military and policy decisions over the long term is therefore a task for historians. The strategic decision maker in the heat of a crisis is unlikely to have the luxury of all this time to reflect on their choices. So, how can they know if they are heading in the right direction? The answer is that they can never know.

What we do know is that tactics can be practiced, tested, and adjusted. They evolve either quickly or slowly, but inevitably they catch-up with reality. Their impact is incremental and cumulative (one localised victory born of clever tactics is usually insufficient to triumph in a conflict, while a thousand similar victories will tip the scales to one side). Therefore, tactics rewards consistency. Strategy does not. Strategic decisions are a high stakes game of commitment. Their effects can rarely be simulated in advance, are long-term, and are seldom reversible. Hence, strategy rewards judgement.

To illustrate, it is often claimed that American forces prevailed in almost every significant military encounter they had with their enemy during the Vietnam War, and against other adversaries such as the Taliban in Afghanistan.[xvii] The consistent effectiveness of US military tactics was therefore rewarded with operational success. However, it was the North Vietnamese and Taliban leaderships who recognised more accurately the contingent conditions of their struggles. They were thus able to sustain their commitment over the longer term and endure the necessary sacrifices to wear down the will of their opponent. This eventually rewarded their strategic judgement.

In contrast, US strategic judgement was flawed in the sense that it failed to recognise what kind of wars it was waging and how resilient its opponents would be. As a result, the US failed to design war goals that would be coherent with both its long-term political objectives and the costs it was willing to pay. Unfortunately, even if one realises mid-way through a conflict that mistakes have been made, it is very hard to ‘correct’ this bad initial judgement and alleviate its consequences, as the wars in Vietnam and Afghanistan reveal.

Context is everything

In the final analysis, any strategy’s effectiveness is dependent upon only one thing: context. It is purely a situational realm that depends on who you and your opponents are, what you are fighting for, and the respective understandings by the actors involved of the field they are playing on. As such, the notion of what comprises objectively good or bad strategy is likely to be irrelevant to the strategic-decision maker about to embark on a choice of action. If anything, their best chance at making the ‘right choice’ lies in finding out what are the key factors that underpin the situation in which they find themselves. In that regard, as any chess player will tell you, the moves themselves are not as important as the process of thought behind them. In the words of Eugene Znosko-Borovsky: ‘It is not a move, even the best move that you must seek, but a realizable plan’.[xviii]

Distilling the essence of this reflection so far, we might suggest that the essential indicators that differentiate good and bad strategy are: Good strategy is self-aware in that it is conscious that an adversarial relationship exists in conditions of uncertainty and that decisions are only likely to be efficacious in the light of the responses they emit from the adversary. This means, among other things, that a conflict actor proceeds with an understanding of the adversary’s motivating value-system and the likely decisions it will make in response, as well as a conscious effort to make its strategy proportionate to the goals it is looking to achieve, all the while seeking coherence with the means at its disposal. Bad strategy, by contrast, is insensitive to its surroundings and intransigent to the extent that it discounts or rejects cost-benefit calculations of proportionality.

The paradoxical insights from wargaming

The distinctions between good and bad strategy outlined above might represent something of a caricature. Few policymakers, one imagines, set out to be negligent of the strategic environment and so intractable in their judgements that they become detached from reality. Invariably it is ideological disposition and group think that predisposes policy makers to think in a particular kind of way, paying attention to factors, and data, whilst ignoring others, and avoiding asking crucial framing questions that might challenge the ideological suppositions that underpin a governing world view. To illuminate the involuntary susceptibility towards bad strategy, then, let us turn to some insights drawn from wargaming, which provides a mirror for our reflections upon what constitutes good or bad strategy.

Analytical wargaming is supposed to be an exploratory tool, focusing on investigating system dynamics and rationales behind decision-making. It aims not at predicting the future, but rather the generation of interesting hypotheses that might have been underestimated or discarded too hastily. In brief, wargaming seeks to explore strategic conundrums through a practical lens that is in touch with the sensibilities, imperfections, and the contingency of human decision-makers.[xix]

Yet, despite the effort to approximate to reality, this is often not what happens in professional wargaming. According to analysis by Jacquelyn Schneider, game design is invariably influenced by the people convening it. Games frequently end with a victory or defeat without further analysis of what this final state of ‘victory’ or ‘defeat’ really means. Objectives are customarily set as absolute and unchanging throughout the game, despite the evolving pace of events. Notably, we can sometimes witness a disproportionate focus on the tactical and operational levels of war, leaving the politics aside.

Yet, politics have to be taken into account, even if it is not the game’s main focus. Indeed, playing out hundreds of iterations of a conflict on NATO’s border at the operational level is not very useful if in the meanwhile no wargame is being convened on the topic of intra-NATO politics, which immensely impacts inter-army operability, rules of engagement, and ultimately, the operational level. Yet, building in the political dimension to game design is not easy to capture. The options of the ‘red team’ playing the ‘enemy’, are also frequently limited and their objectives are designed in sometimes clichéd ways that are strangely amenable to the blue team. In other words, the games are created often to justify a doctrine or prior concepts instead of truly challenging them.[xx]

In such wargames totalising perceptions of war and politics are readily visible, both in the design and in the way in which defence professionals play. Interestingly, when some non-western or ‘unorthodox’ voices are brought to the table, the games can take on a different complexion, moving away from binary thinking and the pursuit of maximalist, unbounded objectives, which usually generates more valuable outcomes to analyse.[xxi]

Professional wargaming, in other words, functionally reflects the propensities towards bad strategy, largely because they are always distillations of more complicated real-world phenomena.[xxii] Wargaming thus contains a dual tension. On the one hand, epistemological questionings that push some wargame designers to build games as rigorously scientific analytical and predictive tools, tend to screen out more intuitive or dissenting forms of reasoning.[xxiii] On the other hand, wargames are limited by the fact that convenors are often more interested in organising games to support a specific agenda rather than understanding an issue better. As Schneider observes, ‘even though war games are ostensibly designed to help people understand how a war might play out, the results of this “inner” game can reveal only so much. Instead, it is the outer game – who convened the game, who is playing it, how the game is played and distributed, and ultimately why it is played – that offers real insight’.[xxiv]

Accordingly, despite its aspiration to provide more sophisticated understandings of decision-making, wargaming ends up all too frequently re-constituting totalising approaches, especially via the ever-present temptation to resolve problems through ‘radical thrusts’ and escalations to reach decisive conclusions. Not only is this symptomatic of the continuing hold of totalising modes of thinking over the Western strategic imagination (and possibly also of the growing polarisation within Western politics more generally) but also of the more human difficulty of retaining a long-term perspective on things.

Indeed, strategic goals are the tributaries of global, long-term ‘visions’ of how things should be, and as such are only ever truly successful when carefully implemented, often in a slow and tedious process. Since this endeavour can span long periods of time, it demands a constant attention to gradations, capacities for adaptation, and an agility of mind, all of which are not easy to acquire, master and maintain, even for those most attuned to strategic affairs.

Wargaming, in the final analysis, merely replicates human frailties. These frailties, along with all the other polarising discourses in contemporary Western politics, conspire to outpace the capacity for context-sensitive approaches to strategy, not least because the context changes way faster than the ability of institutions to re-configure themselves. Wargaming is, thereby, reflective of the general problems in the study and practice within our institutions of strategic learning. For the attentive analyst, of course, this very insight might be the opportunity to step into an understanding of better strategy.[xxv]

Conclusion: What remains? The infinite game?

So, what are we to make of all this? Is it possible to durably improve decision making by nurturing a disposition that seeks to create a framework that contains a strong, concise, foundational baseline about the objective of strategic studies, yet retains the capacity for a flexible, and adaptable conversation? To that end, this essay has suggested that the foundational objective of strategic studies should be a quest to understand how people have sought to think about the achievement of objectives within highly contingent settings. Therefore, someone who aspires to be a ‘strategist’ is first and foremost a learner. Because doing good strategy requires the exercise of good judgement and imagination, through nuance and open-mindedness.

In stating this, of course, one risks not saying anything beyond the banal and trivially obvious. In the end, we may have simply re-stated in less elegant form the principles of thought underlying Isiaih Berlin’s essay on the Hedgehog and the Fox – the hedgehog knowing one big thing (like an ideology for example), while the fox knows many things.[xxvi] The point being that ‘good’ strategists should learn to become ‘foxes’ who are prepared to seek information from multiple sources, receive new knowledge, remain curious about the world, change their thinking in line with the evidence or the demands of the situation, while being aware of their own cognitive processes and shortcomings.[xxvii] Above all they are conscious that provisional forecasts and conclusions are all that can be offered by the analyst.[xxviii] And, all this boils down to the exercise of strategic humility.

To emphasise, the exercise of strategic humility is not about passing judgement on what is good or bad strategy and who might be responsible – or guilty – for particular strategic outcomes. As this article has stated, assessing whether strategies resulted in good or bad outcomes is a matter of continuous reappraisal and therefore a task for historians. The rationale for seeking to introduce humility into a consideration of strategy is precisely to avoid excessive judgmentalism, not least because perfection in strategic affairs, as in many areas of life, is impossible. The importance of doing ‘good enough’ relative to one’s adversary, or in a particular context, is a crucial component of strategic success, regardless of whether that success was obtained in the most optimum or perfectly efficient manner possible. As Thomas Schelling observed, ‘winning in a conflict does not have a strictly competitive meaning; it is not winning relative to one’s adversary. It means gaining relative to one’s own value system’.[xxix]

In this respect, there is certainly a notion of priority and hierarchisation of objectives in strategic practice that is worthy of further exploration as this can play a major role in discerning strategic successes and failures. This involves yet another exercise in judgement and proportionality, except this time it operates one level higher: it is about finding the right balance of strategic objectives that fit one’s political ideal or overall vision for the future (knowing one cannot maximise them all). It is about defining the ends and assessing their respective weight. A decision-maker might have a misplaced ideological obsession for a specific area/objective, whichever nature it is, which simply does not actually do much to fulfil its political goals.

So, ultimately, strategic humility is about the exercise of introspection and being aware of prior assumptions and ideological underpinnings. One final question to pose to the reader in this respect is whether Western nations are predisposed towards bad strategy because they are ideologically torn apart internally. Does a lack of shared sense of national destiny, public morality, collective identity or sense of fate, render governments unable to make considered choices and weigh the principles they want to uphold?

Does this ideological sundering put too much emphasis on pursuing too many strategic goals at once and end up weakening them all? Is this uncomfortable indecisiveness at these higher levels of decision-making the reason why a strict and rigid understanding of strategy, such as the totalising mind, is so appealing, as an attempt to offer clarity through an appeal to easy moral guidelines? These are open questions. Our intuition is that the link between morals, politics, and strategy, requires far more reflection.