On Strategic Thinking

There’s a fundamental distinction to be made between two kinds of thinking: figuring out what we would like to achieve and working out how to achieve it. Or, put another way, there’s a key difference between strategy on the one hand and execution on the other. Strategy is about determining our overall aims, and execution comprises everything that follows once we’ve decided: the practical activities required to put our plans into action.

It’s natural to assume that we would all instinctively spend a lot of time on strategy before we ever turned our attention to execution – given that, however successful we might be in carrying out our plans, what really counts is having the right plans to work from in the first place. Our results can only ever be as good as the aims that first led to them.

But there’s a paradoxical aspect to the way our minds operate: as a general rule we’re a great deal better at execution than at strategy. We appear to have an innate energy for working through obstacles to our goals and an equally innate resistance to pausing to understand what these goals should rightly be. We seem to be as lackadaisical about strategy as we are assiduous about execution. We prefer to zero in on the mechanics, on the means and the tools rather than on the guiding question of ends. We are almost allergic to the large first-order enquiries: what are we ultimately trying to do here? What would best serve our happiness? Why should we bother? How is this aligned with real value? 

There are tragic consequences to this over-devotion to execution. We rush frantically to fulfil hastily chosen ends, we exhaust ourselves blindly in the name of sketchy goals, we chain ourselves to schedules, timelines and performance targets – but all the while, we avoid asking what  we might really need in order to flourish and so frequently learn, at the end of a lifetime of superhuman effort, that we had the wrong destinations from the start.

Perhaps it should not surprise us that our minds have such a pronounced bias towards executive labour over strategic reflection. From an evolutionary perspective, mulling over strategic questions was never a high priority. For most of history, the strategic goals would have been patently obvious: to find sufficient things to eat, to reproduce, to get through the winter and to keep the tribe safe from attack. Execution was where all the urgent and genuine difficulties lay: how to light a fire in wet weather, how to make sharper arrowheads, where to find wild strawberries or the right leaves to calm down an inflammation… We are the descendants of generations that made a succession of complex discoveries in the service of a few basic goals. Only in the conditions of modernity – where we are surrounded by acute choices as to what to do with our lives and when our aim is happiness rather than sheer survival – have strategic questions become at once necessary and very costly to avoid.

Even in daily life, raising strategic questions can feel tiresome and odd. To ask ‘what’s the point of doing this?’ is easy to mistake for a piece of provocative negativity. If we challenge our acquaintances with any degree of seriousness with ‘What is a good holiday?’ or ‘What is a relationship for?,  ‘What is a satisfying conversation?’ or ‘Why do we want money?’, we risk coming across as absurd and pretentious – as though such large questions were by definition unanswerable.

They tend not to be; while the dangers lie in never daring to raise them with enough vigour at the outset. We already possess a great deal of fragmentary, disorganised but important information that could help us to make progress with the larger strategic dilemmas. We have already been on a sufficient number of holidays and shopping trips, we have already had some relationships and been through a number of career shifts, we have had a chance to observe the connections between what we do and how we feel – and so we have, at least in theory, gathered the necessary material from which to draw rich conclusions as to our happiness and our purpose, as to meaning and the right human ends. We have the data; the challenge is to process it by running it through the sieve of the larger questions.

We should dare to move the emphasis of our thinking away from execution and towards strategy. 

Find out more about finding balance in our class on Effectiveness.