Why entrepreneurs need to turn the world of “what if” on its head

One of the reasons why hindsight really is a wonderful thing is that it provides us with an infinite number of “what ifs”. We might remain acutely aware of the futility of imagining what could have been, but we can seldom resist a peek at the road not taken – even when the ultimate effect is merely to reinforce how alarmingly riddled with potholes our chosen route is.

There are occasions, of course, when hindsight proves us right or enhances our grasp of a glorious success over which we have somehow presided. More often than not, though, it lays bare how ill-considered and misguided our decisions have been.

The strange thing is that this seldom comes as a surprise. We reflect on our choices and their consequences, belatedly acknowledge the alternative scenarios to which we gave insufficient attention and essentially admit to ourselves that we always suspected this would happen.

No wonder, then, that psychologists believe our brains are every bit as inherently indolent as our bodies. Nobel Prize winner Daniel Kahneman described the phenomenon in his book, Thinking Fast and Slow, positing that we employ two decision-making systems – one swift but prone to error, the other deliberate but taxing to use.

Most of the time, much as we might like to think otherwise, the first system rules. The best the second system can manage is to rubber-stamp the imprudent inferences of its careless counterpart. “If there are several ways of achieving the same goal,” wrote Kahneman, “people will eventually gravitate to the least demanding course of action. Laziness is built deep into our nature.”

Re-wiring the human brain is probably beyond the powers of even the most celebrated of business schools, but helping to bring about a beneficial change in mindset should be within our collective capabilities. The importance of doing so becomes all the clearer when we pause to ponder the number and significance of the decisions entrepreneurs must face and, just as compellingly, the escalating reach and gravity of those decisions as a business grows.

The unfortunate truth is that acting in haste is too frequently celebrated as some kind of skill. This is a dangerous misconception. There are undoubtedly occasions – in business as in life – when quick thinking is desirable; but there are many others when this apparent facility is actually a rush to judgment that stems largely – if not entirely – from the less attractive of the two brain systems suggested by Kahneman’s research.

This is why the next generation of entrepreneurs would do well to cultivate a mindset that encourages the contemplation of “what ifs” before rather than after the event. They need to appreciate the vast difference between a culture of “What if we were to do this?”, which is rooted in healthy curiosity and rigour, and a culture of “What if we had done this?”, which is mired in helpless retrospect and regret. So how might they go about it?

A fundamental shortcoming at the core of every rash decision-making process is the assumption that the correct answer can be plucked with ease from a set of fully formed and available options. This philosophy may seem perfectly reasonable at first glance, but its inherent pitfalls become obvious when we note how closely it mirrors the act of picking a winner in a horse race.

As any successful breeder or trainer of horses can attest, winners are not picked: they are made. Moreover, while breeders and trainers are relatively constrained in their freedom to think radically – they cannot, for example, build a horse from lighter materials or of dramatically different dimensions – decision-makers in the sphere of business enjoy much more scope in assessing novel yet practical solutions that might be far removed from the rapid and the routine.

To develop a full range of possible answers it is first necessary to grasp fully the question at hand. Exploring the root causes and assorted elements of a problem, especially if it is a complicated one, is vital to the conception of creative responses. Deconstruction must precede reconstruction.

Thereafter the aim should be a flood of informed ideas – good, bad, bold, conservative – anticipating each and every identifiable “what if”. From these, via a process of elimination, the cream of the crop should emerge. Part of the attraction of this approach is that it is mentally stimulating, enjoyable and even amusing; in tandem, the tedious lament that “creatives” have all the fun is exposed as the enduring myth that it most assuredly is.

It is only right to concede that entrepreneurs, not least those in the early stages of their careers, may flinch at the prospect of devoting sizeable amounts of time, energy and even money to pre-empting a multitude of “what ifs”. Yet the urgency and sheer scale of some of the issues many of them are likely to play a role in tackling, however comparatively small their contribution, are sufficient to render ROI-related concerns not just trivial but vaguely preposterous.

As business schools ought to stress to their students at every opportunity, the mind remains the greatest resource humanity possesses. It is readily available, inexhaustible and free at the point of use, and it deals in the invaluable currency of ideas – which, lest we forget, are what enable us to progress. Used well, it does much more than address the problems of the present: crucially, it also lays the foundations for the future. The pain of the road not taken is likely to be particularly severe when, as has become the unhappy norm in so many quarters, long-term benefits are left to play a distant second fiddle to the short-term caprices that laziness of thought is so quick to satisfy.

Martin Binks is the former dean of Nottingham University Business School and a Professor of Entrepreneurial Development at its Haydn Green Institute for Innovation and Entrepreneurship.