When I coach senior executives, they often reveal their inner doubts. It’s a tough job making the big calls. Even with a good and supportive team, the uncertainties and unknowns that surround every substantial strategic decision often leave leaders in a perpetual and unsettling state of self-doubt. And in my coach’s role I can’t help directly. I can’t tell them what to think. But I can and do help them how to think. Or rather, Shakespeare and Darwin can. And they can help you too, if you can spare me the next few minutes.

Let’s begin with the Shakespeare. In Measure for Measure, Lucio points out the damage that doubts can do: ‘Our doubts are traitors, and make us lose the good we oft might win, by fearing to attempt.’ He’s right, of course. How often have you seen companies choose not to do things – not because they weren’t right but because their leaders couldn’t be sure they were right. The nature of corporate life and strategic decision-making is that big decisions often carry the burden of proof we apply in legal cases. We tend to implicitly decide ‘no’ if there is reasonable doubt about the outcome. That way, as Shakespeare’s words were meant to warn, lies inaction and strategic paralysis. What executives need is a way to reduce their doubt. Enter Darwin, stage left.

Well, actually enter Dan Levinthal, Professor of Corporate Strategy at Wharton, who like me applies Darwinian thinking to businesses. He describes strategic choices as a Darwinian selection process, the effectiveness of which determines how well the firm adapts to its changing environment. One of the many insights I took from Dan was that these choices can have three mechanisms. We can select from existing options, choose from untried options or craft new options by learning from past experience. Now, I appreciate this may sound a little abstract and academic to my readers, but it has very useful and practical implications because if you know your mechanism, you can test that it’s working properly.

Imagine, for example, that your firm has been trying several different approaches to shaping treatment pathways in different markets and you need to select the one to adopt in a new market. You must pick the one that works best. To lessen your doubts about that choice, you can critically evaluate how you have measured and compared the different approaches. If you’ve done that well, worry less. If not, your doubts are valid and should be addressed.

Alternatively, imagine if you are choosing between several targeting and positioning options for a new product. You can’t select from previous approaches, so your mechanism is to evaluate them against predicted future outcomes. If you want to be more sure of your choice, then consider how you are doing that evaluation. A rigorous evaluation should reassure you that your decision is sound. But the all-too-common approach of ‘socialisation’, when approval is based on everyone’s gut instinct, means your doubts should push you towards a more exacting and severe calculation of future outcomes.

The third mechanism, learning, applies when you can neither select from tried options nor choose from projected outcomes. For example, imagine a scenario where you have tried various approaches to externalising innovation and you’re trying to craft an approach that learns from previous approaches.

Obviously, this can be a very useful way to make new decisions based on past experience, but only if your learning process is sound. You can assure yourself it is by considering how you are taking lessons from the past. If you have built a deliberate learning process that is deductive, inductive, abductive or a combination of all three, then you can be confident that you’re learning the right lessons. But if you haven’t and you’re just labelling your biased opinions ‘organisational learning’, then you should indeed be doubting yourself and improving how you and your team learn from experience.

My executive mentees furrow their brows when I ask to tell them about Shakespeare, Darwin and Levinthal. But they are usually pleasantly surprised by what they can learn from these unusual sources and how it translates into practical steps for improving their strategic decision-making. The secret is to neither ignore your doubts nor to have them constrain you. Instead, ask yourself if you’re selecting, choosing or learning then, whichever you choose, do it the best way you can.