We fear failure more than we fear losing out on a win. Humans are funny that way. Loss aversion is baked into our psychology. It’s why, when something goes pear-shaped, many won’t just shrug it off. Instead, the tendency is to drag everyone involved, and many who were never involved, through endless rounds of hindsight and finger-pointing. Harry Hindsight becomes a frequent guest in those moments.

Even in a small business like mine, Harry Hindsight gets an invitation from time to time when I reflect on moments where I let caution overtake opportunity.

What happened to markets with the US tariff announcements? Sell, sell, sell. Fear of loss. What is happening in board rooms globally? The highest levels of uncertainty, outside of wartime or a pandemic, seen in decades. Fear of making the wrong call now. Do we bet big that tariffs will last or not last, that markets will adjust reasonably well or not? Or do we wait until we get a little more certainty?

Is this one of those moments in the careers of leaders that provide a stark choice between betting big or bracing for impact. Battening down the hatches and aiming for survival as the impacts of tariffs and the potential removal of tariffs play out. It was interesting to observe the different choices made amongst my clients as COVID hit. Some definitely battened down the hatches. Others leapt into opportunity creation.

Strategic decisions like this are tipping points. They set off a domino effect of choices, actions, and outcomes that ripple across the organisation no matter the decision. As leaders, the challenge is to move beyond fear and embrace rigour. Get the right people in the room. Develop a broad range of scenarios. Pressure test assumptions. Explore opportunities and the downside risks and build a flexible plan. Flexible plans create resilience.

What makes small businesses resilient? Their ability to shift quickly to deal with threats and meet demand.

For C-suite leaders: Design flexibility knowing it builds the resilience you will need.

For risk professionals: Your role is to bring rigour to the scenarios and clarity to the opportunities and risks.

As always, I’d love to hear your thoughts.