We always ask the same question – what does it take to win?

We think through wargame scenarios, develop a strategy, and then try to execute. We predict what the other side might do but we maintain flexibility so we can adjust when something unexpected happens.

But what if we took a different approach?

What if we turned that question on its head and instead asked – how could we lose?

Suddenly the conversation changes.

The goal isn’t to be pessimistic or negative, but rather to open our eyes to a new framework.

When we only plan for success, we can easily make generous assumptions in our favor. And one of these assumptions can be devastating if we later find out that we’ve been working with an inaccurate mental model.

So rather than solely thinking about the path to success, we can work back from a hypothetical failure to identify all of the ways in which things could go wrong – and how we can mitigate the risk of these negative outcomes.

It certainly requires a change in mindset, but I’ve found this approach to be incredibly helpful in times of high stakes and uncertainty.

-Brandon