The nature of the challenge

While working on a strategy this week, I realized that one of the most common missing bits from a well-designed strategy is a discussion of the nature of the challenge.

There are degrees of strategy design quality (that I probably need to write about someday), and at the higher end of the spectrum are strategies that include a problem statement. The problem statement usually briefly describes the challenge that the strategy seeks to wrestle with. For me, this is usually a good sign. I have seen so many docs/decks that call themselves strategies, but are actually just plans or inventories of projects that having a cogent description of the challenge is breath of fresh air. It’s an indicator that the author invested time reflecting on why their set of proposed actions might lead to addressing the challenge.

What would help make a strategy even more effective is capturing why the problem is hard. What is the nature of the challenge? What are the forces at play and which ones of them do we intend to rely on — or contend with — to overcome the challenge? Think of the nature of the challenge as drawing your best approximation of the map of the upcoming quest: here are the tall mountains, here is the dragon lake, here is the fairy meadow. Then, the approach you’ve taken is a path that weaves through this map.

By painting that larger picture around the proposed path, we allow others around us to see it. They might point out that they are seeing a slightly different picture. “There’s no dragon lake here. And the fairy is actually a witch.” They might also point to a different path: “Why not skip visiting the castle? It smells musty and the old duke is not fun to be around.” This might be uncomfortable, especially when so much work went into putting the strategy together, but in my experience, describing the nature of the challenge tends to act as a unifying force: once articulated, it pins down at least one mental model of how the future events will unfold, and this catalyzes sharing and aligning of other mental models — dramatically increasing the overall chances of the strategy succeeding.

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