Anticipation

Sometimes you can't.

Every time you catch yourself saying, "I should have thought of that" or "Why did I not think of that before?" you are reflecting on your (lack of) anticipation.

A more dysfunctional way is to ask, "Why the heck did you not think of this before?" This is the notion of carrying accountability to an extreme. Punitive questioning results in defensive behavior and reduced risk taking.

While there are consequences for not being able to anticipate, sometimes the only thing that can be done is to learn from the experience and improve the planning process.

Effective strategy execution requires improved planning, which in turn requires an ability to anticipate. 'Guessing' is not anticipating. For complex situations, experience from multiple people may have to be pooled together, while guarding against 'groupthink'.