Those index cards are the conversational equivalent of a plan. A plan is nice. With a plan, we get to stop thinking. We can just execute. But a conversation doesn’t work that way, and neither does a work of art. Having an intention and then executing it does not make good art. Artists know this. According to Donald Barthelme, “The writer is one who, embarking upon a task, does not know what to do.

One technique I’ve used to soften the process is to ask everyone in the room to make two lists: the top five things that they would do again and the top five things that they wouldn’t do again. People find it easier to be candid if they balance the negative with the positive, and a good facilitator can make it easier for that balance to be struck.

A Checklist is a good way of reminding you what’s missing.”

Jim Collins and Morten T. Hansen, in their book Great by Choice: Uncertainty, Chaos, and Luck — Why Some Thrive Despite Them All, note: “Greatness is not a function of circumstance. Greatness, it turns out, is largely a matter of conscious choice, and discipline.

A long list of ‘things to do,’ often mislabelled as ‘strategies’ or ‘objectives,’ is not a strategy. It is just a list of things to do. Such lists usually grow out of planning meetings in which a wide variety of stakeholders make suggestions as to things they would like to see done. Rather than focus on a few important items, the group sweeps the whole day’s collection into the ‘strategic plan.

When it came to recommending a course of action, almost everyone chose the first one they thought of.

This is predictable. Most people, most of the time, solve problems by grabbing the first solution that pops into their heads—the first insight. In a large number of situations this is reasonable. It is the efficient way to get through life. We simply don’t have the time, energy, or mental space to do a full and complete analysis of every issue we face.