One of the paradoxes that reveals a great deal about making sense of the world is the tension between uncertainty and action. On one hand, we are often told that being effective relies on decisive reasoning, and quickly choosing a course to pursue even with incomplete information. However, opting to eliminate the discomfort of an uncertain or ambiguous situation by making a quick decision can often backfire, and in predictable ways.
When I recall events in my life where my decisions went sideways, they were often hurried, and driven more by my desire to end a period of stress and insecurity than actually determining what could go wrong… before finding out the hard way.
And the world is more complex than ever, more ambiguous, less predictable. As Margaret Wheatley points out in Willing to Be Disturbed, "We live in a complex world, we often don’t know what’s going on, and we won’t be able to understand its complexity unless we spend more time in not knowing."
Wheatley's formulation, that we need to spend more time in not knowing, is a first step in deconstructing uncertainty. One aspect of contemporary emotional maturity is to accept the state of not knowing. Not having a quick answer for complex questions. Being willing to admit being confused by new situations, or rapid changes in the context we are living and working in. Remaining open to spending more time listening to alternative viewpoints before shutting down gathering inputs. These are all aspects of constructive uncertainty, a term I learned from Howard Ross: "Learning to slow down decision-making".
The poet John Keats once wrote that Shakespeare was able to accept uncertainty in his characters and their context, and coined the term negative capability to capture what he described as "being in uncertainties, mysteries, doubts, without any irritable reaching after fact and reason".
So, too, we need to cultivate a negative capability in our approach to an uncertain world. All too often we approach decision-making or strategy formulation in an overly positive manner, which may have serious downsides. JP Castlin argues for a negative approach, saying "instead of explicitly stating what one might do, and thereby implicitly what one might not do, one does the opposite (explicitly stating what one might not do, and implicitly what one might do)." He believes this leads to a more open-minded approach, spending more time in Wheatley's not-knowing, and avoiding the pitfall of closing off Keat's uncertainties, mysteries, and doubts.
Castlin characterizes the difference as two sorts of people:
"People ingrained in the positive strategic planning mindset (in lack of better words) tend to be heads down; focused on the task at hand, certainly, but ignoring new information in favor of routine, downplaying anything that jeopardizes sticking to the plan. Conversely, people who are encouraged to be curious, challenge ideas, think creatively and adapt to context often notice things previously unconsidered, and thus reveal new and improved ways of doing things."
A great example of taking a negative planning approach is Gary Klein's pre-mortem method. A post-mortem is a technique for analyzing what happened after a failed project, such as a surgical operation in which the patient died (from which the term has been borrowed). Klein's insight is to have a post-mortem in advance of the project -- hence pre-mortem -- where the project members cast their thinking ahead to the end of the project's hypothetical failure, and determine what went wrong and how to learn from it… before the project even starts.
The specifics of conducting pre-mortems vary widely, but the fundamental idea is to start with each individual writing down the reasons why the project failed -- from a future-looking-back perspective. This should be done individually prior to any other discussions other than a facilitator spelling out the premise of the pre-mortem, so as to not bias the outcome.
Then, one by one, each participant shares their top reason for the failed project, which are posted on a board. For many reasons, it may be profitable for the most junior members to start and progress sequentially to the most senior. After that, each participant can upvote the various reasons for impact, likelihood, and avoidability. Other rounds can include averaging these votes, suggesting potential solutions, and weighing solutions against the others.
But the purpose is to sidestep the undertow of positive planning. As JP Castlin puts it, pre-mortems "mitigate pluralistic ignorance [when everyone mistakenly believes everyone else holds a different opinion than their own], eliminate overconfidence, and reduce misinterpretation – while it promotes precisely the curiosity, discovery, and creativity that we sought in the first place".
Had I known about not-knowing and negative planning when I was younger, perhaps I could have pre-mortemed that terrible job I accepted, the dumb investments I made, and other iffy decisions fast-tracked by positive planning, when I failed to embrace constructive uncertainty.