Prospective Hindsight – A Critical Leadership and Life Practice

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  • July 24, 2017


Hindsight has an interesting way of producing an almost universal response: “What was I thinking?!” Whether it was wearing trendy Z-Cavaricci pants in my youth, going to Cancun for spring break in college (twice!), accidentally biking on an interstate highway while training for an Ironman or seeing the less-than-stellar movie Gone Fishin’, hindsight always seems to be 20/20.

Although I am usually in the camp of “start with yes” and “ask questions later,” I have over the years adopted a process in both my personal and professional life of considering how things could go wrong. I see this as an exercise in getting in touch with my fears instead of letting them control me. It’s about staring my fears down and realizing that things are probably not so bad — even if the worst-case scenario plays out in the end. I recently read about a process called a “premortem” that I think can be extremely valuable both personally and professionally when done correctly. I want to share with you the origins of the premortem and steps to implementing a premortem exercise in your life.

What Is a Premortem?

According to Gary Klein, the creator of the management practice, a premortem is the hypothetical opposite of a postmortem. As most people know, a postmortem in a medical setting allows health professionals and the family to learn what caused a patient’s death. A premortem, on the other hand, is a managerial strategy in which a manager imagines that a project has failed, then works backward to determine what could potentially lead to its failure.

Klein writes, “Unlike a typical critiquing session, in which project team members are asked what might go wrong, the premortem operates on the assumption that the ‘patient’ has died.” He cites research that found prospective hindsight, or imagining that an event has already occurred, increases the ability to correctly identify reasons for future negative outcomes by 30 percent.

Steps to Completing a Premortem

Doing a premortem is fairly straightforward. Whether it’s for a high-stakes project at work like launching a new product line or planning a big event at home such as buying a house, these steps could be helpful the next time you embark on any kind of meaningful undertaking.

A few prerequisites that set you up for the best possible outcomes include setting aside at least one hour (preferably two hours) of uninterrupted time, ensuring all stakeholders are present and making the premortem a face-to-face meeting (or video call).

Here are the three simple steps:

  1. Spend one hour listing every possible problem you can imagine.
  2. Pick the top 10 problems.
  3. Spend one hour creating solutions.

My view is that there are several benefits to this process aside from increasing the likelihood of a project’s success. First, a premortem can create better alignment with the team because everyone feels like their opinions and fears have been heard. In addition, this practice increases the confidence level of the team, which is a critical factor in the success of any project. Because it only takes a couple hours of your time, I see very little downside to doing this exercise. What do you have to lose?

Premeditatio Malorum (Premeditation of Evils)

According to Ryan Holiday, the author of several books on Stoicism, the practice of imagining the worst-case scenario goes back many thousands of years. In fact, it can be traced to great Stoic philosophers like Marcus Aurelius, Epictetus and Seneca. They called it premeditatio malorum (premeditation of evils).

A writer like Seneca would begin by reviewing or rehearsing his plans to, say, take a trip. Then he would go over the things that could go wrong or that might prevent it from happening — a storm could arise, the captain could fall ill, the ship could be attacked by pirates, etc. Seneca is quoted as saying, “Nothing happens to the wise man against his expectation … nor do all things turn out for him as he wished but as he reckoned — and above all he reckoned that something could block his plans.”

By completing this exercise, Seneca was always prepared for disruption and was always including that disruption in his plans. He was prepared for defeat or victory. The Stoics knew all too well that our world is ruled by external factors. Therefore, they prepared themselves for this level of uncertainty.

Incorporating the Premortem Into Your Life

It’s possible that many of you will think the premortem isn’t for you at first, perhaps because your to-do list is long enough already and you don’t have time for such intellectual exercises. But try to resist feeling this way. The simple fact is that we have been taught since birth that an ounce of prevention is worth a pound of cure, and for good reason. Life has a way of not going as planned. We know that the data says prospective hindsight, or premortem, significantly boosts our ability to correctly identify reasons for future outcomes. That seems like an “unfair advantage” we should all want in our toolkit.


About Todd Zipper

President & Chief Executive Officer

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