Premortem

I was introduced to the concept of the premortem by Haley Bryant, my COO at Animalz.

A premortem is a structured process for identifying potential flaws in a plan. It requires users to assume the certain failure of their project—whether a product launch, a new customer relationship, even making a new hire—and posit the most likely reasons for the failure.

I started using premortems in the context of onboarding new customers. As I began to research the new customer and theorize the best content strategy to develop for them, I would write a bullet point answer to the following question:

This customer churned 3-months into our relationship. Why?

Based on my knowledge of the customer to date, my experience with similar customers, the perspective of the sales team and my own nascent gut feelings, I would quickly arrive at a handful of potential relationship killers.

Here are some excerpts from my real-world premortems:

• “We didn’t offer enough of an ROI above their existing freelancer process. We’re expensive, and they have years of experience working with freelancers. Our articles have to be better by an order of magnitude.”

• “We required too much oversight from their team. They have extremely high editorial standards and their existing editorial team is extremely stretched. If we can’t ramp up to their standards, we’ll lose them.”

• “We lost access to decision-makers. Our relationship is being run through a third party, and their CEO is extremely busy (and reportedly misses meetings).”

Haley introduced me to the premortem by way of Gary Klein’s research paper, The Misuse of Premortems on Wall Street. The paper’s key point: a premortem isn't a box-checking exercise to validate your latest brainwave. It's an active process designed to increase a project's likelihood of success.

Alongside your reasons for failure, the premortem needs to recommend possible solutions:

• We didn’t offer enough of an ROI above their existing freelancer process ∴ we have to prioritize the highest-leverage concepts to write. Our writing can never be 10x better than their existing content, so we need to focus on the concepts that will have the biggest impact on sign-ups and revenue.

• We required too much oversight from the customer’s team ∴ we need to function autonomously, taking their fledgling ideas and turning them into workable article pitches, ensuring all editors and copyeditors edit according to their brand guidelines, and deliver articles in Markdown.

• We lost access to decision-makers ∴ we should make sure to keep the C-Suite thoroughly aware of our value-add and maintain a direct line of communication with them.

I like the premortem for a host of practical reasons.

For one, it provides a laser focus for your team. Going into any new endeavour, there are always one or two red flags that warrant the bulk of your thought and preparation. The premortem surfaces these out-sized risks, and makes it easy to unify your team around solving them.

The premortem also normalizes failure. Even the most successful career is accompanied by a litany of failures—arguably, the more failures experienced, the greater the likelihood of eventual success. The premortem process sends a clear message: failure is a learning exercise and not something to hide from.

Lastly, it's quick, dirty and extremely effective. It's an easy model for everyone to understand and apply. From my experience, it leads to a marked improvement in project success—and a clearer understanding of failure when it happens.

The premortem resonated with me because it combines elements of three other fantastically powerful mental models:

• Steel-manning: we're creating the strongest possible argument for the failure of a given project—we're working on the assumption that it actually has failed, and forcing ourselves to explain the failure. There is no get-out, no softball questions to answer.

• The Pareto Principle: the premortem lets you home in on the handful of problems (the 20%) that are likely to account for the majority of a project's risk (the 80%). It's a powerful heuristic that even the busiest of teams can adopt and benefit from.

• Negative visualisation: we identify, internalize and become comfortable with the full range of possible outcomes. We admit that failure is not only possible, but likely, and we allow ourselves to prepare for the worst-case scenario.

In many ways, the premortem is pure Stoic philosophy in action, reminiscent of this quote from Seneca:

"Remember that all we have is 'on loan' from Fortune, which can reclaim it without our permission—indeed, without even advance notice. Thus, we should love all our dear ones, but always with the thought that we have no promise that we may keep them forever—nay, no promise even that we may keep them for long.”

Tl;dr - Whatever your next project may be, it's worth taking the time to conduct a premortem and remind yourself that Fortune may well reclaim success at a moment's notice.