How Will the Plan Fail?

Many leaders devise detailed strategies they think will lead to success. But they don't give nearly enough consideration to what losing would specifically look like.

September 08, 2022

The coach has a great game plan. Speed up the tempo, increase the number of possessions, get the opponent out of rhythm, be especially aggressive early.

Except in the first few minutes of the game, the quickest player goes down with an injury, the most-talented player starts fuming over a bad call, and the opponent anticipated its competitor would want to play fast and has counterstrategies.

The season, the school year, the fall cycle are underway in many parts of the world — and countless leaders have painstakingly put together their own respective plans they think will lead to success.

But the vast majority likely haven't considered something that might be just as important: How their plans could ever fail.

A crucial concept we'd be wise to incorporate is the premortem, detailed by former professional poker player and behavioral science author Annie Duke (borrowing on research from psychologist Gary Klein) in her book How to Decide.

A premortem essentially works backwards to consider hypotheticals of how even a seemingly-foolproof strategy could crumble.

It entails five steps:

1. Identify the goal you’re trying to achieve or a decision you’re weighing.2. Decide on a reasonable time period for achieving it or for having your decision play out.3. Imagine it’s a day after and you failed to achieve the goal or it turned out poorly. Then, in reflecting on the disappointment, list as many as five reasons why it failed based on your own choices and actions.4. List five external factors that caused the plan to fail.5. If this is a team exercise, have individual members do steps 3 and 4 independently.

When failure occurs, it’s likely due to a combination of internal factors (jealousy, ego, bad game plan) and external (poor weather, improbable injury, unexpected tech malfunction, etc.), Duke writes.

The key is to anticipate that the plan will go awry because of factors from each category.

This will ultimately lead us to get ahead of potentially fatal issues, while also devising alternative strategies to overcome any hiccups.

“A premortem allows you to do the same examination of the causes of death while the patient is still alive,” writes Duke, who is set to release a new book on the art of quitting next month.

In essence, methodically considering how we will lose may be exactly what inspires our impressive win.