Overcome your fears of failure by preparing for the worst-case scenario. Picture: 123RF/LANGSTRUP
Overcome your fears of failure by preparing for the worst-case scenario. Picture: 123RF/LANGSTRUP

The ancient Stoic philosophers like Marcus Aurelius, Seneca and Epictetus regularly conducted an exercise known as a premeditatio malorum, which translates as a “premeditation of evils”.

The goal of this exercise was to envision the negative things that could happen in life. For example, the Stoics would imagine what it would be like to lose their job and become homeless or to suffer an injury and become paralysed or to have their reputation ruined and lose their status in society.

The Stoics believed that by imagining the worst-case scenario ahead of time, they could overcome their fears of negative experiences and make better plans to prevent them. While most people were focused on how they could achieve success, the Stoics also considered how they would manage failure.

What would things look like if everything went wrong tomorrow? And what does this tell us about how we should prepare today? This way of thinking, in which you consider the opposite of what you want, is known as inversion thinking.

When I first learnt of it, I didn’t realise how powerful a tool it could be in my business for managing and delivering projects within an allocated timeline and budget. Inversion thinking is practised by conducting a pre-mortem. Let’s look at why and how.

Why you must consider failure

Projects fail at a spectacular rate. One reason is that too many people are reluctant to speak up about their reservations during the all-important planning phase. By making it safe for dissenters who are knowledgeable about the undertaking and worried about its weaknesses to speak up, you can improve a project’s chances of success.

Each setback or unexpected problem adds time to your project. If the timeline of a project doubles or triples your estimates, then the first problem is the project timeline itself. A project that gets approved with its original timeline may lose priority and focus if it runs over, as those working on the project may be needed somewhere else. Over time, you can end up starting a lot of projects with nothing to show for it. You waste time and money on failed projects, cripple team morale and lose direction.

To talk about what might go wrong is scary. It acknowledges many things are out of our control and we might mess up the things that are within our control. To talk about what might go wrong and how to adapt to it acknowledges the possibility of failure. But if pre-mortems are held with some regularity, and always with creative problem-solving, it can build a safe space for adaptation in the face of adversity.

How to conduct a pre-mortem

A typical pre-mortem begins after the team has been briefed on the plan. The leader starts the exercise by informing everyone that the project has failed spectacularly. Over the next few minutes those in the room independently write down every reason they can think of for the failure, especially the kinds of things they ordinarily wouldn’t mention as potential problems for fear of being impolitic.

Here are a few steps to follow to conduct a successful pre-mortem, starting with a brief of the plan to the project team. Armed with a white board and some pens and paper, follow these few steps:

  1. Imagine the worst: Start the meeting by exposing that the project at hand has been a complete disaster.
  2. Generate reasons for failure: Ask each person to write down all the reasons they can think of to explain the failure that occurred.
  3. Share reasons for the failure: Ask each person to share one item on their list and continue to go around the room until everyone has exhausted their list. Record all reasons on a white board.
  4. Brainstorm the solutions: Discuss solutions to prevent each problem from happening.
  5. Review the list: After the session, review the list and look for ways to strengthen the plan.

You should revisit the list from time to time for the remainder of the project.

Luthuli is an independent financial adviser and founder of Luthuli Capital.