Every business leader, entrepreneur, and manager is constantly required to make bold decisions. Every decision comes with a high amount of risk, which in turn involves uncertainty. What sets successful leaders apart isn’t just their willingness to take risks. It’s their unique ability to anticipate the results.

When leaders can connect the dots and predict what might go wrong before it does, it creates a better pitfall for taking risks. As a result, the outcomes become manageable, and many times, profitable for them. This behavior sets the direction for a powerful business strategy called Premortem.

A premortem is a proactive exercise where you imagine a project or decision has already failed. Instead of asking- What could go wrong, you ask, What did go wrong? This mental shift is called prospective hindsight, which forces you to confront risks head-on. Unlike a postmortem, which analyzes what went wrong after the fact, a premortem does the opposite.

So, a premortem imagines what could go wrong before the action is taken, and uses that insight to make smarter decisions from the start. This is especially useful because here, leaders don’t wait for the failure to occur to understand it; they simply see it from early on. That means businesses and leaders get the resources and time to pivot and ensure successful outcomes.

It may sound counterintuitive, but thinking about failure in advance can actually lead to greater success. When leaders gather their teams and ask about what went wrong, they’re opening up a space for honest, creative, and risk-aware thinking.

This technique, popularized by psychologist Gary Klein, encourages people to suspend the usual optimism that surrounds new ventures and adopt a healthy dose of productive pessimism. The idea is to protect against blind spots, groupthink, and overconfidence. Research shows premortems improve risk identification by 30% compared to standard methods. Here’s why:

• Defuses overconfidence: Teams often assume success is inevitable. A premortem shatters this illusion, replacing “We’ve got this” with “What if we don’t?”
• Encourages honesty: By framing failure as a hypothetical reality, team members speak freely without fear of blame.
• Sparks creativity: Imagining disaster pushes teams to brainstorm unconventional solutions.

How to Use Premortem for a Regret-Free Leadership

The beauty of the premortem lies in its simplicity and versatility. It doesn’t require a formal process or a big budget. It just takes time, honesty, and the willingness to question your own plan.

You can start by setting the scene. Introduce the situation in which your project, launch, or strategy has failed. Now, work backward. Open, honest, and clear dialogue among employees and management about what went wrong here. This involves considering timeline changes, misjudging the market, communications breaking down, etc.

Once you’ve listed the imagined reasons for failure, turn those into checkpoints and adjustments for your current plan. By identifying these potential pitfalls early, you’re giving yourself the chance to act smarter now, rather than scramble later.

In the end, the goal isn’t to avoid risk altogether. It’s to avoid regret. And the secret to doing that is about having a flexible, thoughtful plan that has already considered the worst and prepared for the best. So, before your next big move, take the time to pause and ask each other- if we fail, why did it happen? Then get to work making sure it doesn’t.