I’m not interested in doing a post-mortem on projects, policies or relationships. In theory, it makes sense to take stock of an event when it’s over. It sounds healthy to compile a list of “lessons learned.”

But you know what happens with a post-mortem? Not much. You make a list, file it away, and forget about it. Then you’re surprised when you fail again.


Over the past six months, I’ve been trying a new approach called a pre-mortem™. Before I do anything, I ask myself a simple question: how could this fail?

Because almost everything breaks and bombs the first time.

Life is sticky. The world doesn’t bend to our will. There are universal forces of failure™ bearing down on us. Sometimes there are no good choices, and we’re victims of a broken system. But, for the most part, that’s not how it works. I believe that most people know how they’re going to fail.

So before you do anything, take a second and ask yourself how you’ll fail.

Yikes, it’s an uncomfortable question and a delicate mental exercise. I don’t expect you to like it. But if you want to stop making the same mistakes over and over again, evaluate your chances of failure (not success) before you even start.

Are you about to finance a car? Are you getting married? Do you want a new haircut? Are you thinking of going back to school? Are you implementing new payroll software?

Take a second. Peer into your shitty future. How will this have failed? Then, you know, maybe plan to do it differently. Give that a go.

Me? I want to get better at the predictive analytics of human behavior without consulting Watson. I want to have quick and honest conversations about mistakes and misunderstandings before I make those mistakes again and again.

So that’s why I’m sticking to my plan and asking myself, “How will this fail?”

The earlier you examine failure, the better your chances of success.

1 Comment

  1. Engineers have a systematic way of doing this, of course, called a Potential Problem Analysis. Major projects will go through a PPA to assure that there is preparation for what could go wrong. Putting some genuine thought into the normally sarcastic question “What could possibly go wrong” can provide insights that end up creating improved outcomes.

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