Years ago, when I served as the President of the Legal Marketing Association, I would get antsy if I looked around the table during board meetings, and all 12 of us were completely on-side with a new idea or project.  I knew it probably meant that we weren’t being critical enough.  So, I would stop the vote, and ask the question – where can this go wrong?  What assumptions are we making that might not pan out?  Who might be opposed to this idea and why?  It caused a break in momentum, but it usually fueled a deeper, more meaningful discussion.  In the end, we usually passed the vote, but with a much stronger product.

In a recent podcast (from Freakonomics), I learned about pre-mortems.  We of course know of post-mortems.  In science they are examinations of a body after death, usually to learn more about the cause of death.   In business, they are conversations after a project has gone off the rails in an attempt to determine how things went wrong, and what lessons can be used to avoid similar problems in the future.  But this was the first I’d heard of pre-mortems. They are held in the final stages of approving a project or event.  They start with a request to imagine the meeting is taking place in the future, after the project has been launched, and has failed.  No question, no debate.  It has absolutely failed.   Participants are then asked to discuss the failure.  What caused it, what did the failure look like, what can we learn from the failure?

In the podcast, the presenter gave an example of his work with a defense contractor working on a particular device that would be used in the battlefield – I believe it identified incoming missiles or something along that line.  The company was ready to show it to the client when they held a pre-mortem.  During that session, eventually, the lowest rank in the room shyly put up their hand, to say that the computer units used in the field were far inferior to the super computers being used to create the device, so it wouldn’t work in the field!  They were able to creatively solve that problem but it illustrates how powerful (and important) a pre-mortem can be.

Hearing the podcast made me realize that I often hold pre-mortems, just as I did on that board.  But these days, it’s more likely to be a pre-mortem of one.  That doesn’t make it any less helpful.

Just imagine that you’ve provided your advice, or you’ve represented your client in court, or you’ve launched you marketing campaign, or held your event. Now imagine that it was a disaster.  What could have gone wrong?  What were the variables that you haven’t thought about until now?  We don’t tend to do this because we see it as being negative, as placing drama where it needn’t exist.  Really, I think we don’t do this because we don’t want to feel that sense of failure that comes from even imagining such a scenario.  But do it anyway: get past the emotion associated with failure as quickly as you can, and move into intense curiosity.  This opens the door for considerations we might not have allowed to the surface before.  In my experience, it broadens the mind and ultimately, you enable yourself to create a better, more rounded and bulletproof solution.

We’re so afraid of failure that, ironically, we fail to see the benefits that it can bring whether it’s real or imagined.  But practice, which most people see as positive, is about failing a bunch of times until you can succeed, and then continuing to fail every so often until you can succeed far more than you fail.  Don’t be afraid of it.  Learn from it. And cherish opportunities to potentially learn before you fail.

The podcast I listened to was part of a three-part series on failure from Freakonomics – well worth the time to listen to all three parts.

Happy New Year, everyone!

Heather Gray-Grant is a business strategist, marketing expert and executive coach for law firms, lawyers and administrators.  She can be reached at