How to do a premortem on your culture

In Ryan Holiday's book, The Obstacle is the Way, the author talks about the value of premortems in business. 

While a "post-mortem" refers to an autopsy, or examination to assess the cause of an unexpected death, a premortem (a term coined by psychologist Gary Klein) is a pro-active exercise in anticipating what might kill something. 

Holiday uses the example of a CEO who calls her staff for a meeting the night they're launching a major project, announcing she has bad news. "The project has failed spectacularly. Tell me what went wrong?"

She posed this question before they even launched. She was forcing them to think about all the possible worst-case scenarios before they could arise. 

"We look to envision what could go wrong, what will go wrong, in advance, before we start," Holiday explains of a premortem. "Far too many ambitious undertaking fail for preventable reasons."

People don't like to imaging worst-case scenarios, particularly when planning something that feels really positive -- like creating your company culture guide, or coming up with your guiding values system. But doing so could help you a) avoid potential disaster, and b) dream bigger.

Doing a premortem on your company culture

Whether you're developing your company culture from scratch or updating it, a premortem could be a healthy part of your assessment when looking at your guiding values, perks, benefits, and other elements of your culture. 

For example, you might be toying with the idea of unlimited vacation time. Before you implement it -- or toss the idea off the table -- conduct a premortem with your core team members to see if you could handle the worst case scenario. 

Some of the things you might worry about: What if people take too much time off? What if people take too much time off? What if people abuse the system? What if people get complacent? 

Holiday recommends going through an exercise in which you ask and answer questions like this: 

What if...

Then I will...

What if...

Instead I'll just...

What if...

No problem, we can always... 

And, he notes, sometimes there is nothing that can be done in a worst case scenario, in which case we can learn to say, "It will suck, but we'll be okay." 

Try it, for anything in your culture. Adding "radical transparency" to your guiding values? Run a premortem first, assess potential what-ifs. Thinking of setting up a remote team? What are the scariest things you can imagine happening? And how could you handle those?

By designing plans based in reality, by not being afraid to imagine worst case scenarios, we can create anything with much more confidence because we know we're prepared for anything.

More articles on premortems 

How to Do a Pre-Mortem (and Prevent a Post-Mortem) - Guy Kawasaki

Simple Way to Prevent Failure: Do a Pre-Mortem - Inc Magazine

Fake Your Own Death: The 4-Step Startup "Pre-Mortem" - Forbes