In the past, running a Premortem has been the single most helpful exercise I’ve found for dealing with complex, risky projects. This is the core idea, but there’s a little more to it.

I’m not joking when I say that a premortem refocused the hardest death-march I’ve been on, and another premortem was a key step in planning for a complicated (and ultimately successful) $12m fund-raise. If all goes well, it’ll help highlight your biggest fears, and proactively figure out steps for how to defuse them.

In short, this is how I run them:

• Gather a couple of other core people/project leads with complementary expertise. Allocate 2 uninterrupted hours (though you might not need all that time once you start to get efficient at them).
• Sit down and read the above Guardian article through together at the beginning of the session.
• Have fun telling each other the nightmare story. I usually set them at the next major milestone, perhaps within the next 6 months or so. Make it specific and vivid, e.g. ‘The CEO of X is on stage announcing their partnership in October with your major competitor’ or ‘We’re out of money and don’t exist, and you’re back to working at your previous job you hated.’
• Set a timer for 15 minutes or so, and separately in silence each scribble down as many potential reasons why this terrible future came to pass, e.g. ‘Their CEO tried it out and happened to get a buggy version and they lost faith in us’, or ‘The lawyers axed the project because of regulatory hurdles’. I usually use either Google Docs or postits to make the following phases easier.
• Race through everyone’s items out loud quickly. There will be duplicates and related issues – as you go through them, place them into groups.
• Then, for each group of issues, ask ‘what could we do to fix/de-risk this?’. [Maybe do this in silence individually first too]. You’ll start to see that there are a few things you could do that will help considerably de-risk multiple issues at the same time. Assign one person to be responsible for each approach you agree to act on.
• By this point, you should have felt like you’ve looked into the abyss, but come out the other side and achieved a measure of catharsis. There’s something about the perspective you get from doing this exercise that makes it much easier to make hard choices (I find).
• Set a date to revisit in 6 weeks (to make sure you actually addressed the risks you’ve just identified, and see where things stand).