Imagine Your Failed Future To Stop It Happening
A Pre-Mortem can help you avoid pitfalls at work by forecasting what the worst outcome might be.
My dearly beloved, we are gathered here today to talk about your project at work.
You know the one I’m talking about: that project where everyone knew it was doomed for failure before it even began. Despite this, your colleagues and you worked diligently on it as best as you could until the inevitable happened and it all imploded spectacularly. Just like you knew it was going to.
Sound familiar?
The reality is that some projects succeed wildly, and others fail dismally. When they do blow up, we tend to pick over the bones to try to find out why it didn’t work, a form of a post-mortem to ascertain the cause of its death. That can be useful, but it’s always too late after a project has died to be helpful.
There is, however, an excellent exercise that you can do before you kick off a project to give it the best chance of succeeding. It’s called a Pre-Mortem, and its a strategic team tool conducted before a project begins where you imagine the project has already failed and work backwards to identify potential causes. Instead of doing an autopsy at the end, you do it upfront, while you still have time to change the plan.
I love Pre-Mortems. This month I gathered around 20 participants of the inagural This Year program together in-person for the first time. For an entire day, we workshopped their 12-month goals and interrogated them from all angles.
One of the exercises we conducted was a Pre-Mortem on their annual goals. If they didn’t achieve them by the end of the year, what would be the primary reasons? From focus to process, once they determined what their biggest obstacles were likely to be, they could devise strategies to stop that from happening. (If you’re interested in joining the waitlist for This Year’s Class of 2027 that will kick off in the back-half of this year, you can do that here.)
You should ideally perform a Pre-Mortem on every large project that you kick off to identify its potential potholes before you start.
This is how you do it:
One Useful Thing: Pre-Mortems
The ideas behind doing a Pre-Mortem are backed up by research, with psychologists saying that ‘prospective hindsight’ helps people generate more specific, concrete risks than when asked abstractly what could go potentially wrong.
They are also, surprisingly, kinda fun to do. You get to think ahead and forecast a story of what might happen if your project crashes and burns. For optimists like myself, it’s a great place to play around with as you give yourself, and your team, permission to be pessimistic, even dramatic, without feeling disloyal or negative. It also helps puncture any overconfidence and stops you from underestimating obstacles and timelines.
This is how to run a Pre-Mortem for your team:
Invite your team to a Pre-Mortem
Choose a project you’re currently working on, or about to kick off, and get everyone in a room together. Open the session by explaining that the goal is to surface risks early, not to assign blame or prove anyone wrong.
Imagine a failed future
Ask everyone to imagine a point in time 12 months from now when the project has been a complete disaster. Explain it in its most failed form: budgets blown out, deadlines missed, customers furious, reputations in tatters. You want to make the failure seem really specific so people can see it and feel it.
Silently come up with ideas on the causes of failure
You should always spend time on individual ideation before coming together as a group (see my Cerebration model). Get some Post-It notes and spend a few minutes in silence as each person writes down their reasons for why this future failure occurred. Encourage them to name operational problems, identify bottlenecks, political or stakeholder issues, behaviours and external shocks. Aim for at least five to ten distinct, concrete causes from each participant rather than general worries.
Share outcomes and group them
I like to share ideas in a random order, by using whoever’s birthday is coming up next. Get each person reads out their reasons and posts them on a board or wall, grouping similar items together. Go around the room in order, and once they are all up and clustered, vote or rank which risks are both most likely and most damaging to the project.
Turn your insights into concrete actions
For each high‑priority risk, agree on specific steps, owners, and deadlines so the pre‑mortem translates directly into the plan (you can even use a RACI if you want). Capture these actions in your usual project tools so they aren’t forgotten after the meeting. Schedule a short check‑in later in the project to revisit the list and update the risks so that the exercise becomes an ongoing discipline rather than a one‑off ritual.
The benefits of a Pre-Mortem are both cognitive and cultural. On the cognitive side, they reduce blind spots and improve the accuracy of people’s predictions by forcing you to search for disconfirming evidence, rather than reassuring data. On the cultural side, they help to create some psychological safety, raising risks as an act of contribution instead of obstruction.
I hope you can use this tool of imagining a failed future to stop it from ever coming to life.
It’s been several years since I’ve spent a full Summer in Australia, and boy I’ve missed it. The days are long and the beaches are even longer. I especially love the added thrill every time you snorkel or dive in the ocean as you really never know what’s going to be down there with you.
After much hard work my new book on conflict is finally taking a wonderful shape, and I’m currently recruiting for some Early Readers to help me make it a truly excellent and useful book. If you’re interested in reading some rough drafts of chapters and giving feedback, you can sign up here.
Thanks in advance, and I’ll write to you again next month.
Yours in usefulness,
Tim