Pre-Mortem: The Art of Failing Brilliantly Before You Actually Do

You know that sinking feeling when your carefully crafted feature launch goes spectacularly pear-shaped? When your team is frantically messaging at 3 AM because the servers are melting, customers are rage-tweeting, and someone's suggesting "have we tried turning it off and on again?" That's the precise moment when your brain helpfully whispers, "We should have seen this coming." Well, what if I told you there's a way to experience all that delightful failure before it actually happens? Welcome to the pre-mortem, where we get to kill our ideas before the market does it for us.

What Is a Pre-Mortem (Or: How I Learned to Stop Worrying and Love Anticipated Disaster)

A pre-mortem is essentially a post-mortem, just without the inconvenience of actual failure. It's the business equivalent of those cheery conversations about what you'd do in a zombie apocalypse, except instead of discussing which neighbour you'd eat first, you're identifying which part of your project might turn into a shambling disaster.

Unlike optimistic planning sessions where everyone pretends everything will go brilliantly, a pre-mortem starts with the cheery premise: "Right, this project has failed catastrophically. Let's imagine why." It's pessimism as a productivity tool. And having walked the founder path where my own business eventually went belly-up (partly because I never bothered doing pre-mortems), I can tell you that planning for failure is counterintuitively one of the most optimistic things you can do.

The concept was popularised by psychologist Gary Klein, who noticed that medical teams who imagined what could go wrong before surgeries had better outcomes than those who didn't. It turns out that collective anxiety, properly channelled, is actually quite useful. Who knew?

Why Pre-Mortems Work Better Than Plain Old Risk Assessment

Traditional risk assessments are where good ideas go to be suffocated by spreadsheets. They're clinical, detached, and about as engaging as watching toast go stale. They also usually happen after you've already emotionally committed to an idea, which means you're just going through the motions while secretly planning the launch party.

Pre-mortems, by contrast, tap into our delightfully negative human nature. We're naturally brilliant at imagining disaster—just look at how well we doomscroll. The pre-mortem harnesses our inner catastrophiser and puts it to work before we've sunk too much time, money, and emotional investment into a potentially flawed plan.

The truth is, nobody wants to be the person pointing out problems during normal planning sessions. It feels like you're raining on everyone's parade. But when failure is the premise, suddenly everyone's free to unleash their inner Cassandra. "The API will definitely collapse under load." "The customers will hate the new interface." "Legal will have seventeen heart attacks when they see this." All the thoughts people usually keep to themselves come pouring out.

How to Run a Pre-Mortem That Actually De-Risks Your Launch

Running a pre-mortem isn't complicated, but like most worthwhile things, it does require fighting against our natural tendencies—in this case, our tendency to rush headlong into disaster while humming cheerfully. Here's how to do it properly:

• Set the scene for spectacular failure. Begin with "It's six months from now, and our launch has failed so badly that people are using it as a business school case study. What happened?"
• Make it safe to be negative. The more senior you are, the more you need to go first with something alarming. "I think my leadership decisions might tank this project" opens the floodgates nicely.
• Collect individual thoughts before group discussion. Have everyone write down their disaster scenarios independently first—this prevents groupthink and ensures the quiet catastrophisers get heard.
• Categorise the horrors. Group similar concerns together and look for patterns. If seven people independently worried the database would melt, that's probably worth addressing.
• Develop pre-emptive countermeasures. For each major failure path, create a specific action plan. Not vague "we'll be careful" nonsense, but actual steps.

I've found that 90 minutes is the sweet spot for a pre-mortem. Less than that and you don't dig deep enough; more than that and people start envisioning asteroid strikes and alien invasions out of sheer creative desperation.

The Psychological Magic Behind Pre-Mortems

Pre-mortems work because they hack several cognitive biases that usually work against us. They neutralise the optimism bias (our tendency to think things will go better than they statistically will), and they counteract the planning fallacy (our charming habit of underestimating how long things take even when we know we always underestimate how long things take).

They also create psychological safety for the pessimists in your team—those invaluable people who see problems before everyone else but have learned to keep quiet because nobody likes a doomsayer. In a pre-mortem, suddenly the pessimists are the heroes, spotting landmines before you step on them.

Having watched my own business gradually unravel through a series of "unforeseen" problems that were, in retrospect, entirely foreseeable, I've become evangelical about pre-mortems. Most business catastrophes aren't actually surprises—they're just things we chose not to see because looking would have been uncomfortable.

Real Pre-Mortem Questions That Saved My Bacon

Over the years, I've collected a set of pre-mortem questions that consistently unearth the most productive disasters. These aren't your standard "what if we go over budget" questions—they're the ones that make people shift uncomfortably in their seats because they hit a nerve.

• What will our most loyal customers absolutely hate about this? Not the average customer—the ones who currently sing your praises. How might you alienate them?
• If our competitors were hoping we'd make a strategic blunder, what would they be praying this launch looks like? Sometimes it's easier to see flaws when you imagine a rival cheering them on.
• Which part of this plan relies on users/customers behaving differently than they do today? Behaviour change is where good ideas go to die.
• What are we assuming will go right that we have no actual evidence for? This one typically opens a Pandora's box of wishful thinking.
• If we had to cancel this project tomorrow, what would be our secret relief? Often reveals the misgivings people are carrying but not expressing.

These questions aren't comfortable, but comfort is overrated. You know what's comfortable? The warm embrace of delusion right before you walk off a cliff.

Pre-Mortem Case Study: The Feature Nobody Asked For

Let me share a situation where a pre-mortem saved a team from a costly mistake. This isn't from my own business (which, let's be honest, could have used more pre-mortems and fewer "it'll all work out" moments), but from a company I advised afterward.

They were planning to launch a complex new analytics dashboard—something the product team had been itching to build for ages. During the pre-mortem, someone raised a seemingly obvious question: "What if users find this too complicated and never use it?"

This triggered a realisation that they'd never actually validated the need. They'd assumed users wanted deep analytics because that's what the product team found interesting. The team was making the classic mistake of listening to what customers asked for (a feature) instead of understanding what they were trying to achieve (an outcome). As Forbes points out, customers are experts in their problems, but founders are the experts in the solution. A quick series of customer interviews revealed that users wanted simple insights, not complex tools.

They pivoted to building three simple automated reports instead of a whole dashboard. Development time dropped from three months to three weeks, and adoption was near-universal. Had they proceeded with the original plan, they'd have spent months building something destined to become a graveyard feature.

When Pre-Mortems Go Wrong

Like any powerful tool, pre-mortems can be misused. I've seen them go sideways in a few predictable ways:

The Blame Game: If your pre-mortem devolves into people pointing fingers ("Marketing will definitely mess this up" or "Engineering always delivers late"), you've missed the point. Pre-mortems are about identifying systemic risks, not personal failings.

The Overwhelm Spiral: Sometimes a pre-mortem unearths so many potential disasters that the team becomes paralysed. Remember, the goal isn't to identify every possible risk—it's to find the most likely and impactful ones.

The No-Action Post-Mortem: The most common failure mode is running a great pre-mortem, generating brilliant insights, and then... doing absolutely nothing with them. Make sure every identified risk has an owner and a mitigation plan.

The "This Is Why We Can't Have Nice Things" Effect: If your team only ever looks for problems and never gets excited about opportunities, you'll kill innovation. Pre-mortems should be balanced with pre-celebrations (imagining wild success and how to maximise it).

The key is to keep pre-mortems focused on constructive pessimism—the kind that leads to better planning, not despair.

Making Pre-Mortems Part of Your Culture

The real power of pre-mortems emerges when they become embedded in your company culture. When "let's pre-mortem this" becomes a natural response to any significant initiative, you've created an organisation that can think clearly about risk without dampening enthusiasm.

Some ways to make pre-mortems stick:

• Start small but visible. Run a pre-mortem on a high-profile project where the stakes are real but not existential. When it helps avoid problems, make sure everyone knows.
• Create pre-mortem rituals. Maybe it's ordering a specific meal, or using a particular meeting room, or wearing black. Rituals make practices memorable.
• Reward the best disaster scenarios. Consider giving a small prize for the most insightful failure prediction. I know a company that has a "Cassandra Award" for the person whose pre-mortem warning proved most prescient.
• Document and review. After the project, compare what actually went wrong with what was predicted. This creates a feedback loop that improves your collective foresight.
• Share pre-mortem stories. When a disaster is averted because someone spotted it in advance, tell that story again and again.

The goal isn't to create a culture of anxiety, but one of clear-eyed assessment. As someone who had to shutter a business partly because we kept sleepwalking into foreseeable problems, I can tell you that realistic pessimism is far kinder than blind optimism in the long run. If you're serious about building something sustainable, you need to start with asking the right questions about whether your idea is worth pursuing in the first place.

Final Thoughts: The Paradox of Planning for Failure

There's something wonderfully contradictory about pre-mortems. By imagining failure in vivid detail, we actually make success more likely. By embracing our inner pessimists, we become more effective optimists. By killing our ideas in a controlled environment, we give them a better chance at surviving in the wild.

The most confident-seeming founders I know are often the ones constantly running pre-mortems in their heads. Research shows that people who spend time evaluating their time investments against subjective value see significant improvements in life satisfaction—even a 1.5-hour shift per day from low- to high-value activities can result in a significant increase in perceived well-being, according to the MIT Sloan Review. This principle applies to business decisions too. It's not that successful founders expect to fail—it's that they've already thought through the failure modes and prepared for them. Their confidence comes not from blind faith but from knowing they've looked the potential disasters in the eye.

So before your next launch, gather your team, order in some food, and spend 90 minutes deliberately killing your beautiful idea. It might feel uncomfortable, even slightly morbid. But remember: in the startup world, the pre-mortem paradox reigns supreme—those most willing to imagine failure are the ones most likely to succeed.