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You're about to launch a new feature. Your team is excited. The plan looks solid. Everyone's aligned on the timeline.

Three weeks later, you're scrambling. A critical dependency you didn't account for. A user flow nobody tested. A technical limitation that "should have been obvious." The launch is delayed, the team is frustrated, and you're wondering how you missed something so fundamental.

Here's the painful truth: you didn't miss it because you weren't smart enough. You missed it because you never asked the team to imagine failure before you started.

Not too long ago, I was talking with a small HR tech company, to go nameless.

The team was building a new AI-powered resume screening feature. They'd talked to customers. They'd mapped out the workflow. They'd estimated three weeks of development time.

Everyone was pumped.

Four weeks into development, they hit their first wall: the AI model they'd planned to use didn't integrate with the systems most customers used. Two weeks after that, they discovered a compliance issue. Some states had laws against automated resume screening without human review.

By week eight, they'd burned through $40K in dev time and still hadn't shipped.

The worst part? When they finally launched a watered-down version, customer adoption was lukewarm. Turns out, the feature solved a problem customers said they had, but not one they were actually willing to change their workflow for.

I kept thinking, 'Why didn't they see this coming?' Then I realized, they never actually tried to.

The team had spent hours planning what could go right. They'd spent zero minutes planning what could go wrong.

You might have heard about a post-mortem where you go over what went wrong, and hopefully learn a lesson or two after things have gone south. Technically, you do a post-mortem when something (or someone) is dead.

So, why wait for things to be dead or on life-support? Instead of a post-mortem, let’s do a pre-mortem.

One 15-minute pre-mortem meeting could have saved them two months and $40K. Or at least given them some time to think about a more valuable pivot.

Here's what happens in most project kickoffs:

You gather the team, or yourself and your cat if that’s all there is. You outline the goal. You talk through the plan. Everyone nods. Someone asks, "Any concerns?" Silence. "Great, let's get started!"

You just fell victim to the optimism bias… the psychological tendency to believe things will go better than they statistically should.

Studies show that 70% of projects run over budget or miss deadlines. Yet when you ask a team at the start, they'll estimate on-time delivery with high confidence. Why? Because humans are wired to focus on ideal outcomes, not realistic obstacles.

Think of project planning like packing for a camping trip.

Most teams pack for perfect weather: sunny skies, warm nights, no bugs. They bring the tent, the snacks, and a Bluetooth speaker for ambiance.

Then it rains. The tent leaks. Someone forgot matches. The "easy 2-mile hike" turns into a 4-mile mud slog.

A pre-mortem is like checking the weather forecast and packing a tarp, backup lighter, and blister kit. Always be prepared, say the scouts.

Big companies have project managers, risk registers, and contingency budgets. If a project hits a snag, they throw more people at it, push the timeline, or absorb the cost.

Microteams don't have that luxury.

For a dinner table-sized team, a project failure isn't just a setback, it can be a catastrophe. Here's why:

The pre-mortem isn’t being Debbie Downer. This is how you protect your Microteam's most valuable assets: time, money, and morale.

By spending 15 minutes imagining failure, you avoid spending 15 weeks cleaning up a mess.

Here's how to run a pre-mortem before every significant project:

Gather the team (in-person, Zoom, or async in a shared doc), or if it’s just yourself, gather yourself together. Frame the exercise clearly:

"Imagine it's [project deadline]. The project has completely failed. It didn't launch, it shipped broken, or nobody used it. We're doing a post-mortem to figure out what went wrong. Your job is to tell me why it failed."

Rather than asking "What might go wrong?" You're saying, "It did go wrong. Why?"

This mental shift unlocks honest thinking. People stop hedging and start naming real risks.

Give everyone 5 minutes to silently write down every reason the project could fail. No discussion yet.

Prompt with categories:

Silence is key. It prevents groupthink and ensures introverts share their concerns.

If you’re using the LLM Prompt we provide in our Premium content below, the tool will help you through this process.

Go around the room (or the doc). Each person shares one failure mode at a time. Keep cycling until all ideas are on the table.

Write everything down. No judgment. No "that won't happen" rebuttals. Just capture.

You'll be surprised how many risks surface that nobody would have mentioned in a regular planning meeting.

If you’re using the LLM Prompt, it will come back with some things you might not have ever thought of.

Now, categorize the risks:

Focus your energy on the top-left quadrant: high likelihood, high impact.

For each high-priority risk, assign someone to either:

Example:

You don't need to solve everything in the meeting. You just need to see the risks and assign owners.

Here's what this looks like in practice:

Example 1: Launching a new pricing tier

Risks identified:

Mitigations:

Example 2: Hiring a contractor for a critical project

Risks identified:

Mitigations:

You don't need to run a pre-mortem for every task. But before your next significant project (new feature, hire, launch, major process change), do this:

That's it. Fifteen minutes of imagined failure to prevent weeks of real failure.

Optimism is necessary if you’re running a Microteam. It’s part of that Spark that got you to launch the company. You need unrealistic optimism to be able to come up with something that no one ever did to solve a problem.. It's what gets you to take the leap, bet on yourself, and build something from nothing.

[Unfamiliar with the Spark? Learn more about the Microteam journey stages here]

Unrealistic optimism is good to keep you motivated and keep the momentum going. But unexamined optimism is a liability.

The pre-mortem helps you channel your optimism in productive ways. It says, "We're going to make this work, and we're going to be smart about how we do it."

The most efficient Microteams see problems coming and neutralize them before they explode.

“Momento Mori” (Remember that you will die) is something the Stoics have always said as a way to guide behavior and avoid the heat of emotion.

Let’s tweak that by saying “Momentum Mori”… let’s use the constant thinking of what can go wrong so that we can keep the train moving forward with momentum.

So before you kick off your next big project, spend 15 minutes imagining failure.

Then go build something that succeeds anyway.

A battle-tested pre-mortem prompt that surfaces project-killing risks before you ship anything.

Instead of running a meeting or managing templates, you paste one prompt into ChatGPT (or your AI of choice), answer a few guided questions, and get back a structured pre-mortem. It identifies failure modes, prioritizes risks by impact and likelihood, and forces concrete mitigation plans with owners.

This is the fastest way for a Microteam to think like a seasoned PM, CTO, and risk officer without hiring any of them.

Most project failures are obvious in hindsight. The risks were always there. They just never made it into a kickoff doc, a roadmap, or a Slack thread.

This prompt creates the same psychological safety and rigor as a great pre-mortem session, without the overhead. No scheduling. No facilitation. No groupthink. No hour-long anxiety spirals.

It gives you brutally honest answers early, when fixing things is still cheap.