♖The Pre-Mortem Party

Hi Moaters,

My former boss, Jason Adams, taught me something counterintuitive about strategic execution:

The best way to energize a team isn't to paint the perfect future. It's to imagine everything going wrong.

I know, it that sounds like motivational malpractice.

But Jason would kick off new product initiatives with what I jokingly called a “failure kickoff.”

Instead of goal-setting, we’d spend 90 minutes as a team predicting all the ways the project could blow up, and then course-correct before writing a single line of code.

The result?

It was the only meeting I saw where engineers left more aligned, more confident, and weirdly more excited to execute.

I've used this practice with nearly every cross-functional team since.

I call it a Pre-Mortem Party.

And it might be the highest ROI 90 minutes your team can invest this quarter.

When should you run one?

• Launching a mission-critical initiative

• Entering uncharted product or GTM territory

• Shifting company strategy

Why does it work?

• Most plans fail because no one plans for failure

• Surfaces blind spots early, before they get expensive

• Builds real momentum instead of fragile optimism

What we'll cover:

• Why do pre-mortems work

• Who should you invite

• A step-by-step breakdown for running one that doesn’t suck

Let’s dig in.

Why This Feels Wrong (But Works)

Most leaders think like skiers: Look where you want to go, not at the trees.

But strategy isn't skiing. It's more like chess where the best players obsess over where they could get checkmated.

The research backs this up:

• Gary Klein found that teams using Pre-Mortems identified 30% more risks upfront.

• NASA runs "failure modes analysis" before every single mission.

• Google discovered that openly discussing risks was the #1 predictor of team performance.

Takeaway: Teams that talk openly about failure execute with more confidence, not less.

Who Should Join a Pre-Mortem Party?

You don’t need the whole org. You need the right five voices in the room.

After dozens of experiments, here’s what I’ve found works best:

✅ Keep it small (5 is the sweet spot)
✅ Choose odd numbers (need tie breakers)
✅ Cap at 7 max (any more, and the signal gets drowned in noise)

Bring these five archetypes:

• Owner: The person who feels the heat if this fails. They're accountable for results and have real skin in the game. Leads the session.
  

• Partner: Someone from a different function who'll feel the ripple effects. They see around corners you can't.
  

• Operator: The person who actually has to make this work day-to-day. They will love having this session.
  

• Loyal Skeptic: Your trusted devil's advocate who knows the details. Someone with no ego in the game who'll say what others won't.
  

• Generalist: The pattern spotter. They've seen this movie before and know how it usually ends.

Takeaway: You're not inviting the biggest titles or loudest voices. You're inviting the people who have the skill, knowledge, and desire for success.

When you get these 5 perspectives in a room, magic happens.

The Pre-Mortem Party Agenda (90 Minutes)

I have a 6-step agenda. Adjust times based on your situation.

Step 1: Set the Tone (5 min)

Owner leads and frames the session with the right mindset:

"We're not here to poke holes. We're here to protect this plan.”

Goals for this step:

• Create psychological safety for honest feedback.

• Align everyone on the purpose and goals (protection, not criticism).

• Set expectations that this builds confidence, not fear.

Step 2: Silent Reflection (15 min)

Prompt the group:

"It's 12 months from now. The [strategic initiative] failed. Why?"

What to do:

• Each person writes down 3 specific reasons privately.

• Push for clarity and avoid generic fluff.

• Examples:

  • Bad: "Lack of buy-in"

  • Good: "Sales ignored the new pricing deck."

Why silence matters: Prevents groupthink and gets unfiltered perspectives.

Step 3: Share & Cluster (30 min)

Process:

• Go around the room one by one.

• Each person shares one risk at a time..

• No debate or discussion, just listen and capture

Cluster risks into themes:

• Internal misalignment

• Execution gaps

• Market shifts

• Customer behavior

• Team or cultural friction

Expected outcome: 10 to 15 risks total. That's a good sign you're being thorough.

Step 4: Prioritize the Top Risks (15 min)

The filter: Only focus on risks that are both:

• High Impact (would seriously damage the plan)

• High Likelihood (realistic chance of happening)

Goal: Create a shortlist of 3 to 5 true threats. Ignore everything else.

Remember: If everything is urgent, nothing is.

Step 5: Add Safeguards & Kill Signals (20 min)

Turn each priority risk into actionable prevention:

For each risk, define:

• Safeguard: What can we do now to prevent this?

• Kill Signal: What's the early warning sign this is happening?

Example:

• Risk: Sales ignores the pitch deck

• Safeguard: Pre-launch training + role-plays

• Kill Signal: Less than 25% deck usage by Week 3

Critical: Make these visible and assign clear owners.

Step 6: Reframe, Align & Close (5 min)

End strong by:

• Reinforcing why this exercise protects the plan

• Assigning owners to each safeguard

• Scheduling the next check-in to review progress

The result: Real momentum and shared accountability.

Closing Thoughts

Here's what Jason understood that others miss:

Teams aren't afraid of failure. They're afraid of preventable failure.

When you surface risks publicly, three things happen:

1. Shared reality: Everyone sees the same obstacles.

2. Collective ownership: The team owns the solution, not just you.

3. Earned confidence: You've stress-tested the plan together.

It's the difference between hope and conviction to achieve your goals.

Til next time,

Ali

P.S. Thanks to you, we're now over 500 strong with a well above average 55% open rate. I’m grateful for every reader. If there’s someone on your team who’d benefit from this issue, don’t keep it a secret.

About Me: I help B2B founders and execs get clear on their strategy, sharpen their story, and build a sales motion that doesn’t fall flat. I’ve spent my career at the messy intersection of product, marketing, and sales. If you’re wrestling with a tough challenge or just want to nerd out on strategy, reach out. I’d love to hear from you.

Learn more about my story on LinkedIn.