/postmortem

name: "postmortem"
description: "Use after a failed launch, missed quarter or bad hire. Runs a blameless 5-Whys with a change register."

/executive-mentor:postmortem — Honest Analysis of What Went Wrong

**Command:** `/executive-mentor:postmortem <event>`

Not blame. Understanding. The failed deal, the missed quarter, the feature that flopped, the hire that didn't work out. What actually happened, why, and what changes as a result.

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Why Most Post-Mortems Fail

They become one of two things:

**The blame session** — someone gets scapegoated, defensive walls go up, actual causes don't get examined, and the same problem happens again in a different form.

**The whitewash** — "We learned a lot, we're going to do better, here are 12 vague action items." Nothing changes. Same problem, different quarter.

A real post-mortem is neither. It's a rigorous investigation into a system failure. Not "whose fault was it" but "what conditions made this outcome predictable in hindsight?"

**The purpose:** extract the maximum learning value from a failure so you can prevent recurrence and improve the system.

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The Framework

Step 1: Define the Event Precisely

Before analysis: describe exactly what happened.

• What was the expected outcome?
• What was the actual outcome?
• When was the gap first visible?
• What was the impact (financial, operational, reputational)?

Precision matters. "We missed Q3 revenue" is not precise enough. "We closed $420K in new ARR vs $680K target — a $260K miss driven primarily by three deals that slipped to Q4 and one deal that was lost to a competitor" is precise.

Step 2: The 5 Whys — Done Properly

The goal: get from **what happened** (the symptom) to **why it happened** (the root cause).

Standard bad 5 Whys:

• Why did we miss revenue? Because deals slipped.
• Why did deals slip? Because the sales cycle was longer than expected.
• Why? Because the customer buying process is complex.
• Why? Because we're selling to enterprise.
• Why? That's just how enterprise sales works.

→ Conclusion: Nothing to do. It's just enterprise.

Real 5 Whys:

• Why did we miss revenue? Three deals slipped out of quarter.
• Why did those deals slip? None of them had identified a champion with budget authority.
• Why did we progress deals without a champion? Our qualification criteria didn't require it.
• Why didn't our qualification criteria require it? When we built the criteria 8 months ago, we were in SMB, not enterprise.
• Why haven't we updated qualification criteria as ICP shifted? No owner, no process for criteria review.

→ Root cause: Qualification criteria outdated, no owner, no review process. → Fix: Update criteria, assign owner, add quarterly review.

**The test for a good root cause:** Could you prevent recurrence with a specific, concrete change? If yes, you've found something real.

Step 3: Distinguish Contributing Factors from Root Cause

Most events have multiple contributing factors. Not all are root causes.

**Contributing factor:** Made it worse, but isn't the core reason. If removed, the outcome might have been different — but the same class of problem would recur.

**Root cause:** The fundamental condition that made the outcome probable. Fix this, and this class of problem doesn't recur.

Example — failed hire:

• Contributing factors: rushed process, reference checks skipped, team under pressure to staff up
• Root cause: No defined competency framework, so interview process varied by who happened to conduct interviews

**The distinction matters.** If you address only contributing factors, you'll have a different-looking but structurally identical failure next time.

Step 4: Identify the Warning Signs That Were Ignored

Every failure has precursors. In hindsight, they're obvious. The value of this step is making them obvious prospectively.

Ask:

• At what point was the negative outcome predictable?
• What signals were visible at that point?
• Who saw them? What happened when they raised them?
• Why weren't they acted on?

**Common patterns:**

• Signal was raised but dismissed by a senior person
• Signal wasn't raised because nobody felt safe saying it
• Signal was seen but no one had clear ownership to act on it
• Data was available but nobody was looking at it
• The team was too optimistic to take negative signals seriously

This step is particularly important for systemic issues — "we didn't feel safe raising the concern" is a much deeper root cause than "the deal qualification was off."

Step 5: Distinguish What Was in Control vs. Out of Control

Some failures happen despite correct decisions. Some happen because of incorrect decisions. Knowing the difference prevents both overcorrection and undercorrection.

• **In control:** Process, criteria, team capability, resource allocation, decisions made
• **Out of control:** Market conditions, customer decisions, competitor actions, macro events

For things out of control: what can be done to be more resilient to similar events? For things in control: what specifically needs to change?

**Warning:** "It was outside our control" is sometimes used to avoid accountability. Be rigorous.

Step 6: Build the Change Register

Every post-mortem ends with a change register — specific commitments, owned and dated.

**Bad action items:**

• "We'll improve our qualification process"
• "Communication will be better"
• "We'll be more rigorous about forecasting"

**Good action items:**

• "Ravi owns rewriting qualification criteria by March 15 to include champion identification as hard requirement. New criteria reviewed in weekly sales standup starting March 22."
• "By March 10, Elena adds deal-slippage risk flag to CRM for any open opportunity >60 days without a product demo"
• "Maria runs a 30-min retrospective with enterprise sales team every 6 weeks starting April 1, reviews win/loss data"

**For each action:**

• What exactly is changing?
• Who owns it?
• By when?
• How will you verify it work