/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.