Executive Mentor

Step 1: STATE THE PLAN
  Describe the plan as if it succeeded perfectly.

Step 2: ASSUME FAILURE
  "It's 12 months from now. This plan failed completely. Why?"

Step 3: IDENTIFY FAILURE MODES
  List every way the plan could fail. Minimum 5 failure modes.
  Rate each: Probability (1-5) x Impact (1-5) = Severity (1-25)

Step 4: FIND THE KILLERS
  Focus on severity > 15. These are the ones that will actually kill you.

Step 5: BUILD HEDGES
  For each killer: What's the earliest warning signal?
  What's the cheapest hedge that reduces severity by 50%?

Step 6: SET TRIPWIRES
  Define specific conditions that trigger plan modification.
  "If [metric] drops below [threshold] by [date], we [action]."

T-48 hours: INFORMATION GATHERING
  - Pull all metrics the board tracks
  - Identify every number that missed target
  - List every hard question they could ask
  - Review previous board meeting action items

T-24 hours: NARRATIVE CONSTRUCTION
  - Build the story: where we said we'd be, where we are, why, what next
  - Prepare the bad news delivery (Framework: State, Own, Understand, Fix)
  - Practice the three hardest questions out loud
  - Prepare specific asks (not "any help appreciated")

T-2 hours: FINAL PREP
  - Review deck one more time
  - Ensure every metric has a target and status
  - Confirm every variance has a one-sentence explanation
  - Know your three key messages cold

During: EXECUTION
  - Lead with the most important thing (slide 3, not slide 30)
  - Deliver bad news early, with ownership and a plan
  - End with specific, actionable asks

Step 1: REVERSIBILITY TEST
  [Is this decision reversible within 90 days?]
  |
  +-- YES --> Make it faster. Speed > perfection for reversible decisions.
  +-- NO  --> Proceed through full framework.

Step 2: 10/10/10 ANALYSIS
  - How will you feel about this in 10 minutes?
  - How will you feel in 10 months?
  - How will you feel in 10 years?

Step 3: STAKEHOLDER IMPACT MAP
  For each stakeholder group:
  | Stakeholder | Impact | Severity | Can You Mitigate? |
  | Team        | [desc] | [H/M/L]  | [Yes/No/Partially] |
  | Customers   | [desc] | [H/M/L]  | [Yes/No/Partially] |
  | Investors   | [desc] | [H/M/L]  | [Yes/No/Partially] |
  | Partners    | [desc] | [H/M/L]  | [Yes/No/Partially] |

Step 4: OPTION MATRIX
  | Option | Upside | Downside | Reversibility | Speed | Regret Risk |
  | A      |        |          |               |       |             |
  | B      |        |          |               |       |             |
  | C (do nothing) | | |                      |       |             |

Step 5: DECIDE AND COMMUNICATE
  - Make the call
  - Communicate to affected stakeholders within 24 hours
  - Own the decision fully -- no "I was advised to"

Step 1: IDENTIFY THE ASSUMPTION
  State it explicitly: "We assume [X]"

Step 2: FIND COUNTER-EVIDENCE
  What data or scenarios would make this assumption false?
  - Historical precedent
  - Competitor actions
  - Market shifts
  - Customer behavior changes
  - Regulatory changes

Step 3: MODEL THE DOWNSIDE
  If this assumption is wrong by 20%, what happens?
  By 40%? By 60%?
  At what point does the plan break?

Step 4: PROPOSE THE HEDGE
  What's the cheapest action that protects against this assumption being wrong?

Step 5: SET THE MONITORING
  What metric tells us earliest if this assumption is weakening?

POST-MORTEM: [Event Name]
Date of Event: [YYYY-MM-DD]
Date of Review: [YYYY-MM-DD]
Facilitator: [Name]
Participants: [Names]

TIMELINE
  [Chronological sequence of events, facts only]

IMPACT
  - Customer impact: [description, magnitude]
  - Revenue impact: [$ amount]
  - Team impact: [description]
  - Reputation impact: [description]

5 WHYS ANALYSIS
  1. Why did [event] happen?
     Because [cause 1].
  2. Why did [cause 1] happen?
     Because [cause 2].
  3. Why did [cause 2] happen?
     Because [cause 3].
  4. Why did [cause 3] happen?
     Because [cause 4].
  5. Why did [cause 4] happen?
     Because [root cause].

ROOT CAUSE: [One sentence]

CONTRIBUTING FACTORS (not root cause, but made it worse):
  - [Factor 1]
  - [Factor 2]

WHAT WENT WELL (always include this):
  - [Thing 1]
  - [Thing 2]

CHANGES REQUIRED
  | Change | Owner | Deadline | Verification Method |
  |--------|-------|----------|-------------------|
  | [Change 1] | [Name] | [Date] | [How we verify it's done] |
  | [Change 2] | [Name] | [Date] | [How we verify it's done] |

FOLLOW-UP REVIEW: [Date to check all changes are implemented]