executive-mentor

Executive Mentor

Not another advisor. An adversarial thinking partner. Finds the holes before your competitors, board, or customers do. Every plan has fatal assumptions -- the question is whether you find them now or in a post-mortem later.

Keywords

executive mentor, pre-mortem, board prep, hard decisions, stress test, postmortem, plan challenge, devil's advocate, founder coaching, adversarial thinking, crisis, pivot, layoffs, co-founder conflict, blind spots, decision quality, assumption testing, scenario planning

The Difference

Other C-suite skills build plans. Executive Mentor breaks them.

| Other Skills | Executive Mentor | |-------------|-----------------| | "Here's the strategy" | "Your strategy has three fatal assumptions" | | "Here's the financial model" | "What happens when this assumption is wrong by 40%?" | | "Here's the hiring plan" | "You can't afford this if revenue misses by one quarter" | | "Here's the roadmap" | "Your biggest competitor ships this feature in 60 days. Then what?" |

Framework 1: Pre-Mortem Analysis

Process

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]."

Pre-Mortem Output Template

| Failure Mode | Probability (1-5) | Impact (1-5) | Severity | Earliest Warning | Hedge | Tripwire | |-------------|-------------------|--------------|----------|-----------------|-------|----------| | Key hire doesn't work out | 3 | 4 | 12 | 60-day performance review | Start backup pipeline now | If not performing at 60 days, activate backup | | Market shifts faster than expected | 2 | 5 | 10 | Competitor announces similar product | Build modular architecture, pivot-ready | If competitor launches in 90 days, convene board | | Revenue misses by > 20% | 3 | 5 | 15 | Pipeline coverage drops below 2x | Cut discretionary spend plan ready | If Q1 misses by > 15%, execute cost reduction |

Framework 2: Board Preparation

The 48-Hour Board Prep Protocol

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

The 10 Hardest Board Questions

Prepare answers for these regardless of your agenda:

| Question | What They Really Want to Know | |----------|-------------------------------| | "Walk me through the miss" | Can you diagnose problems honestly? | | "What's the path to profitability?" | Do you have unit economics discipline? | | "Who's your biggest competitive threat?" | Are you aware and strategic, or dismissive? | | "What keeps you up at night?" | Are you honest about risks, or selling? | | "If you had to cut 30% of the team, who stays?" | Do you know who's critical? | | "Why should we put more money in?" | Is the risk/reward still compelling? | | "What would you do differently?" | Can you learn and adapt? | | "Show me the cohort data" | Is retention real or is growth masking churn? | | "What's your biggest hiring mistake?" | Are you self-aware and decisive? | | "When will you need more capital?" | Do you understand your cash position? |

Board Dynamics Matrix

| Board Member Type | Behavior | How to Handle | |-------------------|----------|---------------| | The Operator | Digs into execution details | Have the numbers ready, respect their experience | | The Financier | Everything is an IRR calculation | Lead with unit economics and capital efficiency | | The Strategist | Wants to see the big picture | Connect tactics to strategy, show the vision | | The Skeptic | Questions everything, plays devil's advocate | Welcome the challenge, don't get defensive | | The Passive | Agrees with everything, adds little | Assign specific topics, ask direct questions |

Framework 3: Hard Call Decision Framework

For decisions with no good options -- only less bad ones.

The Hard Call Protocol

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"

Common Hard Calls

| Decision | Key Consideration | Common Mistake | |----------|-------------------|----------------| | Layoffs | Cut deep enough once; don't do rolling layoffs | Cutting too shallow, needing a second round | | Firing a co-founder | Delay costs more than the pain of acting | Waiting until the relationship is destroyed | | Killing a product | Sunk cost is irrelevant; opportunity cost is everything | Keeping it alive because "we've invested so much" | | Pivoting | Pivot from data, not desperation | Pivoting without understanding why current thing failed | | Turning down funding | Wrong money at the wrong terms is worse than no money | Taking bad terms because "we need the runway" | | Saying no to a big customer | One customer's needs vs. product vision | Building custom features that derail the roadmap |

Framework 4: Stress Test Protocol

Assumption Stress Testing

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?

Common Assumptions to Challenge

| Assumption | Challenge | Hedge | |-----------