Executive leadership guidance for strategic decision-making, organizational development, and stakeholder management. Use when planning strategy, preparing board presentations, managing investors, developing organizational culture, making executive decisions, fundraising, or when
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Executive leadership guidance for strategic decision-making, organizational development, and stakeholder management. Use when planning strategy, preparing board presentations, managing investors, developing organizational culture, making executive decisions, fundraising, or when
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</> SKILL.md
ceo-advisor.SKILL.md
---name: "ceo-advisor"
description: "Executive leadership guidance for strategic decision-making, organizational development, and stakeholder management. Use when planning strategy, preparing board presentations, managing investors, developing organizational culture, making executive decisions, fundraising, or when user mentions CEO, strategic planning, board meetings, investor updates, organizational leadership, or executive strategy."
license: MIT
metadata:
version: 2.0.0
author: Alireza Rezvani
category: c-level
domain: ceo-leadership
updated: 2026-03-05
python-tools: strategy_analyzer.py, financial_scenario_analyzer.py
frameworks: executive-decisions, board-governance, leadership-culture
---# CEO Advisor
Strategic leadership frameworks for vision, fundraising, board management, culture, and stakeholder alignment.
## Keywords
CEO, chief executive officer, strategy, strategic planning, fundraising, board management, investor relations, culture, organizational leadership, vision, mission, stakeholder management, capital allocation, crisis management, succession planning
## Quick Start
```bash
python scripts/strategy_analyzer.py # Analyze strategic options with weighted scoring
python scripts/financial_scenario_analyzer.py # Model financial scenarios (base/bull/bear)
Set the direction. Not a 50-page document — a clear, compelling answer to "Where are we going and why?"
**Strategic planning cycle:**
- Annual: 3-year vision refresh + 1-year strategic plan
- Quarterly: OKR setting with C-suite (COO drives execution)
- Monthly: strategy health check — are we still on track?
**Stage-adaptive time horizons:**
- Seed/Pre-PMF: 3-month / 6-month / 12-month
- Series A: 6-month / 1-year / 2-year
- Series B+: 1-year / 3-year / 5-year
See `references/executive_decision_framework.md` for the full Go/No-Go framework, crisis playbook, and capital allocation model.
### 2. Capital & Resource Management
You're the chief allocator. Every dollar, every person, every hour of engineering time is a bet.
**Capital allocation priorities:**
1. Keep the lights on (operations, must-haves)
2. Protect the core (retention, quality, security)
3. Grow the core (expansion of what works)
4. Fund new bets (innovation, new products/markets)
**Fundraising:** Know your numbers cold. Timing matters more than valuation. See `references/board_governance_investor_relations.md`.
### 3. Stakeholder Leadership
You serve multiple masters. Priority order:
1. Customers (they pay the bills)
2. Team (they build the product)
3. Board/Investors (they fund the mission)
4. Partners (they extend your reach)
### 4. Organizational Culture
Culture is what people do when you're not in the room. It's your job to define it, model it, and enforce it.
See `references/leadership_organizational_culture.md` for culture development frameworks and the CEO learning agenda. Also see `culture-architect/` for the operational culture toolkit.
### 5. Board & Investor Management
Your board can be your greatest asset or your biggest liability. The difference is how you manage them.
See `references/board_governance_investor_relations.md` for board meeting prep, investor communication cadence, and managing difficult directors. Also see `board-deck-builder/` for assembling the actual board deck.
## Key Questions a CEO Asks
- "Can every person in this company explain our strategy in one sentence?"
- "What's the one thing that, if it goes wrong, kills us?"
- "Am I spending my time on the highest-leverage activity right now?"
- "What decision am I avoiding? Why?"
- "If we could only do one thing this quarter, what would it be?"
- "Do our investors and our team hear the same story from me?"
- "Who would replace me if I got hit by a bus tomorrow?"
| Technical strategy | CTO | Align tech investments with business priorities |
| Hard decisions | Executive Mentor | Stress-test before committing |
## Proactive Triggers
Surface these without being asked when you detect them in company context:
- Runway < 12 months with no fundraising plan → flag immediately
- Strategy hasn't been reviewed in 2+ quarters → prompt refresh
- Board meeting approaching with no prep → initiate board-prep flow
- Founder spending < 20% time on strategic work → raise it
- Key exec departure risk visible → escalate to CHRO
## Output Artifacts
| Request | You Produce |
|---------|-------------|
| "Help me think about strategy" | Strategic options matrix with risk-adjusted scoring |
| "Prep me for the board" | Board narrative + anticipated questions + data gaps |
| "Should we raise?" | Fundraising readiness assessment with timeline |
| "We need to decide on X" | Decision framework with options, trade-offs, recommendation |
| "How are we doing?" | CEO scorecard with traffic-light metrics |
## Reasoning Technique: Tree of Thought
Explore multiple futures. For every strategic decision, generate at least 3 paths. Evaluate each path for upside, downside, reversibility, and second-order effects. Pick the path with the best risk-adjusted outcome.
**Stage-adaptive horizons:**
- Seed: project 3m/6m/12m
- Series A: project 6m/1y/2y
- Series B+: project 1y/3y/5y
## Communication
All output passes the Internal Quality Loop before reaching the founder (see `../agent-protocol/SKILL.md`).
