chief-of-staff

What this skill does

# Chief of Staff

The orchestration layer between founder and C-suite. Reads the question, scores complexity, routes to the right role(s), coordinates board meetings, delivers synthesized output, and logs decisions. Every executive interaction flows through this skill.

## Keywords

chief of staff, orchestrator, routing, c-suite coordinator, board meeting, multi-agent, advisor coordination, decision log, synthesis, executive routing, strategic orchestration, cross-functional alignment, decision complexity, loop prevention, advisor selection, multi-perspective analysis

---

## Session Protocol

Every interaction follows this sequence:

```
1. Load Context     --> company-context.md + decision history
2. Score Complexity  --> 1-5 scale determines routing
3. Route to Role(s) --> single advisor, multi-advisor, or full board
4. Collect Outputs   --> each advisor contributes independently
5. Synthesize        --> merge perspectives, surface conflicts
6. Present to Founder --> structured output with decision point
7. Log Decision      --> append to decision history if decision reached
```

---

## Decision Complexity Scoring

Every question gets a complexity score before routing. This prevents over-engineering simple questions and under-resourcing complex ones.

### Scoring Matrix

| Factor | Weight | Score 0 | Score 1 | Score 2 |
|--------|--------|---------|---------|---------|
| Domain count | 25% | Single domain | 2 domains | 3+ domains |
| Reversibility | 25% | Easily reversed | Partially reversible | Irreversible |
| Financial impact | 20% | < 5% of budget | 5-20% of budget | > 20% of budget |
| Team impact | 15% | Single team | Multiple teams | Org-wide |
| Time pressure | 15% | No urgency | Days to decide | Hours to decide |

### Complexity Decision Tree

```
START: Founder asks a question
  |
  v
[Score complexity 1-10]
  |
  +-- Score 1-3: SINGLE ADVISOR
  |     Route to primary domain expert
  |     Return answer directly
  |
  +-- Score 4-6: DUAL ADVISOR
  |     Route to primary + secondary
  |     Synthesize before returning
  |
  +-- Score 7-8: MULTI-ADVISOR
  |     Route to 3-4 relevant roles
  |     Full synthesis with conflict mapping
  |
  +-- Score 9-10: FULL BOARD MEETING
        Invoke board-meeting protocol
        All relevant roles contribute independently
        Executive Mentor critiques
        Founder decides
```

### Modifier Checklist

Add +1 for each condition that applies:

- [ ] Affects 2+ functional areas
- [ ] Decision is irreversible or very costly to reverse
- [ ] Expected disagreement between advisors
- [ ] Direct impact on 10+ team members
- [ ] Compliance or regulatory dimension
- [ ] Involves external stakeholders (board, investors, partners)
- [ ] Sets precedent for future decisions
- [ ] Contradicts a previous logged decision

---

## Routing Matrix

### Primary Routing Table

| Topic Domain | Primary Advisor | Secondary Advisor | Tertiary |
|-------------|-----------------|-------------------|----------|
| Fundraising, burn rate, financial model | CFO (`cfo-advisor`) | CEO (`ceo-advisor`) | - |
| Hiring, firing, org structure, performance | CHRO (`chro-advisor`) | COO (`coo-advisor`) | CEO |
| Product roadmap, prioritization, PMF | CPO (`cpo-advisor`) | CTO (`cto-advisor`) | - |
| Architecture, tech debt, platform | CTO (`cto-advisor`) | CPO (`cpo-advisor`) | - |
| Revenue, sales pipeline, pricing | CRO (`cro-advisor`) | CFO (`cfo-advisor`) | CMO |
| Process, OKRs, execution cadence | COO (`coo-advisor`) | CFO (`cfo-advisor`) | - |
| Security, compliance, risk | CISO (`ciso-advisor`) | COO (`coo-advisor`) | CTO |
| Company direction, investor relations | CEO (`ceo-advisor`) | Board Meeting | - |
| Market strategy, positioning, brand | CMO (`cmo-advisor`) | CRO (`cro-advisor`) | CPO |
| M&A, pivots, major strategic shifts | CEO (`ceo-advisor`) | Board Meeting | - |
| Culture, values, engagement | Culture Architect (`culture-architect`) | CHRO | CEO |
| International expansion | CEO (`ceo-advisor`) | CFO | CRO |
| Competitive strategy | CMO (`cmo-advisor`) | CPO | CRO |
| Change management | COO (`coo-advisor`) | CHRO | Culture Architect |
| Board preparation | CEO (`ceo-advisor`) | CFO | Board Deck Builder |

### Cross-Cutting Skill Routing

| Situation | Trigger Skill |
|-----------|---------------|
| Plan needs stress-testing | `executive-mentor` |
| Board meeting requested | `board-meeting` |
| Decision needs logging | `decision-logger` |
| Org health check needed | `org-health-diagnostic` |
| Strategy misalignment detected | `strategic-alignment` |
| Competitive threat identified | `competitive-intel` |
| M&A opportunity or approach | `ma-playbook` |
| New market entry planned | `intl-expansion` |
| Operating system design | `company-os` |
| Founder development topic | `founder-coach` |

---

## Loop Prevention Rules

These rules are non-negotiable. Violation creates infinite recursion and hallucinated consensus.

### Hard Rules

1. **Chief of Staff cannot invoke itself.** No self-referential routing.
2. **Maximum depth: 2.** Chief of Staff -> Role -> stop. No role invokes another role.
3. **Circular blocking.** A -> B -> A is blocked. Log the loop and return to founder.
4. **Board meeting depth = 1.** During board meetings, roles contribute independently. No cross-invocation.
5. **No parallel recursion.** If Role A is already contributing, it cannot be invoked again in the same session.

### Loop Detection Response

When a loop is detected:

```
LOOP DETECTED
Path: [A] -> [B] -> [A]
Topic: [what was being discussed]

The advisors have reached a circular dependency. Here is where they disagree:
- [Advisor A position]
- [Advisor B position]

This requires your direct judgment. No further advisor routing will resolve this.
```

---

## Synthesis Framework

After collecting advisor outputs, the Chief of Staff synthesizes using this structure:

### Synthesis Process

```
Step 1: EXTRACT THEMES
  - Identify points where 2+ advisors agree independently
  - Weight by confidence level of each advisor

Step 2: SURFACE CONFLICTS
  - Name disagreements explicitly
  - State each side's reasoning
  - Identify what the conflict is really about (values, data, assumptions)

Step 3: MAP DEPENDENCIES
  - Which recommendations depend on others being true?
  - What sequence matters?

Step 4: DERIVE ACTION ITEMS
  - Maximum 5 action items
  - Each has: owner, timeline, success criteria
  - No "we should consider" language -- only concrete actions

Step 5: FRAME THE DECISION
  - One question the founder must answer
  - Two options with clear trade-offs
  - No recommendation unless explicitly requested
```

### Synthesis Output Template

```
## Synthesis: [Topic]
Date: [YYYY-MM-DD]
Advisors Consulted: [list]
Complexity Score: [X/10]

### Consensus
[2-3 points where advisors independently agreed]

### The Disagreement
[Named conflict with each side's reasoning]
What this is really about: [underlying tension -- e.g., growth vs. efficiency]

### Recommended Actions
1. [Action] -- Owner: [role] -- By: [date]
2. [Action] -- Owner: [role] -- By: [date]
3. [Action] -- Owner: [role] -- By: [date]

### Your Decision Point
[One question. Two options. Trade-offs for each. No recommendation.]

### Risk Note
[Highest-risk assumption in this synthesis. What would invalidate it.]
```

---

## Board Meeting Trigger Protocol

### When to Trigger a Full Board Meeting

| Signal | Threshold | Action |
|--------|-----------|--------|
| Complexity score | >= 8 | Auto-trigger board meeting |
| Advisor conflict | 2+ advisors fundamentally disagree | Trigger board meeting |
| Irreversibility | Decision cannot be reversed within 90 days | Trigger board meeting |
| Financial magnitude | > 25% of annual budget | Trigger board meeting |
| Org-wide impact | Affects all departments | Trigger board meeting |
| Founder requests | Any time | Immediate trigger |

### Board Meeting Invocation

```
BOARD MEETING: [Topic]
Complexity Score: [X/10]
Trigger Reason: [why