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Chief Of Staff

  • 97 installs
  • 451 repo stars
  • Updated July 21, 2026
  • borghei/claude-skills

chief-of-staff is a skill that orchestrates a C-suite of advisor roles, routing founder questions, synthesizing outputs, and logging decisions.

About

This skill is a C-suite orchestration layer that routes founder questions to the right advisor role(s), triggers multi-role board meetings for complex decisions, synthesizes outputs, and logs decisions. It scores each question's complexity 1-10 to decide whether to use a single advisor, dual advisors, or a full board. Founders use it to coordinate executive decisions and route strategic questions across advisor skills.

  • Orchestration layer that routes founder questions to the right C-suite advisor role(s)
  • Scores decision complexity 1-10 to pick single-advisor, dual, multi, or full board routing
  • Synthesizes multi-advisor outputs, surfaces conflicts, and logs decisions

Chief Of Staff by the numbers

  • 97 all-time installs (skills.sh)
  • Ranked #4,520 of 16,546 AI & Agent Building skills by installs in the Skillselion catalog
  • Data as of Aug 5, 2026 (Skillselion catalog sync)
At a glance

chief-of-staff capabilities & compatibility

Capabilities
advisor routing · decision synthesis · orchestration
Use cases
orchestration · planning · project management
Pricing
Free
From the docs

What chief-of-staff says it does

The orchestration layer between founder and C-suite.
SKILL.md
Every question gets a complexity score before routing.
SKILL.md
npx skills add https://github.com/borghei/claude-skills --skill chief-of-staff

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Listed on Skillselion
Installs97
repo stars451
Last updatedJuly 21, 2026
Repositoryborghei/claude-skills

What it does

Route strategic founder questions to the right advisor roles, synthesize their advice, and log the decision.

Who is it for?

Founders coordinating executive decisions across multiple advisor roles or board meetings.

Skip if: Simple single-domain questions that do not need multi-advisor synthesis.

When should I use this skill?

You are coordinating executive decisions, routing strategic questions, or managing a board meeting.

What you get

A synthesized, multi-perspective answer routed to the right advisors with the decision logged.

  • routed advisor output
  • synthesized recommendation
  • decision log entry

By the numbers

  • 1-10 complexity scoring
  • 7-step session protocol
  • routing matrix across 14+ topic domains

Files

SKILL.mdMarkdownGitHub ↗

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

FactorWeightScore 0Score 1Score 2
Domain count25%Single domain2 domains3+ domains
Reversibility25%Easily reversedPartially reversibleIrreversible
Financial impact20%< 5% of budget5-20% of budget> 20% of budget
Team impact15%Single teamMultiple teamsOrg-wide
Time pressure15%No urgencyDays to decideHours 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 DomainPrimary AdvisorSecondary AdvisorTertiary
Fundraising, burn rate, financial modelCFO (cfo-advisor)CEO (ceo-advisor)-
Hiring, firing, org structure, performanceCHRO (chro-advisor)COO (coo-advisor)CEO
Product roadmap, prioritization, PMFCPO (cpo-advisor)CTO (cto-advisor)-
Architecture, tech debt, platformCTO (cto-advisor)CPO (cpo-advisor)-
Revenue, sales pipeline, pricingCRO (cro-advisor)CFO (cfo-advisor)CMO
Process, OKRs, execution cadenceCOO (coo-advisor)CFO (cfo-advisor)-
Security, compliance, riskCISO (ciso-advisor)COO (coo-advisor)CTO
Company direction, investor relationsCEO (ceo-advisor)Board Meeting-
Market strategy, positioning, brandCMO (cmo-advisor)CRO (cro-advisor)CPO
M&A, pivots, major strategic shiftsCEO (ceo-advisor)Board Meeting-
Culture, values, engagementCulture Architect (culture-architect)CHROCEO
International expansionCEO (ceo-advisor)CFOCRO
Competitive strategyCMO (cmo-advisor)CPOCRO
Change managementCOO (coo-advisor)CHROCulture Architect
Board preparationCEO (ceo-advisor)CFOBoard Deck Builder

Cross-Cutting Skill Routing

SituationTrigger Skill
Plan needs stress-testingexecutive-mentor
Board meeting requestedboard-meeting
Decision needs loggingdecision-logger
Org health check neededorg-health-diagnostic
Strategy misalignment detectedstrategic-alignment
Competitive threat identifiedcompetitive-intel
M&A opportunity or approachma-playbook
New market entry plannedintl-expansion
Operating system designcompany-os
Founder development topicfounder-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

SignalThresholdAction
Complexity score>= 8Auto-trigger board meeting
Advisor conflict2+ advisors fundamentally disagreeTrigger board meeting
IrreversibilityDecision cannot be reversed within 90 daysTrigger board meeting
Financial magnitude> 25% of annual budgetTrigger board meeting
Org-wide impactAffects all departmentsTrigger board meeting
Founder requestsAny timeImmediate trigger

Board Meeting Invocation

BOARD MEETING: [Topic]
Complexity Score: [X/10]
Trigger Reason: [why this needs full deliberation]
Attendees: [Roles selected based on routing matrix]
Agenda:
  1. [Specific question for discussion]
  2. [Specific question for discussion]
  3. [Decision to be made]

Proceeding to board-meeting protocol...

See c-level-advisor/board-meeting/SKILL.md for the full 6-phase protocol.

---

Decision Logging Integration

After every interaction that produces a decision:

1. Check for conflicts with existing decisions in decision-logger 2. Format the decision entry with owner, deadline, and review date 3. Mark any superseded decisions 4. Flag rejected proposals with DO_NOT_RESURFACE tags 5. Confirm logging to the founder

See c-level-advisor/decision-logger/SKILL.md for the full two-layer memory architecture.

---

Ecosystem Map

The Chief of Staff routes to the entire C-level advisory ecosystem:

C-Suite Advisors (10 roles)

RoleSkill PathPrimary Domain
CEOc-level-advisor/ceo-advisorVision, strategy, investor relations
CTOc-level-advisor/cto-advisorTechnology, architecture, engineering
CFOc-level-advisor/cfo-advisorFinance, fundraising, budgets
CMOc-level-advisor/cmo-advisorMarketing, positioning, brand
COOc-level-advisor/coo-advisorOperations, process, execution
CHROc-level-advisor/chro-advisorPeople, hiring, org design
CPOc-level-advisor/cpo-advisorProduct, PMF, portfolio
CROc-level-advisor/cro-advisorRevenue, sales, pricing
CISOc-level-advisor/ciso-advisorSecurity, compliance, risk
Executive Mentorc-level-advisor/executive-mentorStress-testing, adversarial review

Orchestration Skills (4)

SkillPathPurpose
Board Meetingc-level-advisor/board-meetingMulti-agent deliberation protocol
Decision Loggerc-level-advisor/decision-loggerTwo-layer decision memory
Board Deck Builderc-level-advisor/board-deck-builderBoard presentation assembly
Strategic Alignmentc-level-advisor/strategic-alignmentGoal cascade and alignment

Strategic Skills (6)

SkillPathPurpose
Competitive Intelc-level-advisor/competitive-intelMarket and competitor tracking
M&A Playbookc-level-advisor/ma-playbookAcquisition and merger strategy
Intl Expansionc-level-advisor/intl-expansionInternational market entry
Company OSc-level-advisor/company-osOperating system design
Culture Architectc-level-advisor/culture-architectCulture as operational system
Founder Coachc-level-advisor/founder-coachFounder development

External Integrations

DomainSkill PathIntegration
Productproduct-team/product-strategistProduct strategy alignment
Engineeringengineering/Technical implementation
Marketingmarketing/Campaign execution
Project Managementproject-management/Execution tracking
Data Analyticsdata-analytics/Metrics and analysis

---

Quality Standards

Before delivering ANY output to the founder:

  • [ ] Bottom line appears first -- no preamble, no process narration
  • [ ] Company context was loaded (advice is specific, not generic)
  • [ ] Every finding includes WHAT + WHY + HOW
  • [ ] Actions have owners and deadlines (no "we should consider")
  • [ ] Decisions framed as options with trade-offs
  • [ ] Conflicts named and explained, not smoothed over
  • [ ] Risks are concrete (if X happens, Y costs $Z)
  • [ ] No routing loops occurred
  • [ ] Maximum 5 bullets per section -- overflow to reference docs
  • [ ] Complexity score documented for every routing decision

---

Proactive Triggers

Surface these without being asked when detected:

  • Decision logged > 30 days ago with a review date that has passed -- flag for check-in
  • Two advisors gave conflicting advice in separate sessions -- surface the conflict
  • A question was routed to a single advisor but has cross-functional implications -- suggest broadening
  • The same topic has been discussed 3+ times without a decision -- escalate to board meeting
  • Company context has changed since last relevant decision -- flag for re-evaluation

---

Anti-Patterns

Anti-PatternWhy It FailsCorrection
Routing everything to board meetingDecision fatigue, slow executionUse complexity scoring; most questions need 1-2 advisors
Synthesizing without surfacing conflictCreates false consensusName every disagreement explicitly
Skipping the decision logSame debates repeat endlesslyLog every decision, even small ones
Over-routing simple questionsWastes founder timeScore 1-3 = single advisor, direct answer
Letting advisors cross-pollinateGroupthink riskEnforce independent contributions
Generic advice without contextWorthless recommendationsAlways load company context first

---

Tool Reference

routing_engine.py

Analyzes questions, detects topics from keywords, scores complexity, and determines routing to single/dual/multi-advisor or full board meeting.

# Route a question
python scripts/routing_engine.py --question "Should we raise a Series B now or wait?" --complexity 8

# Specify topic directly
python scripts/routing_engine.py --topic fundraising --complexity 7

# List all topic routing
python scripts/routing_engine.py --list-topics

# JSON output
python scripts/routing_engine.py --question "How should we restructure engineering?" --json

synthesis_generator.py

Merges multi-advisor contributions into decision-ready format. Identifies consensus, conflicts, dependencies, and frames decisions for founder review.

# Run with demo contributions
python scripts/synthesis_generator.py

# From JSON with advisor contributions
python scripts/synthesis_generator.py --input contributions.json

# JSON output
python scripts/synthesis_generator.py --json

ecosystem_mapper.py

Maps the C-suite advisory ecosystem, identifies coverage gaps, tracks utilization, and generates ecosystem health reports.

# Map with default ecosystem
python scripts/ecosystem_mapper.py

# Specify active skills
python scripts/ecosystem_mapper.py --active CEO CFO CTO CMO CHRO

# From JSON
python scripts/ecosystem_mapper.py --input ecosystem.json

# JSON output
python scripts/ecosystem_mapper.py --json

---

Troubleshooting

ProblemLikely CauseFix
Simple questions routed to full board meetingComplexity scoring too aggressive or modifiers over-appliedRecalibrate: most questions need 1-2 advisors; reserve board for score 9-10
Synthesis smooths over real disagreementsChief of Staff optimizing for consensus instead of clarityName every disagreement explicitly; state each side's reasoning and what it's really about
Same debate keeps recurring across sessionsDecision not logged or logged without DO_NOT_RESURFACE flagLog every decision; mark rejected proposals; check history before routing
Routing loops detected (A -> B -> A)Circular dependency between advisorsStop routing immediately; surface the conflict to founder for direct judgment
Advisor outputs feel genericCompany context not loaded at session startMake context loading mandatory in Step 1; verify context is recent (within 30 days)
Founder bypasses Chief of Staff and goes directly to advisorsCoS not adding value or slowing things downReduce friction: for score 1-3 questions, CoS routes silently with no overhead

---

Success Criteria

  • 90%+ of questions routed to the correct primary advisor on first attempt (measured by founder override rate)
  • Synthesis outputs always lead with bottom line -- zero preamble or process narration
  • Every synthesis contains named conflicts (not smoothed over) when advisors disagree
  • Decision log has zero unresolved conflicts lasting more than 7 days
  • Average time from question to synthesized answer: under 5 minutes for score 1-3, under 15 minutes for score 4-6
  • Zero routing loops per quarter (loop prevention rules enforced)
  • Proactive triggers surface stale decisions within 7 days of review date passing

---

Scope & Limitations

In Scope: Question routing, complexity scoring, multi-advisor synthesis, decision logging integration, loop prevention, ecosystem orchestration, proactive triggers.

Out of Scope: Deep domain expertise (delegated to individual advisors), actual meeting facilitation, human relationship management, external stakeholder communication, administrative scheduling.

Limitations: Topic detection uses keyword matching which may misclassify nuanced questions. Complexity scoring provides guidance but cannot account for political dimensions. Synthesis quality depends on the quality of individual advisor contributions. Ecosystem mapper tracks skill availability but not skill quality.

---

Integration Points

SkillIntegration
All C-suite advisorsRoutes to all 9 C-suite roles based on topic and complexity
board-meetingTriggers full board protocol for complexity score >= 8
decision-loggerLogs every decision; checks for conflicts with existing decisions
executive-mentorRoutes for stress-testing when plan needs adversarial review
strategic-alignmentValidates that routed advice aligns with strategic goals
board-deck-builderRoutes board prep questions to CEO + CFO
company-osIntegrates with meeting pulse for decision cadence

Related skills

FAQ

How does it decide who to route to?

It scores decision complexity from 1 to 10 and routes to a single advisor, dual advisors, a multi-advisor group, or a full board meeting accordingly.

Does it track decisions?

Yes, it logs decisions to a decision history when a decision is reached.

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