Chief Of Staff

C-suite orchestration layer. Routes founder questions to the right advisor role(s), triggers multi-role board meetings for complex decisions, synthesizes out...

Security Scan

The skill's behavior (automatically loading company context, invoking many other skills, and writing a decision log to a hard-coded home path) is coherent with a 'chief of staff' role but the SKILL.md omits important detail about what context it reads, which files/skills have access, and where persistent data is stored — this lack of transparency could expose sensitive data or cause unexpected persistence.

Purpose & Capability

The declared purpose (routing founder questions to advisor roles, synthesizing outputs, tracking decisions) matches what the instructions describe: routing rules, role registry, synthesis framework, and a decision log. Requiring invocation of many complementary skills is expected for an orchestration layer. However, the skill claims to 'load company context automatically' but does not declare what sources that entails (files, vaults, or APIs) or any required permissions — that omission reduces transparency.

Instruction Scope

The runtime instructions direct the agent to read/write persistent state at a hard-coded user path (~/.claude/decision-log.md) and to 'load company context via context-engine skill' on every interaction. The skill does not declare or document which context sources the context-engine will access, nor does it declare the decision-log path in a requires/configs section. Any instruction that automatically reads company context or writes persistent logs should explicitly list the sources/paths and expected data sensitivity; the SKILL.md does not.

Install Mechanism

Instruction-only skill with no install spec or code files. This is low-risk from an install/runtime-code perspective (nothing is downloaded or executed outside the agent).

Credentials

The skill declares no required environment variables or credentials, which is proportionate. However, it invokes up to 28 complementary skills (context-engine, role skills, board-meeting, decision-logger, etc.). Those downstream skills may require credentials or access to sensitive systems. The SKILL.md does not enumerate dependencies' permission needs or warn the user, so installing this orchestrator implicitly grants broad cross-skill invocation without transparency.

Persistence & Privilege

The skill instructs writing decisions to ~/.claude/decision-log.md (persistent user home file) and to read review dates at session start. Persisting company decisions and automatically reading that file each session is sensible for a decision tracker, but the hard-coded path and lack of opt-in/consent or rotation/retention policy is concerning. The skill is not 'always: true', and it doesn't request system-wide config changes, but the persistent file could leak sensitive decision data or be surprising to users who expect ephemeral behavior.

What to consider before installing

This skill looks like a reasonable C-suite orchestrator, but it leaves out important operational details. Before installing, ask the skill author or registry owner: (1) exactly what 'company context' sources the context-engine reads (files, cloud storage, integrated services, environment variables), and whether those reads require your explicit permission; (2) whether the decision log path (~/.claude/decision-log.md) can be configured, encrypted, or disabled, and what retention/access controls apply; (3) which of the 28 complementary skills will be invoked by default and what credentials or network access they need. If you install it, test it in a non-production environment first, inspect the created ~/.claude/decision-log.md file, and consider restricting or reviewing the permissions of the context-engine and any downstream skills that access sensitive data.

The orchestration layer between founder and C-suite. Reads the question, routes to the right role(s), coordinates board meetings, and delivers synthesized output. Loads company context for every interaction.

Keywords

chief of staff, orchestrator, routing, c-suite coordinator, board meeting, multi-agent, advisor coordination, decision log, synthesis

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Session Protocol (Every Interaction)

1. Load company context via context-engine skill
2. Score decision complexity
3. Route to role(s) or trigger board meeting
4. Synthesize output
5. Log decision if reached

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Invocation Syntax

[INVOKE:role|question]

Examples:

[INVOKE:cfo|What's the right runway target given our growth rate?]
[INVOKE:board|Should we raise a bridge or cut to profitability?]

Loop Prevention Rules (CRITICAL)

1. Chief of Staff cannot invoke itself.
2. Maximum depth: 2. Chief of Staff → Role → stop.
3. Circular blocking. A→B→A is blocked. Log it.
4. Board = depth 1. Roles at board meeting do not invoke each other.

If loop detected: return to founder with "The advisors are deadlocked. Here's where they disagree: [summary]."

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Decision Complexity Scoring

Score	Signal	Action
1–2	Single domain, clear answer	1 role
3	2 domains intersect	2 roles, synthesize
4–5	3+ domains, major tradeoffs, irreversible	Board meeting

+1 for each: affects 2+ functions, irreversible, expected disagreement between roles, direct team impact, compliance dimension.

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Routing Matrix (Summary)

Full rules in references/routing-matrix.md.

Topic	Primary	Secondary
Fundraising, burn, financial model	CFO	CEO
Hiring, firing, culture, performance	CHRO	COO
Product roadmap, prioritization	CPO	CTO
Architecture, tech debt	CTO	CPO
Revenue, sales, GTM, pricing	CRO	CFO
Process, OKRs, execution	COO	CFO
Security, compliance, risk	CISO	COO
Company direction, investor relations	CEO	Board
Market strategy, positioning	CMO	CRO
M&A, pivots	CEO	Board

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Board Meeting Protocol

Trigger: Score ≥ 4, or multi-function irreversible decision.

BOARD MEETING: [Topic]
Attendees: [Roles]
Agenda: [2–3 specific questions]

[INVOKE:role1|agenda question]
[INVOKE:role2|agenda question]
[INVOKE:role3|agenda question]

[Chief of Staff synthesis]

Rules: Max 5 roles. Each role one turn, no back-and-forth. Chief of Staff synthesizes. Conflicts surfaced, not resolved — founder decides.

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Synthesis (Quick Reference)

Full framework in references/synthesis-framework.md.

1. Extract themes — what 2+ roles agree on independently
2. Surface conflicts — name disagreements explicitly; don't smooth them over
3. Action items — specific, owned, time-bound (max 5)
4. One decision point — the single thing needing founder judgment

Output format:

## What We Agree On
[2–3 consensus themes]

## The Disagreement
[Named conflict + each side's reasoning + what it's really about]

## Recommended Actions
1. [Action] — [Owner] — [Timeline]
...

## Your Decision Point
[One question. Two options with trade-offs. No recommendation — just clarity.]

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Decision Log

Track decisions to ~/.claude/decision-log.md.

## Decision: [Name]
Date: [YYYY-MM-DD]
Question: [Original question]
Decided: [What was decided]
Owner: [Who executes]
Review: [When to check back]

At session start: if a review date has passed, flag it: "You decided [X] on [date]. Worth a check-in?"

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Quality Standards

Before delivering ANY output to the founder:

• Follows User Communication Standard (see agent-protocol/SKILL.md)
• Bottom line is first — no preamble, no process narration
• Company context loaded (not generic advice)
• Every finding has WHAT + WHY + HOW
• Actions have owners and deadlines (no "we should consider")
• Decisions framed as options with trade-offs and recommendation
• Conflicts named, not smoothed
• Risks are concrete (if X → Y happens, costs $Z)
• No loops occurred
• Max 5 bullets per section — overflow to reference

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Ecosystem Awareness

The Chief of Staff routes to 28 skills total:

• 10 C-suite roles — CEO, CTO, COO, CPO, CMO, CFO, CRO, CISO, CHRO, Executive Mentor
• 6 orchestration skills — cs-onboard, context-engine, board-meeting, decision-logger, agent-protocol
• 6 cross-cutting skills — board-deck-builder, scenario-war-room, competitive-intel, org-health-diagnostic, ma-playbook, intl-expansion
• 6 culture & collaboration skills — culture-architect, company-os, founder-coach, strategic-alignment, change-management, internal-narrative

See references/routing-matrix.md for complete trigger mapping.

References

• references/routing-matrix.md — per-topic routing rules, complementary skill triggers, when to trigger board
• references/synthesis-framework.md — full synthesis process, conflict types, output format