chief-of-staff

Overview of chief-of-staff skill

What chief-of-staff does

chief-of-staff is a C-suite orchestration skill for founder decision support. Instead of answering every question from one generic perspective, it routes the issue to the right executive advisor role, decides when a multi-role board meeting is needed, synthesizes competing viewpoints, and records the decision when one is reached.

The real job is not “give startup advice.” The job is to help a founder turn an ambiguous operating question like “Should we raise now or cut burn?” into a structured decision process with the right lenses applied: finance, growth, product, operations, people, technology, and CEO-level tradeoffs.

Best-fit users and decisions

The chief-of-staff skill fits founders, operators, and AI-agent builders who want a repeatable executive advisory workflow. It is strongest for decisions that cross functions, such as pricing, runway, hiring pace, product prioritization, restructuring, fundraising timing, leadership conflict, or whether to convene a simulated board discussion.

It is less useful for narrow single-task work such as writing copy, debugging code, or answering a factual question. Use it when the main risk is choosing the wrong advisor frame, missing a stakeholder perspective, or receiving a pile of role outputs without a clear recommendation.

What makes this skill different

The differentiator is its routing and synthesis layer. The repository includes references/routing-matrix.md, which maps question types to executive roles and complexity scores, and references/synthesis-framework.md, which explains how to integrate multiple role responses into one founder-ready answer.

That makes chief-of-staff for Decision Support more structured than a broad “act as my COO” prompt. It includes loop prevention rules, a maximum invocation depth, routing syntax, and a board-meeting pathway for high-complexity decisions.

How to Use chief-of-staff skill

chief-of-staff install and files to inspect first

If your skill manager supports GitHub skill installation, install with:

npx skills add alirezarezvani/claude-skills --skill chief-of-staff

Then inspect the skill path:

c-level-advisor/skills/chief-of-staff

Read these files in order:

1. SKILL.md — session protocol, invocation syntax, routing behavior, loop prevention.
2. references/routing-matrix.md — which executive role should handle which decision.
3. references/synthesis-framework.md — how multi-role outputs become one recommendation.

There are no scripts or resources to configure, so adoption depends mainly on using the protocol correctly and providing enough company context.

Inputs the skill needs to work well

The skill is designed to load company context through a context-engine skill, but you should still provide the decision facts directly if your environment does not already contain them. Strong inputs include:

• Company stage, business model, market, and current objective.
• Relevant numbers: runway, burn, revenue, growth, margins, sales cycle, headcount.
• Decision deadline and reversibility.
• Options already being considered.
• Constraints: cash, team capacity, investor promises, customer commitments.
• What a good answer should produce: decision, options, risk map, board recommendation, or next actions.

Weak prompt: “Should we hire a VP Sales?”

Better prompt: “We are a B2B SaaS company at $1.8M ARR, growing 6% MoM, 11 months runway, founder-led sales, 4 AEs, weak pipeline discipline. Should we hire a VP Sales now, promote internally, or wait until after Series A? Route this through chief-of-staff and synthesize CFO, CRO, and CEO tradeoffs.”

Invocation syntax and practical workflow

The upstream skill uses this invocation format:

[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?]

A practical chief-of-staff usage workflow is:

1. Start with the founder question and company context.
2. Let the skill score complexity and select one role, multiple roles, or board.
3. Ask it to name assumptions before recommending.
4. For multi-role decisions, request synthesis, not a transcript.
5. End with one decision point, unresolved risks, and next actions.

For high-stakes decisions, explicitly ask: “If this requires a board meeting, convene one; otherwise route to the minimum necessary roles.”

chief-of-staff skill FAQ

Is chief-of-staff better than an ordinary prompt?

Yes, when the problem is cross-functional. A normal prompt often gives a blended answer without explaining which lens is driving the recommendation. The chief-of-staff skill adds routing discipline: CFO for capital and runway, CHRO for people issues, CPO/CTO for product and technical tradeoffs, CRO for revenue, and board mode for complex multi-domain calls.

For simple advice, an ordinary prompt may be faster. For founder decisions with real tradeoffs, the skill reduces blind spots.

What does the skill not do?

It does not replace legal, financial, HR, medical, or investment professionals. It also does not magically know your operating data unless your agent environment has company context loaded or you provide it in the prompt.

The skill coordinates advisory reasoning; it does not execute fundraising, update financial models, change roadmaps, or create a reliable decision log unless your surrounding agent setup supports those actions.

Is it beginner-friendly?

Moderately. The invocation syntax is simple, but the outputs improve a lot when the user understands the difference between a role answer and a synthesized decision. Beginners should start by asking the skill to explain its routing choice:

“Use chief-of-staff. First state which role or roles you are routing to and why, then provide the synthesized recommendation.”

This helps verify that the skill is not over-escalating every question to a board meeting.

When should I avoid this skill?

Avoid chief-of-staff when you need a single specialist answer, a fast content draft, a coding task, or a purely factual lookup. Also avoid it if you cannot share enough business context to make the decision meaningful. Without numbers, constraints, and goals, the skill may produce polished but generic executive advice.

How to Improve chief-of-staff skill

Improve chief-of-staff outputs with decision-grade context

The most important improvement is to feed the skill decision-grade inputs. Include the actual choice, not just the topic. “Pricing strategy” is broad; “Should we move from seat-based to usage-based pricing before Series A?” gives the routing matrix a real decision to classify.

Add the current metric baseline and the consequence of being wrong. A CFO answer changes when runway is 6 months versus 24 months. A CPO answer changes when churn is driven by missing features versus poor onboarding.

Control routing, escalation, and synthesis quality

Common failure modes are over-routing, under-routing, and summary-style synthesis. To prevent them, ask for:

• “Use the fewest roles needed.”
• “Escalate to board only if the decision affects multiple functions or has high downside.”
• “Name conflicts between roles instead of averaging them.”
• “End with a recommended path, not a list of equal options.”

This aligns with the repository’s synthesis framework, where the highest-value output is an integrated decision: consensus, conflicts, gaps, priority actions, and one clear decision point.

Iterate after the first answer

After the first output, do not simply ask for “more detail.” Ask targeted follow-ups:

• “What assumption would change the recommendation?”
• “What would the CFO object to?”
• “What is the lowest-regret option if our growth forecast is wrong?”
• “What should we decide this week versus revisit in 30 days?”
• “Convert this into a decision log entry with owner, date, rationale, and review trigger.”

This turns chief-of-staff from a one-shot advisor into a repeatable operating cadence for founder decision support.