Chief of Staff Advisor
Runs the CEO's leadership rhythm: decision logs that stop re-debates, cross-functional decision framing, commitment tracking, exec comms.
Before & after
Same prompt, same agent — the only difference is the skill.
That's a big strategic question and it depends on a lot of factors—your runway, your growth rate, your competitive landscape, and what the market is doing right now. You'd probably want to talk to people in different roles: someone focused on finance might have different priorities than someone running product. There are pros and cons to both raising and bootstrapping. The right answer depends on your specific situation. What's your current runway and burn rate? How fast are you growing? That would help clarify things.
FOUNDER QUESTION ROUTED → Chief of Staff convening board review (Finance, Growth, Product) BOARD SESSION OUTPUT FINANCE ADVISOR summary: • Current runway: 11 months (if burn stays flat at 85K/month) • Raise pros: 18-month runway gives you market expansion window; easier to hire • Bootstrap pros: avoid dilution; keep full control; prove unit economics first GROWTH ADVISOR summary: • MRR growing 12% month-over-month (trending well) • Market window: 18-month lead on competitor X before they scale • Raise recommendation: Needed IF you want to capture category leadership; otherwise bootstrap works PRODUCT ADVISOR summary: • Roadmap: 8-week sprint to hit "table stakes" features before fundraising makes sense • Risk: Competitor launch in Q4 may force a funding decision SYNTHESIS & DECISION GATE If you want to own the category: Raise Series A in Oct 2026 (after product milestone) If you want to own your destiny: Extend runway to 24 months, hit 30% MoM growth, then decide Nov 2026 Unanswered: Do you want exit in 5 years or long-term business? (CTO needs to weigh in) NEXT STEP: Board reconvenes after Q3 metrics close.
About this skill
If your leadership team keeps re-deciding the same things and spends meetings on status updates, the fix is a few sharp habits, not more process. This skill works like a chief of staff to the CEO: decisions logged with a single decider, meetings that decide, and communications that land.
What it does
- Sets up a decision log with owner, decider, rejected options, and a revisit trigger
- Frames cross-functional decisions so each executive's view and disagreement stay visible
- Redesigns the leadership staff meeting around decisions, not status
- Tracks commitments to closure and flags when overdue means a capacity conversation
- Drafts the weekly CEO update, decision announcements, and pre-reads in the CEO's voice
What you get
One ready-to-use artifact (log entry, agenda, update draft, decision framing) or, on request, a full leadership rhythm.
Best for
CEOs, founders, and chiefs of staff running a leadership team of roughly 4-12 people. For a company-wide operating system use Company OS Designer; for process and capacity problems use COO Advisor.
SKILL.md preview
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name: chief-of-staff
description: Act as a chief of staff to a CEO or founder - run the leadership team's operating rhythm, keep a decision log so settled questions stay settled, frame cross-functional decisions with a clear owner and each executive's view, track commitments to closure, and draft executive communications (weekly CEO update, staff meeting agenda and pre-reads, all-hands notes, decision announcements). Use when the user says "we keep re-deciding the same things", "set up a decision log", "prep my exec staff meeting", "draft my weekly update to the team", "who should own this?", "this decision touches finance and product", or "help me run my leadership team better".
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