CEO Advisor
Ongoing advice on the CEO's job: board handling, investor updates, priorities, exec hires, fundraising timing, and bad news.
Before & after
Same prompt, same agent — the only difference is the skill.
Strategic decisions like roadmap choices depend on several factors. You'd want to consider your market position, customer feedback, resource constraints, and competitive landscape. Both options probably have tradeoffs—revenue potential versus execution risk, speed to market versus quality. It's often useful to run the scenarios past your leadership team. You might also want to gather customer input. What are the two options you're considering? How does your team feel about each?
OPTION A: Build Platform Tools REVENUE IMPACT: 35% potential uplift through ecosystem lock-in (est. Year 2) EXECUTION: 18 months, requires 2 senior engineers COMPETITIVE FIT: Defensible moat; 2 competitors ahead MARKET SIGNAL: 60% customer feature requests align here RISK: High—platform complexity, long payoff OPTION B: Vertical Expansion REVENUE IMPACT: 20% uplift through market penetration (est. Q3) EXECUTION: 6 months, existing team can own COMPETITIVE FIT: Faster to first win; 5 competitors here already MARKET SIGNAL: Enterprise buyers asking for vertical depth RISK: Medium—faster validation, earlier revenue RECOMMENDATION: Start with Option B (6-month runway). Use revenue from vertical wins to fund Option A platform investment. Parallel execution splits focus too thin given your team size. Option B validates demand faster and de-risks platform play.
About this skill
Advice on the parts of the CEO job no one else owns: the board, investors, the exec team, the few priorities that matter, and how the company hears hard news. Calibrated to your stage, with conventions experienced CEOs and board members actually use.
What it does
- Handles the board: no-surprises rule, pre-wiring votes 1:1, pre-reads, consistent KPIs
- Drafts and fixes investor updates in a consistent format with real asks
- Runs the default alive test on your numbers before fundraising talk
- Cuts priorities to 3-5 with owners and metrics, and names what you will not do
- Handles exec problems conversation-first, never jumping to a verdict
What you get
A direct answer for quick questions, edits to your board outline or investor update, and optional templates for both. Every rule of thumb is labeled, and legal or charter questions are flagged for counsel.
Best for
Founders and CEOs of seed to growth-stage companies preparing for board meetings, sending investor updates, or building their first exec team.
SKILL.md preview
---
name: ceo-advisor
description: Ongoing advice on the CEO's actual job - running the board, writing investor updates, setting and cutting company priorities, building and fixing the exec team, fundraising timing and narrative, operating cadence, and delivering bad news - calibrated to company stage. Use when a founder or CEO asks "how do I handle my board?", "what should go in my investor update?", "we have too many priorities", "when should I hire a VP?", "how do I tell the board we missed the quarter?", "what should I be spending my time on?", or "am I default alive?".
---
# CEO Advisor
… (sign up to view the full skill)More business & ops skills
View all Business & Ops skills →Simulated Board Pressure Test
Stress-tests a proposal from each board seat's incentives, forecasts the vote, and names the changes that would get it approved.
New Executive Onboarding Plan
First 90 days for a new VP or C-level hire: decision rights from the founder, a measurable scorecard, listening tour, 30/60/90 check-ins.
Change Rollout Planner
Plans how one reorg, tool switch, or pivot lands: impact by group, who hears what first, resistance diagnosis, and follow-through.
CEO Board Prep and Pre-Wires
Gets a CEO ready for the board: likely hard questions by director, number-first answers, pre-wire calls, and a vote count.