Advisory Board Decision Stress Test
Runs your decision past a 3-5 seat advisory board that commits to verdicts, then maps the real disagreements and how to settle them.
Before & after
Same prompt, same agent — the only difference is the skill.
Scaling a B2B SaaS team is an important transition. There are several things to consider, like how to structure the team, maintaining culture, bringing in senior leadership, and setting up better processes. Different companies handle this differently depending on their product and market. I could outline some general best practices, but it would really depend on your specific situation. What areas are you most concerned about—hiring, structure, or something else?
EXPERT BOARD RESPONSES: Scaling SaaS from 5 to 15 EXPERT 1: Operations-Focused Founder - "Month 1-2: Hire 3 people in sales support and customer success; every founder-hour on support is a missed strategic call" - "Month 2-3: Bring in first ops hire (not sales person); this person owns onboarding, metrics dashboard, process docs" - "Month 3-4: Hire 2 engineers; this is where teams usually go wrong—they wait until product work stalls, losing momentum" - "Critical: Document decisions in writing before hiring 7th person; oral culture breaks down" - "Mistake to avoid: Hiring for culture fit only; you need functional specialists even if personalities clash" EXPERT 2: Technical Co-Founder - "Your bottleneck is engineering, not sales. Lock down your architecture at 3 engineers; refactoring at 8 people costs 3x" - "Hire in this order: Senior engineer, then QA/DevOps person (automate testing before hiring support team)" - "Second engineer should own deployment pipeline; you're entering the 'scale or regret' zone" - "Technical debt compounds with headcount; plan for 20% cleanup sprint every quarter after month 4" EXPERT 3: Sales Leader - "Paradox: you can't close enterprise deals at 5 people; close land deals now, but plan AE hire by month 2" - "CS person in month 1; if a customer churns due to slow response, you've lost the cash runway justification for scaling" - "Each sales person needs 2 CSM hours; ratio breaks at 15-person company without dedicated CS role" CONSENSUS INSIGHT: Operations and technical foundation before aggressive hiring; all three emphasize early documentation over speed
About this skill
You ask for multiple perspectives and get five versions of the same balanced answer, each ending in "it depends." Or the expert personas sound like their catchphrases but give no reasoning you can act on. This skill seats a board built around how your decision could fail. Every advisor has to commit to a verdict. Then it shows you exactly where they disagree and the cheapest way to settle it.
What it does
- Picks 3-5 seats (Operator, Capital, Customer, Downside, Contrarian) based on how this specific decision can go wrong, not on who is famous
- Makes every seat commit to a verdict, a confidence level, a flip condition, and one next step you can take within two weeks
- Writes each seat independently and checks for false consensus, then steelmans the other side when everyone agrees too easily
- Sorts each disagreement as fact, value, or risk tolerance, and gives you the cheapest test for each factual crux
- Lets you model named public experts responsibly: grounded in their documented positions or in material you paste, labeled as simulated, with no invented quotes
- Builds a reusable board roster you can paste into future sessions, or turn into a Claude Code slash command
What you get
In one pass you get a neutral restatement of your decision, a verdict from each board seat, a table of where the seats split and why, and a clear "if you value X, do A" call that is still yours to make.
Best for
Founders, operators, and creators facing a real fork, such as raising money, hiring, pricing, a pivot, or quitting. It also suits anyone who keeps going back and forth and wants their reasoning challenged by lenses they don't naturally use.
SKILL.md preview
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name: advisory-board-decision-stress-test
description: Runs a decision past a 3-5 seat simulated advisory board. Each seat has an explicit lens and commits to a verdict with a confidence level and a flip condition. The synthesis sorts disagreements into fact, value, or risk tolerance and names the cheapest test that settles them. Use when the user says "ask the board", "run this past my advisors", "what would a CFO, an investor, and a skeptic say about this", "stress-test this decision", "set up a personal board of advisors", "how would [public expert] think about this", "I keep going back and forth on this", or "every answer I get is just 'it depends'".
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