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/cs:caio-review <plan

/cs:caio-review — CAIO Forcing Questions

by alirezarezvani · MIT license · ★ 26,349 on GitHub · updated Aug 30

/cs:caio-review — CAIO Forcing Questions cover

/cs:caio-review <plan> — Eval-demanding Chief AI Officer interrogation of any plan that involves AI: model selection, risk classification, cost economics, or AI hiring. Use when shipping an AI feature without an eval set, choosing…

---
name: "caio-review"
description: "/cs:caio-review <plan> — Eval-demanding Chief AI Officer interrogation of any plan that involves AI: model selection, risk classification, cost economics, or AI hiring. Use when shipping an AI feature without an eval set, choosing between API, fine-tune, and self-hosted, or classifying a use case under the EU AI Act."
---

# /cs:caio-review — CAIO Forcing Questions

**Command:** `/cs:caio-review <plan>`

The eval-demanding CAIO pressure-tests any plan that involves AI. Six questions before any AI feature ships, any multi-year vendor commitment, or any AI team expansion.

## When to Run

- Before shipping any new AI-powered feature
- Before signing a multi-year AI vendor contract (API or self-hosted infra)
- Before EU launch of any AI feature
- Before a major AI team hire (especially ML engineer or research scientist)
- Before a fine-tuning project commitment

Overview

The eval-demanding CAIO pressure-tests any plan that involves AI. Six questions before any AI feature ships, any multi-year vendor commitment, or any AI team expansion.

Manual install (npx, ZIP)
Claude Codenpx skills add alirezarezvani/claude-skills --skill caio-review -g -a claude-code
Claude Code (manual)mkdir -p ~/.claude/skills && curl -sL https://codeload.github.com/alirezarezvani/claude-skills/tar.gz/19392f7a0826 \ | tar -xz -C ~/.claude/skills --strip-components=3 claude-skills-19392f7a0826/c-level-agents/skills/caio-review
Windows (PowerShell)New-Item -ItemType Directory -Force "$HOME\.claude\skills" | Out-Null; Invoke-WebRequest "https://m.agentalley.io/zip/9be527537456a946db52/caio-review.zip" -OutFile "$env:TEMP\caio-review.zip"; Expand-Archive "$env:TEMP\caio-review.zip" -DestinationPath "$HOME\.claude\skills" -Force
Claude.ai / desktopDownload the ZIP and upload it under Settings → Capabilities → Skills.
Codex, Cursor, other agentsPoint them at SKILL.md. The other files are plain text.

Connects with Agent Alley MCP · agentalley.io/mcp

Files included

  • SKILL.md5.9 KB
Read the files here
alirezarezvani/19392f71 file
Shared references8SKILL.md reads these from elsewhere in the repo. Not in the ZIP.Get them on GitHub ↗
SKILL.md
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/cs:caio-review — CAIO Forcing Questions

Command: /cs:caio-review <plan>

The eval-demanding CAIO pressure-tests any plan that involves AI. Six questions before any AI feature ships, any multi-year vendor commitment, or any AI team expansion.

When to Run

  • Before shipping any new AI-powered feature
  • Before signing a multi-year AI vendor contract (API or self-hosted infra)
  • Before EU launch of any AI feature
  • Before a major AI team hire (especially ML engineer or research scientist)
  • Before a fine-tuning project commitment
  • Before adopting AI in a regulated domain (employment, credit, healthcare, education, etc.)
  • When the founder uses the word "AI" near "competitive advantage" or "moat"

The Six CAIO Questions

1. What does this AI need to be good at, and how would you measure it?

No eval set = no ship. Before any AI feature deploys, define the eval criteria.

  • 50-100 representative inputs minimum
  • Expected outputs OR rubric for grading
  • Edge cases: ambiguous, adversarial, format-edge
  • If you can't write down what "good" looks like, you don't have a feature; you have a vibe.
2. What's the SLO on hallucination / error rate, and what's the fallback?

Every AI feature has a failure mode. Plan for it.

  • Quantified SLO: "<5% hallucination on factual queries"
  • Detection mechanism: monitoring, sampling, customer feedback loop
  • Fallback: human-in-loop review, lower-risk default response, refuse-to-answer
  • Blast radius if SLO breached: how many users affected, what is the cost?
3. What's the risk tier under EU AI Act, and is conformity assessment required?

Run ai_risk_classifier.py if any EU residents are affected OR domain is regulated.

  • PROHIBITED → cannot launch in EU; re-scope
  • HIGH → conformity assessment + EU DB registration + 10 Articles of obligations (3-12 months, $50-200K)
  • LIMITED → transparency obligations (chatbot disclosure, AI-generated content marking)
  • MINIMAL → no specific obligations; NIST AI RMF voluntary
4. API, fine-tune, or build?

Run model_buildvsbuy_calculator.py for the specific use case.

  • 80% of B2B SaaS use cases: API
  • 15%: fine-tune (when domain-specific behavior + labeled data + ML team + high volume)
  • <1%: build from scratch
  • Decision must consider economic breakeven AND practical feasibility (data, team, compliance)
5. What's the 12-month cost trajectory at expected scale?

Run ai_cost_economics.py for the workload.

  • API: variable, scales linearly
  • Self-hosted: mostly fixed, breakeven typically 1-10B tokens/month for 70B-class
  • Hidden costs of self-hosted: ops, monitoring, model updates, capacity, failover, security
  • Hidden costs of API: vendor lock-in, capability drift, rate limits, data residency
  • Prompt caching is the most underrated lever; check provider support
6. What role unblocks this — and have we hired prerequisites first?

Map AI capability to specific role. Founders confuse AI engineer / ML engineer / research scientist.

  • AI engineer: applied + full-stack + prompts + evals + deployment (most startups need this)
  • ML engineer: fine-tuning + retraining infra (only after platform engineer + labeled data)
  • Research scientist: model invention (only if model IS the product)
  • Don't hire research scientist as first AI hire — they need infrastructure to be productive

Workflow

# 1. Model selection check
python ../../../c-level-advisor/skills/chief-ai-officer-advisor/scripts/model_buildvsbuy_calculator.py use_case.json

# 2. Regulatory classification
python ../../../c-level-advisor/skills/chief-ai-officer-advisor/scripts/ai_risk_classifier.py use_case.json

# 3. Cost projection
python ../../../c-level-advisor/skills/chief-ai-officer-advisor/scripts/ai_cost_economics.py workload.json

Output Format

# CAIO Review: <plan>
**Date:** YYYY-MM-DD

## The Decision Being Made
[one sentence — which CAIO decision: model selection | risk classification | economics | next hire]

## Eval Discipline
- Eval set committed: yes/no
- SLO defined: <metric> < <threshold>
- Fallback behavior: <one line>

## Model Selection (if applicable)
- Recommended: API / FINE_TUNE / BUILD
- 3-year TCO: $X (chosen path) vs $Y (alternatives)
- Breakeven: <volume>

## Risk Classification (if applicable)
- EU AI Act tier: PROHIBITED / HIGH / LIMITED / MINIMAL
- Conformity assessment required: yes/no
- US state triggers: [list]
- Required controls open: N

## Cost Economics (if applicable)
- Monthly cost at current volume: $X
- Breakeven for self-hosted migration: <volume>
- Migration cost if applicable: $X (3-6 months)

## Org (if applicable)
- Next hire: <role>
- Why this, not the alternative: <one line>
- Prerequisite hires in place: yes/no

## Verdict
🟢 SHIP | 🟡 SHARPEN | 🔴 BLOCK

## Next Steps
[3 concrete actions]

Routing

  • /cs:cdo-review — for any training-data implications
  • /cs:gc-review — for AI vendor contracts, output liability, training-data licensing
  • /cs:ciso-review — for prompt injection / jailbreak / training-data poisoning threat model
  • /cs:cfo-review — for multi-year vendor or GPU commitment TCO
  • cs-chro-advisor agent — for AI team hires (comp, ladder, leveling)
  • /cs:decide — log the verdict
  • /cs:freeze 60 — on multi-year AI commitments

Version: 1.0.0

1---
2name: "caio-review"
3description: "/cs:caio-review <plan> — Eval-demanding Chief AI Officer interrogation of any plan that involves AI: model selection, risk classification, cost economics, or AI hiring. Use when shipping an AI feature without an eval set, choosing between API, fine-tune, and self-hosted, or classifying a use case under the EU AI Act."
4---
5 
6# /cs:caio-review — CAIO Forcing Questions
7 
8**Command:** `/cs:caio-review <plan>`
9 
10The eval-demanding CAIO pressure-tests any plan that involves AI. Six questions before any AI feature ships, any multi-year vendor commitment, or any AI team expansion.
11 
12## When to Run
13 
14- Before shipping any new AI-powered feature
15- Before signing a multi-year AI vendor contract (API or self-hosted infra)
16- Before EU launch of any AI feature
17- Before a major AI team hire (especially ML engineer or research scientist)
18- Before a fine-tuning project commitment
19- Before adopting AI in a regulated domain (employment, credit, healthcare, education, etc.)
20- When the founder uses the word "AI" near "competitive advantage" or "moat"
21 
22## The Six CAIO Questions
23 
24### 1. What does this AI need to be good at, and how would you measure it?
25**No eval set = no ship.** Before any AI feature deploys, define the eval criteria.
26- 50-100 representative inputs minimum
27- Expected outputs OR rubric for grading
28- Edge cases: ambiguous, adversarial, format-edge
29- If you can't write down what "good" looks like, you don't have a feature; you have a vibe.
30 
31### 2. What's the SLO on hallucination / error rate, and what's the fallback?
32**Every AI feature has a failure mode. Plan for it.**
33- Quantified SLO: "<5% hallucination on factual queries"
34- Detection mechanism: monitoring, sampling, customer feedback loop
35- Fallback: human-in-loop review, lower-risk default response, refuse-to-answer
36- Blast radius if SLO breached: how many users affected, what is the cost?
37 
38### 3. What's the risk tier under EU AI Act, and is conformity assessment required?
39**Run `ai_risk_classifier.py` if any EU residents are affected OR domain is regulated.**
40- PROHIBITED → cannot launch in EU; re-scope
41- HIGH → conformity assessment + EU DB registration + 10 Articles of obligations (3-12 months, $50-200K)
42- LIMITED → transparency obligations (chatbot disclosure, AI-generated content marking)
43- MINIMAL → no specific obligations; NIST AI RMF voluntary
44 
45### 4. API, fine-tune, or build?
46**Run `model_buildvsbuy_calculator.py` for the specific use case.**
47- 80% of B2B SaaS use cases: API
48- 15%: fine-tune (when domain-specific behavior + labeled data + ML team + high volume)
49- <1%: build from scratch
50- Decision must consider economic breakeven AND practical feasibility (data, team, compliance)
51 
52### 5. What's the 12-month cost trajectory at expected scale?
53**Run `ai_cost_economics.py` for the workload.**
54- API: variable, scales linearly
55- Self-hosted: mostly fixed, breakeven typically 1-10B tokens/month for 70B-class
56- Hidden costs of self-hosted: ops, monitoring, model updates, capacity, failover, security
57- Hidden costs of API: vendor lock-in, capability drift, rate limits, data residency
58- Prompt caching is the most underrated lever; check provider support
59 
60### 6. What role unblocks this — and have we hired prerequisites first?
61**Map AI capability to specific role. Founders confuse AI engineer / ML engineer / research scientist.**
62- AI engineer: applied + full-stack + prompts + evals + deployment (most startups need this)
63- ML engineer: fine-tuning + retraining infra (only after platform engineer + labeled data)
64- Research scientist: model invention (only if model IS the product)
65- Don't hire research scientist as first AI hire — they need infrastructure to be productive
66 
67## Workflow
68 
69```bash
70# 1. Model selection check
71python ../../../c-level-advisor/skills/chief-ai-officer-advisor/scripts/model_buildvsbuy_calculator.py use_case.json
72 
73# 2. Regulatory classification
74python ../../../c-level-advisor/skills/chief-ai-officer-advisor/scripts/ai_risk_classifier.py use_case.json
75 
76# 3. Cost projection
77python ../../../c-level-advisor/skills/chief-ai-officer-advisor/scripts/ai_cost_economics.py workload.json
78```
79 
80## Output Format
81 
82```markdown
83# CAIO Review: <plan>
84**Date:** YYYY-MM-DD
85 
86## The Decision Being Made
87[one sentence — which CAIO decision: model selection | risk classification | economics | next hire]
88 
89## Eval Discipline
90- Eval set committed: yes/no
91- SLO defined: <metric> < <threshold>
92- Fallback behavior: <one line>
93 
94## Model Selection (if applicable)
95- Recommended: API / FINE_TUNE / BUILD
96- 3-year TCO: $X (chosen path) vs $Y (alternatives)
97- Breakeven: <volume>
98 
99## Risk Classification (if applicable)
100- EU AI Act tier: PROHIBITED / HIGH / LIMITED / MINIMAL
101- Conformity assessment required: yes/no
102- US state triggers: [list]
103- Required controls open: N
104 
105## Cost Economics (if applicable)
106- Monthly cost at current volume: $X
107- Breakeven for self-hosted migration: <volume>
108- Migration cost if applicable: $X (3-6 months)
109 
110## Org (if applicable)
111- Next hire: <role>
112- Why this, not the alternative: <one line>
113- Prerequisite hires in place: yes/no
114 
115## Verdict
116🟢 SHIP | 🟡 SHARPEN | 🔴 BLOCK
117 
118## Next Steps
119[3 concrete actions]
120```
121 
122## Routing
123 
124- `/cs:cdo-review` — for any training-data implications
125- `/cs:gc-review` — for AI vendor contracts, output liability, training-data licensing
126- `/cs:ciso-review` — for prompt injection / jailbreak / training-data poisoning threat model
127- `/cs:cfo-review` — for multi-year vendor or GPU commitment TCO
128- `cs-chro-advisor` agent — for AI team hires (comp, ladder, leveling)
129- `/cs:decide` — log the verdict
130- `/cs:freeze 60` — on multi-year AI commitments
131 
132## Related
133 
134- Agent: [`cs-caio-advisor`](../../agents/cs-caio-advisor.md)
135- Skill: [`chief-ai-officer-advisor`](../../../c-level-advisor/skills/chief-ai-officer-advisor/SKILL.md)
136- Adjacent: `../../../c-level-advisor/skills/chief-data-officer-advisor/` (training data rights, data strategy)
137 
138---
139 
140**Version:** 1.0.0
141 
View all files on GitHub →

Details

Updated
Aug 30, 2026
License
MIT
Stars on the repo
★ 26,349
Checked
Source
alirezarezvani/claude-skills ↗
Creator
alirezarezvani · 363 listings
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