Cto Review
/cs:cto-review <plan> — Architecture and scaling interrogation. Tech debt, scaling cliffs, team scaling, build-vs-buy.
Install
Quick install
npx skills add https://github.com/alirezarezvani/claude-skills/tree/main/c-level-advisor/c-level-agents/skills/cto-reviewnpx skills add alirezarezvani/claude-skills --skill cto-review --agent claude-codenpx skills add alirezarezvani/claude-skills --skill cto-review --agent cursornpx skills add alirezarezvani/claude-skills --skill cto-review --agent codexnpx skills add alirezarezvani/claude-skills --skill cto-review --agent opencodenpx skills add alirezarezvani/claude-skills --skill cto-review --agent github-copilotnpx skills add alirezarezvani/claude-skills --skill cto-review --agent windsurfMore install options
Shorthand — useful for multi-skill repos:
npx skills add alirezarezvani/claude-skills --skill cto-reviewManual — clone the repo and drop the folder into your agent's skills directory:
git clone https://github.com/alirezarezvani/claude-skills.gitcp -r claude-skills/c-level-advisor/c-level-agents/skills/cto-review ~/.claude/skills//cs:cto-review — CTO Forcing Questions
Command: /cs:cto-review <plan>
Pressure-tests architecture and engineering scaling decisions. Six questions to surface the next scaling cliff before you hit it.
When to Run
- Before approving a major architecture change
- Before doubling the engineering team
- Before a build-vs-buy decision > $100K/year
- When a system is showing reliability stress (SLOs missed)
- Before committing to a new platform / language / DB
The Six CTO Questions
1. Scaling Cliff
Where does the current architecture break, in terms of users / requests / data volume?- Be specific. "It breaks at 10× current load because the primary DB writes saturate."
- If you don't know, run a load test before deciding.
2. Tech Debt Inventory
What's the top tech debt item, what's it costing per week, and when does it become blocking?python ../../../skills/cto-advisor/scripts/tech_debt_analyzer.py
3. Team Scaling
For each open req, what's the ramp time and contribution model?python ../../../skills/cto-advisor/scripts/team_scaling_calculator.py
4. Build vs Buy
Why are we building this instead of buying it — and what's the 3-year TCO of each?- If "we want control" or "it's not that hard" — push back.
- If the answer is "this is our core moat," build.
5. SLO / Reliability
What are the SLOs for this system and what's the current error budget burn?- Without an SLO, you can't reason about reliability tradeoffs.
- See
engineering/slo-architectfor SLO design.
6. Security & Compliance Surface
What does this expose, and has cs-ciso-advisor signed off?- Architecture decisions are compliance decisions.
- Loop in cs-ciso-advisor before commit.
Workflow
- Run the tech debt analyzer + team scaling calculator
- Define the scaling-cliff hypothesis explicitly
- Cross-check with cs-ciso-advisor for security implications
- Apply the verdict
Output Format
# CTO Review: <plan>
**Date:** YYYY-MM-DD
## Scaling Cliff
- Current capacity: <metric>
- Break point: <metric>
- Headroom: X months at current growth
## Tech Debt
- Top item: <description>
- Cost per week: $X or N eng-hours
- Blocking date estimate: <date>
## Team
- Open reqs: N
- Median ramp: X months
- Contribution model: <pairing / squad / area>
## Build vs Buy
- 3-year build TCO: $X
- 3-year buy TCO: $X
- Strategic fit: <core / context>
- Decision: BUILD | BUY
## Reliability
- SLO defined: yes / no
- Error budget burn: X% (target < Y%)
## Security
- cs-ciso sign-off: ✅ / ❌
## Verdict
🟢 SHIP | 🟡 SHARPEN | 🔴 BLOCK
## Next Steps
[3 concrete actions]
Routing
/cs:ciso-review— mandatory if data surface changes/cs:cfo-review— for build-vs-buy > $100K/cs:execute— quarterly plan/cs:boardroom— for architecture pivots
Related
- Agent: [
cs-cto-advisor](../../../../agents/c-level/cs-cto-advisor.md) - Skill: [
cto-advisor](../../../skills/cto-advisor/SKILL.md) - SLO:
../../../../engineering/slo-architect/
---
Version: 1.0.0
SKILL.md source
--- name: cto-review description: /cs:cto-review <plan> — Architecture and scaling interrogation. Tech debt, scaling cliffs, team scaling, build-vs-buy. --- # /cs:cto-review — CTO Forcing Questions **Command:** `/cs:cto-review <plan>` Pressure-tests architecture and engineering scaling decisions. Six questions to surface the next scaling cliff before you hit it. ## When to Run - Before approving a major architecture change - Before doubling the engineering team - Before a build-vs-buy decision > $100K/year - When a system is showing reliability stress (SLOs missed) - Before committing to a new platform / language / DB ## The Six CTO Questions ### 1. Scaling Cliff **Where does the current architecture break, in terms of users / requests / data volume?** - Be specific. "It breaks at 10× current load because the primary DB writes saturate." - If you don't know, run a load test before deciding. ### 2. Tech Debt Inventory **What's the top tech debt item, what's it costing per week, and when does it become blocking?** ```bash python ../../../skills/cto-advisor/scripts/tech_debt_analyzer.py ``` ### 3. Team Scaling **For each open req, what's the ramp time and contribution model?** ```bash python ../../../skills/cto-advisor/scripts/team_scaling_calculator.py ``` ### 4. Build vs Buy **Why are we building this instead of buying it — and what's the 3-year TCO of each?** - If "we want control" or "it's not that hard" — push back. - If the answer is "this is our core moat," build. ### 5. SLO / Reliability **What are the SLOs for this system and what's the current error budget burn?** - Without an SLO, you can't reason about reliability tradeoffs. - See `engineering/slo-architect` for SLO design. ### 6. Security & Compliance Surface **What does this expose, and has cs-ciso-advisor signed off?** - Architecture decisions are compliance decisions. - Loop in cs-ciso-advisor before commit. ## Workflow 1. Run the tech debt analyzer + team scaling calculator 2. Define the scaling-cliff hypothesis explicitly 3. Cross-check with cs-ciso-advisor for security implications 4. Apply the verdict ## Output Format ```markdown # CTO Review: <plan> **Date:** YYYY-MM-DD ## Scaling Cliff - Current capacity: <metric> - Break point: <metric> - Headroom: X months at current growth ## Tech Debt - Top item: <description> - Cost per week: $X or N eng-hours - Blocking date estimate: <date> ## Team - Open reqs: N - Median ramp: X months - Contribution model: <pairing / squad / area> ## Build vs Buy - 3-year build TCO: $X - 3-year buy TCO: $X - Strategic fit: <core / context> - Decision: BUILD | BUY ## Reliability - SLO defined: yes / no - Error budget burn: X% (target < Y%) ## Security - cs-ciso sign-off: ✅ / ❌ ## Verdict 🟢 SHIP | 🟡 SHARPEN | 🔴 BLOCK ## Next Steps [3 concrete actions] ``` ## Routing - `/cs:ciso-review` — mandatory if data surface changes - `/cs:cfo-review` — for build-vs-buy > $100K - `/cs:execute` — quarterly plan - `/cs:boardroom` — for architecture pivots ## Related - Agent: [`cs-cto-advisor`](../../../../agents/c-level/cs-cto-advisor.md) - Skill: [`cto-advisor`](../../../skills/cto-advisor/SKILL.md) - SLO: `../../../../engineering/slo-architect/` --- **Version:** 1.0.0
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