Architecture Review

/cs:cto-review — CTO Forcing Questions

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

/cs:cto-review — CTO Forcing Questions cover

/cs:cto-review <plan> — Architecture and scaling interrogation. Tech debt, scaling cliffs, team scaling, build-vs-buy.

---
name: "cto-review"
description: "/cs:cto-review <plan> — Architecture and scaling interrogation. Tech debt, scaling cliffs, team scaling, build-vs-buy. Use when committing to an architecture, planning for 10x load, or weighing a rebuild against a vendor."
---

# /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

Overview

Pressure-tests architecture and engineering scaling decisions. Six questions to surface the next scaling cliff before you hit it.

Manual install (npx, ZIP)
Claude Codenpx skills add alirezarezvani/claude-skills --skill cto-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/cto-review
Windows (PowerShell)New-Item -ItemType Directory -Force "$HOME\.claude\skills" | Out-Null; Invoke-WebRequest "https://m.agentalley.io/zip/896fda8dd8ef56575c05/cto-review.zip" -OutFile "$env:TEMP\cto-review.zip"; Expand-Archive "$env:TEMP\cto-review.zip" -DestinationPath "$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.md3.3 KB
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/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 ../../../c-level-advisor/skills/cto-advisor/scripts/tech_debt_analyzer.py
3. Team Scaling

For each open req, what's the ramp time and contribution model?

python ../../../c-level-advisor/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

# 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

Version: 1.0.0

1---
2name: "cto-review"
3description: "/cs:cto-review <plan> — Architecture and scaling interrogation. Tech debt, scaling cliffs, team scaling, build-vs-buy. Use when committing to an architecture, planning for 10x load, or weighing a rebuild against a vendor."
4---
5 
6# /cs:cto-review — CTO Forcing Questions
7 
8**Command:** `/cs:cto-review <plan>`
9 
10Pressure-tests architecture and engineering scaling decisions. Six questions to surface the next scaling cliff before you hit it.
11 
12## When to Run
13 
14- Before approving a major architecture change
15- Before doubling the engineering team
16- Before a build-vs-buy decision > $100K/year
17- When a system is showing reliability stress (SLOs missed)
18- Before committing to a new platform / language / DB
19 
20## The Six CTO Questions
21 
22### 1. Scaling Cliff
23**Where does the current architecture break, in terms of users / requests / data volume?**
24- Be specific. "It breaks at 10× current load because the primary DB writes saturate."
25- If you don't know, run a load test before deciding.
26 
27### 2. Tech Debt Inventory
28**What's the top tech debt item, what's it costing per week, and when does it become blocking?**
29```bash
30python ../../../c-level-advisor/skills/cto-advisor/scripts/tech_debt_analyzer.py
31```
32 
33### 3. Team Scaling
34**For each open req, what's the ramp time and contribution model?**
35```bash
36python ../../../c-level-advisor/skills/cto-advisor/scripts/team_scaling_calculator.py
37```
38 
39### 4. Build vs Buy
40**Why are we building this instead of buying it — and what's the 3-year TCO of each?**
41- If "we want control" or "it's not that hard" — push back.
42- If the answer is "this is our core moat," build.
43 
44### 5. SLO / Reliability
45**What are the SLOs for this system and what's the current error budget burn?**
46- Without an SLO, you can't reason about reliability tradeoffs.
47- See `engineering/slo-architect` for SLO design.
48 
49### 6. Security & Compliance Surface
50**What does this expose, and has cs-ciso-advisor signed off?**
51- Architecture decisions are compliance decisions.
52- Loop in cs-ciso-advisor before commit.
53 
54## Workflow
55 
561. Run the tech debt analyzer + team scaling calculator
572. Define the scaling-cliff hypothesis explicitly
583. Cross-check with cs-ciso-advisor for security implications
594. Apply the verdict
60 
61## Output Format
62 
63```markdown
64# CTO Review: <plan>
65**Date:** YYYY-MM-DD
66 
67## Scaling Cliff
68- Current capacity: <metric>
69- Break point: <metric>
70- Headroom: X months at current growth
71 
72## Tech Debt
73- Top item: <description>
74- Cost per week: $X or N eng-hours
75- Blocking date estimate: <date>
76 
77## Team
78- Open reqs: N
79- Median ramp: X months
80- Contribution model: <pairing / squad / area>
81 
82## Build vs Buy
83- 3-year build TCO: $X
84- 3-year buy TCO: $X
85- Strategic fit: <core / context>
86- Decision: BUILD | BUY
87 
88## Reliability
89- SLO defined: yes / no
90- Error budget burn: X% (target < Y%)
91 
92## Security
93- cs-ciso sign-off: ✅ / ❌
94 
95## Verdict
96🟢 SHIP | 🟡 SHARPEN | 🔴 BLOCK
97 
98## Next Steps
99[3 concrete actions]
100```
101 
102## Routing
103 
104- `/cs:ciso-review` — mandatory if data surface changes
105- `/cs:cfo-review` — for build-vs-buy > $100K
106- `/cs:execute` — quarterly plan
107- `/cs:boardroom` — for architecture pivots
108 
109## Related
110 
111- Agent: [`cs-cto-advisor`](../../../agents/c-level/cs-cto-advisor.md)
112- Skill: [`cto-advisor`](../../../c-level-advisor/skills/cto-advisor/SKILL.md)
113- SLO: `../../../engineering/slo-architect/`
114 
115---
116 
117**Version:** 1.0.0
118 
View all files on GitHub →

Details

Updated
Aug 30, 2026
License
MIT
Stars on the repo
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Source
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