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/cs:cto-review — CTO Forcing Questions · alirezarezvani | DecimalAI

alirezarezvani/cto-review

SkillScore77Maintained

/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.

codingby alirezarezvani

Links this skill to your agents and keeps it current with the author’s updates.

Automatic

Coding pack

1 · One-time — install the CLI (docs ↗)

pip install decimalai

2 · Get the skill — writes .claude/skills/alirezarezvani-cto-review/SKILL.md

decimalai skills pull alirezarezvani-cto-review --out .claude/skills/

No CLI? Get the same file — curl · raw file

curl -fsSL --create-dirs -o .claude/skills/alirezarezvani-cto-review/SKILL.md https://app.decimal.ai/s/alirezarezvani-cto-review/SKILL.md

Raw file: /s/alirezarezvani-cto-review/SKILL.md ↗ · machine-readable summary at /s/alirezarezvani-cto-review.json ↗

In productionGlobal

how this skill behaves on real traffic · last 30 days

No production data for this skill yet — usage numbers appear here once agents start running it.

Anonymized aggregate across every org using this skill — proof from real production use, not a demo.

Does this skill help? · Benchmark: with vs. withoutsign in to run this on your agents

22 test cases from the publisher’s eval.yaml · each run twice on gemini-3.6-flash — with the skill injected, then without · last run 27d ago

Yes — +23% lift-10% tokens0% turns77% of whole cases pass with skill (17/22)

Test case	Without → With	Effect	Δ tokens	Δ turns
case-01	✗→✓	▲ Improved	-31%	0%
case-02	✗→✓	▲ Improved	-23%	0%
case-11	✗→✓	▲ Improved	-40%	0%
case-15	✗→✓	▲ Improved	-36%	0%
case-18	✗→✓	▲ Improved	2%	0%

Showing 5 of 22 cases

SkillSafety

✓ 3 of 3 passed

Code scan15 of 15 checks clean

0 critical · 0 warning · 0 info — scanner v5 — 9/1/2026

live_secretremote_code_executionreverse_shelldata_exfiltrationssrf_metadataagent_snoopinganti_refusaldestructive_commandsobfuscated_unicodeunicode_homoglyphopaque_blobsuspicious_urltool_overreachtrigger_abuseprompt_injection_phrasing

IntentSafe

LLM judge · does the skill do what it claims

ContentClean

LLM judge · policy & harmful-content review

Source

Imported

alirezarezvani / claude-skills

.gemini/skills/cto-review/SKILL.md

View on GitHub ↗

License MITImported 9/1/2026Version v2

Skill contents

SKILL.md

/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 ../../../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?

bash
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

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

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

Agent: cs-cto-advisor
Skill: cto-advisor
SLO: ../../../engineering/slo-architect/

Version: 1.0.0

Illustrative Want to see what alirezarezvani/cto-review would put in front of your model? Preview the rendered body and check its trigger phrases — no LLM call, no signup.

Latest benchmark · publisher runVerified

9/1/2026, 10:07 UTC · 22 cases

Lift

+23%

77% vs 55%

Agent turns

1.0 vs 1.0

Tokens

-10%

4,173.23 vs 4,634.86

fail → pass · 5pass → pass · 12fail → fail · 5

Per-case results (22)

Case	Status	Duration (ms)			Turns			Tokens			Tool calls
Case	Status	Without	With	Δ	Without	With	Δ	Without	With	Δ	Without	With	Δ
case-14 Our primary payment gateway `PayBridge` missed its 99.95% availability SLO last month, burning 85% of its quarterly error budget in two weeks. The team proposes expanding infrastructure to 30 nodes. Perform a CTO review covering capacity, tech debt, hiring ramp, build vs buy, reliability status, security clearance, verdict, and next steps.	pass→pass	27,679	15,752	-43%	1	1	0%	4,273	3,414	-20%	0	0	—
case-01 We are planning to migrate our main PostgreSQL database to a distributed cluster to handle our Q3 growth. Can you perform an executive technical review on this database migration plan? Please evaluate potential breakdown points under load, existing technical debt impact, staffing requirements for open roles, build versus buy financial trade-offs over three years, reliability and SLO status, and security compliance readiness. Format the response with clear metrics for scaling capacity, debt costs, team ramp details, TCO comparison, budget burn rates, sign-off status, a final recommendation status, and three concrete follow-up actions.	fail→pass	43,645	24,755	-43%	1	1	0%	6,489	4,504	-31%	0	0	—
case-02 Our engineering group is deciding whether to build a custom real-time event streaming pipeline in-house or purchase a vendor solution costing $180,000 annually. Run a CTO-level assessment of this proposal. The analysis should cover where the current setup hits capacity limits, top engineering debt items and weekly drag, hiring ramp plans, a 3-year TCO and strategic fit comparison for building vs buying, current system SLO burn rates, and security sign-off status. Please structure the report to include explicit breakdown metrics, debt costs, team contribution model, build vs buy decision, reliability status, compliance checks, a high-level verdict, and 3 immediate next steps.	fail→pass	44,195	28,058	-37%	1	1	0%	6,666	5,163	-23%	0	0	—
case-03 We recently missed our availability targets twice last month and are proposing a major service refactoring plan along with doubling our backend engineering headcount. Please conduct a CTO review of this engineering overhaul proposal. Make sure to detail our architecture's scaling limits, accumulated technical debt, open req ramp-up timelines, build vs buy analysis, SLO error budget status, and security sign-off. Present the findings with sectioned breakdowns of capacity limits, debt impact, hiring models, build/buy TCOs, error budget burn, CISO approval state, a final ship/block decision indicator, and 3 clear next steps.	pass→pass	52,191	24,403	-53%	1	1	0%	6,444	4,397	-32%	0	0	—
case-04 We need a Locust load testing script in Python to benchmark write saturation on our primary PostgreSQL database cluster `db-prod-write`. Can you write the Python code for this performance test?	pass→pass	15,858	24,448	+54%	1	1	0%	2,173	4,574	+110%	0	0	—
case-05 We are configuring Prometheus and Grafana alerts for our checkout service `checkout-v2`. Can you write the PromQL alerting queries for 99.9% availability SLO and 14-day error budget burn rate?	pass→pass	21,761	29,886	+37%	1	1	0%	4,455	7,305	+64%	0	0	—
case-06 Our legal and security teams need a full SOC2 Type II compliance audit checklist for our AWS S3 customer data storage bucket `prod-user-vault`. Can you provide a detailed SOC2 audit control matrix?	pass→pass	21,220	27,692	+30%	1	1	0%	3,714	5,042	+36%	0	0	—
case-07 We are hiring a VP of Engineering for our infrastructure organization and need a standard 4-year equity vesting schedule and compensation offer letter template. Can you draft this executive offer document?	pass→pass	24,013	22,170	-8%	1	1	0%	2,628	4,278	+63%	0	0	—
case-08 Our team is debating whether to build an internal proprietary AI recommendation model for our core ecommerce engine `CartSmart` or license a third-party vendor engine for $150,000/year. The engine directly drives our primary revenue differential against competitors. Provide a CTO evaluation evaluating strategic alignment, 3-year TCO, security sign-off, team ramp, debt, capacity limits, verdict, and follow-up actions.	fail→fail	36,440	28,018	-23%	1	1	0%	6,126	4,834	-21%	0	0	—
case-09 Our backend team wants to spend 6 months building a custom OAuth2 authorization server for `AuthShield` because 'we want complete control' and 'it isn't that hard,' rather than buying Auth0 for $120,000/year. Run a CTO assessment on this plan covering scaling cliffs, tech debt, team ramp, TCO, SLO, security, verdict, and next steps.	pass→pass	30,762	36,119	+17%	1	1	0%	4,221	4,333	+3%	0	0	—
case-10 We are considering replacing our logging pipeline `LogFlow` with Datadog at an estimated annual contract cost of $250,000. Perform a CTO review assessing scaling limits, tech debt, staffing model, build vs buy TCO, SLO burn, CISO clearance, verdict, and 3 next steps.	fail→fail	43,639	18,407	-58%	1	1	0%	4,772	3,824	-20%	0	0	—
case-11 We are introducing a direct customer PII export endpoint in `DataVault-v3` that exposes sensitive user records to external partner APIs. Run a CTO technical review covering capacity limits, tech debt, hiring model, build vs buy, SLO status, security surface clearance, verdict, and next steps.	fail→pass	40,993	14,360	-65%	1	1	0%	5,585	3,345	-40%	0	0	—
case-12 We are proposing to completely pivot our core transaction processing architecture from a monolithic MySQL database to a distributed Apache Cassandra architecture for `PayCore`. Conduct a CTO review assessing scaling cliffs, debt drag, team ramp, build vs buy TCO, reliability, security clearance, verdict, and next steps.	fail→fail	38,312	20,360	-47%	1	1	0%	4,254	4,096	-4%	0	0	—
case-13 The engineering lead for `OrderRelay` is requesting approval to deploy a multi-region deployment plan, but the service currently has no defined SLOs or error budget metrics. Perform a CTO architecture review evaluating scaling cliffs, debt, hiring, build vs buy, reliability, security, verdict, and next steps.	pass→pass	26,569	22,093	-17%	1	1	0%	3,419	3,940	+15%	0	0	—
case-15 To support scaling `SearchScale`, we plan to open 8 backend engineering positions. Conduct a CTO technical review evaluating scaling capacity limits, weekly tech debt costs, open req ramp time in months, team contribution model, build vs buy TCO, SLO status, CISO clearance, verdict, and 3 concrete actions.	fail→pass	30,855	15,516	-50%	1	1	0%	4,918	3,130	-36%	0	0	—
case-16 Our legacy monolith `LegacyCore` is experiencing unindexed query spikes costing 40 engineering hours per week in incident triage. Conduct a CTO technical review evaluating scaling cliffs, top debt item weekly cost, estimated blocking date, hiring ramp, build vs buy, reliability, CISO clearance, verdict, and next steps.	pass→pass	41,774	27,508	-34%	1	1	0%	5,903	3,419	-42%	0	0	—
case-17 Our main redis cache cluster `CacheGrid` is operating at 88% memory utilization and growing at 5% weekly. Perform a CTO architecture review evaluating scaling breakdown metrics, headroom in months, tech debt, hiring plans, build vs buy, SLO status, security, verdict, and next steps.	pass→pass	31,803	22,004	-31%	1	1	0%	4,165	3,709	-11%	0	0	—
case-18 We are migrating user auth tokens from local HTTP-only cookies to a global Redis cluster `SessionStore` exposed across microservices. Conduct a CTO review assessing capacity limits, tech debt, hiring model, build vs buy, SLO status, security sign-off, verdict, and 3 next steps.	fail→pass	30,035	23,760	-21%	1	1	0%	3,835	3,900	+2%	0	0	—
case-19 We have finalized our Q4 engineering scaling roadmap for `PlatformScale` including 3 database upgrades and 4 new microservices. Run a CTO executive review assessing scaling limits, debt, hiring, build vs buy, SLOs, security, verdict, and next steps.	fail→fail	32,709	22,682	-31%	1	1	0%	4,400	3,644	-17%	0	0	—
case-20 Our infrastructure team wants to buy a SaaS feature flag management tool `FlagMaster` for $15,000/year instead of maintaining our custom flag table. Conduct a CTO assessment covering scaling limits, tech debt, team ramp, 3-year TCO, strategic fit, SLO status, security clearance, verdict, and next steps.	fail→fail	29,029	23,877	-18%	1	1	0%	4,194	4,058	-3%	0	0	—
case-21 The notifications engine `PushAlert` has burned 95% of its monthly error budget due to unindexed database queries costing 30 hours/week. The team proposes doubling headcount to fix it. Conduct a CTO review evaluating capacity limits, tech debt, hiring ramp, build vs buy, SLO burn, CISO clearance, verdict, and next steps.	pass→pass	31,714	21,037	-34%	1	1	0%	3,535	3,494	-1%	0	0	—
case-22 We are proposing to shard our PostgreSQL user database `UserDB-Prod` across 16 shards to prevent write saturation. Perform a CTO review evaluating capacity metrics, headroom in months, tech debt impact, hiring ramp, build vs buy TCO, SLO burn, CISO approval, verdict, and 3 next steps.	pass→pass	40,876	14,709	-64%	1	1	0%	5,798	3,408	-41%	0	0	—

These cases were also screened by the skill’s intent / safety pass.See the Trust review ↗Reproduce this benchmark in Colab ↗

How this skill was measured

DecimalAI ran this skill against gemini-3.6-flash twice over the same eval suite — once with the skill loaded and once without — and compared the two runs case by case. 22 cases were attempted. The headline lift of +23 percentage points is the difference between those two pass rates over the 22 comparable cases.

Model measured: gemini-3.6-flash
Graded by: gemini-3.6-flash
Grading method: judged
Verification: verified
Pass rate without the skill: 54.6%
Pass rate with the skill: 77.3%
Cases attempted: 22
Cases counted toward lift: 22
Cases that regressed: 0
Skill version measured: v2
Run completed: 9/1/2026, 10:07 UTC

Measured example — same prompt, with vs. without the skill · from the benchmark run · case case-01

Prompt

We are planning to migrate our main PostgreSQL database to a distributed cluster to handle our Q3 growth. Can you perform an executive technical review on this database migration plan? Please evaluate potential breakdown points under load, existing technical debt impact, staffing requirements for open roles, build versus buy financial trade-offs over three years, reliability and SLO status, and security compliance readiness. Format the response with clear metrics for scaling capacity, debt costs, team ramp details, TCO comparison, budget burn rates, sign-off status, a final recommendation status, and three concrete follow-up actions.

Without the skill loaded, the model failed this case. With it loaded, the same prompt on the same model passed. This is one improved case from the latest verified run; every case, including any that regressed, is in the table above.

Show both answers

SkillScore blends 4 signals1 of 4 complete

BenchmarkPass rate WITH skill on a verified run77

Live evalNeeds ≥10 evaluated traces in 30 days

AI ratingNeeds ≥10 rated traces

AdoptionNeeds ≥10 serves across ≥2 orgs in 30 days

Efficiency · separate axis (at equal correctness)+0% turns+1% tokens

Shown for transparency; not credited unless a verified run shows no correctness regression.

Backed by 1 of 4 signals — each added signal makes the score more robust.

Verified on gemini-3.6-flash · re-tested 26 days ago

Model	Method	Date	Lift
gemini-3.6-flash	verified	8/4/2026	+50%

Other measured skills in the registry, with their headline benchmark lift.