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cto-advisor

Technical leadership guidance for engineering teams, architecture decisions, and technology strategy. Use when assessing technical debt, scaling engineering teams, evaluating technologies, making architecture decisions, establishing engineering metrics, or when user mentions CTO, tech debt, technical debt, team scaling, architecture decisions, technology evaluation, engineering metrics, DORA metrics, or technology strategy.

91

1.43x
Quality

88%

Does it follow best practices?

Impact

92%

1.43x

Average score across 6 eval scenarios

SecuritybySnyk

Passed

No known issues

SKILL.md
Quality
Evals
Security

Evaluation results

82%

40%

Technical Debt Assessment for RapidCart Platform

Technical debt assessment and remediation planning

Criteria
Without context
With context

Uses analyzer script

25%

100%

Critical capacity: 40%

0%

0%

High capacity: 25%

0%

100%

Medium capacity: 15%

0%

100%

Low debt: ongoing

0%

40%

Debt score in report

80%

100%

Category breakdown

100%

100%

Prioritized actions

100%

100%

Strategic recommendations

100%

100%

Risk assessment present

60%

100%

100%

31%

Database Selection for Microservices Migration

Technology evaluation and ADR documentation

Criteria
Without context
With context

ADR file path

40%

100%

ADR status field

100%

100%

Context and problem

100%

100%

All 3 options included

100%

100%

Pros and cons per option

100%

100%

Decision rationale

100%

100%

Consequences documented

100%

100%

Technical criteria: 40% weight

0%

100%

Business criteria: 30% weight

100%

100%

Operational criteria: 30% weight

0%

100%

Decision drivers listed

100%

100%

100%

39%

Engineering Scaling Plan for Series B Expansion

Team scaling and engineering metrics planning

Criteria
Without context
With context

Uses scaling calculator

0%

100%

Manager:Engineer ratio 1:8

100%

100%

Seniority ratio 3:4:2

0%

100%

Deployment frequency target

100%

100%

Lead time target

100%

100%

MTTR target

100%

100%

Change failure rate target

100%

100%

Test coverage target

100%

100%

Unplanned work target

0%

100%

On-call incidents target

0%

100%

Quarterly hiring timeline

100%

100%

Scaling risks

100%

100%

79%

20%

Feature Flag Platform Decision

Build vs buy decision and ADR documentation

Criteria
Without context
With context

Scoring matrix present

100%

100%

Solves core problem: 30%

0%

100%

3-year TCO: 25%

100%

100%

Migration risk: 20%

0%

0%

Vendor stability: 15%

16%

0%

Integration effort: 10%

0%

0%

Buy default rule applied

50%

100%

3-year TCO in ADR

100%

100%

Do-nothing or buy alternative

100%

100%

ADR file path

25%

87%

Reversibility in consequences

70%

100%

ADR status field

100%

100%

README links ADR

83%

100%

96%

5%

Engineering Organization Review

CTO advisory output format and proactive alerts

Criteria
Without context
With context

Bottom Line section

80%

90%

What/Why/How to Act sections

80%

80%

Confidence tags used

70%

100%

Evidence-based reasoning

100%

100%

Deployment frequency alert

100%

100%

Tech debt >30% alert

100%

100%

No ADRs alert

100%

100%

Cloud costs alert

100%

100%

Security audit alert

100%

100%

Build time red flag

100%

100%

On-call red flag

100%

100%

Debt ratio formula reference

66%

83%

95%

31%

Post-Incident Review and Engineering Culture Overhaul

Blameless post-mortem, culture, and team structure planning

Criteria
Without context
With context

Blameless framing

100%

100%

48-hour retrospective

0%

100%

Root cause: system not person

100%

100%

Crisis communication role

25%

37%

Innovation budget 10-20%

100%

100%

Manager:IC ratio 5-8

0%

100%

Senior:junior ratio 1:2

0%

100%

Documentation as first-class

100%

100%

Blameless culture recommendation

100%

100%

Action items with owners

100%

100%

Does NOT blame individual

100%

100%

Repository
alirezarezvani/claude-skills
Evaluated
Agent
Claude Code
Model
Claude Sonnet 4.6

Table of Contents

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