cto-advisor

Technical leadership guidance for engineering teams, architecture decisions, and technology strategy. Includes tech debt analyzer, team scaling calculator, engineering metrics frameworks, technology evaluation tools, and ADR templates. 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.

Install with Tessl CLI

npx tessl i github:majiayu000/claude-skill-registry-data --skill cto-advisor

What are skills?

1.73x

Quality

75%

Does it follow best practices?

Impact

99%

1.73x

Average score across 3 eval scenarios

Optimize this skill with Tessl

npx tessl skill review --optimize ./c-level/cto-advisor/SKILL.md

SKILL.md

Review

Evals

Discovery

100%

Based on the skill's description, can an agent find and select it at the right time? Clear, specific descriptions lead to better discovery.

This is an excellent skill description that hits all the marks. It provides specific tools and capabilities, includes comprehensive trigger terms that users would naturally use, explicitly states both what the skill does and when to use it, and carves out a distinct niche around technical leadership and CTO-level concerns.

Dimension	Reasoning	Score
Specificity	Lists multiple specific concrete actions and tools: 'tech debt analyzer, team scaling calculator, engineering metrics frameworks, technology evaluation tools, and ADR templates' along with specific use cases like 'assessing technical debt, scaling engineering teams, evaluating technologies, making architecture decisions.'	3 / 3
Completeness	Clearly answers both what (technical leadership guidance, specific tools like tech debt analyzer, team scaling calculator, etc.) AND when with explicit 'Use when...' clause listing specific scenarios and trigger terms.	3 / 3
Trigger Term Quality	Excellent coverage of natural terms users would say: 'CTO, tech debt, technical debt, team scaling, architecture decisions, technology evaluation, engineering metrics, DORA metrics, technology strategy.' Includes both formal terms and common abbreviations.	3 / 3
Distinctiveness Conflict Risk	Clear niche focused on CTO-level technical leadership with distinct triggers like 'CTO, tech debt, DORA metrics, ADR templates, team scaling calculator.' Unlikely to conflict with general coding or documentation skills.	3 / 3
	Total	12 / 12 Passed

Implementation

50%

Reviews the quality of instructions and guidance provided to agents. Good implementation is clear, handles edge cases, and produces reliable results.

This skill provides a broad CTO advisory framework with useful structure and some actionable elements (scripts, templates, metrics targets). However, it suffers from verbosity—including generic leadership advice, book recommendations, and weekly cadence suggestions that don't add unique value. The content would benefit from aggressive trimming and better separation between the overview and detailed reference materials.

Suggestions

Move detailed sections (Weekly Cadence, Quarterly Planning, Tools & Resources, Communication Templates) to separate reference files and link from a concise overview

Remove generic advice Claude already knows (basic management practices, book recommendations, community links) to reduce token usage

Add validation steps to workflows—e.g., after running tech_debt_analyzer.py, show how to verify results and handle errors

Make templates fully executable with concrete examples rather than placeholder outlines (e.g., show a complete ADR example, not just structure)

Dimension	Reasoning	Score
Conciseness	The skill is comprehensive but includes significant content that could be trimmed or moved to reference files. Lists of books, communities, and generic management advice (weekly cadence, quarterly planning) are verbose and not specific enough to justify their token cost.	2 / 3
Actionability	Provides some concrete commands (python scripts) and references to external files, but much content is high-level guidance rather than executable instructions. Templates are outlines rather than copy-paste ready, and many sections describe what to do rather than how.	2 / 3
Workflow Clarity	Some workflows are well-structured (Crisis Management, Incident Response with time-boxed steps), but most sections lack validation checkpoints. Tech debt and team scaling reference scripts but don't show verification steps or error handling.	2 / 3
Progressive Disclosure	References external files appropriately (references/architecture_decision_records.md, etc.) but the main file is monolithic with extensive inline content that should be split. The Quick Start section properly points to resources, but subsequent sections embed too much detail.	2 / 3
	Total	8 / 12 Passed

Validation

90%

Warnings & errors only

Checks the skill against the spec for correct structure and formatting. All validation checks must pass before discovery and implementation can be scored.

Validation — 10 / 11 Passed

Validation for skill structure

Criteria	Description	Result
metadata_field	'metadata' should map string keys to string values	Warning

	Total	10 / 11 Passed

Reviewed: 3 days ago

Table of Contents

Discovery Implementation Validation

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