Technical leadership guidance for engineering teams, architecture decisions, and technology strategy.

MITAuto-check passedDevelopment

Install Cto Advisor

skills CLI
$ npx skills add Ibrahim-3d/orchestrator-supaconductor --skill cto-advisor -a claude-code

Project install by default; add -g for ~/.claude/skills/.

GitHub CLI
$ gh skill install Ibrahim-3d/orchestrator-supaconductor cto-advisor --agent claude-code

Project scope by default; add --scope user for a personal install. Needs GitHub CLI 2.90.0 or later (public preview).

Manual copy
$ git clone --depth 1 https://github.com/Ibrahim-3d/orchestrator-supaconductor.git skills-src && mkdir -p .claude/skills && cp -r skills-src/skills/cto-advisor .claude/skills/cto-advisor && rm -rf skills-src

Use ~/.claude/skills/ instead of .claude/skills for a personal install. The folder must contain SKILL.md.

Claude Code skills documentation · loads skills from .claude/skills/

Facts

Skill name
cto-advisor
GitHub stars
381
Used in
4 other repos
Token cost
~2.4k tokens
SKILL.md length
791 words
Files
6 (incl. scripts, references)
Skills in repo
27
Repo updated
First seen
Licence
MIT

At a glance

Technical leadership guidance for engineering teams, architecture decisions, and technology strategy.

  • Works in 5 steps: Technology Strategy → Team Leadership → Architecture Governance → …
  • Assessing technical debt
  • SKILL.md covers Keywords, Quick Start, Core Responsibilities and Weekly Cadence, plus 3 more sections
  • Runs Python scripts from its folder; calls python

What it does

Cto Advisor is an agent skill from Ibrahim-3d/orchestrator-supaconductor. 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…

Its SKILL.md is about 2.4k tokens, which your agent loads only when the skill is triggered. The skill folder holds 7 other files, including scripts and reference files (for example `references/architecture_decision_records.md`, `references/engineering_metrics.md` and `references/technology_evaluation_framework.md`).

It sits in Development, covering Technical debt and Architecture decision records. The repository describes itself as: Multi-agent orchestration system for Claude Code with parallel execution, automated quality gates, Board of Directors, and bundled Superpowers skills. The licence is MIT.

When your agent uses it

  • Assessing technical debt
  • Scaling engineering teams
  • Evaluating technologies
  • Making architecture decisions

Example prompts

  • “/cto-advisor”

Requirements

  • Python 3

Workflow steps

5 steps, taken from the step headings in SKILL.md.

  1. Technology Strategy
  2. Team Leadership
  3. Architecture Governance
  4. Vendor Management
  5. Engineering Excellence

What it can do on your machine

Read from SKILL.md and the folder at commit 76c9b10. It shows what the files ask for, not the result of running them.

  • Tool permissions

    Pre-approves nothing: there is no allowed-tools line, so your agent's usual permission prompts apply.

    From allowed-tools in the SKILL.md frontmatter.

  • Runs code

    Ships 2 files in scripts/ (Python), which the agent can run.

    Shell commands in SKILL.md call:

    • python

    From the folder's file list and the shell code blocks in SKILL.md.

  • Network

    No URLs in SKILL.md.

    From URLs in SKILL.md, links to its own repository left out.

  • Credentials

    Names no API keys, tokens, secrets or passwords.

    From names ending in _API_KEY, _TOKEN, _SECRET, _KEY or _PASSWORD in SKILL.md.

Context cost

Cto Advisor loads about 2.4k tokens when it runs, and up to ~9.8k if it reads all its reference files. Until then it costs about 143 tokens; SKILL.md has 791 words of instructions outside code blocks.

Always · name and description, kept in context so the agent knows when to use it
~143
When it runs · the whole SKILL.md, loaded when a task matches
~2.4k
With references · SKILL.md plus every file in references/, read only if the agent opens them
~9.8k

Estimates: characters ÷ 4, the usual rule of thumb; real counts depend on the model's tokenizer. Scripts and assets cost tokens only if the agent reads them.

Safety

Auto-check passed

The automated check found no risky patterns in SKILL.md.

Automated static check — not a guarantee. Review scripts before installing. It scans the text of SKILL.md for risky patterns (piping downloads into a shell, reading credential files, hidden Unicode, destructive commands); the scripts in this folder are not scanned.

SKILL.md

The full file from Ibrahim-3d/orchestrator-supaconductor at commit 76c9b10, republished under its MIT licence (© Ibrahim-3d). 791 words, ~2,350 tokens.

Download SKILL.mdSave it as .claude/skills/cto-advisor/SKILL.md (or your agent's skills folder). This skill also uses 5 other files; get the full folder from GitHub.
name
cto-advisor
description
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.
license
MIT
metadata.version
1.0.0
metadata.author
Alireza Rezvani
metadata.category
c-level
metadata.domain
cto-leadership
metadata.updated
2025-10-20
metadata.python-tools
tech_debt_analyzer.py, team_scaling_calculator.py
metadata.frameworks
DORA-metrics, architecture-decision-records, engineering-metrics
metadata.tech-stack
engineering-management, team-organization

CTO Advisor

Strategic frameworks and tools for technology leadership, team scaling, and engineering excellence.

Keywords

CTO, chief technology officer, technical leadership, tech debt, technical debt, engineering team, team scaling, architecture decisions, technology evaluation, engineering metrics, DORA metrics, ADR, architecture decision records, technology strategy, engineering leadership, engineering organization, team structure, hiring plan, technical strategy, vendor evaluation, technology selection

Quick Start

For Technical Debt Assessment
bash
python scripts/tech_debt_analyzer.py

Analyzes system architecture and provides prioritized debt reduction plan.

For Team Scaling Planning
bash
python scripts/team_scaling_calculator.py

Calculates optimal hiring plan and team structure for growth.

For Architecture Decisions

Review references/architecture_decision_records.md for ADR templates and examples.

For Technology Evaluation

Use framework in references/technology_evaluation_framework.md for vendor selection.

For Engineering Metrics

Implement KPIs from references/engineering_metrics.md for team performance tracking.

Core Responsibilities

1. Technology Strategy
Vision & Roadmap
  • Define 3-5 year technology vision
  • Create quarterly roadmaps
  • Align with business strategy
  • Communicate to stakeholders
Innovation Management
  • Allocate 20% time for innovation
  • Run hackathons quarterly
  • Evaluate emerging technologies
  • Build proof of concepts
Technical Debt Strategy
bash
# Assess current debt
python scripts/tech_debt_analyzer.py

# Allocate capacity
- Critical debt: 40% capacity
- High debt: 25% capacity
- Medium debt: 15% capacity
- Low debt: Ongoing maintenance
2. Team Leadership
Scaling Engineering
bash
# Calculate scaling needs
python scripts/team_scaling_calculator.py

# Key ratios to maintain:
- Manager:Engineer = 1:8
- Senior:Mid:Junior = 3:4:2
- Product:Engineering = 1:10
- QA:Engineering = 1.5:10
Performance Management
  • Set clear OKRs quarterly
  • Conduct 1:1s weekly
  • Review performance quarterly
  • Provide growth opportunities
Culture Building
  • Define engineering values
  • Establish coding standards
  • Create learning programs
  • Foster collaboration
3. Architecture Governance
Decision Making

Use ADR template from references/architecture_decision_records.md:

  1. Document context and problem
  2. List all options considered
  3. Record decision and rationale
  4. Track consequences
Technology Standards
  • Language choices
  • Framework selection
  • Database standards
  • Security requirements
  • API design guidelines
System Design Review
  • Weekly architecture reviews
  • Design documentation standards
  • Prototype requirements
  • Performance criteria
4. Vendor Management
Evaluation Process

Follow framework in references/technology_evaluation_framework.md:

  1. Gather requirements (Week 1)
  2. Market research (Week 1-2)
  3. Deep evaluation (Week 2-4)
  4. Decision and documentation (Week 4)
Vendor Relationships
  • Quarterly business reviews
  • SLA monitoring
  • Cost optimization
  • Strategic partnerships
5. Engineering Excellence
Metrics Implementation

From references/engineering_metrics.md:

DORA Metrics (Deploy to production targets):

  • Deployment Frequency: >1/day
  • Lead Time: <1 day
  • MTTR: <1 hour
  • Change Failure Rate: <15%

Quality Metrics:

  • Test Coverage: >80%
  • Code Review: 100%
  • Technical Debt: <10%

Team Health:

  • Sprint Velocity: ±10% variance
  • Unplanned Work: <20%
  • On-call Incidents: <5/week

Weekly Cadence

Monday
  • Leadership team sync
  • Review metrics dashboard
  • Address escalations
Tuesday
  • Architecture review
  • Technical interviews
  • 1:1s with directs
Wednesday
  • Cross-functional meetings
  • Vendor meetings
  • Strategy work
Thursday
  • Team all-hands (monthly)
  • Sprint reviews (bi-weekly)
  • Technical deep dives
Friday
  • Strategic planning
  • Innovation time
  • Week recap and planning

Quarterly Planning

Q1 Focus: Foundation
  • Annual planning
  • Budget allocation
  • Team goal setting
  • Technology assessment
Q2 Focus: Execution
  • Major initiatives launch
  • Mid-year hiring push
  • Performance reviews
  • Architecture evolution
Q3 Focus: Innovation
  • Hackathon
  • Technology exploration
  • Team development
  • Process optimization
Q4 Focus: Planning
  • Next year strategy
  • Budget planning
  • Promotion cycles
  • Debt reduction sprint

Crisis Management

Incident Response
  1. Immediate (0-15 min):

    • Assess severity
    • Activate incident team
    • Begin communication
  2. Short-term (15-60 min):

    • Implement fixes
    • Update stakeholders
    • Monitor systems
  3. Resolution (1-24 hours):

    • Verify fix
    • Document timeline
    • Customer communication
  4. Post-mortem (48-72 hours):

    • Root cause analysis
    • Action items
    • Process improvements
Show full SKILL.md (314 more words)Show less
Types of Crises
Security Breach
  • Isolate affected systems
  • Engage security team
  • Legal/compliance notification
  • Customer communication plan
Major Outage
  • All-hands response
  • Status page updates
  • Executive briefings
  • Customer outreach
Data Loss
  • Stop writes immediately
  • Assess recovery options
  • Begin restoration
  • Impact analysis

Stakeholder Management

Board/Executive Reporting

Monthly:

  • KPI dashboard
  • Risk register
  • Major initiatives status

Quarterly:

  • Technology strategy update
  • Team growth and health
  • Innovation highlights
  • Budget review
Cross-functional Partners
Product Team
  • Weekly roadmap sync
  • Sprint planning participation
  • Technical feasibility reviews
  • Feature estimation
Sales/Marketing
  • Technical sales support
  • Product capability briefings
  • Customer reference calls
  • Competitive analysis
Finance
  • Budget management
  • Cost optimization
  • Vendor negotiations
  • Capex planning

Strategic Initiatives

Digital Transformation
  1. Assess current state
  2. Define target architecture
  3. Create migration plan
  4. Execute in phases
  5. Measure and adjust
Cloud Migration
  1. Application assessment
  2. Migration strategy (7Rs)
  3. Pilot applications
  4. Full migration
  5. Optimization
Platform Engineering
  1. Define platform vision
  2. Build core services
  3. Create self-service tools
  4. Enable team adoption
  5. Measure efficiency
AI/ML Integration
  1. Identify use cases
  2. Build data infrastructure
  3. Develop models
  4. Deploy and monitor
  5. Scale adoption

Communication Templates

Technology Strategy Presentation
1. Executive Summary (1 slide)
2. Current State Assessment (2 slides)
3. Vision & Strategy (2 slides)
4. Roadmap & Milestones (3 slides)
5. Investment Required (1 slide)
6. Risks & Mitigation (1 slide)
7. Success Metrics (1 slide)
Team All-hands
1. Wins & Recognition (5 min)
2. Metrics Review (5 min)
3. Strategic Updates (10 min)
4. Demo/Deep Dive (15 min)
5. Q&A (10 min)
Board Update Email
Subject: Engineering Update - [Month]

Highlights:
* [Major achievement]
* [Key metric improvement]
* [Strategic progress]

Challenges:
* [Issue and mitigation]

Next Month:
* [Priority 1]
* [Priority 2]

Detailed metrics attached.

Tools & Resources

Essential Tools
  • Architecture: Draw.io, Lucidchart, C4 Model
  • Metrics: DataDog, Grafana, LinearB
  • Planning: Jira, Confluence, Notion
  • Communication: Slack, Zoom, Loom
  • Development: GitHub, GitLab, Bitbucket
Key Resources
  • Books:

    • "The Manager's Path" - Camille Fournier
    • "Accelerate" - Nicole Forsgren
    • "Team Topologies" - Skelton & Pais
  • Frameworks:

    • DORA metrics
    • SPACE framework
    • Team Topologies
  • Communities:

    • CTO Craft
    • Engineering Leadership Slack
    • LeadDev community

Success Indicators

Technical Excellence

  • System uptime >99.9%
  • Deploy multiple times daily
  • Technical debt <10% capacity
  • Security incidents = 0

Team Success

  • Team satisfaction >8/10
  • Attrition <10%
  • Filled positions >90%
  • Diversity improving

Business Impact

  • Features on-time >80%
  • Engineering enables revenue
  • Cost per transaction decreasing
  • Innovation driving growth

Red Flags to Watch

  • Increasing technical debt
  • Rising attrition rate
  • Slowing velocity
  • Growing incidents
  • Team morale declining
  • Budget overruns
  • Vendor dependencies
  • Security vulnerabilities

© Ibrahim-3d, MIT. Rendered from Markdown: HTML in the file is shown as text, images as links, and headings moved down two levels. Raw file

Files

SKILL.md and 5 other files (scripts, references) in skills/cto-advisor of Ibrahim-3d/orchestrator-supaconductor.

  • SKILL.md
  • references/architecture_decision_records.md
  • references/engineering_metrics.md
  • references/technology_evaluation_framework.md
  • scripts/team_scaling_calculator.py
  • scripts/tech_debt_analyzer.py

Open the folder on GitHubat commit 76c9b10

Used in 4 other repositories

We found 5 copies of this SKILL.md (exact, near-identical or edited) in other folders, from 4 other GitHub owners. This page covers the copy in Ibrahim-3d/orchestrator-supaconductor, which our catalogue first saw on October 7, 2026.

Compare with similar skills

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Categories

Questions about Cto Advisor

What does Cto Advisor do?

Technical leadership guidance for engineering teams, architecture decisions, and technology strategy. Cto Advisor is an agent skill from Ibrahim-3d/orchestrator-supaconductor. Technical leadership guidance for engineering teams, architecture decisions, and technology strategy.

When should I use Cto Advisor?

Cto Advisor fits situations like: assessing technical debt; scaling engineering teams; evaluating technologies; making architecture decisions.

How do I install Cto Advisor in Claude Code?

Run `npx skills add Ibrahim-3d/orchestrator-supaconductor --skill cto-advisor -a claude-code`. Or copy the skill folder (skills/cto-advisor in Ibrahim-3d/orchestrator-supaconductor) into .claude/skills/cto-advisor in your project. Claude Code loads it when a task matches its description.

How do I install Cto Advisor in Codex?

Run `npx skills add Ibrahim-3d/orchestrator-supaconductor --skill cto-advisor -a codex`. Or copy the skill folder (skills/cto-advisor in Ibrahim-3d/orchestrator-supaconductor) into .agents/skills/cto-advisor in your project. Codex loads it when a task matches its description.

Can I use Cto Advisor in Cursor, Gemini CLI or GitHub Copilot?

Cursor, Gemini CLI, GitHub Copilot and OpenCode also load SKILL.md folders. With the skills CLI, run `npx skills add Ibrahim-3d/orchestrator-supaconductor --skill cto-advisor -a cursor` (or -a gemini-cli, github-copilot or opencode for the others). To copy it by hand, put the folder in .cursor/skills/cto-advisor, .gemini/skills/cto-advisor, .github/skills/cto-advisor and .opencode/skills/cto-advisor in your project.

What does Cto Advisor need to run?

Going by SKILL.md and its folder, Cto Advisor needs Python for the scripts in its folder and the command-line tools its instructions call (python). Our summary lists: Python 3.

Does Cto Advisor access the network?

SKILL.md contains no URLs. Any network use would come from the scripts or tools the agent runs. This is read from the text; nothing was executed.

Is Cto Advisor safe to install?

Our automated static check of SKILL.md found no risky patterns, such as piping downloads into a shell, reading credential files or hidden Unicode. It is not a guarantee. The check reads SKILL.md only: the scripts in the folder are not scanned, so read them before running anything.

What licence does Cto Advisor use?

Cto Advisor is published under the MIT licence (declared in SKILL.md). It allows redistribution, so the full SKILL.md is shown on this page.

How many tokens does Cto Advisor use?

About 2.4k tokens (SKILL.md is roughly 9.4k characters). Agents keep only the skill's name and description in context until a task matches; then they load SKILL.md in full. Its references folder adds about 7.5k tokens, read only when the agent opens those files.

What are the alternatives to Cto Advisor?

Skills that share tags, products or a category with Cto Advisor: Cto Advisor (alirezarezvani/claude-skills, 28k stars), Architecture Decision (jwynia/agent-skills, 169 stars), Modernization Assessment (EmeaAppGbb/spec2cloud, 100 stars) and PR Design Doc (OpenHands/OpenHands, 90k stars). The comparison table on this page puts their stars, adoption, token cost, safety result and licence side by side.

Who maintains Cto Advisor?

Ibrahim-3d (a GitHub user) maintains it in Ibrahim-3d/orchestrator-supaconductor, which has 381 GitHub stars. The repository holds 27 skills in this directory. The repository was last updated on September 27, 2026.

Source: Ibrahim-3d/orchestrator-supaconductor on GitHub. Facts on this page come from the repository at the commit we read; the author's words are quoted as theirs.