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/cto-advisor

CTO-level advisory - build vs buy decisions, tech debt quantification, team scaling, ADRs, technology evaluation (RICE), budget planning, TCO, vendor management, DORA/SPACE metrics

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vibecosystem
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$ npx -y skills add vibeeval/vibecosystem --skill cto-advisor --agent claude-code

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  • Fires itselfAuto-invocation. Claude auto-loads it when your prompt matches the work.Auto-invocation is when the right skill fires by itself at the right moment, driven by a FLOW.md router and a hook, instead of you invoking it by name. It is the difference between a skill being installed and a skill actually getting used.Read the full definition →
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  • Slash command/cto-advisor

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CTO-level advisory - build vs buy decisions, tech debt quantification, team scaling, ADRs, technology evaluation (RICE), budget planning, TCO, vendor management, DORA/SPACE metrics

SKILL.md

cto-advisor.SKILL.md
name: cto-advisor
description: CTO-level advisory - build vs buy decisions, tech debt quantification, team scaling, ADRs, technology evaluation (RICE), budget planning, TCO, vendor management, DORA/SPACE metrics

CTO Advisor

Build vs Buy Decision Framework

Decision Matrix

## Build vs Buy Analysis: [Feature/System Name]

### Scoring (1-5 each)

| Factor | Build | Buy | Weight |
|--------|-------|-----|--------|
| Core competency alignment | [1-5] | [1-5] | 3x |
| Time to market | [1-5] | [1-5] | 2x |
| Total cost (3 year) | [1-5] | [1-5] | 2x |
| Customization needs | [1-5] | [1-5] | 2x |
| Maintenance burden | [1-5] | [1-5] | 1x |
| Data control | [1-5] | [1-5] | 1x |
| Integration complexity | [1-5] | [1-5] | 1x |
| Vendor risk | [1-5] | [1-5] | 1x |
| **Weighted Total** | [sum] | [sum] | |

### Decision: BUILD / BUY / HYBRID

Decision Rules

| Condition | Recommendation | |-----------|---------------| | Core differentiator | BUILD (competitive advantage) | | Commodity capability | BUY (focus on core) | | Strict compliance / data sovereignty | BUILD (control) | | Team has no domain expertise | BUY (faster, less risk) | | Vendor lock-in risk > 7/10 | BUILD or multi-vendor | | Time to market < 3 months | BUY (speed) | | Budget constrained, long-term | BUILD (lower TCO) |

Build vs Buy Anti-Patterns

| Anti-Pattern | Neden Yanlis | Dogru Yol | |-------------|-------------|-----------| | "Not invented here" | Wasted engineering time | Evaluate vendors objectively | | "We'll build it in 2 weeks" | Always takes 5x longer | Realistic estimation with buffer | | Buying everything | No differentiation | Build core, buy commodity | | Ignoring maintenance cost | Build looks cheaper initially | Include 3-5 year maintenance TCO | | No exit strategy from vendor | Lock-in trap | Evaluate migration cost upfront |

Tech Debt Quantification & Prioritization

Tech Debt Classification

| Type | Description | Impact | Example | |------|-------------|--------|---------| | **Code debt** | Poor code quality | Developer velocity | No types, huge functions, no tests | | **Architecture debt** | Wrong architectural decisions | Scalability | Monolith that should be microservice | | **Test debt** | Insufficient test coverage | Reliability | No integration tests, flaky tests | | **Dependency debt** | Outdated dependencies | Security | 3 major versions behind, CVEs | | **Documentation debt** | Missing/outdated docs | Onboarding | No API docs, stale README | | **Infrastructure debt** | Manual processes, legacy infra | Reliability | No CI/CD, manual deployments | | **Design debt** | UX inconsistencies | User experience | 5 different button styles |

Tech Debt Scorecard

## Tech Debt Assessment: [Project Name]

| Area | Score (1-10) | Trend | Priority |
|------|-------------|-------|----------|
| Code quality | [X] | [up/down/flat] | [H/M/L] |
| Test coverage | [X%] | [up/down/flat] | [H/M/L] |
| Dependency freshness | [X] | [up/down/flat] | [H/M/L] |
| Build/deploy time | [X min] | [up/down/flat] | [H/M/L] |
| Documentation | [X] | [up/down/flat] | [H/M/L] |
| Security posture | [X] | [up/down/flat] | [H/M/L] |

### Cost of Delay
[If we don't address debt area X, what happens in 6 months?]

### Investment Request
| Initiative | Effort | Impact | ROI Period |
|-----------|--------|--------|------------|
| [debt 1] | [weeks] | [description] | [months] |
| [debt 2] | [weeks] | [description] | [months] |

Prioritization Formula

Priority Score = (Impact * Urgency * Spread) / Effort

Impact (1-5):    How much does it slow the team?
Urgency (1-5):   How quickly will it get worse?
Spread (1-5):    How many areas does it affect?
Effort (1-5):    How hard is it to fix? (inverse: 1=hard, 5=easy)

Tech Debt Budget Rule

RULE: 20% of sprint capacity reserved for tech debt reduction

Sprint capacity: 10 story points
├── 8 points: Feature work
└── 2 points: Tech debt reduction (ZORUNLU, negotiable degil)

Team Scaling Strategies

Hiring Framework

## Hiring Plan: [Quarter/Year]

### Current State
| Role | Headcount | Capacity | Gap |
|------|-----------|----------|-----|
| Backend | [X] | [Y features/quarter] | [shortfall] |
| Frontend | [X] | [Y features/quarter] | [shortfall] |
| DevOps | [X] | [Y deploys/week] | [shortfall] |
| QA | [X] | [Y tests/sprint] | [shortfall] |

### Ratios
- Engineer : Manager = 6-8 : 1
- Senior : Mid : Junior = 2 : 3 : 1
- Backend : Frontend = project-dependent
- Engineer : QA = 4-6 : 1

### Onboarding Milestones
| Day | Milestone |
|-----|-----------|
| 1 | Dev environment running, first commit |
| 7 | First PR merged |
| 14 | First feature shipped to staging |
| 30 | Independent task completion |
| 60 | Contributing to architecture discussions |
| 90 | Fully productive, mentoring others |

Team Topology Patterns

| Pattern | When to Use | Size | |---------|-------------|------| | Stream-aligned | Product features | 5-8 people | | Platform | Internal tooling, infrastructure | 3-5 people | | Enabling | Coach other teams, remove blockers | 2-3 people | | Complicated subsystem | Deep expertise (ML, security) | 2-4 people |

Architecture Decision Records (ADR)

ADR Template

# ADR-[number]: [decision title]

## Status
[Proposed | Accepted | Deprecated | Superseded by ADR-XXX]

## Context
[What is the issue? What forces are at play?]
[Include constraints, requirements, team capabilities]

## Decision
[What is the change that we're proposing and/or doing?]

## Alternatives Considered
### Option A: [name]
- Pros: [list]
- Cons: [list]

### Option B: [name]
- Pros: [list]
- Cons: [list]

## Consequences
### Positive
- [benefit 1]
- [benefit 2]

### Negative
- [tradeoff 1]
- [tradeoff 2]
Read more
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