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cto-advisor skill

/plugins/architecture/skills/cto-advisor

This skill provides proactive technical leadership guidance on architecture, teams, and engineering strategy to balance business needs with engineering

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SKILL.md
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---
name: cto-advisor
description: Technical leadership guidance for architecture decisions, team scaling, tech debt, and engineering strategy. Use PROACTIVELY for technology evaluation, engineering metrics, team structure, or strategic technical decisions.
---

# CTO Advisor

Strategic technical leadership advice. Balance business needs with engineering excellence.

## Core Frameworks

- **DORA Metrics**: Deployment frequency, lead time, MTTR, change failure rate
- **Team Topologies**: Stream-aligned, platform, enabling, complicated-subsystem teams
- **ADRs**: Architecture Decision Records for documenting decisions
- **SPACE**: Satisfaction, Performance, Activity, Communication, Efficiency

## Key Ratios

```
Team Structure:
- Manager:Engineer     = 1:8
- Senior:Mid:Junior    = 3:4:2
- Product:Engineering  = 1:10
- QA:Engineering       = 1.5:10

Capacity Allocation:
- Feature work         = 60-70%
- Technical debt       = 15-20%
- Innovation/learning  = 10-15%
- Unplanned work       < 20%
```

## DORA Targets (Elite Performance)

| Metric | Target |
|--------|--------|
| Deployment Frequency | Multiple per day |
| Lead Time for Changes | < 1 day |
| Mean Time to Recovery | < 1 hour |
| Change Failure Rate | < 15% |

## Decision Framework

1. **Context**: What problem are we solving? Why now?
2. **Options**: List alternatives with trade-offs
3. **Decision**: Clear choice with rationale
4. **Consequences**: What we gain, what we accept

## Technology Evaluation

- **Week 1**: Requirements gathering, market research
- **Week 2-3**: Deep evaluation, POC if needed
- **Week 4**: Decision, ADR documentation

Criteria: Cost, scalability, team expertise, vendor stability, integration effort, exit strategy.

## Red Flags

- Technical debt > 30% of capacity
- Attrition > 15% annually
- Unplanned work > 30%
- Deployment frequency decreasing
- MTTR increasing quarter over quarter
- Team satisfaction < 7/10

## Avoid

- Scaling teams before product-market fit
- Rewriting systems without clear business value
- Ignoring tech debt until crisis
- Over-engineering for hypothetical scale
- Hiring without clear team structure plan
- Architecture decisions without documentation

## ADR Template

```markdown
# ADR-XXX: [Decision Title]

## Status: Proposed | Accepted | Deprecated

## Context
[Why is this decision needed?]

## Options
1. [Option A] - Pros/Cons
2. [Option B] - Pros/Cons

## Decision
[What we chose and why]

## Consequences
[Trade-offs we accept]
```

## Tech Debt Prioritization

| Severity | Response | Capacity |
|----------|----------|----------|
| Critical | Immediate fix | 40% |
| High | Next sprint | 25% |
| Medium | Backlog | 15% |
| Low | Opportunistic | - |

Make decisions with data, communicate with clarity, build teams that scale.

Overview

This skill provides pragmatic CTO-level guidance for architecture decisions, team scaling, tech debt management, and engineering strategy. It balances business priorities with measurable engineering outcomes and offers frameworks, ratios, and templates to drive consistent decisions. Use it proactively to evaluate technology, optimize team structure, and set measurable goals.

How this skill works

The skill inspects current engineering health using proven frameworks like DORA and SPACE, then maps findings to concrete recommendations: team ratios, capacity allocation, and decision records. It guides technology evaluations with a four-week cadence (requirements, deep evaluation/POC, decision, ADR) and provides a decision framework that records context, options, choice, and consequences. It highlights red flags and offers prioritization guidance for tech debt and operational risk.

When to use it

  • Choosing or replacing core technologies or vendors
  • Restructuring teams for scale or faster delivery
  • Prioritizing technical debt versus new features
  • Improving delivery metrics (deployment frequency, lead time, MTTR)
  • Documenting major architecture decisions with ADRs

Best practices

  • Measure before you change: collect DORA/SPACE metrics and team feedback
  • Allocate capacity: 60–70% features, 15–20% tech debt, 10–15% learning
  • Use ADRs for durability: record context, options, decision, consequences
  • Avoid premature scaling or full rewrites without clear business value
  • Treat red flags (attrition, rising MTTR, decreasing deploys) as high priority

Example use cases

  • Run a four-week technology evaluation for a new observability stack with a POC in week 2–3
  • Design a hiring plan to reach a 1:8 manager:engineer ratio while keeping Senior:Mid:Junior at 3:4:2
  • Prioritize backlog items by mapping tech debt severity to sprint capacity (Critical→40%)
  • Create an ADR for migrating to microservices, documenting trade-offs and rollback strategy
  • Improve delivery performance by targeting elite DORA thresholds and tracking progress

FAQ

What DORA targets should I aim for?

Aim for multiple deployments per day, lead time < 1 day, MTTR < 1 hour, and change failure rate < 15% to reach elite performance.

How much capacity should be dedicated to technical debt?

Plan 15–20% of team capacity for technical debt, increasing to higher percentages for critical or legacy-system remediation.