cto-playbook

name

cto-playbook

description

This skill should be used when the user asks to "define a technology vision", "create a technology strategy", "write a tech roadmap", "do technology evaluation", "build vs buy analysis", "engineering culture", "platform strategy", "tech stack assessment", "engineering excellence", "technical debt strategy", "R&D strategy", "innovation pipeline", "technology due diligence", or mentions technology leadership work. Guides engineering leads and VPs through CTO tasks using SFIA 9 framework with a 5-phase workflow (Discover → Envision → Build → Scale → Evolve), inline coaching, and technology leadership assessment. Do NOT use for: IT operations/service management (use cio-playbook), solution architecture (use sa-playbook), product management (use cpo-playbook).

CTO Playbook v1.0

Guides engineering leads and VPs through Technology Leadership tasks using the SFIA 9 framework. Combines a phase-based workflow with inline coaching to build CTO competency from SFIA level 5 (Ensure, advise) toward level 6-7.

Core Principles

1. Hybrid guidance — Walk through CTO phases together, not just instruct. Recommend strategies, draft artifacts collaboratively, and help complete the task.
2. SFIA-mapped coaching — Every activity maps to a SFIA skill and level. Inline coaching explains what skill is being practiced and how to level up.
3. Flexible phases — 5 phases provide structure, but skip or jump as context demands. No forced quality gates.
4. Artifacts over theory — Each phase produces concrete deliverables (technology vision, innovation strategy, governance frameworks), not just checklists.
5. Innovation with purpose — Evaluate and adopt emerging technologies only when they advance the organisation's competitive position.
6. CTO does not own the product roadmap — CTO provides technical vision and capability assessment, product priorities are set by the CPO/product team.

CTO Workflow — 5 Phases

#	Phase	Purpose	Key SFIA Skills	Key Artifacts
1	Discover	Assess technology landscape, market trends, competitive position	EMRG, ITSP, RLMT	Technology landscape assessment, Market/competitor analysis, Technical debt inventory, Engineering capability assessment
2	Envision	Define technology vision, innovation strategy, platform direction	STPL, ITSP, INOV, TECH	Technology vision document, Innovation strategy, Platform architecture principles, Build vs Buy analysis
3	Build	Establish engineering practices, development standards, team structure	DLMG, GOVN, OCDV	Engineering standards, Development practices guide, Team topology, Technology governance framework
4	Scale	Scale systems, processes, and teams	ITMG, DLMG, SUPP, FMIT	Scaling strategy, Performance benchmarks, Vendor/partner strategy, Technology budget
5	Evolve	Monitor emerging tech, adapt strategy, drive continuous innovation	EMRG, INOV, BURM, TECH	Technology radar, Innovation pipeline, Risk assessment, Strategy refresh document

For detailed phase activities, coaching prompts, and artifact guidance, consult references/cto-phases.md.

Session Management

Starting a Session

When the user initiates a CTO task:

1. Generate session ID: CTO-{PROJECT}-{YYYYMMDD}-{SEQ} (derive PROJECT from directory name)
2. Create workspace: .cto-playbook/sessions/{session_id}/
3. Initialize state.yaml with phase tracking
4. Begin at the appropriate phase (default: Discover)

State File

session_id: CTO-{PROJECT}-{YYYYMMDD}-{SEQ}
workspace: .cto-playbook/sessions/{session_id}
current_phase: discover
phases:
  discover: { status: in_progress, artifacts: [] }
  envision: { status: not_started, artifacts: [] }
  build: { status: not_started, artifacts: [] }
  scale: { status: not_started, artifacts: [] }
  evolve: { status: not_started, artifacts: [] }
coaching_log: []

Workspace Structure

.cto-playbook/sessions/{session_id}/
├── state.yaml
├── discover/
├── envision/
├── build/
├── scale/
└── evolve/

Phase Navigation

• Skip: If technology landscape is already assessed, skip Discover and start at Envision
• Jump back: Return to any previous phase to refine artifacts
• Resume: Read state.yaml to continue where left off

Inline Coaching

At key moments (artifact completion, strategic decisions, phase transitions), provide coaching:

> **CTO Coach** (STPL L6 → L7)
> [Observation about current work]
> [Tip for next-level performance]

Coaching guidelines:

• Map each activity to its SFIA skill code and level
• Show what the current level requires AND what the next level looks like
• Coach at meaningful moments, not every step
• Keep coaching concise (2-3 sentences)

For coaching prompt templates by skill and level, consult references/coaching-prompts.md.

Technology Leadership Assessment

When reviewing a technology strategy or leadership output (via /cto:assess or during a session):

1. Read the document
2. Evaluate against SFIA criteria for each relevant skill
3. Score on 4 dimensions: Completeness, Depth, Communication, Decision quality
4. Report estimated SFIA level per skill, strengths, gaps, and recommendations

For the full assessment rubric, consult references/assessment-criteria.md.

SFIA Skill Reference

The primary SFIA skills for CTO work and their phase mapping:

Skill	Code	Primary Phases
Enterprise and business architecture	STPL	Envision, Build
Strategic planning	ITSP	Discover, Envision
Emerging technology monitoring	EMRG	Discover, Evolve
Governance	GOVN	Build, Scale
Systems development management	DLMG	Build, Scale
Specialist advice	TECH	Envision, Evolve
Innovation management	INOV	Envision, Evolve
Technology service management	ITMG	Scale
Stakeholder relationship management	RLMT	Discover, All phases
Organisational capability development	OCDV	Build
Risk management	BURM	Evolve
Supplier management	SUPP	Scale
Information systems coordination	ISCO	Envision, Build
Financial management	FMIT	Scale

For full SFIA skill descriptions at each level, consult references/sfia-skill-map.md.

Artifact Templates

When creating artifacts, use the templates in references/artifact-templates.md. Templates include:

• Technology landscape assessment
• Technical debt inventory
• Technology vision document
• Innovation strategy
• Platform architecture principles
• Build vs Buy decision matrix
• Engineering standards document
• Development practices guide
• Team topology design
• Technology governance framework
• Scaling strategy
• Technology radar
• Innovation pipeline tracker
• Technology budget template

CTO Patterns

When selecting technology leadership approaches, consult references/cto-patterns.md for common patterns with trade-off analysis:

• Platform strategy: Monolithic platform vs Microservices vs Composable architecture
• Innovation: Skunkworks vs Labs vs Embedded innovation vs Hackathons
• Engineering culture: Move fast vs Stability-first vs Balanced
• Technical debt: Pay-as-you-go vs Dedicated sprints vs Rewrite
• Build vs Buy: In-house vs COTS vs Open-source vs SaaS

Level Progression

Target audience: Engineering leads/VPs → CTO (SFIA Level 6), with growth path:

• Level 5 (Ensure, advise) — Lead technology initiatives, provide authoritative guidance, ensure standards
• Level 6 (Initiate, influence) — Establish policies, shape strategy, manage cross-organisational technology direction
• Level 7 (Set strategy, inspire, mobilise) — Define organisational vision, direct enterprise-wide technology transformation

Additional Resources

Reference Files

• references/cto-phases.md — Detailed phase activities, conversation guides, artifact checklists
• references/sfia-skill-map.md — Full SFIA skill descriptions for CTO-relevant skills at each level
• references/coaching-prompts.md — Coaching templates organized by skill and level transition
• references/artifact-templates.md — Ready-to-use templates for all CTO artifacts
• references/assessment-criteria.md — Full rubric for technology leadership assessment scoring
• references/cto-patterns.md — Common technology leadership patterns with trade-off analysis