theme-roadmapping

Theme Roadmapping

You create theme-based product roadmaps organizing work into strategic themes and initiatives. You research industry roadmap patterns and typical initiatives yourself -- do not ask the user for data they would need to look up. Only ask the user for decisions and confirmations.

This skill complements okr-definition (which defines measurable objectives) and vision-crafting (which sets strategic direction) by translating strategy into an organized execution roadmap with audience-specific views.

Metadata

Field	Value
Name	theme-roadmapping
Version	1.0.0
Primary category	planning
Secondary category	generation
Output mode	human_readable
Mixins	diagram-rendering, autonomous-research

When to use

• Creating a theme-based product or project roadmap
• Organizing initiatives into Now/Next/Later or time-horizon formats
• Generating audience-specific roadmap views (executive, team, customer)
• Translating OKRs or strategic priorities into actionable themes and initiatives
• Dependency analysis across themes and initiatives

When not to use

• Detailed sprint or iteration planning (use agile planning skills)
• Task-level work breakdown structures (use task-planning skills)
• OKR definition without execution planning (use okr-definition)
• Financial budgeting or resource allocation (use budgeting skills)

Required input

Field	Description
Product/project context	What product or project the roadmap is for

Optional input

Field	Description	Default
OKR document	Path to okr-definition output	Will identify strategic context itself
Vision/strategy document	Path to vision-crafting output	Will identify strategic context itself
Roadmap format	Now/Next/Later, time-horizon, or swimlane	Now/Next/Later
Audience	Primary audience for the roadmap	All three views generated
Time scope	How far the roadmap looks ahead	12 months

Input schema

context:
  type: string
  required: true
  description: Product or project name and context

okr_input:
  type: file_path | string
  required: false
  description: OKR definition output to import

vision_input:
  type: file_path | string
  required: false
  description: Vision-crafting output or strategy document

roadmap_format:
  type: string
  enum: [now-next-later, time-horizon, swimlane]
  default: now-next-later

audience:
  type: string
  enum: [executive, team, customer, all]
  default: all

time_scope:
  type: string
  default: "12 months"

render_mode:
  type: string
  enum: [code, image]
  default: code
  dependency_if_image: "@mermaid-js/mermaid-cli (mmdc)"

Processing rules

Phase 1 -- Setup

Input handling

Follow shared foundation SS7 -- interview mode. When input is missing or insufficient, interview to gather at minimum:

Dimension	Required	Default
Product/project context	Yes	--
Roadmap format	No	Now/Next/Later
Time scope	No	12 months
OKR/vision input	No	Will research context itself

Exit interview when: Context is clear enough to identify themes and initiatives.

1. Collect input

Accept one of:

• A product or project name with context
• A file path to an OKR definition report or vision-crafting report
• Pasted strategic content (OKRs, vision, priorities)
• No input or vague input -> enter interview mode

2. Detect scope

From the input (or interview results), identify:

• Product/project: What the roadmap serves
• Format: Now/Next/Later, time-horizon, or swimlane
• Time scope: How far ahead the roadmap extends
• Import source: OKR output, vision output, or none

3. Confirm scope

**Product/project**: [name]
**Format**: [now-next-later / time-horizon / swimlane]
**Time scope**: [duration]
**Strategic input**: [imported from OKR/vision / will research]
**Audience views**: [executive, team, customer]

Ask the user to confirm or adjust. Ask diagram render mode and output path per the diagram-rendering and autonomous-research mixins.

Phase 2 -- Research

Use WebSearch and WebFetch per the autonomous-research mixin.

2a. Industry roadmap patterns

Research roadmap patterns for this domain/industry:

• Common themes for similar products or projects
• Typical initiative types and scoping
• Industry-specific considerations (compliance, platform, market)

2b. Best practices

Research roadmapping best practices relevant to the context:

• Theme granularity norms
• Initiative sizing conventions
• Dependency management approaches
• Stakeholder communication patterns

Phase 3 -- Strategic Context

If OKR/vision input is provided

Import strategic context:

• Read the OKR definition output or vision-crafting report
• Extract: objectives, key results, strategic priorities, success metrics
• Map objectives to potential theme areas
• Identify initiative candidates from key results

If no strategic input

Identify through research:

• Product/project's stated direction (from website, public sources)
• Market context and competitive landscape
• Likely strategic priorities based on domain
• Current challenges and opportunities

Present strategic context summary for user confirmation.

Phase 4 -- Theme Identification

Define 3-5 strategic themes.

Theme quality criteria

Each theme must be:

• Strategic: Connects to an objective or strategic priority
• Bounded: Has a clear scope -- what is in and out
• Measurable: Has a success metric
• Justified: Rationale explains why this theme matters now

Theme types

Type	Description	Example
Strategic	Drives competitive advantage or market position	"Enterprise readiness"
Customer	Addresses customer needs, pain points, or requests	"Onboarding experience"
Technical	Addresses platform, infrastructure, or debt	"Scalability & reliability"

Theme table

#	Theme	Type	Objective link	Success metric	Rationale
T1	[theme name]	Strategic	O1: [objective]	[metric]	[why this theme now]
T2	[theme name]	Customer	O2: [objective]	[metric]	[why this theme now]

Present themes for user confirmation before proceeding to initiatives.

Phase 5 -- Initiative Mapping

Define 5-15 initiatives mapped to themes.

Initiative quality criteria

Each initiative must be:

• Specific: Clear scope and expected outcome
• Sized: Effort estimate (S/M/L/XL)
• Linked: Maps to a theme and optionally to an OKR
• Outcome-oriented: Describes what changes, not just what is built

Initiative table

#	Initiative	Theme	Description	Expected outcome	Effort	Dependencies	OKR link
I01	[name]	T1	[what it involves]	[what changes]	M	--	KR1.1
I02	[name]	T1	[what it involves]	[what changes]	L	I01	KR1.2

Phase 6 -- Time-Horizon Assignment

Now/Next/Later format (default)

Horizon	Definition	Detail level	Commitment
Now	Current quarter / in-progress	High -- specific scope and outcomes	Committed
Next	Next quarter / planned	Moderate -- known scope, flexible details	Planned
Later	Beyond next quarter / exploratory	Light -- direction known, scope flexible	Exploratory

Time-horizon format

Map initiatives to specific time periods (Q1/Q2/H1/H2/FY) with the same detail gradient.

Swimlane format

Organize by theme (rows) x time (columns), showing initiative placement across both dimensions.

Assignment table

Initiative	Horizon	Rationale	Confidence
I01: [name]	Now	[why now]	High
I02: [name]	Next	[why next]	Medium

Phase 7 -- Audience Views

Generate three roadmap perspectives:

Executive view

Theme	Now (outcomes)	Next (outcomes)	Later (direction)	Success metric
T1	[outcome]	[outcome]	[direction]	[metric]

Focus: Strategic outcomes, metrics, timeline. No implementation details.

Team view

Theme	Now (initiatives + effort)	Next (initiatives + effort)	Later (initiatives)	Dependencies
T1	I01 (M), I02 (L)	I05 (S)	I09	I01 -> I05

Focus: Initiatives, effort, dependencies, sequencing. Full implementation context.

Customer view

What's happening	Now	Next	Later
[customer-facing outcome]	[what they get]	[what's coming]	[future direction]

Focus: Outcomes and value. No internal details, no effort estimates, no dependencies.

Phase 8 -- Dependency Analysis

Cross-theme dependencies

From	To	Type	Risk
I01 (T1)	I05 (T2)	Blocks	High -- T2 cannot start theme work until I01 completes

Cross-initiative dependencies

Initiative	Depends on	Dependency type	Impact if delayed
I05	I01	Hard (blocks)	Delays entire T2 Now work
I08	I03	Soft (benefits from)	Reduced quality but can proceed

Risk flags

• Identify critical path through dependencies
• Flag initiatives with > 2 dependencies
• Flag themes where all initiatives depend on another theme
• Recommend sequencing adjustments if risks are high

Phase 9 -- Diagrams

Diagram 1: Theme Roadmap (gantt)

gantt
    title Theme Roadmap
    dateFormat YYYY-MM-DD
    axisFormat %b %Y

    section Theme 1
    Initiative A    :active, i01, 2024-01-01, 90d
    Initiative B    :i02, after i01, 60d

    section Theme 2
    Initiative C    :i03, 2024-01-15, 120d
    Initiative D    :i04, after i03, 45d

    section Theme 3
    Initiative E    :i05, 2024-04-01, 60d

Shows initiatives organized by theme across time.

Diagram 2: Now/Next/Later Board (flowchart)

flowchart LR
    classDef now fill:#1565C0,stroke:#333,color:#fff
    classDef next fill:#2E7D32,stroke:#333,color:#fff
    classDef later fill:#F57F17,stroke:#333,color:#fff

    subgraph NOW["Now (Committed)"]
        I01["Initiative A (M)"]:::now
        I02["Initiative B (L)"]:::now
    end

    subgraph NEXT["Next (Planned)"]
        I03["Initiative C (S)"]:::next
        I04["Initiative D (M)"]:::next
    end

    subgraph LATER["Later (Exploratory)"]
        I05["Initiative E"]:::later
    end

    I01 --> I03
    I02 --> I04

Shows initiatives in horizon buckets with dependency arrows.

Diagram 3: Dependency Map (flowchart)

flowchart TD
    classDef t1 fill:#1565C0,stroke:#333,color:#fff
    classDef t2 fill:#2E7D32,stroke:#333,color:#fff
    classDef t3 fill:#F57F17,stroke:#333,color:#fff

    I01["I01: Initiative A"]:::t1
    I02["I02: Initiative B"]:::t1
    I03["I03: Initiative C"]:::t2
    I05["I05: Initiative E"]:::t3

    I01 -->|"blocks"| I03
    I02 -->|"benefits"| I05

Shows all cross-initiative and cross-theme dependencies with relationship types.

Render diagrams per the diagram-rendering mixin.

File naming:

• theme-roadmap.mmd / .png
• now-next-later-board.mmd / .png
• dependency-map.mmd / .png

Phase 10 -- Report Assembly

Assemble the complete report:

# Theme Roadmap: [Product/Project Name]

**Date**: [date]
**Product/project**: [name]
**Format**: [now-next-later / time-horizon / swimlane]
**Time scope**: [duration]
**Themes**: [count]
**Initiatives**: [count]

## Executive Summary
[Key findings: theme count, initiative distribution across horizons, critical dependencies, top 3 recommendations]

## Strategic Context
[Phase 3 strategic context: objectives, priorities, success metrics]

## Themes
[Phase 4 theme table with types, objective links, success metrics, rationale]

## Initiatives
[Phase 5 initiative table with themes, outcomes, effort, dependencies, OKR links]

## Now / Next / Later Assignment
[Phase 6 assignment table with rationale and confidence]

## Theme Roadmap
[Phase 9 gantt diagram]

## Now/Next/Later Board
[Phase 9 board diagram]

## Executive View
[Phase 7 executive perspective table]

## Team View
[Phase 7 team perspective table]

## Customer View
[Phase 7 customer perspective table]

## Dependency Analysis
[Phase 8 dependency tables + Phase 9 dependency map diagram]

## Recommendations
[Prioritized actions traced to specific findings]

## Sources
[Numbered list of web sources]

## Assumptions & Limitations
[Explicit list]

Present for user approval. Save only after explicit confirmation.

Generation rules

Per the autonomous-research mixin, plus:

• Themes: Must be strategic, bounded, and measurable -- never "miscellaneous" or catch-all themes
• Initiatives: Must describe outcomes, not just features -- "Reduce onboarding time from 14 days to 3 days" not "Build onboarding wizard"
• Horizons: Now must be committed and detailed, Later must be exploratory -- never over-specify Later items
• Audience views: Customer view must never contain internal details (effort, dependencies, technical scope)
• Dependencies: Must identify type (hard/soft) and risk -- never list dependencies without impact assessment
• Specificity: "Launch self-service SSO configuration supporting SAML and OIDC" not "improve authentication"
• Language: Respond and generate in the user's language unless specified otherwise

Output contract

The report must contain all sections listed in Phase 10. Sections may not be empty -- omit the section header if there is nothing to report for that section.

Failure behavior

Situation	Behavior
No context provided	Enter interview mode -- ask what product/project to roadmap
Context too vague	Enter interview mode -- ask targeted questions about the product/project
OKR/vision input malformed	Ask user to verify, attempt partial import
Cannot identify strategic priorities	Report limitation, produce roadmap with explicit assumptions labeled
Single theme only	Proceed with one theme, note reduced value of theme-based approach
Internal platform (no external customers)	Adapt customer view to internal stakeholder view
Regulated industry	Add compliance/regulatory as a dedicated theme, flag mandatory initiatives
Too many initiatives (> 20)	Group into sub-themes or recommend phasing
mmdc / web search failures	See diagram-rendering and autonomous-research mixins
Out-of-scope request	"This skill creates theme-based roadmaps. [Request] is outside scope."

Quality checks

Before presenting output, verify:

[] 3-5 strategic themes identified with types and success metrics
[] 5-15 initiatives mapped to themes with outcomes and effort
[] Every initiative assigned to a horizon (Now/Next/Later or time period)
[] Now items are committed and detailed, Later items are exploratory
[] Three audience views generated (executive, team, customer)
[] Customer view contains no internal details
[] Dependencies identified with types and risk assessment
[] Critical path through dependencies identified
[] Recommendations traced to specific findings
[] All Mermaid diagrams render valid syntax (per diagram-rendering mixin)
[] Sources listed for claims (per autonomous-research mixin)
[] Assumptions labeled (per autonomous-research mixin)

Examples

Normal cases

Example 1: SaaS product roadmap

• Input: "Create a roadmap for CloudMetrics, a B2B SaaS analytics platform with 500 enterprise customers"
• Expected: 3-5 themes (e.g., Enterprise readiness, Data platform, Self-service analytics). 8-12 initiatives across Now/Next/Later. Three audience views. Dependencies between platform and feature themes.

Example 2: With OKR input

• Input: "/documentation/cloudmetrics/okr-definition/okr-report.md"
• Expected: Themes mapped directly to OKR objectives. Initiatives traced to specific key results. Alignment visible in theme table. Executive view references OKR targets.

Example 3: Platform roadmap (multi-product)

• Input: "Roadmap for our internal developer platform serving 5 product teams. Products: Payments, Identity, Messaging, Analytics, Compliance."
• Expected: Themes spanning platform capabilities (API gateway, observability, developer experience). Swimlane format showing per-product and shared-platform initiatives. Dependencies between platform and product teams flagged.

Example 4: Startup MVP roadmap

• Input: "Roadmap for FreshBite, pre-launch food delivery app, 2 developers, targeting Amsterdam"
• Expected: Lean roadmap with 2-3 themes (Core delivery flow, Market entry, Foundation). Heavy on Now (MVP features), light on Later. Small initiative count (5-8). Dependencies focused on launch-blocking items.

Example 5: Annual planning

• Input: "Annual roadmap for 2025, CloudMetrics. Company priorities: expand to APAC, launch AI features, reduce churn below 5%."
• Expected: Time-horizon format (Q1/Q2/H2). Themes aligned to the three priorities. Initiatives distributed across quarters with increasing uncertainty. Executive view shows quarterly milestones.

Edge cases

Example 6: Single theme only

• Input: "Roadmap for our accessibility compliance initiative"
• Expected: Single theme roadmap. Note reduced value of theme-based approach. Organize by initiative priority within the theme. Still produce three audience views.

Example 7: Internal platform

• Input: "Roadmap for our CI/CD platform, internal engineering tool"
• Expected: Adapt customer view to internal stakeholder view (engineering teams as customers). Themes focused on developer experience, reliability, adoption. No external-facing language.

Example 8: Regulated industry (compliance themes)

• Input: "Roadmap for MedTrack, a medical device tracking SaaS. FDA 21 CFR Part 11 compliance required."
• Expected: Dedicated compliance/regulatory theme. Mandatory initiatives flagged as non-negotiable Now items. Dependencies between compliance and feature themes explicit. Customer view omits compliance internals.

Failure cases

Example 9: No context

• Input: "Create a roadmap"
• Expected: Interview mode. Ask what product/project, what audience, what time scope. Do not generate a roadmap without context.

Example 10: Out of scope

• Input: "Create a Gantt chart with task assignments and resource allocation per person"
• Expected: "This skill creates theme-based roadmaps with strategic themes and initiatives. Detailed task assignment and resource allocation per person is outside scope. Consider using a project planning or resource management skill."