Roadmap Builder

Roadmap Builder

When to use

Sequence transformation ambition into phased roadmap — dependency map before phase placement, not flat initiative lists.

What this skill does not do

• Does not build business case — route to /transformation:business-case.
• Does not invent capacity — flag overloaded phases.
• Does not use generic Now/Next/Later when profile defines named track model.

Preconditions

Load org + transformation profiles; provisional mode available.

Provisional mode

Defaults: Now/Next/Later; balanced risk — see workflow below.

Trust spine

Structured-aggregation bands; every initiative has phase rationale tied to dependencies; GATE before board/exec final.

Assumption audit

Before dependency mapping, audit initiative-prioritisation assumptions:

Surface audited assumptions in LOAD-BEARING ASSUMPTIONS when any status is assumed or unknown.

Red flags

Initiative prioritisation failures are non-negotiable to flag before governance publish:

• MUST NOT assign initiatives to phases without a one-line dependency rationale — flat lists cause false parallelism.
• Do not proceed to board-final if a phase exceeds plausible capacity without a CAPACITY FLAGS line — overload causes slip cascades.
• Hard stop: sequencing high-variance bets in Now when risk posture is conservative without explicit user override — misaligned posture causes funding for foundations to stall.
• MUST NOT invent dates, FTE, or budget to justify phase placement — use INPUT NEEDED.

Outside-view step

After Step 5 (phase placement), run a reference-class sequencing check:

1. Name comparable transformation or product programs (internal post-mortems or peer benchmarks) with documented phase-slip patterns.
2. Compare this roadmap's Now-quarter load and critical-path length to the class median — if this plan is more aggressive, state the optimism gap.
3. Record: OUTSIDE-VIEW: [reference class] — typical slip [X weeks/quarters]; this plan [aligned/aggressive]; re-sequence trigger if [condition].

Always compare Now-quarter density to reference-class delivery throughput because programs that pack more concurrent critical-path items than peer programs tend to cause milestone slip that invalidates the sequencing argument.

Purpose

Produce a sequencing argument — not a flat initiative list. Each item is placed in a phase because of dependencies, risk posture, and capacity, with explicit flags where the roadmap exceeds what the org can plausibly deliver.

Precondition: load profiles

Before sequencing, read both:

• ~/.claude/plugins/config/claude-for-strategy/org-profile.md
• ~/.claude/plugins/config/claude-for-strategy/transformation/CLAUDE.md

If missing or still template, surface the practice setup bounce (same pattern as business-case) with /transformation:practice-setup or "provisional".

Provisional mode

Defaults: Now (this quarter) / Next (1–2 quarters) / Later (beyond); balanced risk posture; no named governance gates. Tag [PROVISIONAL]. Ask once whether this is portfolio-level (Now/Next/Later) or execution-level (would benefit from a named track model once configured).

Workflow

Before Step 1: Read and apply ../../references/trust-conventions.md — source-tagging, [verify] on model-only numbers, load-bearing assumptions at top, numbers provenance, confidence labeling, and board-ready gate.

Step 1: Orient

If current state or ambition is vague, stop and clarify. A roadmap sequences a gap; vague endpoints produce vague sequencing.

Step 2: Track model routing

Read ## Framework preferences → Roadmap track model from the transformation profile.

Do not substitute a generic model when the profile names a specific one.

Step 3: Dependency mapping

Before assigning phases, map dependencies:

DEPENDENCY MAP (working):
[Initiative A] blocks → [Initiative B] because [reason]
[Initiative C] unblocks → [Initiative D]

Initiatives with unresolved dependency inputs get INPUT NEEDED: confirm whether [X] blocks [Y] — do not guess sequencing order.

Step 4: Risk posture application

Read risk posture from org profile or transformation profile (conservative / balanced / aggressive). State which is applied:

Step 5: Phase placement

Place each initiative in a phase with a one-line rationale — what it depends on, what it unblocks, why this phase and not the next.

Step 6: Capacity and gate alignment

Capacity check: compare phase load to org size/structure from profiles. Flag overloaded phases explicitly.

Gate alignment: check ## Review gates in the transformation profile — note which initiatives require discovery exit, architecture review, investment approval, or release gate before the next phase can start.

Step 7: Kill / revisit criteria

For the overall roadmap and any high-risk phase:

KILL / REVISIT CRITERIA:
- Re-sequence if: [trigger — e.g. dependency slips, funding not approved]
- Pause program if: [trigger]
- Revisit horizon labels if: [trigger]

Step 8: Board-ready gate

Run the trust-spine GATE before a governance-facing or board-final roadmap. Working drafts for the delivery team skip the gate.

Output format

CONFIDENCE: [defensible recommendation | structured first pass]
TRACK MODEL APPLIED: [named model from profile | Now/Next/Later provisional default]
RISK POSTURE APPLIED: [conservative | balanced | aggressive]

LOAD-BEARING ASSUMPTIONS:
- ...

AMBITION: [one sentence]

DEPENDENCY MAP:
- ...

[Track/Phase 1 name]:
  - [Initiative] — [rationale: depends on / unblocks / why here]
  - ...

[Track/Phase 2 name]:
  - ...

DEPENDENCIES (cross-phase): [explicit flags]
CAPACITY FLAGS: [overloaded phases, with rationale]
GATE ALIGNMENT: [initiatives requiring named approval before progression]
KILL / REVISIT CRITERIA: [...]
EVIDENCE GAPS: [INPUT NEEDED items]

Quality checks before delivering

• Both profiles loaded (or [PROVISIONAL] tagged)
• Current state and ambition confirmed before sequencing
• Named track model used when configured — not silently replaced
• Every initiative has phase-placement rationale
• Dependencies mapped before phase assignment
• Capacity risk flagged where phases look overloaded
• No invented dates, costs, or capacity figures

Worked example

Input: Identity platform must precede customer portal; three initiatives in Now quarter.

Expected output (excerpt):

Now: Identity platform — Rationale: blocks portal SSO dependency
CAPACITY FLAGS: Now quarter overloaded — 3 initiatives vs. 2-team capacity [review]

Propose profile update

When a stable convention surfaces during this run (thresholds, naming, tone, output format, or recurring corrections), propose a profile update: show the exact diff against ~/.claude/plugins/config/claude-for-strategy/transformation/CLAUDE.md (org-wide facts go to org-profile.md), ask for confirmation, and write only on yes. Only /transformation:practice-setup auto-applies a full profile write.

Outputs

Follows plugin CLAUDE.md § Outputs. Next: business-case, resolve capacity flags, or GATE before steering publish.