gh-lyndonkl-claude/skills/roadmap-backcast/resources/template.md

Roadmap Backcast Template

Workflow

Copy this checklist and track your progress:

Roadmap Backcast Progress:
- [ ] Step 1: Define target outcome
- [ ] Step 2: Work backward to milestones
- [ ] Step 3: Map dependencies
- [ ] Step 4: Identify critical path
- [ ] Step 5: Assess feasibility

Step 1: Define target outcome

State specific outcome, date, success criteria. See Target Definition.

Step 2: Work backward to milestones

Ask "what must be true just before?" iteratively. See Milestone Backcasting.

Step 3: Map dependencies

Identify sequential vs parallel work. See Dependency Mapping.

Step 4: Identify critical path

Find longest dependent chain. See Critical Path.

Step 5: Assess feasibility

Check time available, add buffers, identify risks. See Feasibility Assessment.

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Roadmap Backcast Template

Target Definition

Target Outcome: [Specific, measurable end state]

Target Date: [Fixed deadline - DD/MM/YYYY]

Success Criteria:

• [Criterion 1]: [Quantifiable measure of success]

Why this matters: [Business impact, strategic importance, consequences if missed]

Constraints:

• Budget: [Available resources]
• Team: [Available capacity, FTEs]
• Dependencies: [External constraints, vendor timelines, regulatory deadlines]
• Scope: [Must-haves vs nice-to-haves]

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Milestone Backcasting Process

Working backward from target date:

Milestone 0: Target Outcome (T+0)

Date: [Target date] Deliverable: [Final outcome achieved] Owner: [Name/Role] Dependencies: [What must be complete for this to happen]

Milestone 1: [Name] (T-[X weeks/months])

Date: [Date] Deliverable: [Specific output, not activity] Owner: [Name/Role] Duration: [X weeks/months] Dependencies: [Requires milestone 2, 3 complete] What must be true before: [State of world needed to start this milestone]

Milestone 2: [Name] (T-[X weeks/months])

Date: [Date] Deliverable: [...] Owner: [...] Duration: [...] Dependencies: [...] What must be true before: [...]

Milestone 3: [Name] (T-[X weeks/months])

Date: [Date] Deliverable: [...] Owner: [...] Duration: [...] Dependencies: [...] What must be true before: [...]

Milestone N: Starting Point (Today)

Date: [Today's date] Deliverable: [Current state, what we have now] Owner: [...] What we need to begin: [Resources, approvals, information to start milestone N-1]

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Dependency Mapping

Dependency Graph:

[Milestone A] ──→ [Milestone B] ──→ [Milestone D] ──→ [Target]
                                      ↑
[Milestone C] ────────────────────────┘

Dependency Table:

Milestone	Depends On (Prerequisites)	Enables (Downstream)	Type	Can Parallelize?
[Milestone A]	None (start)	[B]	Sequential	No (on critical path)
[Milestone B]	[A]	[D]	Sequential	No (on critical path)
[Milestone C]	[A]	[D]	Parallel with B	Yes (non-critical)
[Milestone D]	[B, C]	[Target]	Converging	No (on critical path)

Parallel workstreams (can happen simultaneously):

• [Milestone X] ∥ [Milestone Y]: [Why these can be parallel]
• [Milestone Z] ∥ [Milestone W]: [...]

Converging points (multiple prerequisites):

• [Milestone M] requires both [A] AND [B]: [Coordination needed]

Diverging points (one enables multiple):

• [Milestone N] enables [X], [Y], [Z]: [Handoff process]

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Critical Path Identification

Critical path (longest dependent chain):

[Start] → [Milestone A: 4 weeks] → [Milestone B: 6 weeks] → [Milestone D: 2 weeks] → [Target]
Total: 12 weeks

Alternative paths (non-critical, have slack):

[Start] → [Milestone A: 4 weeks] → [Milestone C: 3 weeks] → [Milestone D: 2 weeks] → [Target]
Total: 9 weeks (3 weeks slack)

Critical path milestones (zero slack, delays directly impact target):

• [Milestone A]: [Why on critical path, impact if delayed]
• [Milestone B]: [Why on critical path, impact if delayed]
• [Milestone D]: [Why on critical path, impact if delayed]

Non-critical milestones (have slack, can absorb delays):

• [Milestone C]: [X weeks slack, latest finish date without impacting target]

Critical path management:

• Monitor: [How will we track critical path progress? Weekly reviews, dashboards]
• Accelerate: [Can we add resources to shorten critical path? Cost/benefit]
• Buffer: [20-30% buffer on critical path tasks built in? Where?]

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Feasibility Assessment

Time Analysis:

Component	Estimate (weeks)	Buffer (%)	Buffered (weeks)
[Milestone A]	[4]	[20%]	[4.8]
[Milestone B]	[6]	[30%]	[7.8]
[Milestone D]	[2]	[20%]	[2.4]
Total (critical path)	12	-	15

Available time: [Target date - Today = X weeks]

Required time (with buffer): [15 weeks]

Feasibility verdict:

• ✓ Feasible if Available ≥ Required (with X weeks margin)
• ⚠ Tight if Available ≈ Required (±10%)
• ✗ Infeasible if Available < Required

If infeasible, options:

1. Extend deadline: Move target date to [new date] (need X additional weeks)
2. Reduce scope: Cut [feature Y], defer [feature Z] to post-launch
3. Add resources: Hire [N contractors/FTEs], cost $[X], reduces timeline by [Y weeks]
4. Accept risk: Proceed with [X%] probability of missing deadline

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Risk Register

Risks to timeline:

Risk	Probability (H/M/L)	Impact (H/M/L)	Mitigation	Contingency
[Vendor delay on component X]	H	H	Contract penalties, alternate vendor identified	Built 4-week buffer in milestone B
[Key engineer leaves]	M	H	Cross-train team, document tribal knowledge	Contractor bench available
[Scope creep from stakeholder Y]	H	M	Requirements freeze by milestone 2, change control process	Reserve 2 weeks flex time
[Technical unknowns in integration]	M	H	Technical spike in milestone 3, architecture review	Parallel path with simpler approach

Triggers for re-planning:

• Critical path milestone delayed >1 week → Escalate, re-assess feasibility
• Scope change >20% → Re-run backcast, adjust target or timeline
• Resource loss >25% → Revisit parallelization, extend timeline

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Resource Allocation

Team capacity:

Role	Available FTEs	Required FTEs (peak)	Gap	Mitigation
[Engineering]	[5]	[7]	[-2]	[Hire 2 contractors by milestone 2]
[Design]	[2]	[2]	[0]	[Sufficient]
[QA]	[1]	[3]	[-2]	[Outsource testing for milestone 4]

Budget:

• Total required: $[X]
• Allocated: $[Y]
• Gap: $[X-Y] → [Source: reallocation, additional funding, scope reduction]

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Communication Plan

Stakeholder alignment:

• Weekly updates: [To whom, what format, starting when]
• Milestone reviews: [After each milestone, with stakeholders X, Y, Z]
• Go/No-Go gates: [At milestones A, C before committing to next phase]

Escalation path:

• Level 1 (delays <1 week): Team lead resolves
• Level 2 (delays 1-2 weeks): Product manager adjusts plan
• Level 3 (delays >2 weeks or feasibility threat): Executive decision on scope/date

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Guidance for Each Section

Target Definition

Good target outcomes (specific, measurable):

• ✓ "1000 paying customers using product by Jan 31, 2025"
• ✓ "SOC 2 Type II certification achieved by regulatory deadline Sept 1, 2025"
• ✓ "Conference with 500 attendees, NPS >40, on Oct 15, 2024"

Bad target outcomes (vague, unmeasurable):

• ❌ "Launch product soon"
• ❌ "Improve compliance"
• ❌ "Hold successful event"

Milestone Backcasting

Ask iteratively: "What must be true just before [current milestone]?"

Example (Product Launch):

• Target: 1000 customers using product
• T-2 weeks: Product in production, scaling, monitoring working
• T-6 weeks: Beta complete, critical bugs fixed, ready for GA
• T-10 weeks: MVP feature complete, QA passed
• T-14 weeks: Design finalized, APIs defined
• T-18 weeks: Requirements locked, team staffed
• Today (T-20 weeks): Feasible if starting now

Milestone quality:

• Clear deliverable: "Design finalized" not "working on design"
• Verifiable: Can objectively check if done
• Owned: Named person responsible
• Estimated: Duration in days/weeks/months

Dependency Mapping

Identify dependencies by asking:

• "Can this start before [X] completes?" (sequential vs parallel)
• "What does this milestone need to begin?" (prerequisites)
• "What can't start until this finishes?" (downstream dependencies)

Common patterns:

• Waterfall phases (design → build → test): Sequential, little parallelization
• Workstreams (frontend ∥ backend ∥ infrastructure): Parallel, converge for integration
• Approvals/Reviews: Often converging (need multiple sign-offs)

Critical Path Identification

Shortcuts for small roadmaps (<10 milestones):

1. Draw dependency graph
2. Visually trace longest path
3. Sum durations on that path

For complex roadmaps (>10 milestones):

• Use project management tools (MS Project, Asana, Jira with dependencies)
• Critical path method (CPM) calculation (forward/backward pass)

Interpreting critical path:

• Critical path length = minimum project duration
• Slack on non-critical tasks = flexibility
• Delays on critical path directly delay target

Feasibility Assessment

Buffer guidance by uncertainty:

• Low uncertainty (done similar work before): 10-20% buffer
• Medium uncertainty (some unknowns, dependencies): 20-30% buffer
• High uncertainty (novel work, many risks): 30-50% buffer
• Regulatory/Compliance: 40%+ buffer (risk intolerant)

Feasibility decision tree:

Available time ≥ Required time (with buffer)?
├─ Yes → Proceed, monitor critical path closely
├─ Within 10% → Proceed with risk acknowledgment, escalation plan
└─ No → Re-plan (extend date, reduce scope, or add resources)

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Common Patterns by Context

Product Launch:

• Critical path: Design → Engineering → Testing (usually 60-70% of timeline)
• Buffer: 20-30% on engineering, 20% on testing
• Risks: Scope creep, technical unknowns, vendor delays

Compliance/Regulatory:

• Critical path: Gap analysis → Remediation → Audit
• Buffer: 40%+ (cannot miss regulatory deadline)
• Risks: Audit findings require rework, controls take longer than expected

Event Planning:

• Critical path: Venue booking (long lead time), content creation, speaker coordination
• Buffer: 10-20% (hard deadline, less flexible)
• Risks: Speaker cancellations, venue issues, low registration

Strategic Transformation:

• Critical path: Foundation work (pilot, learnings) before scaling
• Buffer: 30%+ per phase (unknowns compound)
• Risks: Organizational resistance, scope expansion, funding cuts

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Quality Checklist

• Target outcome is specific and measurable
• Target date is fixed (not flexible)
• Success criteria are quantifiable
• 5-10 major milestones identified working backward
• Each milestone has clear deliverable (not activity)
• Each milestone has owner assigned
• Dependencies explicitly mapped (prerequisites identified)
• Parallel workstreams identified where possible
• Critical path identified (longest dependent chain)
• Duration estimates include 20-30% buffer
• Feasibility assessed: required time ≤ available time
• Risks to timeline documented with mitigations
• Resource constraints identified (team, budget)
• Communication plan for stakeholder updates
• Escalation path defined for delays
• If infeasible, options provided (extend date, reduce scope, add resources)