delivery-plan-and-roadmap

name	Delivery Plan and Roadmap
description	This skill should be used when the user asks to "create a delivery plan", "build a roadmap", "plan the phases", "define milestones", "map the critical path", "estimate the timeline", or needs a structured phased plan for delivering an initiative.
version	1.0.0

Delivery Plan and Roadmap

Produce a realistic, phased delivery plan with milestones, dependencies, and a critical path analysis. Ground estimates in scope and team capacity, not wishful thinking.

Overview

A delivery plan is not a Gantt chart — it is a set of commitments backed by explicit assumptions about scope, team, and risk. This skill produces a plan that delivery teams can execute and sponsors can track.

Delivery Planning Process

Step 1: Define Phases and Objectives

Structure the delivery into phases where each phase delivers standalone business value:

Phase	Name	Objective	Duration	Entry Criteria	Exit Criteria
0	Foundations	Enable delivery	2 weeks	Kick-off complete	Environments ready
1	MVP	Core capability live	6 weeks	Phase 0 exit criteria met	P0 features in production
2	Enhancement	Full feature set	8 weeks	Phase 1 exit criteria met	All MoSCoW Must Haves live

Step 2: Define Milestones and Gates

For each phase, define:

• Milestone: a specific, verifiable event (not "nearly done")
• Gate criteria: the binary conditions that must be met to pass the gate
• Gate owner: who makes the go/no-go decision

Step 3: Identify Dependencies

Map dependencies between work streams:

• Internal: between teams or squads in this engagement
• External: third-party APIs, platform team deliverables, client sign-offs
• Regulatory: compliance approvals, penetration tests, audits

Dependency table:

Dependency	Type	Provider	Required by	Risk if Late
[item]	Internal/External/Regulatory	[who]	[date/milestone]	[impact]

Step 4: Critical Path Analysis

Identify the longest chain of dependent tasks — this is the critical path. Delays on the critical path delay the project; delays off the critical path may have float.

Produce a simple critical path diagram:

Phase 0 (2w) → Phase 1 API (3w) → Phase 1 Frontend (3w) → Phase 1 Go-Live
                                  ↗ (Phase 1 API must complete first)
         Phase 1 Data Migration (4w) — CRITICAL PATH

Step 5: Risk Register

Risk	Likelihood	Impact	Risk Score	Mitigation	Owner
[risk]	H/M/L	H/M/L	H/M/L	[action]	[name]

Flag critical path risks specifically — these are the ones that will delay the whole programme.

Step 6: Resource Plan

Role	Phase 1	Phase 2	Phase 3
Tech Lead	1 FTE	1 FTE	0.5 FTE
Engineers	2 FTE	3 FTE	2 FTE
QA	0.5 FTE	1 FTE	1 FTE

Roadmap Output Format

Produce:

1. Phase table with objectives, duration, and gate criteria
2. Milestone timeline (text-based: Week 1: X | Week 3: Y | Week 6: Z)
3. Dependency table
4. Critical path diagram
5. Risk register
6. Resource plan

Additional Resources

• references/estimation-techniques.md — T-shirt sizing, story points, and reference class forecasting
• assets/delivery-plan-template.md — Blank delivery plan template