When to use
Use this playbook for every strategic project in the coming quarter, once capacity planning has given it a team. A project that continues from last quarter gets a fresh milestone plan too.
Roles
- Project Manager: leads. You write the milestone plan and own its risks and dependencies.
- Product Owner: makes sure each milestone delivers something of value, and turns the first milestone into backlog items.
- Product Manager: checks that the goals still match the outcome in the business case.
- Program Manager: checks dependencies with other projects and confirms capacity.
Before you start
- Get the business case, the high-level design and the capacity plan for the project.
- Book two working sessions with the Product Owner and a senior engineer from the project team.
- Copy the milestone plan template.
Steps
- Write 2 to 4 goals. Each goal is an outcome the business will notice, such as "Agents can bind a small-business policy online without calling us". Tie every goal to the business case.
- Cut each goal into milestones. A milestone is a working, demonstrable step, not a phase like "design done". Aim for one milestone every 2 to 6 weeks.
- Write "done when" for each milestone. Make it testable: "done when three pilot agents bind a policy in production".
- Place milestones on sprints. The quarter has six sprints. Put each milestone at the end of a sprint, and leave the last sprint's capacity at least half free for slips.
- Check the fit. Add up the team-sprints for the milestones and compare the total with the project's capacity. If it doesn't fit, cut or move a milestone. Don't stretch the team.
- List dependencies. For each milestone, name anything it needs from another team or project, with the date you need it. The Program Manager confirms each one with the other side.
- List risks. Note the top risks with an owner and a mitigation for each. Carry over open risks from the design review.
- Prepare the first milestone. With the Product Owner, break the first milestone into backlog items ready for refinement in sprint 1.
- Share the plan two working days before Quarterly Planning.
Outputs
- A milestone plan: goals, milestones with "done when" and target sprint, dependencies and risks.
- Backlog items for the first milestone, ready for refinement.
- Dependency requests sent to the other teams.
Pitfalls
- Milestones that are activities. "Testing complete" doesn't show value. "Claims staff process a real claim end to end" does.
- Back-loading. If most milestones land in sprint 6, nothing is learned until it's too late to change course.
- Treating the plan as fixed. The plan is a forecast. The Project Manager updates it after every sprint review.