Draft: Milestone Planning Process

Problem

The API Security category team needs a repeatable process for planning out milestones.

Proposal

Define a repeatable process for milestone planning.

  1. Identify at risk issues from current milestone
    1. Who: Engineering team
    2. When: Prior to Prioritization of work meeting.
    3. Pre-Tasks:
      1. Create issue with checkboxes for each engineer indicating this work is completed.
    4. Add them to next milestone planning issue
    5. Add weight of work left to be completed
    6. Add workflow status
    7. Add current priority
  2. Identify issues for next milestone
    1. Who: PM, Engineering team
    2. When: Prior to Prioritization of work meeting.
    3. Pre-Tasks:
      1. Create issue with checkboxes for each engineer indicating this work is completed. Could be the same issue as "Identify at risk issues from current milestone"
    4. Add them to the milestone planning issue
    5. Add anyone weight to planning issue
  3. Meeting: Prioritization of work
    1. Who: PM + Engineering team
    2. When: 2 weeks prior to milestone ending
    3. Add milestone priority labels to all items
  4. Engineering team signed up for work items
    1. Pre-Tasks:
      1. Create issue with checkboxes for each engineer indicating this work is completed.
    2. Assign issue to yourself
    3. Adjust weight
    4. Update planning issue 🤖
  5. Meeting: Trim/add work
    1. Who: PM + Engineering team
    2. When: Week prior to milestone ending
    3. Cutdown issue list to milestone capability
    4. Cut issues move to next milestone or backlog

Implementation

  1. Identify roles and responsibilities for each task
    1. Scheduling meetings
    2. Leading meeting
    3. Any other pre-work items
    4. Nudging team members to complete tasks
  2. Document process in handbook
  3. Perform and refine process
  4. Identify areas for automation 🤖
Edited by Michael Eddington