When you are about to start a new milestone for the first time you might want to run a milestone kickoff. This is a discovery exercise like a story kickoff but focussed on the higher level goal of the milestone.

Some key questions:

• who
  • cares about the milestone and when it starts/stops/the scope?
  • should be involved in story kickoffs?
  • is external to the team that we will rely on to complete the milestone?
    • do they need lead time to be able to help us achieve it?
• what
  • is the overall goal and defining achievement of the milestone?
  • do we know about the feature and what don’t we know?
  • is in scope for the milestone vs out of scope?
• why
  • is it important (and more important than subsequent milestones)?
• when
  • do we need to achieve the milestone by?
  • do we need different levels of detail in the plan?
    • if we just need an idea of approach or size we may want to plan some spikes or other investigation sooner rather than later

This is a key time to bring together designers, stakeholders, marketing and anyone involved in a milestone to help plan things out to help guide the completion of the milestone (without prescribing everything up-front).