Milestone is typically associated with reaching a certain goal, before proceeding forward or stopping altogether. Checkpoint signifies points at which the team stops and checks progress against expectations, and possibly adjust.
Milestone (big granularity) means progress checking at iterative way; it is important in overall project progress and if associated goal is not fulfilled, some important analysis and decisions are needed; it is associated with phases and iterations or other important points and it could be related to formal progress tracking. As “no team is an island unto itself”, that “software development” is not a hermetically sealed universe, and that the software development efforts of one team are usually part of a bigger coordinated undertaking / organization.
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