Depends on how much time it takes to make some progress and reassess. For some projects/teams like some I belong to, that's a monthly basis. For others, that's once/quarter. Or, maybe it's very frequent like once every other day during a particularly busy period and then only at the start and midpoint of every project thereafter. Like much of the Playbook, perhaps picking any frequency is fine at first because you'll be able to make more informed adjustments after that.
Many teams ask me this and it does really depend on the project or team. I find that a week or two after a kick off is an excellent time to run a health monitor to work out where the team needs to focus their efforts. Generally, for me, the closer the project gets to completion, the less value a health monitor brings.
Obviously once a project is complete you should have a retro - a brief recap of your project's health monitor can be a nice way to kick it off -great way to see how, over time, the team's health evolved.
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