Question: How many drafts do you typically go through, and how do you know when it’s been too many?

Answer:

Ideally, 6 drafts or fewer. In actuality, it’s often 7-12.

The number of drafts doesn’t depend on the length of the doc, either. I’ve had one-page hardware instruction sheets that went through 17 drafts (due to pop-up stakeholders and differences of opinion amongst people who never talked directly to one another).

If things start to cycle with no end, seek a Higher Power, i.e., your management, or someone’s management. “Decision paralysis” usually means that there’s some dysfunction in the team itself or elsewhere in the organization.

If you’re in a lightweight environment where “drafts and versions don’t matter” then maybe approvals don’t matter, either, and you can try saying that while looking for your next job.