What I've experienced as someone who has helped onboard new-hires is that we meet with the new-hire daily for a week or two, and throughout that process if we f

What I've experienced as someone who has helped onboard new-hires is that we meet with the new-hire daily for a week or two, and throughout that process if we find documentation has gotten stale the mentor usually updates it (e.g., yeah, our baseline OS has changed to xyz, what is here is old, here's where you get the bits for the new stuff), because the new-hire probably has no idea how to fix it yet.