It really depends.
It could be awhile, especially if productivity growth remains high in the early part of the recovery (like it did in the early 2000s recession) causing a lag in job creation, where productivity growth remained high and job creation didn't meaningfully occur till output growth exceeded productivity growth (which wasn't till sometime in Q1 2004).
I have seen this in various parts of San Diego, such as fast food restaurants and grocery stores using automated multiple automated cash registers supervised by one person, instead of multiple lanes.
This might hold true as people are generally risk-averse and would probably have a greater peace of mind with investing in technology first and labor later.
Yes. That has been a concern of mine since 2002, when pundits were talking about a "jobless recovery". I am thinking that there will have been some economic leadership that will create an industry that is not yet automated and still requires a degree of at least initial creativity.