Jack, a renowned adventure reporter, transitions to the role of desk-bound boss, overseeing a team of 20-something journalists, after the founder of the outdoor magazine he works for decides to go to a web-only publication.
The Millenials uncover a secret about Jack's love life while cleaning out his storage unit. In the meantime, Clark and Mason use Jack's old stuff to throw a '90s party at Eddie's bar.
Human Resources forbids Jack from giving his staff any feedback at all after he crushes Clark with a brutally honest performance review. Also, Emma and Mason call out Brooke for being politically incorrect when they try to help her hire a diverse intern.