As a corporate expert in downsizing operations Ryan Bingham’s (George Clooney) job is to fire people. Ryan loved his life on the road and even meets the woman (Vera Farmiga) of his dreams on one of his trips. His boss, however hires an arrogant young lady, Natalie (Anna Kendrick) who threatens his on the road existence when she comes up with a way to terminate people's employment through video conferencing. Ryan tries to show Natalie the error in her judgment by taking her on one of his trips to terminate some employees. Natalie starts to understand the terrible realities of her job, but does Ryan also see the realities as clear as Natalie does?