Mason McGuire (McCormack) and Conner (Cavanagh) are two very different but equally close leaders of the pack in their cutting edge Chicago advertising agency. When Mason is promoted over Conner, the two must learn to navigate their new paths while their personal and professional relationships are tested.
Mason finally gets the recognition he so desperately craves when Denise gives him the credit, and another promotion, for winning a massive account for the team. While Conner gets an update about his short-lived relationship with Diane, Sarah is questioning whether to continue her current relationship or the best way to end it.
Sarah finds herself at odds with both Mason and the director of the team's Dove commercial when she and the director disagree and Mason fails to back her up. Meanwhile, Tony recruits Conner to help him steal a forgotten account from another group, which drives an even larger wedge between Conner and Mason.
Mason questions his career choice when he receives an unsatisfactory job review. In order to deal with the team's neuroses, Tony decides to bring in an expert in business psychology. Meanwhile, Sarah's personal life may be settling down when she and her boyfriend step up their relationship.
Tony loses all control of his anger when Simon and his group jump into the competition for the beer account that Sarah worked so hard to bring to the company, which leaves her feeling torn between the two teams. While Conner works on the bum assignment of making a birthday video for Tony, he unwittingly discovers an interesting office secret.
Conner offers freelance work to his ex-creative partner, only to see that his friend lacks the necessary skills for the job. Meanwhile, Sarah taps into a high-profile beer account, but she draws the attention of Mink nemesis Simon Cochran (Greg Ellis). At the McGuire homestead, Mason tries to help daughter Haley brave romantic growing pains, but his efforts backfire.
The Mink Group is on the front lines of a fierce bidding war for a new energy drink---but a concealed relationship involving a team member could jeopardize the account. Elsewhere, Sarah tries to find a love match via a dating service. And Mason's wife suspects that Mason may have a roving eye, so she pays her husband a surprise office visit.
Financial problems mar both Mason and Conner, prompting each to seek employment elsewhere. But their mutual trust is tested when secrets about one another begin to surface. Elsewhere, Sarah is up to her hair in problems over a shampoo account. And an interoffice romance blooms for Tom.
Mason convinces Tony to allow his group to create a campaign for the potential Chicago Olympics. With the entire team assigned to the project, Mason and Erin have the opportunity to get away for the weekend, leaving Conner at the helm. Sarah and her new partner clash when their two very different lifestyles collide, making them both wonder what they each truly want in life.
Connor makes a bold move by continuing to produce an ad after the client pulls the plug to rethink the entire campaign. Meanwhile, Sarah tries to get back together with her ex-husband and Tony receives devastating news.
Mason's latest pitch falls short after basing his abnormal teenaged daughter's habits which don't exactly translate to all teens her age.
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