Dan Foreman (Dennis Quaid) is a 51-year-old advertising executive and head of sales for Sports America, a major sports magazine. Happily married with two daughters, Dan faces a life-changing event when his magazine is bought out by Globecom, an international corporation that promotes the corporate concept of "synergy". Globecom is headed by Teddy K (Malcolm McDowell) a reclusive billionaire. Dan has been with the company for 20 years and believes in the power of the magazine as a great advertising medium. Dan believes in building relationships with his clients rather than resorting to any aggressive sales techniques. He leaves them a copy of the Magazine as his final argument. One of Dan's prospects is Eugene (Philip Baker Hall with whom he is in the process of building such a long term relationship.Mark Steckle (Clark Gregg) is Carter's boss at Globecom. Teddy K picks Mark to run Marketing at Sports America and Mark picks Carter to run the Advertisements division. Mark intends to "Cut the fat" at Sports America. Carter gets excited when Mark mentions that Carter "is being groomed" by Teddy K, presumably for leadership positions at future acquisitions. After he is forced to fire several of his longtime colleagues (like Enrique (Ty Burrell), Lou (Kevin Chapman) & Morty (David Paymer)), to reduce payroll by $300,000 in the sales team), Dan is demoted and becomes the "wingman" of his new boss, Carter Duryea (Topher Grace), a 26-year-old business school prodigy. While Dan develops clients through handshake deals and relationships, Carter champions the corporate creed of synergy, cross promoting the magazine with the cell phone division and "Krispity Krunch", a snack food also owned by Globecom. Carter has no experience in advertisement sales. He wants to use the synergy concept to increase sales by 20%. The big idea is to put sports factoids in Krispity Krunch boxes and basically force them to buy 28 pages a year in the Sports America magazine, and same with the cell phone division.Dan and Carter are both facing challenges in their personal lives. Dan is supporting two daughters-16-year-old Jana (Zena Grey) and 18-year-old Alex (Scarlett Johansson) who is preparing to enter college and learns that his wife is pregnant with their third child. Alex gets into NYU to study creative writing, which is a much more expensive course as compared to the one she was taking in Newark.Meanwhile, Carter is dumped by his wife of seven months (for being too self-centered and career focused) and focuses all his energy on work. With Dan facing the financial realities of a mortgage, education costs, and a new child, and with Carter needing Dan's practical, real-life experience in the field of advertising, the two form an uneasy friendship.One day, Carter, who has been struggling with loneliness following the breakup of his marriage, invites himself to dinner at Dan's house, where he meets Dan's daughter Alex, and the two quickly form an attraction. Their initial friendship allows Carter to forget his loneliness, and Alex, who is now attending New York University, is able to escape her own loneliness and boredom. Dan is angry at Carter for making him fire the people that he hired himself and had worked with for many years. Dan wants Carter to fire him instead, and Carter retorts that the only reason he doesn't fire Dan is because he has a family that needs him. Dan has to accept his reality and continue to do what Carter tells him to, even if Dan does not agree with it.In the coming days, Carter and Alex spend time together and become romantically involved. Fearful of offending her father, they keep their relationship a secret for the time being. They are successful since Alex has moved into a dorm in NYC to pursue her studies at NYU.Their friendship, however, takes a turn for the worse when Dan discovers that Carter and Alex have been seeing each other, approaches them in a restaurant, and punches his boss in the face when he finds that Alex has been sleeping with Carter. Carter says that he loves Alex. The confrontation with her father (Dan said that he took out a 2nd mortgage so that Alex could study at NYU) convinces Alex to break off the relationship with Carter who is heartbroken. Soon after, faced with a major setback with a longtime client who is unimpressed with Carter's "synergy" and cross-promotional ideas, Carter relies on Dan's personal approach, which ends up saving the account.Later, when Mark tells Carter to fire Dan, he refuses. This is because Dan was honest enough to tell Teddy K in a live office conference that some of his synergy ideas would end up destroying the Sports America brand. Teddy wanted to put a computers section in the Sports America Magazine, and Dan argues that nobody will want to read that and that a sports magazine should remain true to their mandate. Carter stands up for Dan and says that Dan is a hardworking employee. He also threatens Mark that he would call Teddy K and reveal how Mark took his most profitable magazine and drove it into the ground with all the layoffs. To top it off, he says that he and Dan have been working on a huge account, that would save the magazine. The duo approach Eugene and convince him to make a large purchase of ad space in the magazine, thus proving to Mark that their bluster was not bluff.Following another corporate shakeup, Sports America is sold off, Carter is let go, and Dan returns to his former position as head of sales. Having developed fatherly feelings toward Carter, Dan offers him a position in his new department as his "wingman", but Carter refuses, admitting he needs to take some time off and examine what he really wants to do in his life, and the two part as friends.On his way out of the building, Carter runs into Alex, and they exchange pleasantries. Dan's wife gives birth to a girl. He calls Carter-who is jogging outdoors for the first time and feels like a new man-in Los Angeles with the news.