McCann posed as Patrick O'Reilly, an out-of-work house painter, and made stops in 1-800-Flowers locations in New Jersey, Ohio, Massachusetts and New York. On his first stop in New Jersey, McCann meets floral designer/arranger Pauline. When he couldn't keep up with her flower arranging prowess, he listened to her express her frustrations with the company. She and other designers had ideas for new floral arrangements, she told him, but she felt the company didn't listen to their ideas, forcing the designers to do the same old thing every day. Even in his disguise, McCann's surprise at this revelation was easy to see.
Next, McCann went on to Ohio, where he worked at the company's Fanny May chocolate factory in Canton. Like Lucille Ball in the classic "I Love Lucy" chocolate factory episode, McCann couldn't keep up with the conveyor belt's speed - chocolate-covered pretzels were soon covering the factory floor. His new co-worker, Nicole, tells him not to worry about his poor performance, because the goals that employees are mandated to meet are ridiculously high, and set by men "upstairs" who have never even visited the factory.
In Boston, McCann works with Dee, a 25-year veteran of the flower business, in one of 1-800-Flowers' most successful stores. However, his cover is almost blown when Dee's general manager, Steven, shows up at the store - and recognizes the company's president. McCann goes on a delivery with Steven and reveals his identity, and the manager agrees to keep his secret.
McCann makes another visit to a Massachusetts store, but in this one, nothing is going on. When McCann asks store manager Cheryl what she thinks the problem is, she tells him she's frustrated by the lack of advertising and misconceptions about the store's name. She tells McCann that some people think 1-800-Flowers is just an Internet business, or that the storefront is just full of telephone operators. Others won't buy from the store because of the name. Still, she tells him, she's determined to be nice to customers and to show them what the store has to offer.
McCann makes his final stop in Brooklyn, N.Y., where he works with 19-year-old store manager Jose and gets a surprise visitor - his older brother, Jim McCann, who founded 1-800-Flowers and is now the CEO. Jim seemed to take pleasure in pointing out everything his younger brother was doing wrong, but didn't break his cover. Over pizza, Jose tells Chris about the struggles in his life.
After his undercover work, Chris and Jim sit down to talk about what Chris learned undercover, and decide to reward a few of the employees Chris met along the way. Pauline will get a chance to design her own floral arrangements, Cheryl received help to develop a better marketing program, Dee had a floral arrangement named after her and Nicole inspired Chris to create an incentives program for meeting goals. Finally, young Jose will receive money and mentoring in hopes of eventually becoming a franchise owner.