In 1952, Shepherd Mead's satirical book, How to Succeed in Business Without Really Trying, became a bestseller. Playwright Willie Gilbert and fellow playwright Jack Weinstock created a dramatic interpretation in 1955 that was unproduced for five years. Agent Abe Newborn brought the work to the attention of producers Cy Feuer and Ernest Martin, with the intention of retooling it as a musical. Feuer and Martin had great success with the 1950 adaptation of Guys and Dolls and brought in the creative team from that show to work on How to.... Abe Burrows and Frank Loesser set to work on the new adaptation, with rehearsals beginning in August 1961. Burrows collaborated on the book with Jack Weinstock and Willie Gilbert, also serving as director. Their new adaptation became even more satirical and added romance to the story. Loesser wrote both music and lyrics for the show, which was orchestrated by Robert Ginzler.
The original Broadway production credited the choreography to an obscure dance director named Hugh Lambert, while the much better-known Bob Fosse received only a "musical staging by..." credit. Abe Burrows explains this in his autobiography Honest, Abe. While How to Succeed... was in its early development, producer Cy Feuer attended a trade show and was extremely impressed by an elaborate dance number created by Lambert, prompting Feuer to hire Lambert to choreograph the new musical. According to Burrows, it soon became clear in rehearsals that Lambert's creative abilities were completely used up in that one elaborate dance number. Bob Fosse was brought in to replace him, but Fosse was unwilling to hurt Lambert's career by having him fired. Lambert's trade-show dance number was recycled as the "Treasure Hunt" dance in How to Succeed..., while Fosse agreed to take a "musical staging" credit for choreographing all the other dance numbers. Burrows also reveals that another crisis arose in rehearsals when former recording star Rudy Vallee wanted to interpolate some of his hit songs from the 1930s.
J. Pierrepont Finch, a young window cleaner, has a mind for advancement. A "Book Voice" tells him that everything he needs for success is contained within the book in his hand, How to Succeed in Business Without Really Trying. He enters the World Wide Wicket Company searching for a job.
Finch knocks J.B. Biggley, the president of the company, to the ground. Finch presses Biggley for a job, who dismisses him to the personnel manager, Mr. Bratt. Rosemary Pilkington, a secretary, is impressed with Finch and offers to help him meet Mr. Bratt. Bratt treats Finch brusquely until Finch mentions he was referred to Bratt by Mr. Biggley. Finch is given a job in the mailroom, where he works with Mr. Biggley's lazy and nepotism-minded nephew Bud Frump. Rosemary dreams of a life with Finch in the suburbs and tells her friend Smitty that she'd be "Happy to Keep his Dinner Warm".
The fatigued workers rush to get their "Coffee break", only to find it bone dry. The Book Voice warns Finch, "One word of caution about the mailroom: it is a place out of which you must get." Twimble, head of the mailroom, is moving to the shipping department. He tells Finch that the secret to longevity at the company is to play things "The Company Way". Twimble appoints Finch as his successor, but Finch, heeding the words of his trusty book, declines the promotion, saying that Bud Frump is more qualified. Frump accepts, vowing to play things "The Company Way", too. Twimble and Bratt are impressed by Finch, and Bratt offers him a job as a junior executive in the Plans and Systems department, headed by Mr. Gatch. Frump, seeing that he has been outdone, fumes.
A sexy but air-headed woman named Hedy LaRue calls the office searching for a job, and Bratt brings her in to be assigned secretary. The employees see her and are instantly attracted to her, but Bratt, in order to assert his claim to Hedy, reminds them "A Secretary is Not a Toy."
It is Friday afternoon, just after five o'clock. As the employees make their way to the elevators, the ever-alert Finch learns that Biggley is extremely proud of his alma mater, Old Ivy, and learns that he will be in the office Saturday morning. Rosemary and Smitty encounter Finch at the elevator. They agree that it's "Been a Long Day", and Smitty helps them arrange a date. Frump runs into Biggley and Hedy, arguing about her job. Frump realizes their relationship and blackmails Biggley into giving him a promotion.
Finch arrives early Saturday morning in order to appear that he has been working all night. Biggley arrives and witnesses Finch "asleep" at his desk. Finch "absent-mindedly" begins humming "Grand Old Ivy", the Old Ivy fight song. Finch convinces the Old Man that he, too, is a proud alumnus. Biggley insists that Finch be given his own office and secretary, Hedy, prompting the Book Voice to warn Finch to beware of secretaries who have many talents, none of them secretarial. Finch realizes that Biggley must be her advocate, and sends her on an errand to Gatch, knowing that he won't be able to resist making a pass at her. Finch is soon seated behind Gatch's desk, Gatch having been dispatched to Venezuela.
A reception for the new Advertising Department head, Benjamin Burton Daniel Ovington, is being held, and Rosemary hopes to impress Finch with her new "Paris Original", but all the women of the office are wearing identical copies of the dress. Hedy tipsily exits to shower in Biggley's office, and Frump, hoping to trap Finch and Hedy, tells Finch that Biggley is waiting in his office for him. In the office, as Hedy and Finch are kissing passionately, Finch realizes that he is in love with "Rosemary", who enters as Hedy returns to the bathroom. After some farcical complications, Finch and Rosemary embrace—just in time for Frump and Biggley to walk through the door.
Ovington resigns after being prompted for his alma mater by Finch; Biggley realizes that Ovington matriculated from Old Ivy's bitter rival. Biggley a loyal "Ground Hog" cannot stand another day of the "Chipmunk" Ovington. Then, Biggley names Finch Vice-President in Charge of Advertising, just in time for a big meeting two days hence. Biggley leaves as Finch and Rosemary declare their love for "J. Pierrepont Finch", and Bud Frump vows to return.