Published in 1958—two years before Mathew Weiner’s Mad Men begins—Amy Vanderbilt’s Complete Book of Etiquette: A Guide to Gracious Living includes a useful chapter on business manners. Emphasizing the importance of clear-cut boundaries in the workplace, Vanderbilt writes: “A really experienced and urbane executive keeps his relations with his secretary on a friendly but purely business basis.”
But over the course of the AMC series’ six-and-a-half gloriously boozy, adulterous seasons, we’ve seen these boundaries tested and crossed to yield a wide variety of results for Sterling Cooper’s secretarial staff. From drunken office hookups to literal bloodshed (who can forget the infamous John Deere incident?), relationships between secretaries and their bosses have brought about promotions and proposals, redundancies, and resignations. Women, it seems, are damned if they follow the rules and damned if they don’t. Heading into the second half of the final season, if Mad Men’s exploration of office politics has taught us anything at all, it’s that the work of a secretary is nothing if not personal.
As green as green can be when she arrives at Sterling Cooper, Peggy Olson learns everything she needs to know about the realities of her job within a few short days on Don Draper’s desk. “He may act like he wants a secretary,” Joan tells her on her first day at work, “but most of the time they’re looking for something between a mother and a waitress and the rest of the time, well…” She trails off. Sexual expectations are virtually written into the job description; it’s already been decided by the men that Peggy will sleep with one of them, it’s just a matter of who and when. “You’re the subject of much debate,” Ken Cosgrove tells her over lunch on her second day, “there’s money riding on it.”
While every able-bodied suit is driving hard to Peggy’s hoop, Don draws that particular line in the sand pretty quickly—he rebuffs the subtle but awkward pass she makes at him, and their relationship remains wonderfully platonic for the remainder of the show. But even though they never sleep together, the job demands a certain level of intimacy. “You probably know more about him than I do,” Betty says the first time they meet. While the comment is particularly pointed given that Don’s secret past is the dramatic crux of the first season, Peggy happens to have overheard a phone conversation between Don and his mistress of the hour, Midge, arranging a little afternoon delight. So when he’s late to meet his wife and kids for their family portrait, she panics. “I don’t know who to lie to!” she whispers breathlessly to Joan, desperately seeking her seasoned advice.
Discretion, Peggy discovers, is the most important part of her job and it comes part and parcel with knowing things about her boss’s life she would rather not. Her unfaltering loyalty is contrasted against the fundamental incompetence of Lois Sadler, the switchboard operator who takes over Don’s desk when Peggy is permanently promoted to copywriter. “He said he was going to a movie,” Lois tells Peggy when she inquires as to his whereabouts, “Pinocchio.” She delivers the information with a tone of clueless bemusement and Peggy chastises her harshly for insinuating too much. (Lois winds up crying in the break room, which earns her a second scolding from Joan—the poor girl can’t seem to catch a break).
Poring over the early seasons for a second time, the extent to which Weiner expertly uses repetition to test and differentiate between his characters becomes abundantly clear. Lois finds herself in precisely the same sticky spot as Peggy was just one season earlier, but where Peggy succeeded in leveraging the situation to move up a rung on the corporate ladder, Lois fails and is pushed further down.
The hapless secretary is blissfully unaware that she’s done anything remotely wrong and thus repeats the same mistake twice: When Don tells her diplomatically that she’s simply not suited for the job she blinks at him in desperate confusion, “But I always cover for you!” “You do not cover for me,” he responds sternly. “You manage people’s expectations.”
It’s a subtle but critical distinction and her inability to see it proves fatal to her career. Don sends her swiftly back to the switchboards and the next time we see Lois she’s amputating someone’s foot with a lawnmower—a blunder which ironically goes unpunished. Administrative skills are shown to be far less important than interpersonal savvy time and time again as professional mistakes are excused, while mishaps that meddle with bosses’ personal lives are not. When Joan learns Harry Crane’s secretary Scarlett skipped out of work and had Dawn punch her time card, for example, Harry makes sure she keeps her job; when Lane’s secretary Sandi mixes up the cards on two sets of apology roses—one to Joan and one to his wife—she’s fired on the spot.
Mrs. Vanderbilt is careful to warn men against the specific perils of having a pretty woman on his desk: “The more attractive she is,” she writes, “the more, for his own and her protection, he must treat her with careful, polite objectivity. The quickest way to trouble, a straight line into the maze of gossipy office politics, is for a man to pay more than business attention to his secretary.” It’s a risk Don is all too aware of—after all, Joan puts Miss Blankenship on his desk specifically to liberate him from sexual temptation following the mess he caused by sleeping with Allison. (Though it’s revealed with comedic irony in Roger Sterling’s memoirs that the 80-something year-old woman with glasses as thick as goggles was a “hellcat” in her day).
Before she quits and throws a cigarette lighter at his head, Allison was one of Don’s best girls. She was competent, sweet, and patiently tended to his increasingly personal needs as he plummeted deeper into alcoholism. Painfully aware of his split from Betty and the effect it had on his relationship with his children, Allison is brought to tears when reading Sally’s letter to “Santa” aloud that declares all she wants for Christmas is for her father to come home. By the time Don asks her to deliver the keys he drunkenly leaves at the office Christmas party, her guard is down and she’s ill-equipped to refuse the inebriated advances in his sad bachelor pad. That Don wants to pretend nothing ever happened the next morning is compounded by the fact that he seems to be buying Allison off with a $100 Christmas cash bonus, and she runs out of the office in tears, never to return.
Another leggy brunette transplant from the reception desk, Megan ostensibly makes the identical mistake—only she does it on purpose and with a greater sense of self-awareness. “Let’s be clear,” she tells him, “I’m not going to run out of here crying tomorrow. I just want you right now.” The sexual encounter is the kind of no muss, no fuss, good-time-was-had-by-all Mrs. Vanderbilt actually finds acceptable: “If it happens that both are free to have some social life together, if they wish, they should still maintain formal relations in the office if their efficiency is not to suffer,” she writes. Indeed, Don is still dating Dr. Faye Miller at the time and he and Megan manage to maintain a level of professional decorum—at least for a while. (It’s not until Megan accompanies Don to L.A. as a last-minute nanny that he spontaneously proposes).
Executives, it seems, are free to cross as many lines as they please, while secretaries may do so only at their own risk. It works well for Megan, who winds up married and gets promoted to copywriter, but poor Allison finds herself jobless and without even a letter to recommend her.
Between 1960 and 1969, Sterling Cooper & Partners—in all its iterations—has born witness to some pretty major managerial changes, from the acquisition of a clunky photocopier to the installation of a monstrous IBM computer. And while it may seem like the secretarial class has remained stagnant, there’s nothing like revisiting the pilot to realize how much subtle change has unfolded over the course of a decade.
There’s a particularly telling moment in the latest season in which Dawn and Shirley, the company's only two black employees, have a quick tête-a-tête in the break room: Shirley complains that Peggy has selfishly stolen her Valentine’s Day roses assuming they were hers, and Dawn advises her to just keep pretending. “It’s part of the job,” she says. After all, Dawn has been maintaining the illusion to Megan in California that Draper still has a job (he’s still on leave at this point).
The advice neatly mirrors the wisdom Joan imparts to Peggy in the first season, which she in turn tries to pass onto Lois in the second—but later in that same episode, both women stage small-scale revolutions. Shirley gets her roses back and Dawn tells Lou Avery off for wasting her time with his personal errands. That Lou wants her off his desk ultimately works in her favor: recognizing her merits, Joan promotes Dawn to office manager and she gets a room of her own. Boundaries finally being drawn by the secretaries rather than the executives? Oh, my! What would Mrs. Vanderbilt say?