Blogs & Comment

In praise of demanding bosses

Being uncompromising isn’t a fashionable management style these days—but you can’t coddle your employees to greatness

Don Draper scowling

Impress me. (AMC)

As Mad Men winds to a close—its seventh and final season is now airing on AMC—I still vividly recall a scene that perfectly sums up just how much work has changed between its 1960s setting and today: Promising copywriter Peggy Olson has just presented her boss, Don Draper, with a mediocre campaign pitch for Samsonite luggage. As her team files out, she steels herself for what she clearly knows will be Draper’s withering critique.

He doesn’t disappoint: “I gave you more responsibility, and you didn’t do anything,” he barks, later adding, sarcastically, “I’m glad this is an environment where you feel free to fail.” The dressing-down goes on for an uncomfortably long time, leaving Olson frustrated and embarrassed­—but also galvanized.

To modern viewers, such callous disregard for an employee’s feelings is hard to watch. Draper could certainly stand to deliver his disparagement with a bit more tact, but he’s not wrong in holding the people who work for him to high standards. His managerial behaviour is steeped in the premise that all parties—employee, boss, company—are better off when people are pushed to live up to their potential, when “good enough” isn’t good enough. That’s why his actions seem so shocking. He is what fewer and fewer managers want to be today: a difficult boss.

The move toward more comfortable workplaces (perhaps the defining trait of early-21st-century management) has, in too many cases, mutated into environments in which bad ideas aren’t dismissed and poor behaviour isn’t punished, lest someone’s feelings get hurt. Factor in other trends—a fear that employees will balk at criticism and defect; a post-recession tendency to promote people who aren’t trained to handle tough situations; a general shift to a more litigious environment all around—and you get a situation in which many managers aren’t pushing their staff to do significantly better work because, frankly, it’s just easier to uphold the status quo. In a recent U.S. survey of HR executives, 63% said their biggest performance management challenge is that managers simply can’t­—or won’t—have hard conversations with their staff.

This is antithetical to the kind of innovation to which most forward-thinking enterprises aspire. As leadership consultant Mark Murphy writes in his 2009 book Hundred Percenters: Challenge Your Employees to Give It Their All, and They’ll Give You Even More, people can’t be coddled into greatness. Only when their bosses “care enough” (his words; the real impetus may be less altruistic) to push them do they start performing to the best of their abilities.

Why? Brain-chemistry studies show that, as a species, humans need to be pushed out of their comfort zones in order to grow. “There needs to be a hole in the force field that protects their sense of reality before they will actively explore, examine and change their beliefs and behaviour,” writes executive coach Marcia Reynolds in her 2014 book The Discomfort Zone: How Leaders Turn Difficult Conversations Into Breakthroughs. So if professional growth is the goal (and plenty of employee engagement studies suggest it should be), it’s better to honestly challenge people than to blindly shower them with praise and perks. Framed this way, Don Draper’s brand of tough-love leadership isn’t sadistic or even mean—it’s practically enlightened.

Of course, it takes real finesse to push people effectively. There’s a fine line between prodding and bullying, and the difference often depends on the temperament of the subject. Draper’s approach worked because he was hardest only on those he knows could handle it—people like Peggy Olson. As Mad Men approaches its finale, the fictional Olson, once a bright talent prone to impatience and impulse, is delivering the best work of her career and bringing in marquee clients. While it would be simplistic to attribute her rise solely to Draper’s mentorship (she was asking for her own office five decades before Lean In), it’s clear that her drive to excel stems from the critical voice she’s internalized. Such self-motivation doesn’t come when every action gets a gold star.