The Millennial Managers Have Arrived

As they move into management, many Generation Y'ers are discovering some unexpected challenges.


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Senior vice presidents are expected to manage a significant amount of work and people, and Samuel Boyd is no exception. At Capital Asset Management Group, a financial planning firm in Washington, DC, he oversees a staff of nine while bringing in money from clients—$120 million over the last five years. He’s been an active member of his industry’s leading trade association since 2016. Most recently, he bought a 15 percent stake of the firm and began working with the firm’s founder on a long-term succession plan.

That’s a lot of responsibility—especially for a 31-year-old. And Boyd isn’t even the only millennial-aged senior leader in the office. The firm’s chief operations officer hasn’t had her 30th birthday yet. Boyd keeps telling himself that the age number is irrelevant, but sometimes it isn’t so easy. “It all comes down to respect,” he says. “Be tactful when the discussions are hard and try to lead by example. Don’t ask anything of others that you wouldn’t ask of yourself.”

Managing a team is challenging at the best of times. It’s always a balancing act of meeting business goals while juggling a workplace full of different generations, all with their own set of wants and needs. But in offices around the world, there’s a growing number of leaders who are bright, talented, and most critically, young. Millennials—that massive cadre of 75 million Americans born between 1981 and 1996 (there are 2 billion millennials worldwide)—already entered the workforce en masse years ago, and now they are rapidly becoming managers and even senior executives.


The shift may sound ridiculous to baby boomers and Gen Xers, many of whom still hold false notions that millennials as a group are averse to working hard and have lightning-short attention spans. But it shouldn’t be a surprise. The average age of a first-time manager in the United States is about 30, an age milestone that half the millennial generation has now reached. Indeed, one recent study found that 83 percent of US employees have already seen millennials managing boomers and Gen Xers in their offices.

But interview these newcomers to the boss title, and many will quietly express anxiety about moving into management. It isn’t about not wanting to lead—a majority of them do; rather, it’s about not getting the right training, or developing the right skills or emotional intelligence to lead effectively. Millennial managers face a challenge that their older predecessors haven’t faced in decades—how to balance their generation-­specific tendencies with the attributes of great leaders. There’s another related challenge for organizations, too: how to develop these young managers now so they grow into great C-suite executives a few years from now.

Millennials are already the driving force in employment. In 2016, 54 million millennials were either working or looking for work, making it the largest generation in the US labor force for the first time. The group might not have taken over the C-suite yet (only two Fortune 500 companies have millennial-aged CEOs), but they’ve made plenty of inroads in management levels throughout organizations. As of last year, there were anywhere from 5 million to 11 million millennials in management, business, or financial operations roles, according to the US Department of Labor.

Nevertheless, millennial managers are still trying to dispel the labels put upon them years ago by older generations. The one particular mark that stands out is that millennials feel an overwhelming sense of entitlement. Millennials, or so the theory goes, want the keys to the kingdom immediately, even though they don’t have a large depth of experience or skill.

It’s a perception Sunaina Mehra encounters all the time. The 27-year-old earned three degrees as an undergraduate and is a black belt in karate. After two promotions in five years, she’s now the director of marketing at a New York-based wealth management firm, and her days are filled with giving advice to, or making decisions with, her Generation X-aged CEO, and making sure her team does the needed work. It’s another story outside the office, however. “I’ll go to some C-suite networking event, and they think I don’t know what I’m talking about,” Mehra says.

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That kind of intergenerational warfare can be tricky. In fact, according to one survey, the top two things millennials said their education did not prepare them for was managing others and working with older people. It isn’t surprising that millennials are charting their own leadership course.

For one thing, many millennial managers are driven by a sense of purpose. In a study by American Express, 68 percent of millennials said they want to make a positive difference in society and expect their company to do the same. Even more clear-cut, 81 percent said that you must have a higher purpose in order to be truly successful, and 78 percent want their firms to share their own values.

That sense of purpose is driving the vanguard of millennial-aged managers. By her mid-20s, Michaela Shiloh had produced music for multiple megastars, including Janet Jackson, Britney Spears, and Pitbull. But she’d seen the music industry’s underbelly—artists get locked into terrible long-term contracts, and she had been kept from getting a fair share of royalties.


So the 27-year-old started her own Los Angeles-based company, BDRM Records, and hired a team that shared her goal of changing the industry’s tune. “We are having a lot of fun coming up with new standards and creating better contractual agreements for artists,” Shiloh says.

Millennials are also trying to develop a flexible management style early. When millennials began entering the workforce in droves starting in the mid-aughts, they saw firsthand how well—or poorly—baby boomer and Gen X bosses treated their own teams. The best managers, they saw, could adapt their leadership styles to get people engaged.

Savvy millennial managers have picked up this agility right away. Sam Boyd has been charged with digitally transforming the office, including using virtual files over paper ones and email over phone calls. But he saw that certain clients and employees were struggling and, in some cases, frustrated. So he set up a rule: anyone born before a certain date, client or employee, would be exempt from the transformation. “That’s the way many older clients like to communicate, and it’s important to be cognizant of that,” Boyd says. “If you send an email to 70-year-old clients, they may not read it.”

But perhaps the biggest trait of millennial managers is feedback—giving and receiving a lot of it. Members of the generation have been hearing about performance from sports coaches, music instructors, after-school dance teachers, and a litany of others since they were born. They’ve always known where they stood, so it isn’t surprising, as at least one polling firm surmised recently, that millennials are building that feedback loop with their subordinates.

For instance, Mehra expects end-of-the-week reports from her team letting her know what each individual accomplished, what’s on the docket for next week, and if there are any issues she can help out with. But she’s also talking to them throughout the day using the workplace communication software Slack, and once a month talks to team members individually about their top three personal and professional goals. “We want to be able to see what is going on, without having to micromanage anybody,” Mehra says.


That feedback loop is part of an overarching desire by millennials for transparency. More than half of millennial-aged managers want what’s called “active transparency,” meaning companies should make all financial information available to employees. Only 37 percent preferred partial transparency—the status quo at many firms now—according to a survey done by Inc. and Fast Company magazines in conjunction with the career website The Muse.

To be sure, there are plenty of issues millennial managers are struggling with. Some of those boil down to a lack of experience, but not all of it. They are disdainful of the work of their predecessors. More than 80 percent of millennial bosses say prior leaders have done a poor job of addressing issues of gender and racial diversity in their workplaces, according to the Inc. survey.

Indeed, learning how to manage people, regardless of their ages, who recently used to be your peers, requires some tact. “You don’t want to make them feel stupid or spoken down to,” says Samara Cooperberg, a 28-year-old public relations executive who oversees six people.

Some assistance from their employers could help, but at least right now, many organizations don’t prioritize grooming millennials as leaders. To some degree, the shift has caught many off guard. According to the Harvard Business Review, the average age for leadership development training is up there in years—at 42. (See “Management Training for the Younger Set” on page 45 for steps companies can take.)

But at the end of the day, the millions of millennials who are managers or soon will be are going to have to learn to own the fact that they are now bosses. Don’t make excuses. Hold yourself accountable. Recognize problems and find solutions for them. And don’t apologize for being there. Cooperberg says the best advice she ever got was from a former supervisor. “Run with it, and know you were promoted for a reason,” she says. “So just go out and get it done.”

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