Millennials have officially overtaken Generation X as the largest cohort of managers in the American workforce in 2025. This generational handoff marks more than a demographic curiosity—it’s potentially a major shift in how organizations are led, as millennials have a different management style than their predecessors.
According to the semiannual Worklife Trends report by Glassdoor, millennials became the largest share of the managerial workforce in late June 2025, overtaking Gen Xers, who dominated leadership during the past two decades. At current aging trends, according to projections from Glassdoor lead economist Daniel Zhao, Gen Z will provide a greater share of managers than baby boomers in late 2025 or 2026. Already, Gen Z makes up one in 10 managers.
Since becoming the most populous generation in the labor force in the mid-2010s, millennials have steadily risen through the ranks, propelled by demographic inevitability, retirements among baby boomers, and new attitudes toward organizational leadership . This ascent caps years of warnings and speculation about how millennial values would shape the workplace.
In an interview with Coins2Day, Zhao said millennials are inheriting a tough situation, but it could be worse. Workers by and large “don’t feel like they’re in a great situation” right now, but Zhao noted things have not deteriorated for workers since the last edition of the report in January 2025.
Although Zhao didn’t use this particular Gen Z slang, the state of the workforce that is now majority managed by millennials is mid. “At the very least it doesn’t seem that workers are feeling worse,” Zhao said. “I don’t know if you can call that a silver lining.”
Millennials managing through the ongoing ‘burnout crisis’
Millennials are widely credited with pushing “empathy” and “well-being” to the forefront of management culture. They prioritize policies such as remote work, mental-health benefits, and boundary-setting—yet there’s a reason millennials stress mental health so much: They are experiencing record levels of burnout, stress, and job insecurity themselves, leading some workplace experts to warn of a looming “manager crash” in 2025. Zhao agreed this lines up with anecdotes in Glassdoor reviews, but not the data in his research.
Zhao, for his part, writes that the mental-health challenges facing the current workforce show “no signs of abating.” He writes of burnout as an “ongoing crisis,” with mentions in Glassdoor reviews spiking 73% year over year as of May 2025. “Reviews about burnout often refer to the cumulative effect of several years of layoffs and understaffing wearing on employees who remain.”
Of course, the term “burnout” became largely synonymous with the millennial generation in Anne Helen Petersen’s viral 2019 Buzzfeed article on the subject, which morphed into a book and a deep vein of reporting for years to come. Speaking to Petersen’s thesis, that millennials were born into a culture and climate of constant work from a young age, the average number of direct reports per manager has almost doubled in recent years, piling burnout levels of stress onto the burnout generation, just as they become the majority of managers.
Zhao declined to comment on Petersen’s thesis directly, but on the subject of burnout more generally noted that many millennial managers, especially those in their forties and late thirties, are aging into the “sandwich generation,” with responsibilities that have been typical for Gen X: “Millennials right now are in a place where their career pressures might be highest, but there are also these other personal pressures that are really stressing millennials out.” Zhao added that “in a sense, they’re stuck between a rock and a hard place.”
Despite their ambitions, many millennial managers report receiving little to no formal leadership training, often feeling unprepared for the complexities of managing teams across multiple generations and responding to rapid organizational change. This is bound to worsen with double the reports of the historical average. And while they stress empathy, millennials are the generation that invented the term “ghosting” for their avoidant behaviors on social media, and many struggle with assertiveness and managing workplace conflict head-on. Finally, millennials are the “participation trophy” generation, and some bruising TikTok videos have argued that millennial bosses have a toxic tendency to try to befriend all their direct reports. “Wolves in sheep’s clothing,” they were called. Ouch.
The flip side of emotional intelligence
Zhao told Coins2Day that the well-worn cliché about millennial managers being known for their focus on empathy has a flip side. Glassdoor has seen a change in how people talk about management over the past five years since the pandemic, he said: “Reviews that discuss management increasingly emphasize terms related to emotional intelligence, like ‘respecting boundaries,’ ‘being empathetic,’ ‘promoting employee well-being,’ and ‘addressing burnout.’” Zhao noted it shows that workers’ expectations have increased: “The bar on what constitutes a good manager has been raised.”
It doesn’t mean millennials are inherently gifted at emotional intelligence, Zhao said, just that it’s an expectation of their reports, be they fellow millennials, Gen Z, or perhaps even Gen X or boomers. Zhao referenced research that the phrase “emotional intelligence” really started picking up in the 21st century. How ironic, then, that the population that mainstreamed emotional intelligence when they entered the workforce is now responsible for managing it.
Although millennials generally seek to build trust and provide recognition, generational divides persist: A notable minority of employees, especially Gen Z, remain neutral or uncertain about the recognition they receive . According to a comprehensive Deloitte survey, millennials themselves want more feedback, mentorship, and growth opportunities, both for their teams and for their own careers .
This may be why millennials are getting saddled with a dreaded moniker: the so-called cool boss. Recent reporting and viral social-media content have fueled criticism of millennial managers for blurring the line between manager and friend—sometimes to detrimental effect. Sketches and first-person accounts highlight a stereotype of the millennial manager who is eager to be seen as hip, adopting a laid-back attitude, casual communication, and a friendly rapport with direct reports. Critics argue this style can be toxic in creating a “false sense of warmth” that masks underlying power dynamics. In terms of achieving results, the cool boss act leads to inconsistent or unclear expectations, fueling anxiety among staff. And when negative feedback is necessary, the cool boss dropping the mask can come as a shock to their subordinates.
Many millennial managers report difficulties in setting clear boundaries with their teams as they struggle to code-switch from friendly to authoritative as situations demand. Setting boundaries is further complicated by generational shifts: Younger employees, particularly Gen Z, also favor fluid boundaries and a flat hierarchy, sometimes intensifying the ambiguity around roles and expectations .
While Zhao did not comment directly on the so-called cool boss meme, he said millennial managers are walking an “extremely tough line right now.” Millennials are supposed to be at the peak of their career, but many are also taking care of kids, parents, even elder family members. “On the care aspect,” Zhao said, “there’s been a lot of discussion, especially since the pandemic, on the gaps … in the American economy today.”
Are you a millennial who’s a manager, or do you have a millennial for a manager? Coins2Day would love to hear from you: get in touch at [email protected].
For this story, Coins2Day used generative AI to help with an initial draft. An editor verified the accuracy of the information before publishing.