As of mid-2025, millennials have officially overtaken Generation X as the largest cohort of managers in the American workforce, according to Glassdoor’s Worklife Trends report. While this marks a generational shift, it also signals a broader transformation in how organizations are led—with potential implications for workplace culture, employee well-being, and leadership expectations.
Millennials have been steadily ascending through the ranks since becoming the largest generation in the labor force in the 2010s, propelled by retirements among baby boomers and changing attitudes toward leadership. Gen Z is also making inroads: Already, one in 10 managers belongs to Gen Z, and Glassdoor projects they’ll surpass baby boomers in managerial representation by late 2025 or 2026.
Leading Through Burnout
The rise of millennial leadership comes at a complicated time. Millennials are widely credited with pushing empathy, flexibility, and mental health to the forefront of management. They’ve championed remote work, work-life boundaries, and employee well-being. But there's a reason for that: They’re also among the most burned-out generations themselves.
Glassdoor’s report highlights a 73% year-over-year spike in mentions of burnout in employee reviews, indicating an “ongoing crisis.” Many cite the cumulative effects of layoffs, understaffing, and increased workloads. The average number of direct reports per manager has nearly doubled, adding stress to already overwhelmed middle managers—especially millennials, often dubbed “the burnout generation.”
Lead Glassdoor economist Daniel Zhao described the workforce as “mid”—not improving, but not worsening either. “At the very least,” he said, “workers aren’t feeling worse.”
Millennials, now entering their late 30s and 40s, are also aging into the “sandwich generation,” balancing career demands with caring for children and aging parents. “They’re stuck between a rock and a hard place,” Zhao told Fortune.
Under-Trained and Overloaded
Many millennial managers report they’ve received little to no formal leadership training—despite now being responsible for guiding teams across multiple generations in rapidly changing organizations. While they value collaboration and inclusivity, some struggle with conflict resolution and clear boundary-setting. As a result, experts are warning of a possible “manager crash” in 2025, fueled by exhaustion and unpreparedness.
The management style millennials are known for—empathetic, participatory, and informal—has drawn criticism in some circles. Viral social media content paints millennial bosses as “cool bosses” trying too hard to befriend direct reports. Critics argue that this blurred line between friend and manager can create confusion, inconsistency, and even toxic dynamics when hard decisions or negative feedback become necessary.
The “cool boss” persona may generate a casual workplace culture, but it often masks the underlying power imbalance inherent in all managerial relationships. When tough feedback is needed, the sudden shift in tone can catch employees off guard, damaging trust and morale.
The Double-Edged Sword of Empathy
The emphasis on empathy and emotional intelligence is reshaping what employees expect from their managers. Terms like “boundary-respecting,” “empathetic,” and “burnout-aware” are increasingly common in Glassdoor reviews, Zhao noted. “The bar for what constitutes a good manager has been raised.”
However, empathy isn’t a silver bullet. Emotional intelligence is now seen not just as a nice-to-have, but as a baseline expectation from leaders across generations. Millennials—who helped mainstream this value—must now operationalize it, not just express it. This includes balancing emotional connection with clarity, structure, and accountability.
Despite their reputation for being collaborative and feedback-hungry, millennials also struggle to receive enough of it themselves. A Deloitte survey found millennial managers often feel unsupported and are seeking more mentorship, career development, and guidance—not just for their teams, but for their own growth.
A Generation Caught in Transition
As younger generations like Gen Z enter management, the workplace will continue evolving. But for now, millennial managers are navigating a difficult stretch: undertrained, overextended, and facing rising expectations on every front. They are tasked with rebuilding a workforce strained by years of layoffs, economic instability, and rapid change—all while trying to balance personal and professional demands.
Zhao summed it up best: Millennials are walking an “extremely tough line.” They may have reached the top of the org chart—but it's clear the weight of leadership in 2025 is heavier than ever.