The Unspoken Truth for Millennial Senior Leaders

Kimberly Surko • July 29, 2025

Beyond the "Cool Boss" and Burnout

Congratulations, Millennials! We've officially become the dominant force in management, and many of us are now stepping into senior leadership roles. This is a monumental shift, full of exciting opportunities to shape the future of work.

However, let's talk about the unique challenges we face, especially as we climb higher. Our Boomer predecessors, who built their careers in a different era, might not fully grasp the intensity of the landscape we're navigating. They rose through ranks with different communication norms, workplace expectations, and often, without the constant "always-on" culture that defines our professional lives. Their valuable advice, while foundational, may not directly address the intricate modern challenges tied to digital fluency, intense burnout, or navigating empathetic leadership while setting firm boundaries in today's hybrid world.

The "loneliness at the top" isn't just a cliché; it's compounded by the pressures of being the "burnout generation." Many of us are juggling demanding careers with caregiving responsibilities, and Glassdoor data even shows a 73% surge in burnout mentions year-over-year among managers. Beyond the relentless pace, we often find ourselves walking a nuanced line between being an empathetic leader focused on well-being and the need to set clear boundaries. The desire to be the "cool boss" can inadvertently blur professional lines, making tough conversations even harder and leading to inconsistent expectations—a challenge less prevalent in more traditional, hierarchical structures our predecessors knew.

Plus, many of us entered these roles without the formal leadership training designed for leading multi-generational teams in a hyper-connected world or handling a nearly doubled number of direct reports. The playbooks from previous generations don't always apply to today's fluid, fast-paced environment.

If you're a millennial senior leader feeling the weight of these unique pressures—whether it's managing burnout, setting firmer boundaries, or simply needing an objective sounding board who truly gets it because they've navigated similar waters—know you're not alone. The most impactful insights often come from those who've walked a similar path in this new leadership era.

What's one aspect of senior leadership that has surprised you the most, or felt uniquely challenging as a millennial manager?

If you're seeking a confidential partnership to navigate these modern leadership challenges, gain clarity, and truly thrive in your senior leadership journey, let's connect.



Fortune: Millennials are officially a majority of managers—so get ready for a combination of burnout, buddy vibes, and boundary issues





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