Changing of the Guard: When the Legacy Shifts

As we enter 2025, a quiet but seismic shift is occurring in workplaces across the country. Baby Boomers, many of whom postponed retirement, are now exiting the workforce in large numbers. And while the torch is naturally passed to Generation X, we’re seeing another wrinkle: there simply aren’t enough Gen X leaders to fill all the seats.

Millennials—who once challenged traditional leadership paradigms—are now stepping into the executive suite. Many are doing so earlier than expected and with a lingering feeling: Am I ready for this?

This leadership gap isn’t just a matter of numbers. It’s a shift in mindset, culture, and expectations. Millennials view leadership through a different lens: relational over transactional, feedback over formality, flexibility over rigidity. And yet, many find themselves caught between honouring the legacy and pioneering change.

So how can we make this transition less turbulent and more transformational?

Two Ways Retiring Leaders Can Develop Their Successors:

1. Shift from Command to Coaching: Boomers hold a wealth of knowledge that can’t be captured in handbooks. Instead of giving instructions, retiree leaders can take on coaching roles—asking questions, offering frameworks, and helping younger leaders think strategically. As Stephen M.R. Covey notes, “Trust is the highest form of human motivation.” This trust-building mentorship gives Millennials the confidence to lead their own way.

2. Name the Legacy—Then Let Go: The healthiest transitions happen when a leader affirms what was, without clinging to what must be. Boomers can help name the values, wins, and wisdom of their era—while encouraging successors to adapt those principles to a changing world. This public demonstration of trust and permission to build on the vision and strengthen the culture is critical for future innovation. Leaders can remove the shackles of tradition from future leaders while holding great pride in all they have done to bring the organization to where it is now. Legacy is not a script; it’s a springboard.

In Part 2, we’ll explore how Millennial leaders can rise to the occasion—rooted in gratitude, but unafraid to reimagine.