Posted December 12, 2025

A significant shift is happening in the workplace. Baby boomers and older Gen X leaders are moving into retirement, and the question rises quickly. Are the next leaders ready. This is not just a challenge for a handful of companies. It is something that will shape communities, industries, and the health of our entire economy. In a recent conversation with Jennifer Hawkins, we explored why developing the next generation of leaders cannot wait.

The Impending Leadership Exodus

Across the country, seasoned leaders are preparing to step away from the workforce. Jennifer Hawkins pointed out that roughly one third of Gen Xers over age fifty are transitioning into retirement or already have their plans in place. That means a large portion of our leadership bench will soon be unavailable.

Most organizations receive only a few months’ notice before a leader exits. Yet executive roles require long-term development. Without preparation, companies face performance drops, instability, or even the possibility of closing their doors. The problem grows worse when organizations fail to track how many of their executives and board members are approaching retirement. Too many leaders simply do not know how deep the gap truly is.

The Missing Skill: Strategic Acumen

One of the greatest challenges facing emerging leaders is the ability to think strategically. Many rising leaders excel at execution. They know how to run meetings, manage teams, and deliver results. Yet once they step into higher-level roles, they struggle with building strategy from the ground up.

Jennifer Hawkins explained that many mid-level leaders wait for instructions. This works well in operational roles, but executive leadership requires something different. Leaders must anticipate what is ahead, create vision, and build long-term plans that guide the entire organization. When someone is promoted before developing these skills, they often flounder. Some last only a few months. It is not due to lack of knowledge. It is due to lack of strategic experience.

Cultivating Tomorrow’s Strategists

Developing strategic leaders begins with exposure. Organizations need to pull mid-level leaders into the room where strategy is built. They should be part of budgeting cycles, growth planning, and conversations that shape the future. This allows them to learn the rhythm of strategic thinking long before they step into an executive office.

Shadowing alone is not enough. Emerging leaders need hands-on involvement. They need to help build plans, offer ideas, refine them, and watch how those ideas play out across an organization. This iterative experience shifts them from waiting for direction to learning how to provide it.

Expanding Beyond Silos

Good leadership requires a wide perspective. Leaders cannot remain locked inside one department and expect to succeed at the executive level. Jennifer Hawkins underscored the importance of cross-department mentoring. Leaders should seek out opportunities to work with other areas of the organization so they understand how every function contributes to the mission.

Siloed thinking limits growth. A leader who excels in one area must learn the pressures, responsibilities, and obstacles faced by others. Regular conversations with department heads create a fuller picture of how an organization operates. This builds empathy, insight, and the strategic awareness required for executive leadership.

Proactive Personal Development

Aspiring leaders also carry responsibility for their own growth. Jennifer Hawkins credits her own advancement to lifelong learning, coaching, and mentorship. Leaders should not wait for a formal program to appear. They should reach out to senior leaders, ask questions, seek guidance, and show genuine interest in understanding the entire organization.

Mentors can also be found outside someone’s immediate location or even outside their industry. Challenges in leadership often overlap across fields. Expanding one’s network creates new opportunities and new ways of thinking. Hunger for learning is one of the greatest predictors of long-term growth.

The Value of Investing in People

Some leaders hesitate to invest heavily in developing their teams because they fear losing their talent to other companies. Jennifer Hawkins takes the opposite approach. She believes in investing in everyone she leads. When people grow, they carry that growth into every environment they enter. They may become partners, collaborators, or advocates in the future.

She shared her own experience at The Hartford, where strong leadership development programs shaped her career and left her with deep respect for the organization. Investing in people builds loyalty, strengthens communities, and enhances the reputation of the organization. The benefits extend far beyond the time an employee remains on the payroll.

Moving Beyond Micromanagement

Many organizations operate at a fast pace and rely on top-down leadership. This leads to micromanagement. Staff execute while leaders strategize, and little room is left for creativity or ownership. Jennifer Hawkins noted that telling people what to do does not develop them. It leaves them uncertain, disengaged, and afraid to make mistakes.

This approach creates stress and contributes to mental health struggles in the workplace. When people feel unsafe, they cannot bring their best selves to their work. Leaders must shift toward an approach that builds confidence, strengthens capability, and identifies individual gifts. The goal is to create an environment where people rise, not shrink.

Conclusion: A Call to Action

The need to develop the next generation of leaders is urgent. A wave of retirements is coming, and strategic skill gaps are widening. Organizations must take action now. Bringing emerging leaders into strategic conversations, encouraging cross-department collaboration, and supporting personal development will create a strong leadership pipeline for the future.

This investment strengthens companies and communities alike. It ensures that the next generation is ready to carry the responsibility of leadership with clarity, courage, and skill. As Jennifer Hawkins and I discussed, the statistics are clear. The time to prepare is not someday. The time is now.

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