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Ch-Ch-Ch-Changes: Navigating Late Transitions of “Executive Seasons”

The transitional leader phase is the most critical to long-term company sustainability, as executives must work toward building confidence in incoming leaders and ensuring a smooth transition of leadership.

I have several friends who recently sold their companies in large multi-million deals. Both individuals built their businesses from scratch, regularly putting in 16-hour days, investing profits back into the company, and accepting sacrificing in their personal lives as the businesses grew in power and size. The sales had the potential to make them both very happy: they were pre-retirement age, successful and well-liked in their respective fields, and had the financial means to start new endeavors.

Instead, both founder/CEOs fell into dark places, purposeless and paralyzed about the next steps of their professional and personal lives.

A landmark Korn Ferry survey of top executives found 73 percent believe their work has purpose and meaning. In my work counseling private and public companies, working with management on strategic planning and execution, and training and developing high performing management teams and executive talent, I’ve found that as many chief executives transition from the pinnacle of their career success to a slow exodus toward a new role or retirement they suffer more from anxiety and depression, measuring their self-worth by their purpose and level of success.

But resisting change, even a planned course, doesn’t stop it from happening. The key is to find meaning and purpose in each phase of an executive career, especially in the later “seasons.”

Broadly speaking, the average chief executive career unfolds in phases: the emerging leader (lower management), the developing leader (upper management), and the strategic leader (CEO). To that list I would add the “transitional” leader, when the executive steps down and reins of leadership are transferred to a successor.

Arguably, this phase is the most critical to long-term company sustainability, as executives must work toward building confidence in incoming leaders and ensuring a smooth transition of leadership. It is also fraught with risk to one’s long-term professional stability and personal contentedness and happiness. Yet, even in the “transitional” season, CEOs can reject the potential of their final season being marked by a cliff trajectory.

First, they should take concrete steps to decrease the possibility of surprise potholes that will complicate the transition. Some of these steps are obvious: ensuring financial stability, preparing an exit narrative that lessens the likelihood of rumors. But others are less obvious. For example, updating a personal mission statement and following a personal development plan can make the transition less like a bookend and more like a roundabout, with potential offramps representing to-be-realized opportunities.

Those CEOs without a personal mission or development plan need to rectify this immediately. CEOs like Sir Richard Branson, founder of The Virgin Group (“To have fun in [my] journey through life and learn from [my] mistakes.”) and Amanda Steinberg, founder of DailyWorth (“To use my gifts of intelligence, charisma, and serial optimism to cultivate the self-worth and net-worth of women around the world.”) embrace personal missions. Some of the top executives I’ve worked with have personal development plans that they revisit on an annual basis or, for some, even weekly. High-level aspirations should drill down to achievable milestones and bite-size outcome goals, and the personal plan should become a transitional executive’s North Star through the transition and beyond, with enough flexibility to ensure “planning” doesn’t impede seeing and seizing new opportunity.

In addition, chief executives should reframe how they can contribute to “success,” either in their current organization or in the next career opportunity. In an emerging leader, success is equated with personal growth and rising up the corporate ladder. For the developing leader, it is attaining the skills to achieve organizational success, and the strategic leader is creating a vision and attaining buy-in to further the organization’s future.

For a transitional CEO, the wisdom from the journey means more than the knowledge of how to keep the trains running. There is great value – and new personal validation – in experience-based counsel. Through periods of stability and disruption, profit and loss, market growth and contraction, each phase of leadership provides the opportunity for key takeaways. Ultimately, those learnings culminate in a unique long-term vision of an organization – and important insight on what the current organization (or the next one) can do to maintain its unique culture, enhance the customer and employee experiences, and remain profitable in periods of change.

Acknowledging this essential value aids in coping with transitions, but also offers opportunity to find new “second-half significance” – both behind a c-suite desk and elsewhere. Rod Stewart, a master certified coach for the Halftime Institute, said about the ending of his career as an electronics market executive, “Over a period of time, and with the help of a structured thinking process, I developed a vision for my second half – a life mission statement that carried forward what I enjoyed the most about my first-half career: coaching others to help them achieve their goals. Along the way I discovered what many already know – that one of the keys to experiencing joy is in giving myself away to others.”’

While change and exit planning is an essential part of every career, it doesn’t have to be a closed door. Chief executives who prepare for that inevitability and take charge of their futures will find, to their surprise, that they embrace the later seasons of executive life.


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