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The Big Story:  When Is the Right Time to Call It Quits? Ask These Stars and CEOs

“It’s one of the toughest moments in any career: deciding when, and how, to leave a job. Plenty of people want to step down at the top of their professional game, yet struggle in making a well-timed exit… In business, government, entertainment and more, many have wrestled with how to step aside, a career decision that is often agonizing.”

The art of knowing when to stay strong or leave well

By David Jarrard
3-minute read

“They just won’t quit.” It’s a compliment of someone’s indomitability or a curse at their stubbornness.

Unless you’ve been blissfully (and, maybe, wisely) living under a rock lately, you know the national conversation about the exits and entrances of current and future political leaders is at a boil.

Since his disastrous debate performance last month, President Joe Biden, 81, continues to fend off a rising chorus of calls within his party to quit the race for a second term and make way for a candidate to represent a new generation of leadership. “It is now time to pass the torch,” said one Democratic representative on Friday.

Last week, after escaping an attempted assassination, former President Donald Trump, 78, named relative youngster J.D. Vance, 39, as his vice-presidential running mate, effectively “anointing a successor” as the “heir-in-waiting” of his political movement.

It can feel as if we’re living in a twisted new season of Succession. Even Teen Vogue is writing about the “American gerontocracy.”

“Bombarded with speculation about the president’s physical and cognitive health, and about the health and age of Donald Trump, observers want answers,”  Harvard Business Review stated last week in its post “When Should an Aging Leader Step Aside?”

“Are they too old to lead? Are they cognitively intact? Do they lack the ability to be effective? The current discussion offers us a broader opportunity to reflect anew on aging and leadership transitions in politics and business, a process driven both by interested stakeholders and by leaders themselves.”

It’s a question for senior leaders in every organization: When is the right time to resolutely stay and when to gracefully go?

The correct answer must be more than a reflection of an individual leader’s personal desires. It’s about the future of an organization. Or a country. What direction will it take, and who will guide it? How will one generation of leaders make way for the next?

Healthcare organizations are not immune from this question, of course. Executive search firm WittKieffer says retirement ages for healthcare leaders are increasing from one decade to the next.

“The retirement age for healthcare CEOs has demonstrated a consistent increase over the years: starting at 62 from 2000 to 2009, rising to 64 from 2010 to 2019, and further increasing to 65 since 2020,” a WittKieffer executive told Becker’s last March.

It’s not just CEOs. The average retirement ages for COOs, CFOs and CMOs have trended upward over the last two decades. Says Beckers: “COOs now retire around the age of 64, CFOs at 65, and chief medical officers opt for retirement at age 68” aligning with traditional retirement ages.

In healthcare and elsewhere, leaders and employees are hanging on longer.

But how long is too long? When do you know it’s time to let go?

Maybe you won’t.

“Most leaders, left to their own devices, will not know when it’s the right time for them to leave,” Harvard Professor Ranjay Gulati told The New York Times. “It’s really hard to stay grounded and humble when everyone is telling you you’re right.”

After all, leaders have often dedicated decades of their life to attain their positions and can wield extraordinary power to shape an organization and do good through it. The position itself can define a leader’s personal identity. To not lead can be, literally, unimaginable.

Again, The New York Times: “Everywhere you go, people defer to you,” is what Bob Sutton, a former Stanford professor and an executive adviser, often hears from those [executives] resisting retirement.

One corporate leader, Toby Cosgrove, told him: “When I became CEO of the Cleveland Clinic, I became better-looking, and my jokes got funnier.” (“There’s no question my jokes got funnier,” Cosgrove told me.) Sutton describes why executives overstay in leadership using a mnemonic device, the four Ps: power, prestige, privilege and pay.”

It’s better to ask the hard question yourself than be forced to act or be acted upon by your board, or donors, the public, or that boisterous med exec committee that has opinions.

“A good leader asks whether it is time to pass the torch,” writes Paul Irving, a senior leader at the Milken Institute and a distinguished scholar at the University of Southern California Leonard Davis School of Gerontology.

“Am I the leader I used to be? Do I have the same drive? Are my skillsets relevant to the challenges of the future? Rather than leading a transition process, do I want to have the keys taken away?”

We’ll add these questions, too: What do you want to do with your time? Given that, how do I best serve my organization now?

Authentic leaders ask challenging questions of themselves and seek honest brokers to help them answer candidly.

Of course, someone’s age is only one factor in answering these questions and may be inconsequential in the resolution of them. People age differently, have different skills and energy they bring to the work, and different life goals. Warren Buffett is 93; Mick Jagger is 80 and still onstage seeking satisfaction.

But at any age, one of a leader’s greatest acts of leadership is preparing well for his or her succession. The work begins long before your retirement party.

It’s not merely a matter of crowning an individual to inherit your title, though that might be part of it. It’s the long work of leadership development across a team of professionals who reflect the spirit of your culture as well as the skills needed for the organization to thrive in the future.

You might find that the structure and type of leadership your organization has today is inadequate for addressing tomorrow’s needs. Succession planning and leadership development can be an exciting act of institutional creativity. To have no plan is an abnegation of a leader’s responsibility.

“While succession planning may feel challenging in the current environment, organizations that do not make time for ongoing focus on the future of their leadership may find themselves in difficult situations,” the American Hospital Association quietly understates in their succession planning guide.

“Given the talent shortages, turnover and retirements, the talent landscape in health care is rapidly shifting and efforts are needed to consider and plan for the future of leadership.”

There are many “to do’s” for smart succession planning. You can imagine the list: Involve your senior leadership team. Define the key positions needed in the ever-evolving industry. Assess the current talent pool. Establish skills training and mentorship initiatives. Consider external successors. Keep the plan alive, pivoting with the industry’s transformation.

Someday you – and your entire leadership team, for that matter – will surrender your title and role and responsibilities and privileges and power and pay to others. It’s gonna happen. But how it occurs is your work today.

The first step is the hardest one and is yours alone to take. It’s to know yourself well. To be candid with yourself about your desires and abilities and the future needs of the organization that trusts in your guidance. It’s to be mindful of the importance of leaving well. After all, one of the greatest contributions of your leadership may be your relinquishment of it.

Contributors: Emme Nelson Baxter, David Shifrin

Image Credit: Shannon Threadgill