Christina Wing in Harvard Business Review: Talking Honestly About Age and Succession

Christina Wing
October 20, 2026

For 15 years, Christina Wing saw the same dentist, and she adored him. Then one morning she noticed his hands shaking. Over the next few visits he dropped instruments and shuffled when he walked. His son, also a dentist in the practice, couldn’t convince him to retire and eventually left. Patients followed, and within months the practice closed, the staff lost their jobs, and father and son stopped speaking. When he died not long after, the town remembered him less for his years of good work than for refusing to put down his drill.

Christina opens her piece for Harvard Business Review, “Leaders Must Speak Honestly About Aging at Work,” with that story because it shows what happens when nobody is willing to have a hard conversation. The article is adapted from her book, Unspeakable: The Taboo Topics We Avoid and How to Talk About Them.

Why we avoid the topic

Christina spends a lot of time with founders of family enterprises talking about when to hand over the reins. Those talks touch on competence, but also money, identity, whether the next generation is ready, and whether the leader has kept up with the industry. Between employment law and plain good manners, most people would rather not bring it up. So organizations carry on as though skills never fade, a pattern Christina sees more often as Baby Boomer founders reach their 80s with no plans to step down.

Four rules for the conversation

Separate succession from age. Keep the discussion on the role, performance, and what the organization needs. A simple “Where do you see yourself in five years?” works at any age and can ease an older employee into talking about retirement.

Keep the conversation going. Succession plans should cover every role, from the CEO down. When managers talk regularly about growth and what’s next, the topic won’t come as a shock when someone reaches a certain age.

Talk about identity and purpose. Leaders who won’t step aside are often afraid of losing who they are. You can’t talk about whether and when someone will retire without also talking about how they’ll spend their days and find meaning.

Factor in the next generation. Sometimes a strong leader should move on because the successor is ready. Christina points to Doug McMillon, who stepped down as Walmart’s CEO at 59 partly for that reason. Framing succession as a responsibility to the organization makes the conversation less personal.

Two leaders, two choices

Christina contrasts two cases she wrote. One is about a European businessman in his 90s who still runs the IT company he cofounded, with a board that keeps extending his term. He doesn’t need the money, but he says he has no idea what he’d do if he stopped. Meanwhile his adult children are ready to lead and stuck waiting.

Gera Developments, a real estate firm in India, went the other way. Rohit Gera had watched his father wait decades to take over from his grandfather. So in 2020, at 55, Rohit started a leadership change himself and brought in a nonfamily leader to run the firm while the next generation is mentored. Today the company and the family are both doing well.

For Christina, the timing should depend on the leader, the successors, and the organization, more than on a birthday. As she puts it:

“The right time to start these conversations is often sooner than you think.”

Christina has written a book on these topics, Unspeakable, with practical guidance for raising the subjects most of us would rather avoid.

Link to the full article below.

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About Christina Wing

Christina founded Wingspan Legacy Partners to help Founders and Families navigate the intersections between Family dynamics, business operations, wealth, legacy and philanthropic impact.