Why your most senior leaders won’t tell you when they’re leaving

Most organizations assume senior leaders go quiet about retirement because they are reluctant. Our research suggests a less comfortable explanation: the process is built to reward silence.

The cost is already visible. 67% of Baby Boomer leaders have no plans to leave their roles within three years. Gen Z, Millennial and Gen X executives name career progression as their top reason for considering a move. Baby Boomers name work-life balance. The ladder is blocked at the top and the talent beneath it is looking elsewhere. Our survey of 2,531 executives shows a contradiction: 87% say their career path is clear and 71% say a succession plan is documented, yet 48% are still considering a change.

Four retirement discussion design flaws

Our research with Harvard Business School Professor Rebecca Karp found that four common features of executive transition processes can limit honest conversations about what's next.

1. Notice can cost money. One HR leader explained that executives who volunteer their plans may lose severance, so they are incented to wait for the company to ask.
2. The asker reports to the asked. The person who should raise the topic is, in effect, raising it with their boss.
3. Disclosure rules reward vagueness. Conversations stay deliberately imprecise so they do not trigger public disclosure.
4. Announcing early costs authority. Once people know a leader is leaving, influence fades.

Each of these is rational for the individual. Together they guarantee that planning starts late.

What HR leaders say works

• Reward notice. Tie part of the exit package to how early a leader gives notice, so planning ahead pays.
• Take the conversation out of the reporting line. Make succession a standing board agenda item, not a private exchange between a leader and their boss.
• Ask successors what they want. A name on a plan is not a candidate until someone has asked. One HR leader described naming a successor who, at the moment of truth, wanted nothing to do with the role.
• Run a fair process. Internal candidates who believe they had a real chance are more likely to stay when they lose.
• Design the next role. Build tailored executive encore careers based on the person, not their end-date.

The takeaway: If your late-career leaders are not talking about their exit, examine what’s preventing the conversation. It may be incentive-related in the interest of a severance package, or it may be a physiological aversion in retirement altogether.

Is it a financial play or an identity construct?

Increasingly, executives are rejecting the perceived retirement script and working later in life. In partnership with Harvard Business School Professor Rebecca Karp, our research found that late-career executives look at retirement as losing their identity, relevance and decision rights. The distinction between the motivators matters because a leader staying for financial reasons is a different planning variable than one staying for engagement.

If you’re finding your senior leadership is pushing back retirement to stay engaged, take a good look at the executive transition plan. Redefine your executive encore careers not as a full career exit, but as redirected work at a different pace. Our research identified four retiring executive archetypes all looking for different career contributions in their next career stage.