The Last 100 Days: Mastering the Art of the Executive Exit
Leadership transitions are pivotal moments. A CEO’s first 100 days in a role are exhaustively studied; the last 100 days far less so, despite the steep costs of poor exits and the compounding benefits of good ones. For organizations, mishandled transitions can erode shareholder value, destabilize strategy, and undermine trust. For individuals, they can unsettle identity, strain relationships, and tarnish reputations.
Done well, however, a CEO transition can reaffirm direction, reinforce values, and strengthen trust. And yet few leaders or boards show real mastery when it comes to managing executive exits.
Drawing on our combined 60 years of experience working with hundreds of departing executives and our recent interviews with a dozen CEOs, CFOs, equity analysts, and recruiters across geographies and industries, we argue for a more intentional approach to CEO transitions. While the departing CEO is the public face, successful exits are always co-created. We offer operating guidance for board chairs and outgoing CEOs to forge more purposeful transitions.
When CEO Transitions Go Wrong
Even seasoned leaders and boards struggle with CEO exits. Every transition is shaped by a unique mix of people, politics, and circumstances, but all have an emotional undercurrent. They can expose fault lines between individuals and institutions and stir up powerful feelings like shame, embarrassment, fear, relief, bitterness, and sadness. Unlike onboarding, there’s rarely a plan to navigate this difficult terrain.
In an ideal exit, all parties create a virtuous cycle of candor and trust. Organizational stability is maintained, the chair and departing leader reflect and learn, and the business moves forward smoothly. Unfortunately, such exits are rare. The specific causes vary, but we’ve seen these problematic patterns come up again and again:
No clear owner: When no one owns the transition, things drift. Messaging is inconsistent, decisions are delayed, and opportunities for alignment are missed. “Who runs or plans it? The answer is usually no one,” said one recruiter. “It can be a governance vacuum.”
Abrupt or poorly timed decisions: Exits that catch teams off guard and compress timelines erode trust and close the window for a planned handover. They fuel media speculation, sap morale, and create internal noise that distracts from the business.
Board misalignment: Even capable boards can fracture under pressure. A single dominant voice can skew the process. Private doubts go unspoken. Consensus is assumed but not tested. “The board was pushed around by one member,” said one executive. “When they aren’t aligned, or one person dominates, it shows.” Sometimes the chair becomes overly preoccupied with optics. Another executive told us, “They start thinking: ‘How does this look for me?’ rather than ‘What does the business need?’”
Departing CEO behavior: Outgoing leaders often avoid the hard conversations—or worse, sabotage the process. Common failures include delayed announcements that compress timelines and fuel rumors; passive resistance to successor selection or messaging; shadow leadership, where the former CEO lingers, exerts influence, or withholds full support; and emotional denial, where the former CEO ignores their heightened state.
“There’s sometimes a palpable fear that the newcomer will do better,” one recruiter noted. “That doesn’t lend itself to making their successor’s life easy.” Another added: “Shadow CEOs can be a malign force. Passive detraction, faint praise, partial truths—it’s corrosive.”
In many cases, the CEO leaves without being emotionally ready. They’ve delayed the personal reckoning, and that delay distorts how they show up in the final weeks and beyond.
Despite this, we’ve found that boards tend to focus on the costs associated with severance, stocks, and media risk, overlooking the broader cultural and strategic consequences. As one recruiter commented, “If a botched transition throws a company back six months, the cost isn’t counted. Boards only focus on hard costs.”
Getting CEO Transitions Right
Too many exits are treated like terminations, not transitions. Organizations fall back on legal boilerplate—don’t poach, don’t disclose, don’t disparage—rather than crafting a deliberate plan for continuity, culture, and leadership. The result is defensive, transactional, and cold.
Winning CEO transitions require structure, intent, and shared ownership. Based on our interviews and experience, we define three interlocking domains—one individual, two organizational—where exits can create value and reduce risk when handled well:
Personal transitions: Preparing emotionally, exiting with restraint, and handing over with care.
Cultural signaling: Reinforcing values, tone, and continuity through symbolic acts and clear signals.
Strategic inflection: Reaffirming or resetting direction, aligning leadership to the next chapter.
Real benefits accrue when these are handled together with explicit roles and a coherent shared plan that creates space for the human dimension of leaving.
How Departing CEOs Can Successfully Transition
Departing CEOs often underestimate the emotional weight of transition. Even when the decision is mutual or well timed, exits stir up questions of identity, force shifts in status, and deliver the discomfort of the empty calendar. Many assume they’ll take it in stride, but in practice, unacknowledged emotion can leak into unproductive workplace behavior and derail a successful transition. Here are a few ways to avoid that trap:
Do the emotional work early
Several CEOs we interviewed deliberately created space to reflect before stepping away. One revisited every notebook from their tenure to extract lessons. Another packed up weeks early, giving themselves a psychological runway. A third handwrote notes and brought gifts for receptionists and security staff who wouldn’t be at their farewell dinner. These are all intentional acts of closure. “I’m doing my emotional processing now so that when I leave, I leave,” said one departing CEO.
Hand over with grace
Leaders need to create tiered handover strategies mapped around their responsibilities, relationships, and institutional knowledge. This requires structure, of course, but also restraint. One departing CEO aspired to being “the best predecessor [their] successor could have” by taking care of lingering difficult decisions before they left. Another executive described their strategy this way: “I moved from being the driver to being the passenger to not being in the car.” Another executive told colleagues she would be implementing a new rule: “The bar is high for me to speak. If you want to hear from me, call on me.” And another person we interviewed spoke of the humility required in this phase, noting that “the Serenity Prayer is great for transitions.” In the final weeks, contributing less, not more, is often the harder discipline.
Use tone, symbols, and actions to signal culture
Several leaders we spoke to choreographed meaningful actions to reinforce culture on the way out. One, inspired by attending Olympic athletics events, used the relay as a metaphor: “I bought batons and used them in every forum with my successor…I told everyone: ‘Winning relay teams win on the handover.’” Another wrote and recorded her own farewell message to preserve her tone and authenticity: “I didn’t let the dead hand of corporate comms edit it.” Both of these specific gestures reflected the individual leader and signaled respect, continuity, and shared values.
How Boards Can Use the CEO’s Exit to Move the Business Forward
A leadership transition is a symbolic moment. It signals what an organization values, how it treats people, and whether its values are lived or only laminated. Here’s how boards can reinforce identity, continuity, and respect during the transition:
Reinforce with incentives
Forward-thinking firms reinforce good exit behavior by aligning incentives with transition success. “Best-practice CEO transitions involve an economic glide path that gives the departing CEO an interest in their successor’s success,” said one recruiter. For example, we spoke to the retiring CEO of a $1 billion company who agreed to transition out over the course of one year and remain engaged as an active adviser for two more years. Such arrangements are designed to support continuity, protect reputations, and reward clean exits.
Orchestrate endings and create continuity
“Companies and teams need a mourning period to make it clean: organizational Shiva,” said one recruiter. Farewells matter, because the tone of a CEO’s departure leaves a cultural imprint. The board can set a positive tone by allowing the time and space for farewells while remaining forward-looking by helping craft a single, simple narrative about what the departing CEO has achieved, who’s coming in and what they stand for, and how the transition fits into the organization’s story. While departing executives often want to tell their own story, it’s usually more effective for there to be a shared narrative that all key actors can deliver to all stakeholders.
Build alumni relationships with intent
The most effective transitions leave room for alumni to remain close without casting a shadow. Firms that do this well treat former CEOs as long-term assets—advisers, ambassadors, and cultural carriers—not as ghosts at the feast. This doesn’t happen by chance, but requires boards to be intentional about keeping past colleagues in the fold. For example, McKinsey’s alumni program is a dedicated effort to maintain ties with former leaders through relationship managers, alumni communications, curated events, and ongoing access to intellectual capital. As one interviewee put it, “McKinsey’s alumni carrot forces continued engagement.”
Use the moment to reaffirm or reset
Leadership transitions are natural inflection points. They’re an opportunity to signal direction and clarify not just who but also what comes next. Yet boards often miss this opportunity. They focus on the mechanics of the transition and sidestep the deeper questions: What does this transition mean in the next phase of our organizational journey? What kind of leadership does the next chapter require?
Some boards use the CEO’s exit to recalibrate the strategy, shift investor expectations, or send a signal to the organization. Boards need to determine the strategic opportunities presented by an exit and seize the momentum they offer. “Every time someone leaves, there’s a ripple of opportunity. I always portrayed it that way,” said one executive and board member. Departures can consolidate a shift already underway or justify one that’s needed. The key is intention: What should this departure signal?
Clarify the narrative
Leadership transitions are vulnerable to mixed messaging: The outgoing CEO projects continuity, the board wants change, and the new CEO is navigating contradictory cues. The result is drift. The best transitions land a coherent message that links past performance with future ambition and places the emphasis on the business and not the individual. For example, one board member told us, “We timed the announcement to coincide with an earnings upgrade. It was least disruptive and most forward-looking.”
Reinforce governance ownership
Strong board chairs reaffirm expectations and clarify accountability throughout a CEO’s tenure. Conducting succession interviews while the CEO is still in the role ensures that tenure is an ongoing conversation and helps remove the awkwardness that can come from discussing an eventual departure. One of the CEOs we spoke to told us that the chair had never broached the topic with her during her tenure. When she resigned, the organization was unprepared. Another firm included succession readiness in the incentive package for the CEO who was told “We bonus you to take the business to point X by time Y and develop a credible successor.” That created a strategic arc and embedded accountability into the role, making the eventual transition a planned—but not fixed—part of the firm’s evolution.
Handled with skill, a leadership exit itself becomes an act of leadership. It clarifies direction, reinforces values, and models what it means to leave well. That requires intention, structure, and emotional maturity by the outgoing CEO and the board. If the first 100 days define ambition, the final 100 days reveal character. Treat them accordingly.
By James Fulton and Kate Lye
Kate Lye is the founder of The Savoir Group and a trusted partner to C-suite leaders. Her work focuses on how executives in extreme-pressure roles perform, evolve, and thrive. To enquire about partnering with Kate, please get in touch.
