Most CEOs know succession planning matters. They also know it is easy to delay.
The business is running. The leadership team is in place. There may even be someone who could step in if something unexpected happened. That can make succession feel partly handled, especially when there are more immediate issues competing for the CEO’s attention.
But having a name in mind is not the same as having a plan.
That was one of the central issues discussed in a recent Chief Executive Coaching webinar with Greg Kaufman, former CEO of Amstore and Chief Executive coach, and Mark Debinski, founder and president of Bluewater Advisory.
Succession often gets delayed not because CEOs are avoiding reality, but because it raises difficult questions that do not always need to be answered right away. How much of the company still depends on the current CEO? Is the next generation of leadership truly ready? What does the outgoing CEO want their own next chapter to look like?
Those questions can sit quietly in the background for years. Then a health event, family issue, board concern or leadership gap can suddenly make them urgent.
The better approach is to treat succession as a strategic discipline before the timeline is forced. That means looking beyond who might take over and asking whether the business is being built to keep moving without depending too heavily on the person currently leading it.
One of the easiest succession mistakes is confusing emergency coverage with true succession planning.
Mark shared the example of a business owner who believed he had a succession plan because he had written a potential successor’s name on a piece of paper and put it in a safe. That answered one narrow question: who might get called if something happened tomorrow?
But it did not answer the larger questions that determine whether a transition will actually work.
A real succession plan should clarify what the business will need in its next phase, how the future CEO role should be defined, whether internal leaders are being developed against that role and how authority will shift when the time comes.
Every company needs a contingency plan. But the name in the drawer is not Plan A. The deeper work is preparing the company for a leadership transition that does not rely on assumptions, personal loyalty or last-minute decisions.
The wrong first question is, “Who can replace me?”
The better question is, “What kind of leadership will this company need next?”
Greg made the point clearly: the next CEO is rarely supposed to be a “mini-me” version of the current CEO. The business has changed. The market has changed. The team has changed. The next stage may require a different kind of leader than the one who built the company to this point.
That can be hard for a founder or long-tenured CEO to accept. The company may have been built around their instincts, relationships, technical knowledge or way of operating. But succession planning should not be an effort to preserve the past. It should be a way to prepare the company for what comes next.
The next CEO may need to steward what has already been built, lead a turnaround, accelerate growth, professionalize operations, deepen the management team or bring more discipline to a more complex organization. Those needs should shape the role before candidates are evaluated.
Mark described this as creating a clear benchmark for the future CEO role.
That work matters because successors often default to what they already know well. A leader who grew up in sales, product, engineering or operations may over-invest there unless the CEO role is clearly defined.
A strong process forces the company to define the job before deciding who should hold it.
Internal succession can look cleaner than it really is.
A CEO may believe a person has the right potential. The board may assume someone is next in line. Employees may already view a senior leader or family member as the likely successor.
But potential is not readiness.
Greg shared the example of a next-generation leader in a family business who did not simply step into the role because of her last name. She had built experience outside the company first. When she entered the business, she began by leading the strategic planning process. That gave her a way to work with the board, engage the management team and help shape a long-term vision for the company.
That kind of process gives a potential successor something more valuable than a title. It gives them a chance to build credibility before the formal transition. It also gives the company evidence of how they lead, communicate, make decisions and work across the enterprise.
A future CEO should not be evaluated only on functional performance. The best salesperson, operator or finance leader may not automatically be the right CEO. The role requires broader judgment: setting direction, making tradeoffs, building alignment and carrying the weight of the whole business.
That is why stretch assignments matter. A potential successor might lead strategic planning, present regularly to the board, take ownership of a cross-functional initiative or manage a major customer, acquisition, expansion or operating challenge.
The goal is not to create a ceremonial path to the title. It is to determine whether the person is truly ready, what gaps still need to close and whether the company needs additional options.
Succession planning often focuses on the next leader. That is necessary, but incomplete.
The outgoing CEO also needs a plan.
Greg called this one of the most underestimated parts of the process. For many CEOs, leaving the role is not just a professional change. It is one of the biggest personal transitions they will make. The company has often been the center of their identity, relationships, reputation and purpose for years, sometimes decades.
If that reality is not addressed directly, it can complicate the handoff.
A CEO may say they want to step back but continue to weigh in on decisions. They may support the successor publicly but remain the person everyone turns to privately. They may want the business to become less dependent on them while still struggling with what that means day to day.
That is not a character flaw. It is a predictable part of the transition.
Greg’s guidance was to treat the CEO’s next chapter with the same seriousness as a major business decision. What does the outgoing CEO want their role to be after the transition? What do they want their life to look like? How will they stay engaged in work that matters without preventing the next CEO from fully leading?
Mark framed this as the predecessor’s need for a personal strategic plan. That could mean becoming executive chair, serving as an advisor, focusing on ownership matters, joining outside boards, returning to school, spending more time with family or stepping into something entirely separate from the business.
The specific answer will vary. What matters is that it is intentional.
Without that clarity, the outgoing CEO can unintentionally stay in the way. With it, the transition is more likely to feel less like a loss and more like one of the CEO’s most important contributions to the company’s future.
A former CEO can stay involved after a transition. In some cases, that is helpful. In others, the company needs a cleaner break.
The real risk is unclear involvement.
If employees still believe the former CEO has the final say, the new CEO’s authority is weakened. If senior leaders keep going around the successor to get the former CEO’s opinion, the transition is incomplete. If the outgoing CEO continues to influence decisions through back channels, the organization receives mixed signals.
Greg and Mark both emphasized that the symbolism matters. Who holds the microphone at company events? Who sits at the head of the table? Who keeps the big office? Who runs the board meeting? Those details may seem small, but employees notice them.
The company should be clear about what decisions the new CEO owns, what role the former CEO will play and how the two will communicate. A former CEO may serve as an advisor, board member, industry ambassador or source of institutional knowledge. But the boundaries need to be agreed to and documented.
A good handoff gives the new leader access to the former CEO’s wisdom without leaving anyone confused about who is actually running the company.
Succession decisions are rarely neutral.
Internal candidates come with history. A past mistake may be remembered longer than it should be. A trusted executive may be viewed more favorably because of years of loyalty. A family member may face either inflated expectations or unfair skepticism. External candidates may seem stronger simply because their weaknesses are not yet visible.
That is why objectivity matters.
Greg emphasized the value of having a board or board-like group involved in the process. Not every company has a formal board, but most can create a small group of trusted advisors to provide discipline, accountability and perspective.
Mark also noted the role of assessments, as long as they are used appropriately. They can help clarify communication style, behavioral tendencies, motivations and fit against the future CEO role. But they should not become the decision by themselves. They are inputs, not verdicts.
The company still needs judgment. It needs real observation, honest discussion and a process that keeps personal preference from overtaking business need.
Outside perspective also helps with communication. Employees do not need every detail, and the process should not become a public horse race. But silence creates its own risk. People can usually sense when a transition may be coming. If they hear nothing, they may start to wonder whether the company has a plan at all.
Greg’s guidance was to communicate transparently, but generally. Let people know the company is planning carefully. Reassure them that continuity matters. Avoid creating unnecessary competition or anxiety by naming candidates too early or sharing details the broader organization does not need.
Succession planning does not have to start with a final decision. In many cases, it starts with the questions a CEO, board or ownership group has been avoiding because the answers are not yet clear.
Those questions are where the real work begins:
The answers do not need to be perfect at the start. But the questions move succession out of the abstract and into the work of preparing the company, the successor and the outgoing CEO for what comes next.
Succession planning is most useful before the timeline is forced.
In an ideal world, companies give themselves several years to define the future role, develop internal talent, evaluate options and prepare the outgoing CEO for the transition. Mark noted that five years can provide a strong runway, though many companies work with less time.
Greg put the timing question more simply: the best time to plant the tree may have been years ago. The second-best time is today.
Starting early does not mean the CEO has to announce a retirement date. It does not mean naming a successor immediately. It means beginning the work while there is still time to do it well.
That work may include defining the future CEO role, identifying where the business still depends too heavily on the current CEO, developing internal leaders through stretch assignments, clarifying the board’s role and thinking honestly about what the current CEO wants next.
Succession planning is often treated as a question of who comes next. That is too narrow.
The real goal is continuity: continuity of leadership, strategy, culture, customer trust and enterprise value.
Handled well, succession planning does more than prepare for a transition. It strengthens the company now by forcing clarity around leadership, authority and the future of the business.
For a CEO who has spent years building the company, that may be one of the clearest signs that the business is ready for what comes next.
Succession planning is easier to work through before the decision becomes urgent.
Chief Executive Coaching helps CEOs think through the leadership, timing and personal questions that come with preparing for a transition. Our coaches are all former CEOs, matched by stage, industry and the challenge you are working through.
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