The question arises not just because Oracle recently announced that two executives are the company’s new CEOs, succeeding Safra Catz, who had been CEO or co-CEO for the past 11 years. Making the succession more intriguing, Catz has been elevated to the board of directors with a previously unheard-of title, while founder Larry Ellison continues as chairman of the board and chief technology officer, but with duties that are by no means transparent. Result: We know who Oracle’s CEOs are by title, but who they are in reality may be less obvious.

The stakes in Oracle’s unique succession experiment are extraordinarily high. The company’s stock has suddenly rocketed, doubling in the past four months, making Oracle the world’s 12^th most valuable company. It’s a magnificent performance, but investors might like to know, especially now—who’s really running the show?

In the plain vanilla version of managing a big corporation, it’s simple: The CEO runs the show, and the board oversees the CEO and overall management of the company. It doesn’t wade into day-by-day decisions. But in some companies, 11% of the Fortune 500, the board is led by an “executive chair” who is not the CEO but who participates in the company’s management while also running the board. Typically, the executive chair is the previous CEO, and the new CEO typically reports to that person. “When you’re executive chair, the buck stops with you,” says Charles Elson, a corporate governance expert who has served on multiple boards. “It’s a title change with little meaning. You’re still running the show, period.” Think of it this way: “executive chair” = “real CEO.”

At Oracle, the board made long-time CEO Ellison executive chair in 2014, and Catz and Mark Hurd became co-CEOs. But then things get murky. Ellison quickly stopped calling himself executive chair and adopted his current title, though the company doesn’t seem ever to have announced any change in his role. (Oracle has not responded to queries.) Catz and Hurd continued as CEOs until Hurd took a leave of absence then died in 2019, after which Catz carried on alone.

With that as background, look at Catz’s new title: Executive Vice Chair of the Oracle Board of Directors. It’s a bit odd because in corporate governance, “there is no such title as vice chair of the board” says Elson. Corporations are required to have boards, and boards must have chairs, but that’s it. In addition, it’s hard to see how a board could include Catz as executive vice chair, even as an honorific title, unless it includes Ellison as executive chair, in reality if not in title; otherwise the vice chair would hold more power than the chair.

All of which suggests that Oracle’s new CEOs, Clay Magouyrk and Mike Sicilia, may not quite be CEOs in the usual sense. With two of them, the corporate bucks never fully stop with either. Plus, with at least one board member who is also a declared executive, they’re outranked.

So how many CEOs does Oracle have? Officially two, arguably four. And who knows, maybe it will all work spectacularly. What we know for sure is that no matter how this set-up goes, CEOs, directors, and ambitious executives will study it for years.

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“Should I stay or should I go now?” Although the phrase brings to mind The Clash’s punk rock classic, it’s a weighty question for leaders contemplating a career move.

A record number of CEOs left their roles last year, according to the 2024 Global CEO Turnover report by Russell Reynolds Associates (RRA), a global leadership advisory firm. The analysis, which tracks CEO departures from 13 global indices, indicates 202 CEOs left their roles in 2024, up 9% from 2023.

RRA broadly attributes the global increase to investor activism and technological change, but it was also likely a deeply personal decision for each of those leaders. Whether you helm a worldwide powerhouse, a Main Street staple or a treasured family business, the decision to leave is influenced by a multitude of factors requiring careful consideration.

Engage in self-reflection

Ashwini Nadkarni, M.D., assistant professor of psychiatry at Harvard Medical School, says the decision to step down should come after a process of self-reflection.

“I think it’s helpful for leaders to ask themselves a set of questions to arrive at that conclusion and take some time to be thoughtful when they assess their decision,” she says. “Some important questions to ask oneself include…”

• How have I grown?
• What skills did I gain?
• What have I achieved?
• How have I contributed to other people’s development or success?
• Am I still professionally fulfilled in this position?

Nadkarni explains that those answers then must be weighed against the leader’s goals. If a leader is considering retirement, these answers could determine if they’ve accomplished all they hoped for during their career. If a leader is not considering retirement, but instead contemplating a career move, they must examine their answers and ask if their current position and company will enable them to continue growing and help others do the same.

“Leaders have to ask themselves, ‘Is there that space for me?’” Nadkarni says. “The other question that they have to ask themselves is, ‘Will my departure create space for others?’… There’s that tipping point where our growth compromises the growth of others.”

Nadkarni says it’s also important for a leader to consider how they’re handling the challenges of their position. What was once exciting and invigorating may now be exhausting and overwhelming.

“People can end up becoming increasingly cynical or experience emotional exhaustion, and so when that point comes, it’s a great time to hand over the role to somebody else because you know that they’ll apply a new energy,” she says.

Although every leader would prefer to exit on their own terms, sometimes external stressors lead to a departure. Nadkarni says if a leader is consistently receiving negative feedback, it may be time to make a change. Unexpected life events such as health problems or the death of a spouse can also require a person to leave a position.

Seek support

Even if all signs are pointing to resignation or retirement, it can still be a difficult transition, especially if it’s a long-held position or a role in a family business. Nadkarni says seeking support from friends and family, consulting with a career coach or seeking mental health support can help leaders reconcile their personal emotions and the company’s needs.

If a person is “not in a place of acceptance about the fact that the organization and the individual are moving in two different directions… to get to that place of acceptance, it probably requires some additional reflection,” she says.

Nadkarni acknowledges that leadership changes in family businesses can sometimes be especially stressful or intense due to the emotions that come into play with family dynamics.

“There are actually organizational psychiatrists and behavioral health specialists who specialize in that specific area of focus, where they consult families in that setting,” she says. “Seeking out advice from such a person who’s had that experience and expertise in those specific situations is important.”

Leave a legacy

As leaders prepare to leave a role, they may want to solidify their legacy to ensure their time spent was meaningful.

To do so, a leader should first identify their values, which will in turn define their sense of legacy. For example, many people value relationships within the business or visibility of specific projects or work, so Nadkarni advises shoring up those things in the months leading up to an exit.

“I think most people would probably agree that a legacy as a leader is certainly defined by your impact on your team and mentorship that you’ve had, the career advancement that you’ve facilitated for others,” she says. “Continuing to amplify that over time, I think that that is really critical.”

She says leaders can build on that outside their role and continue to share their expertise in their next professional chapter through consultant work, writing and teaching, or even “creating your own content platform for people or exploring things like social media as a way to offer that information.” She adds, “A lot of times people will move from a leadership role to teaching at a college.”

She also notes that many of the skills used at work are also needed in nonprofit organizations and can be shared through volunteer work.

Activate a plan

Nadkarni suggests, if the leader is leaving on their own terms, to allow at least a year for the exit process and transition to a successor. It’s important to allow enough time to talk to key stakeholders and help develop the incoming leadership team.

“Having those meetings and ensuring you have a good runway… that’s key,” she says.

Although the idea of leaving a leadership role can be overwhelming and the exit process can be exhausting, it’s best to be proactive. Otherwise, those Clash lyrics may come back to haunt you: “If I go there will be trouble, and if I stay it will be double.”

By planning ahead and working thoughtfully through the transition process, you will not only promote and facilitate the company’s next chapter but also blaze a new trail for yourself. 

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If you’ve ever seen the HBO original series Succession or have heard of the Murdoch family’s succession drama, you might already know that succession planning can get messy. A succession plan needs a lot to succeed, and gaining the support of key stakeholders, such as the board of directors or investors, is essential.

When developing a leadership pipeline, be it the CEO position or other major role, securing the support of these integral members of your company will ensure your plan runs smoothly. And while the ideal scenario would be for your stakeholders to embrace your plan with open arms, unfortunately, this is often not the case. To help facilitate an easier transition for your company, we spoke to experts to understand how to gain buy-in from investors and the board on a succession plan.

3 tips to ensure a succession plan goes over smoothly 

To develop a succession plan that stakeholders will support, experts agree that it comes down to clear communication, identifying the right talent and preparing them for the role early on.

1. Focus on Communication

The most important action a leader can take to ensure a trouble-free transition is to communicate clearly and often with the investors and the board of directors about the plan, says Marissa Rodriguez, the founder and CEO of Through Experience, a platform that helps CEOs grow their e-commerce business. 

“Uncertainty can often breed confusion and chaos,” she says. “This is why it’s so important that leaders overcommunicate, have clear intentions and can give others a sense of direction.”

To provide clarity on the process, Rodriguez advises developing a plan with key milestones and dates that everyone can reference, from identifying and training potential successors to their eventual assumption of the role.

2. Create a culture of succession planning

Raising a succession plan to your investors and board of directors might cause concern, but if your company is always planning for leaders’ replacements, it will feel like the norm to key stakeholders.

Mary Josephs, founder and CEO of Verit Advisors, an investment banking advisory firm, recommends giving “constant attention to succession for all major roles across the organization. This means early talent identification, coaching and training, exposure, and support.”

To build a company accustomed to succession planning, Christine Edwards, principal at The Red Bee Group, a business consulting firm, recommends that the CEO and CHRO identify potential leaders who are two to four levels down on the organizational chart and begin orienting them early on. “A process by which directors can meet with those leaders earlier on in their careers is helpful, as is bringing those leaders to the board or committees to discuss issues,” she explains. 

For potential leaders outside of the organization, Edwards says, “benchmarking external candidates with a smaller group of directors is also healthy and provides the ability to compare skills and accomplishments.”

3. Invest in potential talent

Once potential leaders are identified, it’s critical to invest in them to ensure they are ready to fulfill the role when it’s time. Having talent pinpointed and already familiarized with the role prior to their transition will help investors and board members feel confident in your plan.

To prepare a successor for the job, Josephs recommends giving them time to shadow the exiting leader before they assume the position.

“This is expensive, as it often includes the next executive shadowing the previous executive for six months to a year. However, it is well worth the investment. It provides time for transitioning key relationships and trust (investors, team, clients, industry, COIs, etc.), understanding client and team nuances to be effective, [and a] safe space to practice decisions,” Josephs says.

Getting key stakeholders’ buy-in

To gain your investors’ and board members’ support, you’ll need to have plenty of discussions about the plan in order for everyone to feel comfortable moving forward.

According to Edwards, the leader or CEO should begin the conversation by discussing any upcoming leadership shifts before they happen and delving into why they are happening. “Repeating those discussions a few times before the changes are made provides ample time for the board to reflect, ask questions and signal agreement with the changes,” she says.

Josephs recommends the CEO share their vision on what strengths and capabilities will best serve the organization. “It [might] paint the picture on why we would look outside the organization, or why there are strong internal candidates,” she says.

To gain buy-in from your investors and board of directors on your succession plan, Rodriguez says you’ll need to be aligned on these five issues:

• Why are we doing this succession plan?
• What does success look like at the end of the transition?
• What does success look like long term?
• What could go wrong? How are we going to mitigate those possibilities?
• What benefits emerge from this transition to the overall business?

Challenges to succession planning 

When succession planning, roadblocks are inevitable. Here are some challenges that might arise during the process and ways to navigate them.

1. Conflict of interest

Be wary of conflicts of interest when doing succession planning. For example, if the incumbent has shares in the company, this could lead to bias in their decision-making during the process, such as supporting a potential successor who would increase or maintain their financial interests rather than choosing a candidate that is best for the company’s long-term success.

To navigate these issues, Henry Penix, CEO and executive chairman of Soaak Technologies, which specializes in sound frequency composition therapy, says to look to your company’s bylaws or operating agreement to locate what your business has decided when it comes to succession. 

“These documents will also mention what happens with shares in a company owned by a majority or significant shareholder. Typically, things like voting control, the purchase of shares outstanding and management are clearly and legally defined,” Penix says.

The board of directors will use these internal rules to ensure that the succession planning process is fair and unbiased.

“Conflicts of interest should always be monitored,” Josephs says. “One should not stay in a position if they are no longer the best leader to drive shareholder value. But it can be enticing to stay if stock prices are growing, increasing personal wealth. The culture needs to be about the organization’s overall growth.”

2. Lack of buy-in from the board of directors or investors 

Even if you have spent months developing a concrete succession plan, there’s always the possibility that the board of directors and investors won’t give their support.

“If the investors/board of directors do not align with the initial intention of the succession plan, it will be a challenge for the leader,” Rodriguez says. “If they do not want the leader to leave and are not receptive to this intention and idea, then the leader might have to sell them on the reasons why it is to their advantage to bring in a new leader.”

3 Personnel issues

It can get sticky when someone who’s seen as a natural choice to succeed a leader is not picked for the job.

“Perhaps the obvious internal candidate has been your right and left hand as you led the company. Perhaps the company has a history of promoting from within. Yet you know this No. 2  is not the right leader to hold the CEO spot. These are tough decisions,” Josephs says.

“All stakeholders and candidates need to understand this is not personal; it’s business,” she adds. “Those not chosen are not inferior candidates. They’re just not the best choice now.”

Having these difficult conversations upfront can mitigate potential upset later. “Clarity always wins,” Rodriguez says. “The more clear one is about the intention and what is required in order to achieve success (and the desired outcome) the better for everyone involved.”

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