Scott Boatwright always aimed to be a CEO. Not just any CEO but the leader of a Fortune 500 company. That moment arrived in late 2024 when he was elevated to the top job at Chipotle after Brian Niccol left to lead Starbucks. But as Boatwright shared at the recent Fortune COO Summit, the jump from second-in-command to chief executive is less a step up and more a transformation.

A CEO today has to run a great business, manage a great stock, and, ultimately, shape a lasting organizational legacy, Boatwright said. As COO, he and Niccol were a strong pairing, he said, because he focused on operations, while Niccol excelled at communicating the company’s growth story to investors. One of the hardest adjustments as CEO, Boatwright admitted, is shifting from pulling the levers himself to managing outcomes through others—and doing so while building investor confidence and long-term vision. “It’s just a completely different job,” he said.

Other newly minted CEOs echoed that learning curve. Howard Hochhauser, the CEO of Ancestry.com and its former COO and CFO, stepped into the role earlier this year at the private equity-backed company. Although he’d previously served as interim chief executive, the weight of the job still caught him off guard once permanently in the role. “Everybody wants a successful exit,” he said. “To do that, you have to grow the company. And now I’m spending 110% of my time on growth.”

At Xerox, Steve Bandrowczak stepped into the CEO role in 2023 following the sudden passing of John Visentin. He had spent five years as COO, was a seasoned CIO, and had attended numerous board and committee meetings. But once he became CEO, the stakes shifted. 

“COOs drive change. COOs make cultural shifts, drive outputs,” Bandrowczak said at the Fortune COO Summit. “The difference as a CEO is you’re now the leader, the face of the company. So you’ve got to be able to drive the culture with shareholders, with employees, with partners, but more importantly, understanding things that you did not know, and the admission of the things that you did not know.”

Bandrowczak encouraged aspiring CEOs to take governance and leadership courses to prepare for the transition to the corner office. And as a teacher of rising executives himself, he offered one consistent piece of advice: “Get comfortable being uncomfortable.”

Ruth Umoh
[email protected]

Today’s newsletter was curated by Lily Mae Lazarus.

This story was originally featured on Fortune.com

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For many senior executives, the COO role is viewed as a pivotal on-ramp to the CEO seat. In fact, last year, 57% of new S&P 1500 CEOs were promoted from COO roles. And some of today’s most notable business leaders, including Apple’s Tim Cook and Chipotle’s Scott Boatwright, made the leap from COO to CEO. But leadership experts warn that what looks like a fast track can just as easily become a dead end.

Stephen Miles, founder and CEO of leadership consultancy The Miles Group, shared two critical missteps for CEO aspirants during Fortune’s 2025 COO Summit. He recounted a story of one COO who began referring to themselves as the company’s heir apparent and not just within the company, but in the boardroom too. The fallout was swift, prompting an emergency board meeting to decide on whether or not to dismiss the executive.

“The board had to be talked off the ledge,” says Miles. “They want the ultimate decision to choose their next CEO.”

This kind of overreach, whether motivated by ambition or miscommunication, can be fatal to a leadership trajectory and demonstrate characteristics counterintuitive for those in the top role, namely arrogance and hubris. More broadly, the COO role, as Miles notes, is often a highly customized position designed to achieve specific outcomes. Treating it as an automatic stepping stone to CEO can alienate key decision-makers.

Aside from overstepping, Miles cites a COO’s failure to align tightly with the CEO as another succession roadblock. Organizations, he says, will constantly test the blueprint for synchronizing and reducing friction between COOs and CEOs. 

“What they do is they go to you as COO and say, ‘Make a decision,’ and then they try to take that decision to the CEO, assuming they want a different decision, or slightly different and see if the CEO will bite,” Miles explains. “As soon as they bite, they erode the entire construct of the CEO-COO relationship, and generally that goes really poorly for the COO.”

While the COO’s job is to “win in the business of today,” as Miles puts it, the CEO’s role is to “build the business of tomorrow.” The leap from one to the other requires more than operational excellence. It demands strategic vision, leadership acumen, and humility.

This story was originally featured on Fortune.com

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For women with ambitions to become CEO, the most reliable path appears to be through the chief financial officer role. Ten percent of women CEOs reached the top after serving as CFO, compared to just six percent of men, according to the Eos Foundation’s 2025 Women’s Power Gap CEO Report. But even this promising route often comes with an added step, writes Fortune’s Lily Mae Lazarus.

Often, women are also expected to serve in an additional position—typically as president—before being deemed ready for the top job. The report found that 32% of women CEOs had to take this extra step, a proving ground that is rarely required of men.

While 11% of Fortune 500 companies are now led by women—a record high—the data shows that progress masks persistent obstacles. Women in the S&P 100 hold 24% of typical pre-CEO roles yet make up only 8% of CEO appointments from those positions.

Andrea Silbert, president of the Eos Foundation, says the imbalance reflects systemic bias in the final stretch of succession. “We can only surmise that there’s bias in that final selection process,” she tells Fortune.

Silbert notes that unconscious bias shows up in small but consequential ways. Boards often demand more proof of readiness from women, including language that suggests women are less visionary or assertive. “We’ve heard, ‘He has more potential.’ We’ve heard, ‘She doesn’t have executive presence,’” Silbert says.

Women are also overrepresented in C-suite roles that rarely lead to the CEO position, such as CHRO. In contrast, CFO roles offer board exposure and financial leadership, which are critical for being seen as CEO-ready.

The takeaway is clear. Women need early P&L experience, visible ambition, and strong internal sponsorship to move up. It falls on companies to foster this, but women also have some agency. “You can’t just keep your head down and work hard,” Silbert says. “You need to build your brand, network, and have coffee with the right people.”

Read the full story here.

Ruth Umoh
[email protected]

Today’s newsletter was curated by Lily Mae Lazarus.

This story was originally featured on Fortune.com

Female leaders are increasingly landing roles that traditionally serve as launchpads to the corner office. A record 11% of Fortune 500 companies are now led by women. But behind that milestone lies a more sobering truth: Women still face a steeper climb to the top, often required to take more steps and log more experience than their male counterparts to be seen as ready.

According to a 2025 Women’s Power Gap CEO Report from the Eos Foundation, a philanthropic organization focused on advancing gender and racial equity in leadership, women in the S&P 100 now hold 24% of the most common “launchpad” roles for CEOs, including chief operating officer, president, and division head. Yet they account for just 8% of CEO appointments from those positions. 

This gap is not due to a lack of qualifications. The data shows that women are equally, if not more, capable than male CEO candidates. In fact, 32% of women CEOs took an additional step as president before being elevated to the CEO seat.

“We can only surmise that there’s bias in that final selection process,” Andrea Silbert, president of the Eos Foundation, tells Fortune. 

Silbert explains that unconscious bias can emerge both before and during the CEO selection process, often in subtle but consequential ways. One telling example is the unspoken expectation that women must prove themselves in an additional proving ground—typically as president—before being deemed CEO-ready. This extra step, she notes, serves as a form of risk mitigation that is rarely required of men, reinforcing the notion that women must be overprepared to be considered equally qualified.

During the actual selection process, gendered assumptions about leadership can further place women candidates at a disadvantage. “We’ve heard, ‘He has more potential.’ We’ve heard, ‘She doesn’t have executive presence.’ At the worst end of things, we’ve heard of women told that they are shrill,” Silbert says. 

The structure of the C-suite also plays a role. While women are increasingly making inroads into the C-suite, they remain concentrated in roles that rarely lead to the very top, such as chief human resources officer, chief marketing officer, and chief sustainability officer. Women occupy 76% of CHRO positions and 56% of CMO roles, according to the report.

By contrast, roles with direct financial and operational oversight remain a more straightforward path to the CEO seat. While women are often siloed into non-P&L-facing functions, they still hold 19% of CFO roles—a position long seen as a primary gateway to CEO. The CFO-to-CEO pipeline is more common among women than men: 10% of women CEOs followed that path, compared to just 6% of men. 

Ultimately, for women aspiring to be CEOs, the data indicate a higher likelihood of success for those with extensive P&L experience.

“Even the women who made it to CEO through the CFO route had, in many cases, held a prior P&L role. It’s another way that the companies assure that the woman has that rounded experience [and] that they are 110% qualified for the job when they’re being appointed,” says Magdalena Punty, the Eos Foundation’s director of research.

For aspiring women CEOs, Silbert and Punty’s advice is clear: pursue P&L roles early, be vocal about your ambitions, and approach your career with intentionality.

“You can’t just keep your head down and work hard,” says Silbert. “You need to build your brand, network, and have coffee with the right people. A friend of mine used to say, ‘It’s a campaign to break the glass ceiling.’”

This story was originally featured on Fortune.com

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