How to Ensure Your Next CEO is Always in the Room

Twilio CEO Khozema Shipchandler outlines a strategy for developing future CEOs from within the company, emphasizing cross-functional rotations, mentorship, and permission to think bigger. He argues that building internal leadership pipelines is critical amid record CEO turnover driven by AI disruption and economic uncertainty.

“Why can’t you be the CEO?” It’s a question I regularly ask my senior leaders at Twilio. Historic leadership factories like General Electric GE , Procter & Gamble, and Ford embody this better than most. True corporate training grounds cultivate talent and chart years-long development pathways. More mobility. More exposure. Programs that teach flexibility and encourage risk. I came up at GE, where I rotated through different programs and took on new roles over two decades. Thanks to that experience, I spend a lot of time thinking about how to make sure each employee at Twilio sees possibility in their careers. How to invest in roles, development, and training to make that possibility real. I believe the next generation of executives is always in the room. It’s especially important now, as AI https://www.fastcompany.com/section/artificial-intelligence disruption and economic unpredictability are driving record CEO turnover at public companies. Boards and leadership teams are tapping operational leaders for the top job, often from outside their ranks. They’re choosing steady hands to steward organizations through unknown waters. The thing is, there is always something transforming the business world. Twenty-six years ago it was the internet, then mobile, then the cloud. Today, it’s AI. Change is constant: The ability to adapt is the thing that matters. I want my teams to benefit from a new kind of leadership factory that draws on the legacy of those storied training programs, and cultivates the most important skills for CEO’s today: agility and adaptability. So, how do organizations ensure that successors built to lead through change are already in the building? While on stage at our company’s annual sales kickoff, I planted the idea that the next CEO is in the room, saying “Somewhere in the audience sits a member of our future C-suite. They just don’t know it yet.” I’ve benefited from this exact idea. My predecessor bet big on me. He routinely gave me the chance to grow beyond my finance roots, take on different operational roles, and learn the full 360 degrees of the business. I have tremendous respect for this approach. I think it’s important to be clear-eyed about what you’re not good at and hire https://www.fastcompany.com/section/hiring people who are, who can complement your skills. And it’s also important to help your team see experience gaps as opportunities. Building leadership pipelines starts with giving people permission to think bigger and imagine themselves at the helm. It sounds simple. But for someone just starting their career, the distance between where they are and where they could be is overwhelming. Permission is just the point of entry. To turn ambition into action you need structure. This means cross-functional, hands-on rotations across the organization. Built-in experiences that close the gap between the idea of the C-suite and the skills you need to run it. Face time with investors one quarter. Earnings preparation the next. Product roadmapping the quarter after. At every stop, mentorship and feedback cycles provide guidance and safe harbor to ask questions, share ideas, and take risks. At Twilio, executive leaders increasingly expand responsibilities and run new departments. We encourage rotations through other teams at different levels. These are some of the most effective ways to build flexible leadership. Moving from a department where you’re a subject matter expert to one where you’re less experienced forces you to manage teams and make decisions without complete information. It creates more cognitive flexibility. You no longer see goals through the lens of your specific department, but through the company’s overall needs. Finally, it teaches professional code-switching, so you can adapt your communication style to the moment at hand. In my more than 20 years in senior leadership roles, aside from permission, the biggest barrier to executive development is desire. The reality is, the higher you climb the corporate ladder, the thinner the air. More responsibility. Longer days. Heightened pressure. It’s not for everyone. Leaders can’t be forced to lead. They have to do it because they want to. At junior levels, I tend to see greater appetite to move between functions, to accept a non-linear experience that speeds up career growth. But the higher up the org chart, the more entrenched people tend to become. I’ve seen careers get stalled by resistance to different experiences and more responsibility. Identifying and honing leaders was the blueprint behind GE’s 110-year-old Corporate Audit Staff program. It was one of the original executive bootcamps I had the privilege of being selected for and eventually leading. Its intensity produced generations of division presidents, C-suite executives, and Fortune 500 leaders. I’ve always found it interesting how many graduates of these programs landed at tech companies, in Silicon Valley and beyond. The rigorous training breeds a kind of adaptability well-suited to the tech world. This serves as the inspiration for how we invest in leaders at Twilio. We have a handful of intensive development programs to grow the next generation of leaders, including a four-month accelerated program for VPs and SVPs identified as top talent and potential successors, and a manager-level program focused on upskilling younger leaders. This has to be part of the value proposition for employees: As organizations grow, so will careers. Leaders have to demonstrate that periods of career uncertainty and risk won’t stall momentum. Leadership doesn’t just mean more work, but more opportunity. Companies everywhere are facing unpredictability: AI-driven disruption is speeding up CEO and C-suite churn, exposing gaps in leadership pipelines. To ensure that the next generation of adaptable leaders is always in the room, create the permission. Build the development structure. Find the willing. This is the design of true leadership factories. The companies set up for transition and long-term stability aren’t the ones looking to fill their leadership rosters from outside the company. They’re the ones constantly building them from within. Khozema Shipchandler is the CEO of Twilio.