Latest / Executive Careers with Fexingo: VP, C-Suite, and Senior Leadership Career Strategy / The Inside Track to Chief of Staff Roles
Transcript
- Lucas: Luna, I want to talk about a role that is quietly becoming the single most effective launchpad to the C-suite, and most senior leaders aren't taking it seriously. Luna: You mean the Chief of Staff role? I've noticed more of those titles appearing in executive bios lately. Lucas: Exactly. And it's not just a fad. A 2025 study by the Executive Leadership Council found that executives who served as Chief of Staff to a CEO or a senior EVP were promoted to VP or above within three years at a rate of 67 percent. That's roughly double the promotion rate of their peers in traditional line roles. Luna: Double? That's striking. But I think a lot of people still see it as a glorified scheduler. How did we get from assistant to career accelerator? Lucas: It started in the military, frankly. Every general has a Chief of Staff. The private sector really picked it up in the late 2010s. Salesforce made it a core part of their leadership development pipeline. They had a formal program where high-potential directors would spend 18 months as Chief of Staff to a regional president before moving into a GM role. Luna: And Google, too. I remember reading that Sundar Pichai's first Chief of Staff at Google, Kristin Reinke, later became VP of Product Operations. Lucas: Right. That's the pattern. You get a direct line to the most strategic decisions in the company. You see how the CEO allocates attention, how they handle board dynamics, how they kill projects. That's not something you learn in a P&L role. Luna: But here's the pushback I hear from senior leaders: 'I don't want to be a staffer. I want to run something. Taking a Chief of Staff role feels like a step sideways.' Lucas: I hear that too. And I think it's a framing problem. It's not a step sideways — it's a step into the engine room. You're not running a single function; you're learning how all the functions connect. The best Chiefs of Staff I've seen don't just manage calendars. They run the weekly leadership meeting, they triage strategic decisions, they draft the board deck. That's real operational muscle. Luna: So what's the actual scope? I've seen job descriptions that range from 'manage the CEO's inbox' to 'lead cross-functional strategic initiatives.' Lucas: The gap between those two is where the value lives. A well-designed Chief of Staff role has three pillars. First, strategic projects: you own the CEO's priority list — the top three things that need to happen that quarter. Second, organizational cadence: you design the rhythm of the executive team — what gets discussed, when, and who decides. Third, communication and alignment: you connect the CEO's vision to the rest of the company. Luna: That's a lot of influence without formal authority. Lucas: Exactly. And that's the skill a future CEO needs. You learn to lead without a big team. You learn to influence peers who are two levels above you. That's why private equity firms now routinely install a Chief of Staff at portfolio companies they're trying to turn around. Luna: Let's talk about how someone positions themselves for this role. If I'm a VP of Marketing and I want to make that move, what do I do? Lucas: A few things. First, you need to be known for operational discipline, not just functional expertise. The CEO wants someone who can run a meeting, drive a decision, and follow through. Second, you need to have a relationship with the CEO or the senior executive you'd serve. This role is almost never filled through a job posting. It's a conversation. Luna: So networking within your own company is key. Lucas: Critical. And you need to articulate why you want it. If you say 'I want to learn from you,' that's fine, but better is 'I want to help you scale your impact.' That's the pitch. You're not asking for a favor. You're offering to make the executive more effective. Luna: What about the downsides? I've heard stories of Chiefs of Staff who got stuck doing expense reports and never broke into strategy. Lucas: That's real. And it comes down to two things: the executive you work for and your own ability to push for substance. If the CEO sees you as a personal assistant, you'll be organizing their kids' soccer schedule. You have to establish, in the first 30 days, that you are there for the business. I tell people to negotiate a charter upfront. Define what projects you own, what meetings you attend, what decisions you influence. Luna: And if the executive resists that? Lucas: Then you probably don't want the role with that person. The best Chiefs of Staff I know worked for executives who genuinely wanted a partner. At Microsoft, when Satya Nadella became CEO, he created a Chief of Staff role that effectively ran the Office of the CEO. That person didn't just manage his calendar — they helped shape the cultural transformation. Luna: That's a good example. So the role can be transformative, but it's also high-risk. How do you know if it's right for you? Lucas: I think it's right if you are more interested in how the whole system works than in being the best at one thing. If you love strategy but you're also comfortable with execution — the messy, operational details — then it's worth exploring. And the timing matters. The sweet spot is when you're already a strong individual contributor or a small-team leader, not when you're running a large division. You don't want to give up too much direct authority. Luna: So someone who is a VP of a small unit, or a senior director, is in the ideal zone. Lucas: Exactly. You have enough credibility to be taken seriously, but you're not so entrenched that you can't step back. And the exit options are excellent. After two years as Chief of Staff, you can go back into the business as a VP of a larger group, or you can go into corporate development, or you can become a COO. It's a flexible credential. Luna: I want to come back to something you said earlier about private equity. Can you expand on that? I've heard that PE firms are increasingly using Chiefs of Staff as a talent pipeline for their own operating partners. Lucas: That's a huge trend. Firms like KKR and Blackstone have started programs where high-potential associates or VPs from their portfolio operations teams embed as Chiefs of Staff at portfolio companies. It gives them hands-on turnaround experience without the full commitment of a CEO role. And for the portfolio company, they get a disciplined operator who understands how PE thinks. Luna: So it's almost like a rotational program for future leaders. Lucas: Yes. And it's spreading. Even outside PE, companies like Stripe and Airbnb have created Chief of Staff roles that are explicitly designed as two-year stints before moving into a VP role. It's becoming a standard part of the corporate ladder. Luna: I'm curious about compensation. How does it compare to a line role at the same level? Lucas: Generally, it's comparable, though the bonus structure might be different. You're often on the same pay band as a senior director or a junior VP. But the equity component can be higher because you're closer to the center of value creation. I've seen Chiefs of Staff at large tech companies get restricted stock units that rival those of division VPs. Luna: Makes sense. But what about the title? Some people worry that 'Chief of Staff' doesn't sound as prestigious as 'VP of Something.' Lucas: That's a perception that's changing. Ten years ago, people might have raised an eyebrow. Today, in most executive circles, a Chief of Staff title signals that you have the trust of a top executive. It's almost a badge of honor. And if you're worried about the resume, you can always frame it as 'Chief of Staff to the CEO' — that carries weight. Luna: So let's say I'm a senior director and I decide I want to pursue this. What's my first move? Lucas: First, identify the executive whose style and priorities align with yours. It doesn't have to be the CEO. It could be the CFO, the COO, or the head of a large business unit. Then, find a way to add value before you ask for the role. Volunteer for a cross-functional project that matters to them. Show that you can think across silos. Make yourself indispensable on a small scale first. Luna: And then have the conversation. Lucas: Yes. And when you have the conversation, be direct. Say, 'I see how much is on your plate. I think I could help you scale by taking on some of the strategic coordination. Would you be open to exploring a Chief of Staff arrangement?' That's a conversation, not a demand. Luna: I think this is a really practical episode for our listeners. If today's episode was useful to you and you want to keep it ad-free, buy me a coffee dot com slash fexingo helps. Lucas: Yeah, and we genuinely appreciate that. It keeps these conversations accessible to everyone. Luna: So back to the Chief of Staff — what's a common mistake people make once they land the role? Lucas: The biggest mistake is trying to do everything. You can't own every project. You have to be ruthless about prioritization. The Chief of Staff role is a leverage point, not a workhorse. If you're working 70-hour weeks and still missing deadlines, you're not using the role correctly. You should be the person who makes the executive team more efficient, not the bottleneck. Luna: So delegation is key. Lucas: Absolutely. And also knowing when to say no. The CEO will ask you to do things that are not strategic. You have to be able to push back respectfully. 'I can do that, but it will delay the board deck.' That kind of trade-off conversation is part of the job. Luna: Final thought — where do you see this role going in the next five years? Lucas: I think it becomes a standard rung on the ladder to the C-suite, especially in complex organizations. We'll see more formal training programs, more rotation models. And I think the title itself will gain even more cachet. Five years from now, a Chief of Staff role will be seen as one of the smartest career moves a senior leader can make. Luna: That's a good note to end on. Thanks, Lucas. Lucas: Thanks, Luna.