Everything you need to know about becoming a Chief of Staff (with Clara Ma)
what do Chief of Staffs actually do? how should you navigate your way to the job?
You hear the word “Chief of Staff” more and more these days. It is certainly one of the most popular positions we hear about through the next play network. But what do Chief of Staffs actually do? If you’re interested in becoming one, how should you navigate your way to the job? If you’re a founder, when does it make sense to hire a Chief of Staff versus when is it more of a waste of time? We talked to Clara Ma to help answer those questions and more in this deep dive. Clara was previously a Chief of Staff at a fast-growing Silicon Valley tech company and now runs a community helping people become and thrive as Chief of Staffs at many of the best startups in the world. She’s got a lot of very useful thoughts on how to think about the Chief of Staff position that we think would benefit anyone exploring the role. Hope you enjoy!
Quick disclaimer we always give before diving in: you should read the below as ideas and perhaps some suggestions but NOT prescriptive advice. There’s more than one way to live your life, and so our only advice is that you should think for yourself (if you want 🙂).
Tell us a bit about your background.
I like to say I grew up in the “original” Silicon Valley. My dad was an electrical engineer who programmed computer chips back when Silicon Valley was more about tech innovation than venture capital. As the eldest of three and the daughter of immigrant parents, I experienced firsthand the values of hard work, trust, and a lifelong commitment to learning—principles that have guided me throughout my career.
Growing up, I always straddled two identities: being Asian, yet also American; a competitive dancer, yet a dedicated honor roll student. I loved being close to home but dreamed of big cities like New York. My parents encouraged my siblings and me to pursue our creative passions while emphasizing the importance of education. Having the freedom to chase my curiosities is something I know not all of my peers with similar backgrounds had, and I’m incredibly grateful for it.
After earning my undergraduate degree from UC Berkeley, I began my career with a deep interest in strategy and operations. I quickly found myself drawn to roles that allowed me to work cross-functionally and drive meaningful impact at scale. That curiosity eventually led me to the Chief of Staff role, where I’ve had the privilege of partnering with leaders to solve complex challenges and build organizational alignment.
Today, as the founder of Ask a Chief of Staff, I’ve been able to take those experiences and channel them into helping others navigate their own career journeys. It’s incredibly rewarding to demystify the Chief of Staff role, connect people with opportunities, and watch them flourish in what can be a transformative position.
Why do you think so many people want to become a Chief of Staff?
The Chief of Staff role is uniquely appealing because it offers something rare in the professional world: a front-row seat to leadership while allowing you to shape strategic decision-making behind the scenes. It’s a role that combines influence, impact, and variety in ways that few positions do.
For many, the allure lies in the exposure it provides. As a Chief of Staff, you get to work directly with executives, gaining insights into how decisions are made at the highest levels of an organization. This access is particularly attractive for those who want to broaden their understanding of business or prepare for future leadership roles.
The diversity of the role is another draw. Chiefs of Staff wear many hats—from strategic advisor to project manager to problem solver. No two days are the same, which makes the work dynamic and intellectually stimulating. For professionals who enjoy variety and thrive in ambiguous environments, it’s the perfect fit.
There’s also a growing recognition that being a Chief of Staff is a career accelerator. Whether you’re transitioning from an individual contributor role or exploring the operational side of leadership, this position offers unparalleled learning opportunities. It allows you to build relationships across the organization, expand your skill set, and create a lasting impact—all of which can open doors to future roles like COO, founder, or investor.
Finally, the rise of the Chief of Staff role in tech and startups has made it more visible than ever. As more companies embrace the position, it’s no longer seen as just a political or corporate title—it’s becoming a key driver of organizational success. This visibility has inspired many ambitious professionals to see the role not as a steppingstone, but as a meaningful career path in its own right.
What does a Chief of Staff do? What does success look like? What is the typical day-to-day like? Who do they typically work with and how do they coordinate with the rest of the organization?
A Chief of Staff (CoS) is a strategic enabler who empowers their Principal—often the CEO or a senior executive—to focus on their “Zone of Genius,” the areas where they can deliver the most impact. Their responsibilities typically fall into three categories: Culture, Operations, and Strategy (COS). They uphold the organization’s culture by aligning teams around the Principal’s vision, streamline operations to enhance efficiency, and act as a trusted advisor to shape and execute long-term strategies.
Day-to-day, a CoS serves as a bridge between the Principal and stakeholders, ensuring clear communication and alignment across the organization. Their activities might include leading cross-functional projects, preparing for leadership meetings, filtering and synthesizing information for decision-making, and resolving bottlenecks that could hinder progress. They are often described as the “connective tissue” of the organization, facilitating collaboration and ensuring that the Principal’s time is spent on the most strategic priorities.
Success in the role is measured by the Principal’s increased capacity to focus on high-impact work, the seamless execution of strategic initiatives, and enhanced organizational alignment. A great CoS not only amplifies the effectiveness of their Principal but also creates a more cohesive and high-performing team around them.
What is the biggest misconception people have about the Chief of Staff role? Who - what type of person - do you see as a good fit for becoming a Chief of Staff? Who is less of a good fit? Why?
One of the biggest misconceptions about the Chief of Staff (CoS) role is that it’s purely administrative or simply a “steppingstone” to a more defined leadership position. In reality, the role is dynamic, strategic, and tailored to the unique needs of the Principal and organization. It requires balancing high-level strategy with day-to-day execution, often in ambiguous and evolving circumstances.
The best fit for a Chief of Staff is someone who thrives in ambiguity, enjoys solving complex problems, and can navigate different challenges without requiring constant direction. They should have excellent emotional intelligence, adaptability, and the ability to manage up, down, and across an organization. Ideal candidates are often curious generalists with a “big picture” mindset and a knack for turning ideas into action.
Conversely, individuals who need a clearly defined job description or a linear career path may struggle as a CoS. The role demands flexibility and initiative—success often comes from proactively identifying and addressing what needs to be done rather than waiting for instructions. For someone who prefers a more structured environment or predictable responsibilities, the inherent fluidity of the CoS role might feel frustrating or overwhelming.
How long does the Chief of Staff role typically last? What do most Chief of Staffs do afterwards?
The Chief of Staff role is often a transitional position, with a typical tenure lasting around 18 to 24 months. This timeline reflects the intensity of the role and its focus on equipping individuals with broad organizational knowledge and leadership exposure. However, some Chiefs of Staff stay longer, particularly if their Principal’s needs evolve or if the role grows in scope alongside the organization. I’ve started to observe Chiefs of Staff staying in their roles longer if they enjoy working with their Principal and want to continue in the partnership that they’ve both invested in.
When it comes to what’s next, Chiefs of Staff tend to follow one of four main career paths:
Founding a Company: Many Chiefs of Staff use their proximity to leadership and strategic decision-making as a launchpad to start their own ventures. It’s a natural step for those inspired by observing the inner workings of a business and eager to build something of their own.
Specializing in a Function: After managing cross-functional responsibilities, some Chiefs of Staff identify a specific area they’re passionate about—such as operations, business strategy, or finance—and transition into leadership roles like Head of Operations or VP of Business Development.
Staying in the Role Long-Term: Some Chiefs of Staff thrive as generalists and choose to remain in the role beyond the typical tenure, growing alongside their Principal and continuing to serve as a trusted partner as the organization scales.
Exploring Diverse Opportunities: Given their broad skill set and exposure, Chiefs of Staff can transition into a wide variety of roles, from consulting to investing to other executive positions. The challenge here lies in crafting a compelling narrative that ties their unique experience to the new opportunity they’re pursuing.
The Chief of Staff role is as much about growth as it is about impact. It equips individuals with the tools to carve their own career path, making it a pivotal stepping stone for those eager to lead and innovate.
What advice do you have for someone who wants to become a Chief of Staff but does not know where to get started? Additionally, if there is any content you suggest reading, what would that be?
If you’re aspiring to become a Chief of Staff (CoS), the first step is to understand the role and assess if it aligns with your skills and career goals. A great Chief of Staff thrives in ambiguity, enjoys solving cross-functional challenges, and is motivated by driving impact behind the scenes. Start by reflecting on your strengths—are you an effective communicator, a strategic thinker, and someone who builds trust quickly? These traits are crucial for success.
Next, begin building your network and knowledge base. Reach out to current or former Chiefs of Staff on LinkedIn and ask about their experiences. These conversations will provide valuable insights into the day-to-day responsibilities and challenges of the role. Additionally, explore communities like Ask a Chief of Staff, where you can join conversations, access resources, and connect with others navigating the CoS journey.
For reading, start with our Ask a Chief of Staff Substack, which offers practical advice, industry insights, and real-world stories from Chiefs of Staff at all stages of their careers. Sharing some links to some of my favorite articles below:
Ask a Chief of Staff Newsletter
Chief of Staff Compensation Survey
What a Chief of Staff Should Be Doing for Your Company
What is a Chief of Staff job interview typically like? Any general guidance for succeeding?
The Chief of Staff interview process is designed to evaluate your strategic thinking, relationship-building skills, and alignment with the organization’s needs. It typically starts with a short chemistry check with the Principal, where they’ll ask questions like, “Why do you want to be a Chief of Staff here?” and “Why is now the right time for you to step into this role?” This initial conversation is about building rapport and showing your enthusiasm for the role while demonstrating your understanding of the company’s challenges and goals.
Next, you’ll likely complete a take-home assignment simulating real-world tasks, such as creating a strategic plan or operational roadmap. This step allows you to showcase your problem-solving and prioritization skills. Afterward, you’ll present your project to the Principal and possibly the leadership team. This phase assesses your communication skills, executive presence, and ability to adapt to feedback. Additional interviews with members of the leadership team may follow to gauge how well you’d collaborate across the organization.
The final stage is often a casual meeting, such as coffee or a meal with the Principal, to solidify mutual trust and chemistry. Throughout the process, it’s critical to prepare thoughtful answers, demonstrate your ability to navigate complex challenges, and show you can build strong relationships across teams. By focusing on strategic impact, collaboration, and alignment with the organization’s vision, you can stand out as a strong candidate for the Chief of Staff role.
For more on nailing your Chief of Staff interview, refer to this article:
If I am a Chief of Staff candidate and I am talking to lots of founders, how can I best vet them? How can I know who is a good person to partner closely with versus someone I should probably stay away from?
Vetting a founder is one of the most important steps when considering a Chief of Staff role, as the working relationship you build with them will define your experience and impact. To identify a strong partnership, focus on understanding their leadership style, the company’s health, and how well your values align.
Start with the Founder’s Vision and Leadership Style
Ask about their top priorities and biggest challenges. Can they clearly articulate their vision and where they need the most support? This will tell you how focused and self-aware they are. Dig into how they make decisions, delegate responsibilities, and communicate expectations for the CoS role. Look for someone who views the role as a true partnership, not just a “catch-all” for tasks they want to avoid.
Do Your Homework on the Company
Take the time to ask thoughtful questions about the company’s financial health, team dynamics, and culture. For example: “What’s your financial runway?” or “How would you describe your approach to building the leadership team?” High turnover or vague answers about strategy might signal issues to watch for. Offer to sign an NDA if needed to get access to data that will help you evaluate the business more thoroughly.
Assess Cultural and Values Fit
Pay close attention to the culture and how the founder treats their team. Ask questions like, “What’s your philosophy on talent development?” or “What’s it like to work here day-to-day?” Speaking to references—both about the founder and the company—can also give you an honest perspective on what it’s like to work alongside them. Look for alignment between their values and your own, as this is often what makes or breaks a strong partnership .
Ultimately, the best founder to partner with is someone whose leadership style inspires you, whose values align with yours, and who is ready to empower a Chief of Staff to truly make an impact.
If you could plaster a few sentences in the sky for every Chief of Staff to read that would help them be more effective in their jobs, what would it say? What should people be doing differently?
“Busyness doesn’t equal productivity. Stop measuring your value by how full your calendar is or how many tasks you’ve crossed off your list. Your job is to create clarity, not chaos.”
As a Chief of Staff, it’s easy to get caught up in the whirlwind of meetings, emails, and endless to-dos, but the real impact comes from stepping back and asking: Am I focusing on what matters most? Chiefs of Staff should prioritize outcomes over outputs—fewer, more meaningful actions that drive alignment and progress are far more valuable than juggling dozens of low-impact tasks.
What could people do differently? Spend time proactively identifying bottlenecks and high-leverage opportunities rather than just reacting to what’s urgent. Simplify systems, create space to think strategically, and ensure your Principal and team are working in their “Zone of Genius.” Productivity isn’t about doing everything—it’s about doing the right things well.
What do you think is the biggest difference between a highly effective Chief of Staff and perhaps just a mediocre one? What habits or practices do the highly productive Chief of Staffs do differently?
The difference between a good Chief of Staff and a great one often comes down to proactivity and strategic focus. A mediocre Chief of Staff tends to stay reactive—saying “yes” to every project, solving problems as they come, and keeping things moving. In contrast, a highly effective Chief of Staff operates a few steps ahead, anticipating needs, preventing issues, and ensuring their efforts drive long-term value.
Great Chiefs of Staff build systems and empower others, creating capacity for the organization to thrive without bottlenecks. Instead of executing every task themselves, they focus on delegation, team development, and prioritizing high-impact initiatives. They’re not just focused on this week’s to-do list—they’re strategically planning how today’s work ties into the bigger picture.
The most effective Chiefs of Staff also actively seek out feedback and act on it. They aren’t afraid to question whether they’re solving the right problems or delivering on their Principal’s most important goals. Ultimately, it’s this blend of foresight, empowerment, and intentionality that sets great Chiefs of Staff apart—they’re not just busy; they’re driving meaningful impact.
The Chief of Staff role often involves lots of context switching between problem areas. What advice do you have for managing this context switching?
Context switching is a core part of the Chief of Staff (CoS) role, but it can be mentally taxing if not managed intentionally. The key is building habits and systems that allow you to move fluidly between topics without losing focus or energy.
Ruthlessly Manage Your Calendar
Your calendar is your first line of defense. Group similar types of meetings together to minimize the mental energy spent switching between topics. Build in buffer time between back-to-back meetings to reset and prepare. For instance, consider scheduling 25- or 50-minute meetings instead of the typical 30 or 60 minutes to allow breathing room. Protect blocks of time for deep, strategic work and hold those boundaries firmly .
Create Clear Transition Routines
Small rituals between tasks can help signal your brain to shift gears. This could mean standing up, stretching, taking a short walk, or even jotting down quick notes about where you left off before jumping into the next meeting. These micro-resets prevent brain fog and help you show up sharper for the next topic .
Organize for Efficiency
Keep your workspace and digital tools set up to support quick transitions. Use tools like pre-linked calendar entries with relevant documents to reduce friction, and maintain a running priority list so you always know what’s next. Simplifying these processes can save precious minutes when juggling multiple areas of responsibility .
The goal isn’t to eliminate context switching—it’s to manage it in a way that protects your mental energy while ensuring you’re effective across all areas.