Clara Ma, through her influential "Ask a Chief of Staff" newsletter, podcast, and community, has emerged as a leading voice on the strategic and often misunderstood role of a Chief of Staff. Drawing from her experiences as a CoS at startups like Hugging Face and her current role at Notion, she provides a masterclass in operational excellence, career navigation, and the art of being an effective force multiplier. Her insights are essential reading for anyone in or aspiring to a strategic operator role.

On the Chief of Staff Role & Responsibilities

Direct Quotes:

  1. "The Chief of Staff role is a rotation. It is not a forever role."
  2. "Your job is to make the entire company and your principal better. It’s not about you."
  3. "The CoS role is about filling the white space. You have to be comfortable with ambiguity and with carving out your own job."
  4. "You are a router and a resolver of information. Your job is to make sure the right people are talking to each other at the right time."
  5. "A good CoS tells their principal what they need to hear, not what they want to hear."
  6. "You're not the 'Chief of Stuff.' Don't fall into the trap of just being an executive assistant. You have to be strategic."
  7. "The three buckets of a CoS are typically People, Projects, and Process."
  8. "You're playing organizational Jenga. You're trying to remove blocks to make the whole structure more stable without it collapsing."
  9. "Success in the role means you’ve worked yourself out of a job, because the organization is now running so smoothly."
  10. "The CoS role is an apprenticeship in executive leadership. You have a front-row seat to how decisions are made."

Key Learnings:

  1. It's a Tour of Duty, Not a Career: Ma emphasizes that the CoS position is typically an 18-24 month role designed to solve a specific set of organizational problems before the CoS "graduates" into a line role. (Source: Ask a Chief of Staff, "Is the Chief of Staff Role a 'Forever' Role?")
  2. Define Your "Swim Lane": To avoid being a catch-all, it's crucial to work with your principal to define your specific areas of ownership and impact. Ma advocates for creating a clear job description, even if one doesn't exist. (Source: The Logan Bartlett Show, "How To Become A Chief Of Staff")
  3. Master the Art of "Managing Up": A huge part of the job is managing your principal. This means understanding their priorities, protecting their time, and ensuring they are focused on the most important things. (Source: Ask a Chief of Staff Podcast, various episodes)
  4. Your Success is Invisible: A great Chief of Staff makes the leader and the organization more effective, often without leaving their own fingerprints. The credit goes to the team. You must have a low ego. (Source: Lenny's Podcast, "The Chief of Staff role")
  5. Be a "Shit Shield": One of the key functions of a CoS is to absorb the chaos and ambiguity within an organization, filtering and clarifying issues before they get to the principal. (Source: Ask a Chief of Staff, "What does a Chief of Staff actually do?")

On Career Strategy and Finding the Role

Direct Quotes:

  1. "Don't just look for a Chief of Staff title. Look for the experiences and skills you want to gain."
  2. "The best CoS candidates are often generalists with a spike in one or two key areas."
  3. "You don't need to have been a consultant or a banker. The best Chiefs of Staff often come from operational roles."
  4. "The most important factor in a CoS role is your relationship with your principal. You have to have deep trust and chemistry."
  5. "When interviewing, ask the principal: 'What are the top three things keeping you up at night?' Your job is to solve those."
  6. "Your network is your superpower. Most CoS roles are filled through referrals, not job boards."
  7. "Be a 'painkiller,' not a 'vitamin.' Show how you can solve a company's immediate, tangible problems."

Key Learnings:

  1. Optimize for the Principal, Not the Company: The success of your tenure is almost entirely dependent on your relationship with your executive. Ma advises to interview the principal as much as they interview you. (Source: The Logan Bartlett Show, "How To Become A Chief Of Staff")
  2. Build a "Portfolio of Evidence": To land a CoS role, you need to demonstrate your ability to be a strategic operator. Proactively take on cross-functional projects, solve ambiguous problems, and document your impact. (Source: Ask a Chief of Staff, "How to Land a Chief of Staff Role")
  3. The Best CoS Hires Come From Within: Ma notes that some of the most successful CoS transitions happen when an internal candidate who already has context and trust is promoted into the role. (Source: Ask a Chief of Staff Podcast)
  4. Craft Your Own CoS Role: If your company doesn't have a CoS, you can effectively create the role for yourself by identifying "white space" problems and stepping up to solve them, eventually making the case to formalize the position. (Source: clara.ma Substack)
  5. The "Off-Ramp" is as Important as the "On-Ramp": Before you even take a CoS job, you should be thinking about what comes next. Discuss your long-term career goals with your principal from the start. (Source: Lenny's Podcast, "The Chief of Staff role")

On Operational Excellence and Getting Things Done

Direct Quotes:

  1. "Your job is to be the connective tissue of the organization."
  2. "Run meetings like a product. Have a clear agenda, desired outcomes, and follow-up actions."
  3. "Don't just be a note-taker. Be a synthesizer. What were the key decisions? Who is doing what by when?"
  4. "A lot of being a CoS is just doing the unglamorous work that needs to get done to move the company forward."
  5. "You need to be able to zoom in and zoom out. You have to connect the 30,000-foot strategy to the 3-foot execution."
  6. "Frameworks are your friend. Use them to bring structure to chaos."
  7. "Over-communicate. You can never assume that everyone has the same context you do."

Key Learnings:

  1. Weaponize Your Calendar: The calendar is the most powerful tool a CoS has. Ma advises using it not just to schedule meetings, but to drive strategic priorities, force decision-making, and manage the cadence of the entire company. (Source: Ask a Chief of Staff, "The Art of the Calendar")
  2. Become a Master of Written Communication: Clear, concise writing is essential for a CoS. You are often the person responsible for drafting company-wide announcements, board decks, and strategic memos. (Source: clara.ma Substack, "Writing is Thinking")
  3. Build Systems, Not Just Solutions: Don't just solve a problem once. Create a process or a system so that the problem solves itself in the future. This is how you scale your impact. (Source: Ask a Chief of Staff Podcast)
  4. Gain Leverage Through Others: A CoS has high influence but low authority. Your job is to lead through influence, build relationships across the organization, and empower others to get things done. (Source: Lenny's Podcast, "The Chief of Staff role")
  5. The "First 90 Days" are Critical: Ma provides a framework for how a new CoS should spend their first 90 days: focus on learning, building relationships, and identifying a few quick wins to establish credibility. (Source: Ask a Chief of Staff, "Your First 90 Days as a Chief of Staff")

On Mindset and Personal Growth

Direct Quotes:

  1. "Be relentlessly curious. You have to want to learn about every part of the business."
  2. "You need to have a high tolerance for ambiguity."
  3. "Stay humble. The moment you think you know everything is the moment you stop being effective."
  4. "You have to be comfortable being behind the scenes."
  5. "Take care of yourself. The CoS role can be incredibly demanding. You have to set boundaries to avoid burnout."
  6. "Your superpower is context. You see more of the business than almost anyone else."

Key Learnings:

  1. Be an Information Sponge: Your primary goal, especially early on, is to absorb as much context as possible. Sit in meetings, read everything, and talk to everyone. Your value is directly proportional to the breadth and depth of your context. (Source: The Logan Bartlett Show, "How To Become A Chief Of Staff")
  2. Develop Radical Candor: Building the trust required to give your principal direct, unfiltered feedback is one of the most valuable things a CoS can do. This requires courage and psychological safety. (Source: Ask a Chief of Staff)
  3. Embrace Imposter Syndrome: Nearly everyone in a CoS role feels imposter syndrome. Ma advises reframing it as a sign that you are in a role that is stretching you and pushing you to grow. (Source: Ask a Chief of Staff Community)
  4. Find Your "Kitchen Cabinet": The CoS role can be lonely. Ma strongly advocates for building a personal board of directors—a trusted group of mentors and peers you can turn to for advice. (Source: clara.ma Substack)
  5. Always Be Graduating: Constantly look for opportunities to hand off your responsibilities. As you build systems and empower others, you free yourself up to tackle the next big, ambiguous problem for the organization. This is the path to growth. (Source: Lenny's Podcast, "The Chief of Staff role")