This masterclass by Ben Casnocha explores the role of a Chief of Staff (CoS) in startups, addressing their functions, the ideal time to hire, and the hiring process. Casnocha, drawing from his experience as CoS to Reid Hoffman, emphasizes the diverse nature of the role, which can range from high-level Executive Assistants to operating executives. He suggests that founders define their needs, considering internal resources and potential overlap with existing roles before hiring. He also distinguishes between CoS and EA roles, suggesting the former is more strategic and often involves speaking on behalf of the founder. The masterclass includes insights from founders Laura Crabtree (Epsilon 3) and Zinchen Zhang (Waypoint Bio), who share their experiences hiring and utilizing CoSs, and a Q&A session covering candidate assessment, role definition, and career paths for CoSs.

Metadata

Summary

  • A Chief of Staff (CoS) can significantly boost founder productivity.
  • The CoS role varies greatly, from executive assistant tasks to operational leadership.
  • Key CoS functions include operations, strategic projects, communications, and advising the founder.
  • Consider internal resources and potential role overlap before hiring.
  • Determine if an EA or a CoS better suits your needs. EAs handle logistics, while CoSs take on more strategic tasks.
  • Hiring a CoS is generally recommended post-Series A funding.
  • Look for versatile generalists, not necessarily candidates with prior CoS experience.
  • Key CoS qualities include detail orientation, excellent communication skills, and adaptability.
  • Treat the CoS role as an 18-24 month tour of duty.
  • Plan for the CoS's career progression after their tenure.

What makes this novel or interesting

  • Clarifies the often-ambiguous CoS role in startups.
  • Provides a practical framework for evaluating the need for a CoS.
  • Offers actionable advice on hiring and managing a CoS.
  • Includes real-world examples and insights from founders.

Verbatim Quotes

  • Role of a CoS: "Imagine you had someone on your team who could 2-extra your productivity as a founder who's a versatile generalist—someone who could fill in and pick up one of those one-off strategic projects that you never quite have the time to do."
  • CoS vs. EA: "It may be that you actually need an EA, not a chief of staff. Many founders… advertise for Chief of Staff roles when what they really want is an EA… It's okay to advertise for a chief of staff if what you really want is an EA. Just be really clear about that…"
  • Hiring: "You're not looking… for someone that has the job title chief of staff… Most great Chiefs of Staff are not career Chiefs of Staff.”
  • Key Qualities: "You're looking for versatile, adaptable generalists… phenomenal detail orientation… phenomenal communicator… someone who can write well or speak well on your behalf…"
  • Tour of Duty: "Think about it as an 18- to 24-month tour of duty. These are not lifetime jobs…"
  • Career Path: "…tell CEOs or founders… to scope a tour of duty, and then to be transparent and commit that you will help them land a great job after… at your company."
  • Challenges: "Chiefs of Staff can step on toes because it's so undefined; it can cause internal strife… around, 'Wait, that's my job.'"

How to report this in the news

Founders struggling to keep up with the demands of running a startup now have a better path to regaining control of their time and boosting productivity, thanks to expert advice on leveraging the power of a Chief of Staff. Ben Casnocha, drawing on years of experience, offers a practical guide to understanding this versatile role, which can be tailored to fit the unique needs of any early-stage company. Think of it like having a high-level "right hand" who not only handles day-to-day tasks, but also anticipates needs and tackles critical projects, freeing up the founder to focus on the big picture.

Detailed Recap

A. Signs you will benefit from hiring a Chief of Staff

Do any of these scenarios sound like your current struggles?

1. Strategic Capacity & Execution

  • Strategic Projects Are Stalled: Important cross-functional initiatives such as product launches, partnership negotiations, or internal restructuring, lack a clear owner and are not progressing due to competing priorities or a lack of dedicated resources.
  • Preparing for Rapid Growth: You anticipate significant growth in the near future and need someone to help manage the increasing complexity and scale of the organization.
  • Building Out a New Function or Team: You're establishing a new department or team and need someone to handle the operational setup, hiring, and initial management.

2. Time Management & Prioritization

  • The Founder's Time is Highly Fragmented: You're constantly context-switching between meetings, fire-fighting, and small tasks, leaving little time for strategic thinking or deep work.
  • Meeting Overload & Follow-Up Fatigue: You're attending too many meetings, many of which could be delegated, and struggling to keep track of action items and follow-ups.
  • Difficulty Prioritizing Competing Demands: You're constantly bombarded with requests and find it challenging to prioritize effectively across different functions and stakeholders.
  • Founder is Spending Time on Tasks Beneath Their Pay Grade: You're spending significant time on administrative tasks, scheduling, and logistics that could be delegated to someone else.

3. Information Flow & Communication

  • Communication is Inconsistent or Ineffective: Investor updates, board materials, internal communications, and public-facing content are not being created consistently or lack polish and clarity.
  • Information Flow is Bottlenecked: You're not receiving timely or accurate information from different parts of the organization, hindering decision-making.

4. General Oversight & Control

  • Sensing a Lack of Control: You feel overwhelmed by the day-to-day demands and feel a lack of control over your schedule and priorities.
  • "Things are Falling Through the Cracks": You have the nagging feeling that important tasks, details, or opportunities are being missed due to a lack of capacity or oversight.

5. Specific Events/Needs

  • Fundraising is Imminent or Ongoing: You need support with investor relations, preparing materials, and managing the fundraising process.

B. Founders considering a Chief of Staff/EA should:

1. Assess current needs and gaps:

  • List tasks/projects falling through the cracks, not being addressed effectively, or overwhelming you.
  • Categorize these into operations, strategic projects, communications, and general advice/counsel.
  • Identify who's currently responsible for these tasks (if anyone) and potential conflicts/overlap.
  • Consider whether existing team members would feel threatened by a new CoS/EA.

2. Differentiate between CoS and EA:

  • EA: Primarily focused on administrative tasks, scheduling, logistics, and organization. Great for early-stage founders needing support with day-to-day activities. Can often be hired virtually.
  • CoS: More strategic role involving project management, cross-functional communication, representing the founder, and providing high-level advice. Better suited for post-Series A startups with more complex needs.

3. Keep these in mind if hiring a CoS:

  • Look for: Versatile generalists with strong communication, detail orientation, adaptability. Experience in Biz Ops, Corporate Strategy, Finance, or even ex-founders could be beneficial. Don’t prioritize candidates solely based on previous "Chief of Staff" titles.
  • Interview Process: Use take-home tests to assess work ethic, judgment, and fit. Include scenarios related to expected tasks (e.g., drafting comms, addressing sensitive situations). Be upfront about the diverse nature of the role and the inclusion of mundane tasks.
  • Onboarding: Clearly define 70% of the role upfront, allowing flexibility for the remaining 30% based on the CoS's skills and evolving company needs. Get buy-in from existing team members.
  • Management: Establish clear communication channels, regular check-ins, and feedback mechanisms. Address potential role overlap and conflicts proactively.
  • Career Development: Frame the CoS role as an 18-24 month tour of duty. Discuss long-term career goals early on and commit to supporting their transition to their next role, even if it's outside your company.

4. Keep these in mind if hiring an EA:

  • Look for: Strong organizational and logistical skills, responsiveness, and discretion. Prior EA experience can be helpful, but not essential. Consider virtual EAs for cost-effectiveness.
  • Interview Process: Assess their ability to anticipate needs, prioritize tasks, and handle various administrative duties. Include practical scenarios in the interview.
  • Onboarding: Provide clear expectations, processes, and access to necessary tools and information.
  • Management: Regular communication and feedback are crucial. Provide opportunities for growth and development.