Check it out on a much prettier version on this Notion page
⚡️ A great Chief of Staff (Cos) is a high-EQ, operationally excellent, and strategic leader who helps move the entire organization forward every single day.🎯 The primary objective of a great Chief of Staff
- To increase the effectiveness of the entire organization
- If successful, a great Chief of Staff creates business value by propelling the business towards its objectives through increased pace of execution, decision making, communication and learning
🤔 Why the Chief of Staff role is needed by startups today
- The growth of a startup is fundamentally constrained by leadership capacity. Teams can only go as fast, far, and efficiently as their leadership enables them.
- The Chief of Staff role is needed to expand leadership capacity without adding managerial overhead.
🧠 Personality traits that matter most
- Gravitas and emotional maturity to work in a productive and cooperative way with a variety of personalities and levels.
- Big, positive energy that lifts up team members
- Able to maintain good judgment in fast-paced, complex environments
- Exceptional collaboration skills
- Excellent Interpersonal and communication skills
- Grit, breaks through barriers
- A learning machine who can quickly get from 0 → 1 on any topic
- Organized, meticulous, dependable
🛠️ Key decision making tools
- Diagnosis: SCQA
- Decision making: RAPID
- Project plan: Objective/Outcomes/Outputs/Projects/DRIs
The SCQA (Situation, Complication, Question, Answer) is the most powerful framework for quickly driving clear decisions. Every Chief of Staff and executive team should be using this multiple times a week.
📝 Requirements to fully leverage your Chief of Staff
- Honesty - The principal must be willing to be honest about the company and themselves. A lack of honesty, which is typically due to fear rather than anything nefarious, will limit the effectiveness of a Chief of Staff as a true partner.
- Sparring partner - The principal must be willing to hear real pushback from their Chief of Staff. Intellectual honesty is the only way to make progress on problems facing a startup, and a CoS must be able to surface hard truths.
- Access - Chief of Staff impact will be limited by the information they have access to. For example, if a Chief of Staff is not observing board meetings, they will be less able to provide insight on how to manage board dynamics. The more information access a Chief of Staff has, the more impact they can have.
- Trust - All of this requires deep trust between the principal and Chief of Staff. I find Tobi Lütke’s idea of the “trust battery” to be helpful.
👨💼 Key Experience
- Operating experience - Deep experience of how startups function, the emotional ups & downs team members face, and how to lead teams through it all.
- Student of startups, business — Constantly studying what other startups and businesses are doing, who is new on the scene, what new trends are emerging, and so on. StrictlyVC, Stratechery and TechMeme are my three go-to sources, though I also have Twitter/X lists curated for this purpose.
- Venture Capital - Important for understanding investor motivations, board management and fundraising dynamics.
📚 3 books every chief of staff should read
- Scaling People
- The Great CEO Within
- Peopleware
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