How to Hire Your First Chief of Staff

Hiring a Chief of Staff is a significant milestone for any organization, and understanding the role, crafting a compelling job description, and following a thoughtful hiring process are crucial steps in finding the right fit for your team and goals.

How to Hire Your First Chief of Staff

Hiring your first Chief of Staff (CoS) is a significant step for any organization. It's a move that signals growth, complexity, and the need for strategic alignment at the highest levels. The CoS role, often seen as the right hand of the CEO, can vary widely from one organization to another, but it fundamentally revolves around enhancing the effectiveness of the CEO and, by extension, the entire organization. Let's dive into how you can approach hiring your first Chief of Staff, ensuring you find the right fit for your team and goals.

Understanding the Role of a Chief of Staff

Before you start the hiring process, it's crucial to have a clear understanding of what you expect from your Chief of Staff. Typically, the CoS acts as a force multiplier for the CEO, taking on strategic initiatives, managing stakeholder relationships, and sometimes even handling operational tasks. They can also serve as a confidante and advisor, helping navigate the complexities of running an organization.

Key Responsibilities

  • Strategic Planning: Assisting in formulating and implementing the strategic plan to guide the organization's direction.
  • Project Management: Overseeing key projects or initiatives, ensuring they align with the organization's goals.
  • Communications: Acting as a liaison between the CEO and other stakeholders, including employees, board members, and external partners.
  • Operational Efficiency: Identifying and addressing inefficiencies within the organization, streamlining processes for better productivity.

Crafting the Perfect Job Description

A well-crafted job description is your first step in attracting the right candidates. It should clearly articulate the role's responsibilities, required qualifications, and the qualities you're looking for in a CoS. Be sure to highlight the unique aspects of your organization and the role, as this will help candidates assess their fit.

Essential Elements

  • Overview of the Role: A brief summary that captures the essence of the role and its importance to the organization.
  • Key Responsibilities: A detailed list of the tasks and areas the CoS will oversee.
  • Qualifications: Both the hard skills (e.g., strategic planning, project management) and soft skills (e.g., leadership, communication) required for the role.
  • Organizational Culture: A description of your company culture to help candidates understand the environment they'll be entering.

The Hiring Process

With your job description in hand, it's time to embark on the hiring process. This journey involves several key steps, each critical to ensuring you find the right person for the job.

Sourcing Candidates

  • Leverage Your Network: Reach out to your professional and personal networks for recommendations. Often, the best candidates come through referrals.
  • Use Professional Platforms: Platforms like LinkedIn can be invaluable in finding candidates with the right background and skills.
  • Engage a Recruiter: If you're looking for someone with a very specific skill set or background, a specialized recruiter can help narrow down the field.


  • Initial Screening: Begin with a phone or video interview to gauge the candidate's interest and fit for the role.
  • In-depth Interviews: Conduct several rounds of interviews, involving different members of your team. This can include direct reports, key stakeholders, and even board members, depending on the role's scope.
  • Case Studies or Projects: For a role as critical as the CoS, consider asking candidates to complete a case study or project. This can provide insight into their problem-solving abilities and how they approach strategic challenges.

Making the Decision

  • Reference Checks: Always conduct thorough reference checks. Speaking with former colleagues and supervisors can provide valuable insights into the candidate's work style and effectiveness.
  • Cultural Fit: Ensure the candidate aligns with your organization's culture and values. The CoS will be a key figure in your organization, and it's crucial they embody the principles you stand for.
  • Alignment of Vision: The CoS should share your vision for the organization's future. This alignment is critical for a successful partnership.

Onboarding Your Chief of Staff

Congratulations, you've hired your first Chief of Staff! Now, the focus shifts to ensuring a smooth transition into the role. Onboarding is a critical phase where your new CoS will learn about the organization, its people, and the specific challenges they'll be tackling.

First 30 Days

  • Orientation: Introduce them to the team and key stakeholders. Provide an overview of the organization's structure, ongoing projects, and strategic priorities.
  • Learning: Encourage them to spend time understanding the business's ins and outs, from operations to finance to marketing.
  • Goal Setting: Work together to set short-term goals for the first few months, aligning with the organization's broader objectives.

First 90 Days

  • Strategic Initiatives: Begin assigning specific projects or initiatives for them to lead. This will help them make an immediate impact and start building credibility within the organization.
  • Feedback Loops: Establish regular check-ins to provide feedback, discuss challenges, and adjust goals as necessary. This ongoing dialogue is crucial for their development and success in the role.

Hiring your first Chief of Staff is a significant milestone for any organization. It's a decision that can enhance your effectiveness as a CEO and accelerate your organization's growth. By understanding the role, crafting a compelling job description, and following a thoughtful hiring process, you can find a CoS who will be a true asset to your team. Remember, the right Chief of Staff can be a game-changer, providing strategic insight, operational efficiency, and leadership that propels your organization forward.