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Chief of Staff Interview Questions

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  1. What is the most challenging part of being a chief of staff? See answer
  2. As chief of staff, what was your role in the strategic planning process? See answer
  3. Tell me about the types of projects you led in your last chief of staff position. See answer
  4. Do you have experience rewarding and motivating staff for good work? See answer
  5. In your opinion, what is the most important skill to have as chief of staff? See answer
  6. As chief of staff, how would you shape hiring policies and determine best practices for staff management? See answer
  7. Are you comfortable being flexible and taking on additional duties to support company staff through transition periods and busy times of year?
  8. The chief of staff is in charge of managing the CEO’s schedule. What would you do if you weren’t sure which responsibilities to prioritize when scheduling a busy day or week?
  9. How does change management impact your work as chief of staff and what change management strategies do you find most effective?
  10. Do you have experience managing workplace communications on behalf of a company leader?
  11. Explain how you keep track of all important action items when delegating responsibilities to others on your team.
  12. As chief of staff, you may act as a strategic advisor to company leaders for matters related to staffing and operations. Are you comfortable giving feedback and advice to your direct supervisor?
  13. What steps would you take if a majority of your staff were failing to meet performance benchmarks?
  14. How do you strengthen relationships between an organization’s leaders and employees to create a successful team dynamic?
  15. Describe your experience planning company events or conferences for a team.
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6 Chief of Staff Interview Questions and Answers

Q:

What is the most challenging part of being a chief of staff?

A:

The chief of staff deals with many stressful situations, which is why it is critical that the applicant knows how to remain calm and collected under any circumstance. A good candidate will explain how they choose whose guidance to seek to solve unfamiliar problems for their advisee.

What to look for in an answer:

  • Awareness of the difficult duties of the job
  • Critical thinking skills
  • Delegation of tasks to people with the right skill set

Example:

“The most challenging part of being chief of staff is keeping up with multiple projects at once. I always hire a capable assistant and have a list of experts that I consult for ideas. “

Q:

As chief of staff, what was your role in the strategic planning process?

A:

The chief of staff plays a significant role in determining internal priorities within a business. When the head of a company sets a goal, it is the chief of staff’s duty to figure out how to delegate these duties to other staff members. The ideal candidate should have experience being a key player in both the development and implementation of the strategic planning process for a company.

What to look for in an answer:

  • Ability to provide accurate results promptly
  • Experience determining main priorities for staff
  • Excellent communication skills

Example:

“In my previous chief of staff position, I met with the CEO about all staff-related plans. During these meetings, I would delegate priorities for different staff departments to focus on.”

Q:

Tell me about the types of projects you led in your last chief of staff position.

A:

A candidate’s answer may vary greatly depending on industry experience and previous job. Focus on the types of projects the individual has experience with, such as technology-based projects. Does the candidate have experience with cybersecurity, risk management or data management? Does the applicant mention any software they use? Identify any client-related projects the individual has experience with, such as creating a process to transition to a new system or program.

What to look for in an answer:

  • Aware of solutions implemented by other companies
  • Knowledge of different departments within a company
  • Applicant’s level of expertise with client management software

Example:

“I worked heavily with the IT department in my last position, so many of my projects were technology-based. I also have six years of experience working directly with clients on projects. “

Q:

Do you have experience rewarding and motivating staff for good work?

A:

The ideal candidate will know many methods to reward and motivate staff. A chief of staff typically has teams working on multiple projects at once. Being able to show appreciation for employees can result in them working more accurately and efficiently. Focus on what types of situations the applicant has rewarded their teams for in the past. Note creative rewards that inspire staff.

What to look for in an answer:

  • Shows interpersonal skills
  • Influential personality
  • Understands the importance of providing staff with incentives

Example:

“In my last position, I would provide staff with lunch in the office every Monday. Each week, a different team would select where we would order our food. I felt that it helped keep my staff happy with their work environment.”

Q:

In your opinion, what is the most important skill to have as chief of staff?

A:

A chief of staff wears many different hats during the workday, from creating plans to following up with executives. The ideal candidate will be able to easily decide on what abilities are essential to them and defend their opinion. Does the candidate take an innovative approach or do they emphasize a common skill set?

What to look for in an answer:

  • Demonstrates decision-making skills
  • Open-minded personality
  • Ability to innovate

Example:

“Being adaptable is the most important skill to have as chief of staff. It is essential to be able to think critically and have alternative options when something does not go as planned.”

Q:

As chief of staff, how would you shape hiring policies and determine best practices for staff management?

A:

A chief of staff is responsible for managing the recruitment and hiring process for key roles at a company. The chief of staff may have additional involvement in hiring and interviewing people who directly report to the company's president or CEO, making it important for them to be strategic when setting expectations for new employees. Strong candidates should have a plan for making sure they hire the best team possible and uphold consistent standards.

Try to identify these key parts of a strong response:

  • Responsibility and accountability
  • Research skills
  • Foresight and planning

Here is one sample response:

Example:

"I'd start by assessing the current policies in place and conducting research to measure their impact on employee performance and satisfaction. I'd compare current practices to the organization's strategic goals and explore how other businesses implement successful hiring and performance management policies. I'd seek feedback from long-term employees about the patterns they see in hiring and employee retention to identify and address the core pain points for the organization. When implementing new policies, I'd continue measuring their impact, making changes and documenting policy updates as needed."

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