Chief of Staff Interview Questions

Responsibilities

A chief of staff’s responsibilities include:

• Reporting directly to the CEO regarding current operations and advise accordingly
• Overseeing the individual departments that make up the business
• Overseeing the projects assigned to each department
• Ensuring goals set by the office of the CEO are being met
• Leading the hiring process
• Leading strategic planning
• Making sure that all issues regarding staff are handled appropriately

Skills

A chief of staff’s skills should include:

• Good managerial and communication skills
• Being detail oriented with skills in analyzing data
• Hiring and delegating tasks
• Planning skills and effective decision making
• Experience in business administration

Qualifications

This position at any company will require a graduate degree in business administration or a related field. They will also need several years of experience in a chief of staff position at a different company or in a closely related executive administration role. This is never an entry-level position in the field of business and requires ample training and experience.

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Chief of Staff Interview Questions

Question: Can you give me an example of the types of projects you led in your last position as chief of staff?

Explanation: This is a general question the interviewer will ask you early in the interview to get you talking, learn about your background, and gather the information they can use for subsequent questions.

Example: “During my most recent position as chief of staff, I handled a wide variety of projects for the CEO I reported to. These included staff reviews, strategic planning, speech writing, and event planning. While performing most of these tasks, I collaborated with the appropriate people who had subject matter expertise in these topics.”

Question: How do you maintain communications with the key stakeholders of the organization, including governing boards, senior staff, and department heads?

Explanation: This is an operational question which the interviewer is using to assess your communication style. Operational questions are best answered succinctly and directly. The interviewer will ask you a follow-up question if they need additional information.

Example: “I have found the best way to maintain communication with the key stakeholders of the organization is to first develop a relationship with them that is appropriate for the positions they hold. I then try to communicate directly and clearly, providing the information they need in oral or written formats. I then make myself available for questions or follow-up action items.”

Question: Tell me about your experience recruiting, interviewing, and hiring employees. What methods did you find most effective in finding the appropriate person for the job?

Explanation: This is another operational question in which the interviewer is trying to understand your ability to attract, recruit, and bring qualified candidates on board. This question can best be answered by detailing the steps you take to make sure you hire the right people.

Example: “I have a great deal of experience hiring staff members for the organization. I take my time to write extremely specific job descriptions that attract the right type of applicants. I then screen them by reviewing their resume, looking for any online presence they may have, using thorough and detailed interviews and speaking to the references.”

Question: Have you ever coached or mentored a staff member, and if so, what were the results?

Explanation: This is yet another operational question. As chief of staff, you can anticipate that the majority of questions you will be asked during an interview will be operational or technical in nature. Practicing questions like these will help you be prepared to respond to them.

Example: “As a chief of staff, I’ve done a great deal of mentoring and coaching of the staff members who report to me. My goal with these activities is to improve each staffer’s capabilities and prepare them for promotion to positions with more responsibility. This approach has been very successful. Many of the staffers I’ve worked with have moved on to better positions, some even as the chief of staff for other organizations.”

Question: Can you give me an example of when you organized a diverse group of people to accomplish a task?

Explanation: Diversity and inclusion are a key element of any organization in today’s business world. You should be able to talk about how you promote these important initiatives within the organizations you’ve worked with.

Example: “In virtually every organization I’ve worked for, diversity and inclusion were key initiatives. These were mandated by the CEO and the rest of the senior management team, and I was responsible for designing programs and implementing them across the organization. When putting together teams to accomplish a specific task, the first selection criteria was their qualifications, followed by whether they would bring diverse perspectives to the situation.”

Question: What experience do you have analyzing information and evaluating results to choose the best options for a new initiative?

Explanation: The ability to analyze information and make a recommendation to the CEO for a course of action is critical for any chief of staff. You should be able to easily talk about your approach to this and give an example of when you did it successfully.

Example: “I have a great deal of experience in collecting information, analyzing the data, and making a recommendation to the CEO. I methodically do this, using tools such as spreadsheets, Google, industry reports, and other sources. Once I have the information, I sort and select the best options and provide a recommendation for the course of action which should be taken. I also include one or two alternatives that either support my recommendation or can be used in place of it."

Question: Can you give me an example of a time when you were able to avoid a problem because you foresaw the reaction of the people affected by the issue?.

Explanation: This question helps the interviewer understand how you approach issues from a strategic perspective. Effective managers foresee challenging situations and develop solutions in advance of the event to prevent it from happening or minimize its impact.

Example: “One of my jobs as the chief of staff is to help prevent those “CNN” moments. I do this by becoming keenly aware of potential threats and challenges to the organization and creating contingency plans to avoid or minimize them. I also maintain open communications with the employees of the company who are on the ground and have a great perspective on issues that senior management may not yet be aware of.”

Question: Has a situation ever risen where your ethics were tested, and if so, how did you respond?

Explanation: By asking this question, the interviewer is interested in whether you would be willing to compromise your ethics or standards to accomplish a task. The correct answer is to maintain your ethical standards and find other ways to either accomplish the task or avoid this situation.

Example: “When you reach a certain level within an organization, you are often tempted to cut corners or compromise your ethics to accomplish a task. Doing this will have serious repercussions, if not immediately, then in the long term. The best course of action is always to do the right thing, even if it isn’t easy or effective. I try to look for alternative solutions which will get the job done while still maintaining my and the organization’s integrity.”

Question: As chief of staff, would you be willing to take on additional responsibilities that are not part of your job description?

Explanation: This question addresses your ability to be flexible and willing to go above and beyond your role to help the organization move forward or accomplish its objectives. Your answer should demonstrate a balance between willingness to take on additional responsibilities and commitment to doing your job.

Example: "As one of the senior offices of the company, it is my responsibility to do whatever it takes to help the organization reach its business objectives. However, I also have a responsibility to the CEO to make sure that I am doing what they want me to. If the additional responsibilities do not interfere with my role as chief of staff, I willingly take them on. If I sense there will be a conflict, I discuss it with the CEO before committing myself."

Question: How do you balance cooperating with others and acting independently?

Explanation: The purpose of this question is to determine whether you’re willing to take the initiative, even if it conflicts with other staff members' opinions or priorities. Again, you need to carefully balance these two objectives and demonstrate that while you are independent and willing to take the initiative, you are also sensitive to other people’s ideas and want to make sure the entire organization is moving in the right direction together.

Example: “Balancing between taking the initiative and working together as a team is critical for a chief of staff. There’s a saying that if you want to move fast, you go alone, but if you want to move far, go with a team. I am willing to take the initiative if I believe I can accomplish a task quickly and without repercussions across the organization. However, I prefer to collaborate with other staff members to achieve the company’s business objectives and have a greater impact on the organization.”

• What is your first step in implementing goals set by the office of the CEO?

• When managing cross-departmental projects, how do you ensure proper communication?

• How would you handle disagreements with the office of the CEO?

• What was the most challenging part of your previous (or current) position?

• What is your typical role in the strategic-planning process?

• How do you motivate subordinates in the workplace?

• What personal skills do you think are most helpful for the role of chief of staff?

• How do you implement new strategies in the workplace?

• What is your first step when analyzing productivity?

• What is your process for determining the viability of long-term goals?