A Guide to Interviewing Candidates for a Fractional Position

Our five-step process will help you identify the candidate who’s best able to make an impact.

Interviews can be stressful, no matter which side of the table you’re on. When you’re a job seeker, you may feel that you’re on trial, having to prove that you’re good enough. But when you’re the hiring manager, you may feel a lot of pressure to ask the right questions.

This is because the typical interview tends to set up a false power dynamic. There’s an assumption that what the employer has to offer is more valuable than what the employee has to offer, when that’s simply not the case.

When hiring for a fractional chief of staff, we recommend taking a collaborative approach. It’s just as important to make sure the job gives the candidate what they’re looking for as it is to make sure the candidate has what you’re looking for.

Here’s the five-step process we recommend to all our clients to follow in order to quickly identify a candidate who’ll excel as a fractional Chief of Staff.

Step 1: Accelerate the Process

Hiring a fractional executive is all about efficiency and speed. The goal is to hire someone as quickly as possible to get the project up and running. To achieve this, it’s important to accelerate the hiring process by eliminating unnecessary steps. For example, you can skip exercises typically given to prospects and limit the number of interview rounds. While this may increase the risk of a bad fit, the short-term nature of a fractional hire allows for parting ways if needed.

It’s also important to make room in your schedule for the interviews as soon as possible, rather than looking for the next convenient slot in your calendar. Some executives might not have availability for weeks or even months. Even if you have to shuffle things around or skip a meeting, it’s better to get the help you need sooner rather than later.

Step 2: Clarify Your Scope of Work

The chief of staff role is very flexible and can look very different from one company to another, so it’s important to get clear on what you want the role to look like. Take the time to outline the specific responsibilities and tasks associated with the role. If possible, provide a percentage breakdown for different work streams as a guide. How much of their time will be spent on project management vs. hiring support vs. communications? This clarity will help you evaluate candidates more effectively and ensure they understand the expectations of the position.

Step 3: Know the Profile of the Ideal Candidate

Three candidates may be equally qualified for your position based on their resumes, but in order to determine which one will mesh best with your team and drive results fastest, you need to come up with a list of skills, specific experiences, and personality traits that you believe are essential for the role. For example, for a major overhaul of your financial software and reporting workflows, technical accounting experience might be much more important than relationship-building skills. In contrast, good people skills might be the most important thing for a CoS who is covering for an executive absence.

Step 4: Provide Context for the Interviewee

Before you ask the candidate any questions, it’s important to provide thorough context about the job. Clearly communicate your expectations, including the scope of work, breakdown of different types of tasks, and where the project fits within your organization’s priorities. Discuss who the candidate will collaborate with or be supported by and outline the intended outcomes of their project. This context will allow candidates to provide more insightful answers during the interview.

Step 5: Ask Targeted Questions

Finally, we get to the questions. There’s nothing magical about these questions if you skip the previous four steps. But when you combine the right prep work with targeted questions, you’ll find yourself in an interview that feels like a collaborative problem-solving session, where you and the candidate are on the same team, trying to figure out if you’re a good match for each other.

To gauge a candidate’s aptitude for the role and their alignment with your organization’s needs, consider asking the following questions during the interview:

  • What excites you about this work?
  • What questions do you have about the job duties?
  • What past experiences have equipped you with the skills needed for this role?
  • Do you anticipate needing support or lacking experience in any specific aspects of the work?
  • What support would you require from me or my team to be successful?
  • How would you prioritize and spend your time in the first week?
  • Do you prefer collaboration or independent work time? How do you approach collaborative work?
  • What is your communication style, and how do you prefer to keep in touch with colleagues and leaders?
  • What role do you typically play on a team?
  • Share your experiences managing various personalities.

By following these steps and asking targeted questions, you can adopt a more collaborative approach to interviewing, which can increase your chances of finding a well-suited candidate who can quickly make a positive impact in the fractional chief of staff role.

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