The Chief of Staff Hire: How to Get it Right


With the recent buzz about the growing trend of Chief of Staff (COS) roles in the private sector, let’s highlight a few considerations when hiring for this critical position. Prime Chief of Staff specializes in placing Chiefs of Staff with companies across industries from rapidly-growing startups to established corporations. We help companies identify the need for the role, work with them to find exceptional talent that complements their executive, and stay engaged throughout the onboarding process to ensure productivity and integration.

The Chief of Staff role is different than most in an organization. First, the success of any COS is highly dependent on a strong relationship with the executive. Second, a COS is a “catch all” job managing a variety of responsibilities and special projects that are not easily or entirely defined through a position description. Third, how each leader decides to utilize this position can vary—from mostly administrative to highly strategic. With this broad spectrum, finding the right mix of experience, background, skills, and personality traits in COS candidates is paramount.

I speak to companies regularly that tell me how they fill the COS position—post the opening on an online job portal, screen candidates over the phone, and bring in the best ones for an interview with the executive (with possibly a few additional interviews sprinkled in). Once a candidate is hired, they are immediately thrown into the chaotic, demanding deep end of an executive’s workload with little or no onboarding plan. This spaghetti-to-the-wall approach, albeit quick, is doomed to fail. The COS search requires more—more thought, more time, and more conversations. Here’s why:

Your best candidates may be passive job seekers

Finding high-quality talent for your COS role is no easy feat and can rarely be accomplished from a public search on your company’s website alone. Some of your most-qualified, best-fit candidates for this role are already in jobs they like and, therefore, will never see your posting. However, a great COS opportunity may be enough reason for someone to leave a great job for a one-of-a-kind job. Be sure to cast a wide net when sourcing candidates for this search, including both passive and active job seekers.

The focus is on the relationship

The Chief of Staff/executive relationship should be a strong, trusting partnership where the COS enhances the productivity of their executive. As my former boss used to say, “Two plus two should equal five.” This equation requires high EQ from the COS to read situations and respond accordingly. The COS must complement their leader—smoothing over harshly-stated messages and providing rational decisions in times of chaos. The COS also must get along with their boss with whom they spend countless hours on a regular basis. Therefore, vetting candidates on the right behavioral traits is even more critical than their technical competencies. Doing such vetting cannot be done in just one interview. It takes time and several interactions with a candidate to uncover their personality and behavioral traits. Reputable personality assessments and strong referral vetting also helps.

Biased decisions are bad decisions

Executives are strong at decisive action—it’s what helped get them to the top. However, when it comes to hiring a COS, additional input helps. As human beings, we hire people like us. But in this role, two of the same can be a surefire disaster. Therefore, others who work closely with the executive and the COS position should also conduct thoughtful interviews. They may provide a differing perspective, but a needed one. The Chief of Staff role must work well with many people throughout the organization. Interviewing candidates with different employees allows you to understand how the candidate’s communicate and jive with others besides just their boss. It also provides candidates with more insight into the role, the executive, and the team. We all need to reduce bias in the interview process, and this approach helps.

“Date before you marry”

The Chief of Staff/executive relationship is an intimate one by its very nature. Therefore, your executive has to spend quality time with finalist candidates. One interview is like the awkward first date. It’s an interrogation round where both parties leave feeling like they didn’t fully convey their personality. Therefore, at least two or three interviews/conversations should conducted. This additional time also allows for comfort and rapport to develop without having to sign on the dotted line just yet.

If you leader does not have a lot of time for formal sit downs with candidates, consider having them shadow the executive for 1 or 2 days. You can get to know someone much better after a solid 8 hours together, and it won’t disrupt your leader’s busy schedule. They will also see whether each candidate can put into practice the skills and strengths they touted during their interviews.

Onboarding cannot be an afterthought.

The hiring process should not end on a Chief of Staff’s first day. I understand the urgent need for a COS to get up-to-speed quickly, but that’s even more reason for a thoughtful onboarding plan versus overwhelming immersion. An onboarding plan, in place over several months, is critical to a COS’ lasting success in the role and at the company. According to a Brandon Hall Group/Glassdoor study, companies with a strong onboarding process improve new hire retention by 82% and reported a more than 70% increase in productivity. That is reason enough.

The Chief of Staff is a critical role for your company and your leader, and hiring for this position should be done thoughtfully and thoroughly. As former Chiefs of Staff, our Prime team brings a unique perspective and deep experience into the fold. If you want to discuss your company’s search for a Chief of Staff, please contact us to learn more.

{"email":"Email address invalid","url":"Website address invalid","required":"Required field missing"}


It all starts with a conversation.

We love to collaborate with great people at great organizations. Put the power of Prime to work for you to find the Chief of Staff that will help you reclaim your time, your impact, and, of course, your A-game.