The Chief of Staff Role: How To Find the Right Fit in the Interview Process

“Before the Interview”
— CEOs
— Candidates

“During the interview”
— CEOs
— Candidates

“So, what exactly does a Chief of Staff do?”

The startling thing about this question is that I got it as often from people inside my company as people outside of it. I am my company’s first Chief of Staff (CoS), a title that’s developed a bit of a cache in the startup scene. I get a lot of questions both from candidates interested in being a Chief of Staff and CEOs excited about getting one. After all, who wouldn’t love the idea of a capable and ambitious person who is fully dedicated to leveraging you and your time? But because of how intertwined a CEO and a Chief of Staff’s experiences are, the role can be high risk, high reward: at its best, you’re two peas in a pod, an incredibly effective team that massively expands the CEO’s impact; but at its worst, it can turn sour and be a uniquely emotionally draining professional relationship.

Depending on the company, the role of Chief of Staff can span from high functioning and strategic admin, to Jack- (or Jill!)-of-all trades, to early COO, to dedicated leverager of the CEO’s time, and everything in between. Regardless of where they fall on the spectrum, successful CoS’s tend to be smart, ambitious, extremely organized, and have high EQ. Because the role is just taking off in the private sector, and because of its inherent ambiguity, finding the right CoS, particularly the first, can be tough for a CEO, as well as for her team. For candidates, it can be difficult to distinguish a great opportunity from a potential career landmine.

To help all parties find their ideal arrangement, here are some suggestions for both CEOs and potential Chiefs of Staff to consider during the interview process.

Before the Interview

CEO

Make sure you really need a Chief of Staff.

Understand what you’d like to move off your plate, and assess whether these tasks really belong with the executive or should be delegated to a yet-to-be-hired individual in a function. Many folks have shared helpful thoughts on this, but here are some potential indicators that a CoS makes sense for you:

• 1. You are the bottleneck to growth or progress — it’s not a lack of general bandwidth across the team, but of yours specifically. You can’t delegate more to your existing team, and you know that hiring more folks into other executive roles isn’t going to solve your problem.
• 2. You have a senior team — a key responsibility of a CoS focused on CEO leverage is to ensure that your senior team is aligned and is driving progress in their respective areas of the business. As CEO, if you don’t already have your leadership team built out, there is a natural ceiling to how much a CoS can really leverage you. Before hiring a CoS, consider investing in making key senior hires first. For example, if you find yourself spending too much time on product vision, should you be hiring a stronger product leader for your team, versus finding ways to devote more of your own time to it?

Vet your own comfort with the level of access you are willing to grant a CoS

• Many Chiefs of Staff accompany their CEO everywhere. Many have unrestricted access to their boss’s e-mail. Many are in the room for almost every meeting the CEO is in, including 1:1’s, brainstorms on sensitive topics, and board meetings. Ask yourself honestly: Are you the type of person who will be comfortable with the level of access and transparency required to make a CoS effective? The single most important thing in a CEO-CoS relationship is trust. Knowing your own limits on the logistics of trust prior to bringing someone in makes it exponentially more likely the role will be successful. Put another way, is there any information, process, or relationship you consider off-limits? Boundaries (e.g., compensation data, full company performance data, performance reviews) don’t have to be a deal-breaker, but they should be clear from the get-go

Clearly articulate to your team why you need a Chief of Staff, what you expect this person to do, and what they will have access to

• Differing expectations between an incoming CoS and a CEO’s senior team can be a kiss of death: to set both sides up for success, make sure your team is aligned on the need for the role, is on board with your vision for it, and is willing to be part of the interview process. Other senior leaders shouldn’t see this hire as a threat or a buffer between them and the CEO — rather, they should view this role as a multiplier to the entire senior team’s efficiency.

CANDIDATE

Ask yourself: Why the Chief of Staff role?

What makes you interested in a CoS role specifically, versus a role that offers similar strategic or operational experience within a function (e.g., biz ops, product management, etc.)

Consider the traits you find inspiring in a manager

Come ready to vet whether the CEO is someone you think you would jive with and enjoy learning from

Prepare to solve problems you don’t understand yet

To be successful in this role, it’s important to be comfortable with ambiguity (e.g, finding solutions to ill-defined problems that no has explicitly asked you to solve)

• Ahead of the interview, prepare your best diagnosis of challenges the business is likely facing along with solutions you would put into place as CoS. You won’t be exactly right, but you will show the CEO two critical things: that you can be a thought partner to the CEO about her business (e.g., leverage!), and that you can be helpful without someone explicitly telling you how to be

During the interview

CEO

Get to know candidates in a variety of settings

• Unlike many colleagues, you want to be comfortable with this person in a meeting, at a power lunch, at the airport waiting on a 12-hour-delayed flight, at a party, and everything in between
• Hang out with the candidate and team members or even your significant other; see how comfortable you are having them around in non-office situations. This is will surely occur during their tenure, so better to know now
• Imagine your worst day as CEO. Your investors are angry, your team is frantic, and on top of that, your child is sick. Now ask yourself: Am I comfortable with a CoS being around to help right now? Spend enough time with them to be able to answer that type of question

Understand candidates’ personal motivation

• Ask the candidate about their long-term goals. By now, both of you know that the expectation is for them to outgrow the position — what do they want to do next? How will this role inform that future? Do you think you can help them? The question around expected tenure as CoS will arise naturally and, like, everything else, should be discussed candidly.

Test for EQ

• Besides being trustworthy, I would argue that this is the most important trait for a great CoS, above even intelligence or organization
• This person will represent you, your office, and your opinions in a variety of both internal and external situations — you need to be able to trust them to respond maturely and appropriately without you being there to supervise, particularly when interfacing with your team
• To get a sense of their EQ and style, present them with a tough interpersonal scenario and have the candidate talk through how they would handle it. For example, two executive team members have come to them with conflicting accounts of a situation and are asking what the CEO would want to do. Ask the candidate to talk you through how they would approach the situation, and potentially even demonstrate how they would communicate with each team member

Test for ability to work autonomously, even in the face of ambiguity

• For this role, many people prefer candidates with backgrounds in highly structured professional services (consulting, banking etc.) — and for good reason, those jobs provide great training on business acumen, organization, and professionalism
• But what they don’t prepare you for is ambiguity — they tend to be very regimented programs with abundant infrastructural support. So come up with scenarios or questions that will test how the candidate deals with ambiguous situations, particularly where they asked to independently design OR implement a solution

‍

CANDIDATE

Think critically if you could really root for this CEO.

• You will spend an inordinate amount of time laser-focused on them, so it’s important that you believe you will actually like them and want them to be successful. You will inevitably need to defend this person and their perspective, so make sure it’s someone you’ll want to stick up for even if a decision they make is unpopular

Ask them to articulate what the role is — many times

• You need to make certain the CEO actually needs a CoS, and knows why. Ask them to articulate to you specifically what they believe the role entails. Ask them firmly, and in many different ways. For example, you could ask “What’s a recent situation that would have gone better if you had a Chief of Staff? What role would the CoS have played in solving that problem?” If they have trouble articulating the role to you, try to help them: you will need to be their thought partner in a huge range of situations, this can be your first practice!
• Assuming there are multiple rounds of interviews, definitely ask to meet several members of the CEO’s team — and ask them to articulate the role to you, as well. Look for consistency, and if there are inconsistencies, bring them up with the CEO in final conversations
• Another question you can try: what other titles were considered for this role? Why was Chief of Staff the winner?
• If you get a sense that the opportunity for a CoS isn’t meaty enough, or the team isn’t on board with a CoS, this may not be a situation you want to get yourself into.

Figure out how things work right now

• Who manages cross-functional projects today? How is conflict within the team currently resolved? How do big decisions get made? Who would the CEO consider her “right hand” at the company today? Try to understand the status quo. You want to be positioned to be additive very quickly; and you want to avoid causing any internal issues as you integrate

Find out about their working styles

• Ask the CEO how she likes to be communicated with — Frequent check-ins? Structured emails? Convos on the fly? Scheduled meetings? You should be able to flex to their style, but this is important information to know from a fit perspective
• It was weird, but one of the most important questions I asked my CEO when I was interviewing was “show me what you’re like when you’re mad”. You will, with 100% certainty, see your CEO at her most stressed: you should know in advance if their type of stress is one you think you can handle well, and whether you could be helpful to her in tougher, emotionally charged situations
• Ask the CEO what they think the hardest thing about working with them is — and listen to them. If someone says they’re difficult, disorganized, late, temperamental, etc. believe them: your job as CoS is to leverage them, not to change them. Honestly assess if you think their Achilles heel is one you can work with and/or build around
• Ask the team: What’s the one piece of advice you’d give me about working well with the CEO?

Gauge their level of self awareness

• Ask them: What feedback have you received from your team? This will help you gauge their level self-awareness about their own areas of growth — and how much flexibility they’re likely to give you to provide them with (constructive) feedback on their leadership style
• As a note: most CEOs are looking for an extension of themselves, but often would be better served by someone with complementary skills. This is certainly a generalization, but often a CEO who says they need someone “who can help keep the trains on track” is a big picture thinker that will be less excited about engaging with systems and processes you put in place to track initiatives. CEOs who say they need “to get out of the weeds and spend more time thinking high level” are likely detail-oriented, potentially even micro-managers, and won’t be too excited about getting actually pulled out of those weeds.
• You should compare what you learn about their style with your own style to see if they are complementary. You will provide enormous value to the company by taking on necessary executives tasks that your CEO is less excited about. After all, a pair of micro-managers doth not a productive Office of the CEO make!

So, is Chief of Staff the right role for you or your organization? All my fellow ex-consultants out there will recognize this answer: it depends. My experience as Chief of Staff at Group Nine Media has been the most exciting and rewarding job of my career to date, and I’m very proud of the impact I get to have on the strategic and operational leadership of my company. Finding the right fit can be tricky, but done well, it can be extraordinarily fruitful partnership and a major unlock for a company’s growth.

Still have questions about the Chief of Staff interview process? Email me at mlitre@gmail.com.