Part 3: How Do I Find and Hire a Corporate Chief of Staff?

Published in

The Startup

10 min readFeb 24, 2019

Now that we know what a Chief of Staff (CoS) is, and the profiles of typical CoS’s, we’ll look at the Chief of Staff role from the executive’s lens.

This article discusses:

How to define the CoS role for your specific needs
How to find and hire the right CoS for you

Define the role

In order to successfully define this role, the executive should answer these three key questions:

(1) What is the purpose of this role?

At a high level, what is the key purpose of the CoS role? What gives meaning to this role? What is the “why” behind it — why would someone devote their time and energy to filling this role? Is it to help the company grow during a period of hyper-scaling? Is it to project manage cross-company initiatives? Clearly defining the role’s purpose will help you articulate it to colleagues and candidates.

(2) Why is a separate CoS position necessary?

You should answer this question for any new role, but because your team might not be familiar with the function of a CoS, it’s even more important here. What will the CoS do that your Executive Assistant (EA) cannot do? Or your COO? How will the CoS interact on a daily basis with the other people who also report to you?

(3) What specific traits and skills does this CoS need to have?

Analytical skills

Your CoS needs to be able to analyze and draw insights from business data. In order to do that, they’ll need strong quantitative and analytical skills, including an understanding of corporate finance, accounting, and statistics.

High EQ

In addition to analytical skills, your CoS needs to have people skills. Do they have an accurate pulse on employee sentiment at the company? Your CoS’s presence in a meeting (even if you are not there) will likely alter how comfortable employees feel sharing their honest perspectives. They need to balance their relationships with colleagues and their relationship with you.

Effective communicator

Mark Organ, CEO of Influitive, says that a CEO spends much of their day communicating, so you want to look for a CoS that is an effective communicator. Your CoS should be an effective communicator in both verbal and written contexts, and in both public forums and in private meetings.They represent you and your thinking — so it’s in your best interest to make sure it’s an accurate representation. Ash Athawale, Senior Managing Director at Robert Half Executive Search, notes that, “Because the Chief of Staff’s goals should mirror the Chief Executive’s, companies need to ensure candidates are in alignment with the executive’s thoughts, leadership and values. It’s almost like the two should be able to complete each other’s sentences.”

Brian Screnar, former CoS to Nathan Myhrvold, says that a CoS is often a “discreet envoy that communicates sensitive information through back channels”. By laying the groundwork, your CoS can clear a smoother path for you — especially when it comes to difficult announcements.

Project management skills

Project management skills are critical for a CoS. This includes the ability to track multiple projects or priorities at once. When I worked for Tony Hsieh, CEO of Zappos, he would have 50-100 discrete projects that he was following at any given time. I would keep track of all of these projects and have a weekly summary ready to present to Tony. Most weeks, he didn’t need to know more, but when he wanted to drill down on any one project, I had the information handy.

Can-do attitude

Although your CoS likely has a wide range of abilities, they won’t be an expert in everything that you throw their way. At that point, it’s more about their attitude and how they figure out how to complete the task.

When I worked for Tony, the tasks that I worked on could be as diverse as planning a 200-person party or figuring how to scale a new business line. If Tony asked me to accomplish a task and I didn’t have the skillset needed to finish it myself, he empowered me to outsource it. I could recruit someone else within the organization to help me, or hire an external consultant or agency. In those situations, my utility was finding someone with the right skillset — or even at times, one step beyond that: finding someone who knew how to find someone with that skillset. Tony trusted that I could get the task done in the best way, with minimal direction, regardless of whether I completed it myself or not.

Adaptable

Your CoS should be comfortable working in ambiguous environments. Ryan Metcalf, CoS to Max Levchin, writes that he was truly able to hit his stride because he “thrives in ambiguity”. He was able to identify gaps and either find someone to bridge those gaps or fill them himself.

Comfortable with disagreement

Finally, your CoS should feel comfortable disagreeing with you. Robert Half’s Athawale believes that, “your Chief of Staff also needs to be comfortable sharing opinions, including ones that may be different from yours.” When I worked at McKinsey, the management consulting company, we emphasized the “obligation to dissent”. If you had an opposing viewpoint from someone else on the team, even if they were more senior than you, you had to speak up.

Although this is by no means an exhaustive list, a CoS with these core traits will be set up for success. Another way of approaching the role definition is to make a list of all the tasks — big or small — that you are looking to offload onto your CoS and group them by skillset. Chris Hutchins, CEO of Grove, writes here: “I asked each candidate to rank his or her interest and abilities across 12 different functional areas in real time. This allowed us to identify any overlaps that existed between each candidate’s unique skills and expertise with my own expertise, as well as the actual needs of our organization.”

Source, interview, and hire a CoS

Now that you have a clear idea of what you’re looking for in a CoS, it’s time to begin sourcing and interviewing candidates.

Write a job description
Work with your recruiter to write a job description. Part 1 covers the major categories of CoS responsibilities. I also went through recent CoS postings from Away, theSkimm, Knotel, Reddit, Lyft, and Gusto to pull out sample specific responsibilities, which are included in the Additional Resources section at the end of this article.

Source candidates
Should the CoS be an internal or external hire? There is no right answer. It depends on the specific role that the CoS is filling, and CoS’s can be equally successful if hired internally or externally. Sometimes, the CoS benefits from knowing the company dynamics and other members of your executive team. In other cases, the CoS might be more focused on special projects and growth initiatives that don’t require many pre-existing touch points.

Interview candidates
Maren Donovan, Founder of AVRA Talent, has written a comprehensive guide for hiring an EA or CoS based on her experience hiring over 500 EA’s and CoS’s. First, articulate approximately 5 outcomes that the CoS must complete within their first few months in order for the hire to be considered successful. These outcomes must be both objective and quantifiable. Then, during the interview, test for how the candidate’s experiences and strengths align with the outcomes for this role. While this might seem obvious, Maren notes that the process of explicitly writing down these outcomes helps generate critical alignment.

I don’t recommend the standard office conference room interview for this position. It’s too controlled of an environment. Ideally, you would spend time with the candidate in different contexts. Is it possible for them to shadow you for half a day and provide input on what they observed? If not, can they observe a meeting? I know an executive who conducts walking interviews, where he literally walks around a lake with candidates.

While I highly recommend more than one interview before hiring a CoS, many executives are intuition-driven and feel comfortable extending an offer after just one meeting. Richard McLean noted that after just one interview, his executive quickly realized that their values were aligned and that they would complement each other well.

While you may rely on your intuition to determine fit, you also want to back that up with a skillset evaluation. To test this, give the candidate a sample assignment to see how they would approach a typical task.

Additionally, have the candidate spend time with the colleagues on your team who they’ll be interacting with on a daily basis. What does your Executive Assistant think of the candidate? How did the candidate act towards the team when they were going through the interview process? For example, Zappos is known for the “shuttle bus driver test”. Zappos sometimes sends a shuttle bus to pick up candidates at the airport. At the end of the day, in addition to asking interviewers what they thought of the candidate, they also ask the shuttle bus driver. If the driver vetoes the hire, the candidate isn’t hired regardless of how well they did during their actual interviews.

Ultimately, there needs to be a personality fit between you and your CoS, and you need to have trust in each other. The CoS will have access to much of not just your professional life but also your personal life. You need to find someone who you can spend significant amounts of time with, who you are excited to mentor and develop, and who you feel is a good reflection of you and your reputation.

In Part 4, I’ll discuss what to do to ensure your relationship is set up for success.

Additional Resources

Sample Job Responsibilities

Filling holes: Identify cross-functional opportunities that don’t have a clear home within the organization and assume ownership to project manage and execute, with direct approval from leadership team and founders (Away)
Leading cross-functional initiatives: Develop business and project plans for initiatives that cut across the organization, including new offerings, partnership opportunities, and improvements to internal operations (Knotel)
Communications: Drafting external and internal founder communications, including board decks, team presentations, blog posts, network e-blasts, press responses, etc. (theSkimm)
Network management: Managing the founders’ network of contacts and connections. (theSkimm)
Screening opportunities: Vetting new business and partnership opportunities on behalf of the founders before passing to relevant team members (theSkimm)
Meeting prioritization: Work closely with the co-founder’s executive assistant to manage prioritization of schedules and meetings (Away)
Project management: Track and follow up on what appear to be Smouldering Issues and alert before they become fires (Reddit)
Leading new initiatives: Develop new programs to support the strategic direction of the organization (Reddit)
Planning: Own the quarterly strategic planning process (Lyft)
Board meeting preparation: Project manage Board meeting prep and creation of Board meeting materials. Provide regular written updates to the Board on key business moments and progress against goals. (Gusto)

Articles

Harvard Business Review on “The Case for a Chief of Staff”
Tyler Parris, author of “Chief of Staff: The Strategic Partner Who Will Revolutionize Your Organization”, discusses how having a COS can benefit you — read it here
Chris Hutchins, CEO of Grove, on why he needs a Chief of Staff — read it here
Fantastic piece on what to look for during a COS interview by Maxine Litre, COS at Group Nine — read it here
Long piece by First Round that is worth reading. Discusses how to determine if you need a COS, how to scope the role, and what questions to ask COS candidates — read it here

Recruiters

Kathy Macdonald Associates — Founder Kathy Macdonald has over 25 years of experience sourcing talent for CEOs of Fortune 500 companies and Silicon Valley startups
Group Insearch — Specializes in EA/COS roles for CEO’s and VC’s in the Bay Area
AVRA Talent — Founder Maren Kate Donovan also founded Zirtual, a leading Virtual Assistant provider
Prime Chief of Staff — Specializes in CoS searches. They also have an FAQ page that answers some common questions about the role of a CoS and how to hire one
Robert Half Executive Search — One of the larger executive search agencies. Make sure you’re talking to recruiters within the company who have relevant experience, such as Ash Athawale (who was interviewed for this piece)

Consultants

Virtual Chief of Staff — vChief maintains a robust Chief of Staff network that provides CoS support to executives nationwide
McChrystal Group — McChrystal Group provides advisory services based on the book Team of Teams, written by General Stanley McChrystal. They also host an annual Chief of Staff Summit (next happening March 22–23, 2019)

Next: Part 4: Chief of Staff — The First 90 Days

Read All 5 Parts:
Part 1: The Role of a Corporate Chief of Staff
Part 2: How to Become a Chief of Staff
Part 3: How to Find and Hire a Chief of Staff [this article]
Part 4: Chief of Staff — The First 90 Days
Part 5: Chief of Staff Best Practices