How to Hire a Chief of Staff
A step-by-step overview of the hiring process for Chiefs of Staff
Congratulations! You've decided to hire a Chief of Staff. But what are the critical steps in the hiring process that you need to take to recruit an all-star? Read on for step-by-step advice to ensure that you get the right person on the bus.
Step 1: Define the Chief of Staff role
It can't be overstated that having a crystal-clear understanding of the role and responsibilities of a Chief of Staff is the most important step of the process, not only for you as a CEO, but for the candidate you're hoping to attract to your company. I've interviewed many Chief of Staff candidates for Right Hand clients, and there are a few questions that strong candidates always ask:
What are the specific strategic initiatives that I will be working on?
What sets someone apart in this role?
What does success look like after 30/60/90 days?
The biggest risk for the candidate in taking a Chief of Staff role at your company is that they'll spend a lot of time on low-leverage, low-impact, and low-visibility work because your definition of what they'll be doing (and at what level) is unclear. While it's understandable that, as a private company, you might not want to advertise your next moves in a job description, you have to share this information at least in the initial screening interview. If you don't, you'll lose out on candidates that could be perfect fits but need something to chew on and get excited about early in the hiring process.
Examples of the types of Chief of Staff candidates that need something big to chew on beyond what's in the job description*:
Director of Biz Dev @ $XXB public company
Senior leader @ Big 3 management consulting firm
Ops Director @ $XXXM Series A start-up
*Candidates in the Right Hand pipeline
Beyond highlighting their specific initiatives, you'll want to know get clear on what sets a great candidate apart. The ideal Chief of Staff is usually a hunter-killer type that will run through walls to get things done and level-up the executive team, and there are specific questions you can ask in the interview to get to the heart of a candidate's true nature and experience.
Finally, every employee needs to know the standard against which their performance is measured. The Chief of Staff role is notorious (in many cases) for being one of the only roles at the company that doesn't have specific OKRs. While the projects they're working on may ladder up to company-wide OKRs, they can be nebulous at best. Think about how your Chief of Staff will be goaled in their new role -- while in the first 30 days they may still be ramping and end up more task/project-oriented, eventually your high-utility hire will need to spread their wings and start tackling big, hairy, audacious goals beyond 60-90 days.
Step 2: Define the interview process for the Chief of Staff role
The typical hiring process for a Chief of Staff goes something like this:
Initial phone screen
Multiple rounds of virtual and/or in-person meetings with (nearly) every member of the executive team
Somewhere in the middle of the executive meet & greets, a take-home or live case study is slotted in
Final round (could be another quick call or meeting with the Principal, or you'll even see an investor/board member thrown in here for more senior candidates)
Reference checks
Offer
The few major decisions to make before moving forward are how long you want the interview process to be and if you want a case study. My advice here is to keep it on the shorter side, ideally 2-3 weeks. For case studies, I've seen these structured as live walkthroughs of past executive or board meeting decks with the aim of assessing the candidate’s consulting and strategy & ops toolkit, as well as how they think through problems and recommending solutions. They could also be take-home assignments like working in a spreadsheet, building a TAM for a specific product, or doing a website/product audit. Usually, these mini cases are representative of the type of work the candidate will be expected to do on the job and exemplify the desired skillset.
Step 3: Draft a killer Chief of Staff job description
Let's face it -- if you're reading this, you're probably not so familiar with the Chief of Staff role that you could punch out a job description in 15 minutes (and your recruiting team is likely far less equipped). It's more probable that you're sharing a voiceover or a couple of bullets with someone on your team leading recruiting, they're crowd-sourcing Chief of Staff job descriptions from existing posts on LinkedIn, and the final product is customized to your specific needs.
There's nothing inherently wrong with that approach, but the issue arises when there's too much copy-paste going on. I've seen Chief of Staff job descriptions at late-stage companies mirror those of early-stage companies, which is to say, they were equally vague. This is patently Not Good™. Leading cross-functional initiatives at a Series A vs Series C company is very different for many reasons. The best advice I could give here is get as granular as you comfortably can with each bullet point -- think about the teams your Chief of Staff will be working closely with, how matrixed your organization is, and what the next 3-6 months, 6-12 months, and 12+ months look like. Make it worth their (and your) while.
Step 4: Consider hiring a recruiting firm specialized in Chief of Staff placements
A recent client of mine (PE-backed, $XB AUM) had posted their Chief of Staff role on LinkedIn, received over 200 applicants, and closed the application after 3 days. Why? The quality of applicants was less than ideal. For certain roles, you can't count on great candidates to just walk through the door -- you have to find them (and they have to be sold on you). That's why companies hire recruiters to find the perfect person for their executive-level openings, a search which usually start many months in advance of the candidate's anticipated start date.
The Chief of Staff role isn't much different when you're hiring at the Senior Director+ level. In fact, there are certain aspects of the Principal/Chief of Staff relationship and dynamic that are unlike any other and deserve special attention, but are no less important than the typical aspects of a CEO/CXO relationship. There's definitely an edge to be had when you outsource your recruiting to a firm like Right Hand Talent, where we know what it's like to work with founders and CEOs, have been in the role before ourselves, and are maniacally focused on getting stellar Chief of Staff candidates in your pipeline.
Step 5: Post the Chief of Staff job description
Share the role on LinkedIn, Twitter, and any other distribution channel where you might have significant reach, and utilize your network and referrals to help identify potential candidates. Here are some surprising facts about referrals from GoRemotely:
Employees who get referred are 4x more likely to get hired
82% of employers think referrals yield a better return on investment
45% of people employed through referrals stay with the company for >4 years
Step 6: Conduct initial screenings and interviews and review case studies
By now, you've already prepared interview questions that assess qualifications and fit for the role. If you haven't, you can view a teaser of the interview cheat sheet that I made specifically for Chiefs of Staff below, and access the full version on our other Substack post.
At this stage, it's also helpful to have a standardized interview assessment scorecard and feedback process so that all your interviewers are assessing candidates across similar parameters, and importantly, to reduce bias.
Step 7: Select and hire your Chief of Staff
Review feedback from interviews and candidate assessments. I've seen this done in a group setting where individual interviewers give their feedback out loud, or completely async based on scorecards alone. While both extremes have their positives and negatives, some combination of live feedback with the hiring manager + scorecard review is best.
Once you've honed in on your ideal Chief of Staff candidate, it's time to complete reference calls and required background checks, and make the offer. One piece of advice I have for CEOs: this is not the time to be opaque about the value of the candidate's equity. That means that it's unacceptable to just share the stock option grant as a raw number without additional context.
You're at the finish line with the person you're excited to bring on board as your right hand. Don't lose your Chief of Staff at the 11th hour because they can't adequately compare your equity offer with that of Startup B, C, and D (who they're also interviewing with). It's crucial to share the nitty gritty details -- the last preferred price and post-money valuation -- so that the candidate understands their ownership percentage in your company. I wrote extensively about why it's important to be as transparent as possible at the offer stage particularly with respect to equity compensation in this post.
Step 8: Set expectations between now and Day 1
Keep your new hire warm! Ask your executive team members to reach out and welcome your new Chief of Staff to the company. Follow up with your new hire and outline what the next 1-2 weeks will look like. If your onboarding process is already buttoned up, a lot of this will be automated and delegated to your HR and IT team.
The important thing to remember is that you've been leaving an impression on your Chief of Staff since your first interaction, and the time between their hire date and start date is crucial for ensuring a positive onboarding experience. It's important to use this time to provide clear communication and resources and answer any questions they may have. By creating a supportive and welcoming environment during this time, you can set the tone for a productive working relationship with your Chief of Staff from Day 1.
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Until next time, Right Hand fam! 👋