How to Hire Your Chief of Staff

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So is your company going to hire a Chief of Staff? Well, cheers then! As it’s a big kickoff for the future of your Startup.

The CoS role uniquely provides access to decision making, planning, and even network building. It's a huge responsibility. The right person in the role wields enormous influence and will level up your entire organization's strategy and execution.

Why a High Performing Startup Needs a CoS

Let's start with a fundamental question: Why hire a Chief of Staff?

Your Exec team often has 36 hours of work to fit into a 24 hour day. Simply put, an Exec isn't an eight-armed octopus who can handle everything at the same time. The Exec already has a lot on their plate, and it's hard to get everything on track when you’re on the edge of losing it.

A CoS isn't just an assistant – They are someone who acts as a stunt double for an Exec and reads their mind like an identical twin. Their responsibilities include:

attending meetings and rolling out the strategy;
communicating the company vision and coordinating the organization smoothly even when the Exec is not around;
protecting an Exec from burnout;
and percolating up decisions that can only be made by the Exec while resolving issues that do not require their attention.

A good heuristic for a CoS is that they make the same decision you would make 80% of the time without consulting you. And for the other 20%, they can correctly identify that they need to check in with you.

Those X-Factors You Should Look For in a CoS

First, decide what type of Chief of Staff you need to hire. Their responsibilities and skills may vary, so check out this handy framework to gain some insight about CoS types.

The CoS role requires influence and often doesn’t have authority. It means, in most cases, they're neither the manager nor more experienced than those they need to direct, so they have to have what it takes to earn the team's respect.

Therefore, a CoS should be formidable at communication, business savvy, and understand what needs to be done. At the end of the day, one of the most valuable skill sets in a CoS is pragmatism.

How to Find One

I know it sounds like we’re looking for Professor X, but hey! Don’t look for your perfect match in far-far lands. Actually, the right fit for the job might be someone you already know.

So here are the ways to find your best candidates:

Inside the company

Before going on the expedition, make sure that you didn't overlook the hidden gem in your company. Choosing a Chief of Staff from your employees is usually a better idea.

Here is why:

They already know the vision and policies of the company, so you do not need to explain everything over and over again. Being your team member will allow them to convert themselves into your alter ego easily.
They already have relationships with their co-workers. So they’ll skip the "get to know each other" and adaptation part, which will save you lots of time and money throughout the process.
And they already know your dark and bright sides. They’ll quickly fill the gaps as they know what your strong suit is and where you can leg behind.

The failure case in this strategy is to be aware of is that they are too accustomed to how things are already done and won’t challenge your thinking enough. As mentioned before, the best CoSs are pragmatic – they care about achieving outcomes. If they overweight the ideas based on tenure or experience instead of evaluating an idea on its merits alone, they’ll be severely handicapped.

Another thing to be aware of is the perception changes that may be required from the rest of your team. You want to be sure your new CoS is able to wield the right influence necessary to drive priorities across the team, regardless of their previous role.

You can help by giving your management team and their direct reports a clear understanding of how you expect your CoS to work with them and reaffirming this plan directly and often. Make sure to also define the CoS level to give visibility on how your CoS will work with the senior leadership team and their decision-making capabilities within other cross-functional projects.

Evaluating candidates

Now that you know what category of CoS you need to hire, here are some tips to help you make sure you are effectively evaluating for this role:

Define the outcomes they’ll drive;

Launch a new OKR system
Improve cross-functional communication
Save Exec team time
Create leverage in the fundraising process
Create systems that will scale in a high growth phase
Act as a strategic partner

List out what success will look like in 30, 90, 180 days.

‍Here is an example for “Launch a new OKR system” from above to give you a sense of the granularity I would recommend:

30 days:

Demonstrate a mastery of all pros and cons from each function of the current goal-setting process.
A clear understanding of how these differ across different levels of the org because individual contributor’s pain points are almost always different than managers’ or leadership’s.

90 days:

Evaluate other models by speaking with other companies’ representatives and reviewing potential tools on the market.
Present a clear recommendation and drive towards an implementation plan that has cross-functional and multi-level approval.

180 days:

80% of teams follow the new system, and when polled randomly, individuals in the company are aware of why the new system is being rolled out and how it relates to their work.

Define the characteristics they need to have to achieve these.

Continuing with the OKR example:

30 days skillset:

High EQ
Active listener
Self-directed

90 days skillset:

Proactive
Synthesis
Strategy

180 days skillset:

Communication
Change management
Project management

Create an interview scorecard with example questions.

‍Sticking with how to evaluate High EQ as one example:

Tell me about a time you championed someone else's idea.

Good: Specific examples of disagreement, debate, and changing one’s mind based on evidence.
Bad: Lack of examples, can’t explain why their position changed.

Tell me about a time you failed. What did you learn? How has what you learned changed since then?

Good: Examples of introspection that change over time. Continuous reflection and learning.
Bad: Learning a specific lesson once and never reflecting on it or extracting new learnings as their knowledge expands.

How do you malfunction?

Good: Insight into how they succeed and fail, and examples of how they self-manage this.
Bad: Lack of examples and understanding.

The general recommended questions should follow a theme of testing introspection and knowledge of self drive, understanding, empathy, and knowledge of others.

The Best Candidate has a lot of Other Options

Interviewing your Chief of Staff candidates is a bigger deal than you might imagine. That is why it’s more than a traditional questions-answers ceremony.

So here are some tips and tricks to prepare you for an interview journey:

Don't make it look like an interview

Your relationship with your Chief of Staff is not the same as it’s with an average employee. A good CoS will make you look very very good, and will receive none of the credit. You are giving them incredible influence over your life, and in exchange, they are going to work tirelessly to accomplish your goals.

Pick a context that allows for questions that will give you more insight into the candidate's personality. Because both of your personalities should fit, and you should expect to show vulnerability. Your CoS cannot succeed if they don’t know all of the light and dark sides of the business and often parts of your personal life.

More about them

Learn as much as you can about their motivations:

What are their beliefs and visions?
What do they expect from helping you?
What do they want to do next?
Talk to them about the characteristics of the best team they’ve ever worked with.

These questions will make it clear if your company is suitable to prepare them for their next step.

Send up a trial balloon

If possible, put them into scenarios where you can test their emotional intelligence rather than rational decision-making. Come up with unique and various business cases and ask how they would react. Challenge them and check their soft skills when facing actual, real issues.

Preferably, have them shadow team meetings and then ask them to provide insights into strategic decisions about the matters discussed and suggestions on improving the meeting.

Depending on the category of candidate you want to hire, look for someone who is willing to take risks, doesn’t mind being wrong, and provides insights you might otherwise have missed. If their reaction is “everything was great”, they probably aren’t cut out for the role because, let’s be honest - something can always be better.

A few closing words of advice

Maybe you already admire the CoS of ABC company and think that this person would get along well with you. I can’t blame you. In general, the best candidates need to be enticed away from other promising opportunities.

And it’s best to keep in mind that people rarely choose CoS as their primary career. So if you can recognize the CoS potential in someone working in a completely different position, don’t hesitate, invite them for a short conversation. At worst, you’ll get to know one more interesting person. A word of caution: most CoS roles typically encompass some type of tour of duty, often for 18-24 months before being placed in a Director or VP level role in the business.

When you’re ready to start recruiting, the best candidates (if not internally sourced) generally come through referral and word of mouth. One good option is to consider the Chief of Staff Network or the BizOps Network as these communities and their associated job boards have strong peer groups building the skills to excel in these roles.

How to Hire Your Chief of Staff