Why I Need a Chief of Staff and You Probably Do, Too

Forget what's been happening at the White House and in Silicon Valley. A chief of staff can actually help your company soar.
Why I Need a Chief of Staff and You Probably Do, Too
Image credit: Andrew Harrer | Getty Images
Guest Writer
Founder and CEO of Grove
8 min read
Opinions expressed by Entrepreneur contributors are their own.

Being the founder of a business, especially one in the early stages, can feel like a constant struggle to be in multiple places at the same time. Your desire to see the business grow and thrive tempts you to have your hands in every single project. And even if you have co-founders, or early employees you trust, you may still feel the need to be in every meeting or on every call.

But this just won’t scale.

Related: The Importance of Candor and Other Lessons From a Former White House Chief of Staff

During a particularly busy stretch earlier this year, I found myself wishing that cloning, in terms of technology, were a bit more advanced. Trying to stay involved in every aspect of the business was making me inefficient across the board. This wasn't about ego, or believing no one else could “do the thing” as well as I.

It was simply a lack of the time I would need to turn some of my knowledge, and ultimately responsibility, over to another capable person. What I needed was ... a chief of staff.

I know, I know: Chiefs of staff don't always get good press when you consider what's gone on in the White House or Silicon Valley. But one problem here is the very definition of the role a chief of staff plays within an organization. There still doesn’t seem to be a consistent definition of what this position actually is, and perhaps for good reason.

I think one reason why definitions here are so varied is that this position  has to be tailored to meet the specific needs of each organization. For one company, a chief of state might take on duties similar to that of a COO, while in another organization this person might tackle some of the work an executive assistant typically owns. Sometimes it’s a mix of both!

Like many roles in the startup space, the duties and responsibilities of a chief of staff can be ambiguous, but this individual's impact is unquestionable.

From my perspective, the main purpose of a chief of staff is to add firepower to the person he or she has been hired to support. This is why anyone you hire for this "chief" job needs to be good at executing, i.e., getting stuff done. A good chief of saff should double -- or even triple -- the boss’s capacity and productivity.

Related: What White House Chiefs of Staff Can Teach About Running Your Business Better

So, how exactly do you go about finding this unicorn?  

1. Add firepower.

If you’re starting from scratch, a great first step is to conduct an organizational audit to surface areas of your organization's inefficiency. Where are you losing time? What recurring tasks are stealing too much of your focus? At Grove, for example, we had just closed our Series A round and knew we were about to start to grow the team. So, we had an immediate need for someone who would be comfortable tackling the recruiting and onboarding of all those new employees.

However, we also knew this role had enormous opportunity to grow and change because of unparallelled access to nearly every function across the business. Because of that scenario, during the interviewing stage, 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.

2. Keep an open mind.

This brings me to my next point: Keep an open mind. Throughout the interview process, my perspective on the “perfect” profile for my company's chief of staff job changed dramatically. We interviewed dozens of incredibly qualified candidates ranging from an ambitious recent graduate to an admiral in the Royal British Navy, and each one helped us crystalize a little bit more of what the role should be for our organization.

In young companies like ours, special projects and initiatives often pop up that don’t squarely fit into the realm of any specific function (marketing, engineering, product, etc.) -- and in many instances, in-house expertise in that area might not even yet exist! It used to be that those projects ended up on my incredibly long list of to-do’s, and would often be ignored as my focus was pulled to more pressing priorities.

At this point, however, my chief of staff has become an extension of me, meaning that one of this person's main duties is managing any ad-hoc projects (which have no clear owner) on my behalf. As the chief of staff's tenure in the role advances, this management role becomes an iterative process whereby he or she and I continually evaluate whether those projects are areas our chief of staff wants to own.

We also ask whether or not the need has grown large enough to warrant hiring in-house functional expertise.

It’s important to note that the benefits of a chief of staff are not limited to startups of any one size. A quick jobs search on Google shows a seemingly never-ending list of startups at all stages that are looking to hire one. Some are even hiring a chief of staff by strategic category, separated out into growth, product or even government relations. This got me thinking about how my network views the role of a chief of staff  -- and whether it differs from ours at Grove.

What I learned about the chief of staff's role from two people close to me.

My search for the answer began close tohome because my wife, Amy Fox, was chief of staff to Lyft’s co-founder during a period of rapid growth from 2012 to 2014. From her perspective, Amy told me, a chief of staff serves as the right-hand man -- or in cases like hers, woman -- of the executive being supported.

When Amy was chief of staff, Lyft was growing so quickly that everything was moving at hyperspeed. It was her responsibility to be “another brain” to help the co-founder think through, navigate and manage the rapid evolution of business needs. My wife pointed out that when your startup is addressing so many important initiatives simultaneously, some get dropped or deprioritized. That's when it’s probably time to hire a chief of staff.

Next, I happened to speak about this question with my friend Kanjun Qiu, CEO of Sourceress, who'd worked with the entire executive team at Dropbox as chief of staff from 2013 to 2015, which was also a period of accelerated growth. Qiu viewed her role as someone who “kept the trains running on time.” She did everything from conducting analyses on high-priority topics to running meetings and ensuring the executive team's members were communicating with one another effectively.

For her, she said, determining when it’s time to hire a chief of staff comes down to the mental state of the CEO. If he/she is managing too many business categories at once and isn’t sure which of them will require subject matter experts, hiring a chief of staff will increase productivity. The most important skill for this job from Qiu's perspective? Sound judgment.  

Specific tips for whom to hire

Once you’ve sorted out the skills and interests your organization needs in a chief of staff, here are some tips that can not only help you hire the right candidate, but help you make sure that you're building a productive working relationship from day one:

Related: This Founder Shares the One Trait He Looks for in Every Hire

  • Look for someone who is willing to disagree with you. Yes, your goal is for this person to be an extension of you, but if you hire your exact mirror, you will almost definitely miss out on getting a different opinion or perspective. That perspective can lead to a better outcome and increase your company’s chance of success.

  • Understand that relaying your wealth of institutional knowledge to this new asset takes time. Give yourself a solid six months or more to spend as much time together as possible. Bring your chief of staff to every meeting. Give this person the access, tools and information needed to learn your style, so he or she can approach situations similar to the way you would.

  • Do whatever you can to prioritize establishing trust with your chief of staff right away. In order for this person to be your extension, you need to adopt an unwavering commitment to sharing your thoughts and opinions on everything (minus sensitive HR issues). Only when you trust your chief of staff will this trusted employee truly start to help you increase your capacity.

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