What Does a Chief of Staff Do, and Does Your Company Need One?

The case for hiring a Chief of Staff for your startup or small business

Jessica Donahue, PHR
Jun 10 · 5 min read
What Does a Chief of Staff Do, and Does Your Company Need One?
Photo by Sora Shimazaki from Pexels

Before getting into consulting, I spent more than a decade leading HR teams in the corporate world. I worked for companies that had anywhere from 500 employees to 25,000 employees, and these organizations operated in industries that ran the gambit from retail to manufacturing.

I’ve helped executives build organizational structures and subsequently tear them down depending on the needs of the business and how they evolved over time. I thought I had seen it all, but I’ve never worked for an organization with a Chief of Staff (COS) before. Sure, I’d heard about this role in the government or the military, but not in corporate America.

In my HR consulting practice, I focus on helping small businesses and startups implement talent strategies to power their growth and increase employee engagement. So when I noticed the COS job title popping up in more and more Linkedin profiles at these types of organizations, I had to take note.

And, now that I have, I can’t help but think this role is a critical missing piece in so many organizations, both small and large.

According to Forbes, the Chief of Staff “is generally positioned as the CEO or executive’s ‘right-hand person’” and is charged with ensuring their staff works as efficiently and effectively as possible while, at the same time, allowing the executive to focus on the strategic direction of the business.

Julia DeWahl wrote about her experience as COS to the CEO at Opendoor, describing the role as one that “can change over time, but typically encompasses managing the executive’s priorities, overseeing staff/internal operations, and spearheading special projects.”

On the surface, this definition might sound a lot like what we expect out of a COO. However, several key differences delineate the two and thus warrant both positions.

In Tyler Ferris’ book, Chief of Staff: The Strategic Partner Who Will Revolutionize Your Organization, he explains the COS role as “a catch-all role, filled by someone with exceptional organizational and people skills, who handles all manner of tasks not covered by an existing member of an executive’s leadership team or administrative staff.” Additionally, he says the:

“COS is committed to his or her principal executive, not the board or staff — except through that principal executive. The COS represents the principal executive but isn’t a principal executive, and thus leads from behind. The principal executive maintains control and supervision of communications, governance, technological progress and, perhaps most of all, confidentiality with a trusted thought partner in that isolated space known as the top. Whereas the COO might have designs on the CEO’s office some day and have his or her own agenda for influencing the CEO, the COS is enough steps removed to not be an immediate threat and can therefore be an even more deeply trusted advisor.”

DeWahl explains that the right time to bring in a COS is when “your company is scaling quickly, and the organization needs to uplevel its operating procedures, including All Hands meetings, staff meetings, company-wide comms, board meetings, OKR processes.”

A recent article from Harvard Business Review suggested leaders ask themselves several questions to help determine whether a COS role is needed. They include:

  • Are you spending enough time on the vital A items on your agenda, or are you frustrated by time spent on B and C items?
  • Do you have enough “white space” in your calendar to consider future opportunities, or is most of your time spent reacting to what has already happened?
  • Are problems identified early enough that action can be taken before they create damage, or is it common for large problems to occur unexpectedly?
  • When you direct that some action be taken or ask for data on a particular issue, do you often not hear back until you remind people?

If it turns out that you’re spending too much time on low priority items, you don’t have enough — or any — “white space” on your calendar, or you find that problems aren’t being identified before they cause significant damage to the business, it might be wise to invest headcount in a COS.

If you’re anything like me, you may have assumed that only large organizations can benefit from investing in a COS. But startups and small businesses are, in fact, uniquely positioned to benefit from the COS role.

Why? Because so many of the things a COS will be responsible for establishing and shepherding across the finish line (OKRs, internal meetings, staff communications) have not yet been implemented in any measured or intentional way.

In the end, it is far more effective — and less damaging to company culture — to design these things with the time and attention they deserve now when you’re still relatively small.

The alternative to scaling the business without these things in place is that you will ultimately have to circle back to untangle whatever mess they organically morphed into down the road.

Having worked with several small business owners who are scaling successful startups, one of the biggest challenges I see owners wrestle with is how to most effectively use their most precious resource — their time.

When you start out owning a small business, you can — and arguably should — spend your time getting intimately familiar with every detail of your business. Every customer interaction, staff dispute, and product issue likely flows through you. And that’s okay.

But when we look to scale, the challenge becomes figuring out how to pull yourself out of the minutiae to spend less time working in the business and more time working on the business.

And, at that point, bringing in a Chief of Staff just might be the perfect solution.

My free mini-course will provide you with actionable tips on how to become a better, more effective leader for your team. Sign up for free.

Work Today

A publication about work life, remote work, productivity and the labor market

Jessica Donahue, PHR

Written by

I help startups and small businesses design and implement HR solutions at AdjunctLeadership.com → Join my free mini leadership course: bit.ly/307AheB

Work Today

Work Today collects stories and insights on work life, productivity and the transformation of modern work.

Jessica Donahue, PHR

Written by

I help startups and small businesses design and implement HR solutions at AdjunctLeadership.com → Join my free mini leadership course: bit.ly/307AheB

Work Today

Work Today collects stories and insights on work life, productivity and the transformation of modern work.

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