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Chief of Staff is an Essential & Misunderstood Position, Here’s What Enlightened Founders & CEOs Already Know

First and foremost, let’s be clear about what a Chief of Staff is and is not. A surprisingly common misconception is that a Chief of Staff is a glorified executive assistant. While an elite group of executive assistants may one day become Chief of Staff, those are very different roles.
Aron Kressner

A CoS is really meant to handle important cross-functional projects that a founder just can’t actively manage due to time constraints. That’s for the expected items that are still very much a priority but might not be the most important item of the day for the top executive, like pitching the board a new line of business, a rebrand with a new agency, or restructuring the sales team. Because the Chief of Staff is also there to take ownership of critical projects, they need the ability to ingest the founder’s point of view, run with it, and process ambiguity in real time. In short, CoS must effectively move things forward as a founder or CEO would.

More often than not, this means handling projects that require the creation of a new process or system, and then autonomously deciding how long they should maintain that oversight before offloading that responsibility to the appropriate leaders.

The first time I saw a Chief of Staff in the wild was during my time at Vox Media. There was a particularly talented project manager who had been working with design teams and dev teams who also happened to be a very dynamic personality. Even before she got the title she had established herself as someone who could seamlessly work across teams and functions (a very good listener) and help flatten stalemates and power struggles by deploying reason, logic, and when all else failed, humor (see above: very dynamic).

In this particular instance, I was working in a cross-functional capacity myself, a member of the strategic team that worked across all editorial leadership through the lens of data and analytics. Really, we worked with the editorial leadership across all Vox Media to help them understand their audiences at a granular level across all platforms and help them set new priorities and quarterly goals.

I was the dedicated resource translating all those editorial-side best practices, trends, and insights to the internal agency – Vox Creative. Essentially saying some version of here is what works for us editorially right now (say, Eater content about sushi has usurped burger content as the top performer on YouTube this month) and then working as a strategist to brainstorm how that trend should inform a new pitch (say an RFP from Lexus) for a branded lifestyle video series with a strong dining lean (and yes, that content is popping with upwardly mobile women ages 35-54 who have also attended a live music event in the last 90 days).

So when I got a slack message from said Chief of Staff-to-be, who also sat about 10 feet away, saying that she was scheduling a meeting for me and another team member that would include my manager, I was confused. Maybe a little scared too. Alas, the meeting was pretty boiler plate and fully just meant to appease a particularly difficult team member.

But it worked!

Shortly after the meeting she reached out to follow up on a few things. I sent over the materials requested and asked what that was actually all about. I got a smiley face in return. Apparently there had been a road block, at least a speed bump, that was slowing me down from afar. I knew there was a lag but never realized the extent of the issue. She caught wind of the issue and handled it for me by explaining that I had developed a very unique skill set pairing successful content with targeted audiences from RFPs and then crossing over into the realm of a strategist. It took me a week or two to realize that she was speaking for Jim Bankoff, Chairman & CEO. It was a clear message and it worked.

Top 5 most important skills for a Chief of Staff

  1. Communication skills: Chiefs of staff need to be able to communicate effectively with a wide range of people, including their executive, other senior leaders, and employees at all levels. They need to be able to clearly articulate their executive’s vision and goals, and they need to be able to listen to and understand the feedback and concerns of others. This is how my old friend discovered my issue in the first place.
  2. Organizational skills: Chiefs of staff need to be able to manage multiple projects and tasks simultaneously. They need to be able to prioritize and delegate effectively, and they need to be able to meet deadlines. Of course, and I would argue that a PM or scrum master with a background in product, dev, and design is a good path to develop these skills.
  3. Problem-solving skills: Chiefs of staff need to be able to identify and solve problems quickly and effectively. They need to be able to think critically and creatively, and they need to be able to weigh the pros and cons of different solutions. My old friend didn’t threaten an adversarial colleague, but she made it clear that my work was distinct from that team’s work and recognized at the top.
  4. Relationship-building skills: Chiefs of staff need to be able to build and maintain strong relationships with a wide range of people. They need to be able to trust and be trusted, and they need to be able to collaborate effectively with others. Dynamic people who know when to let others shine are important.
  5. Adaptability: Chiefs of staff need to be able to adapt to change and uncertainty. They need to be able to think on their feet and to come up with new solutions to new problems. This same individual taught me a great trick when I was working to fix a problem with an internal contact at Google. Apparently we’d reached a limit and they were threatening to cut off a vital service. In asking for some leniency that should have been offered alongside the alert itself, I replied cc’ing the aforementioned executive – it’s not the most honest tactic but it works in a pinch.

In addition to these five skills, chiefs of staff also need to have a strong understanding of the business world and the industry in which they work. They need to be able to think strategically and to develop and implement plans to achieve their executive’s goals.

Most important interview questions for a chief of staff candidate

  • Tell me about a time when you had to manage multiple projects and tasks simultaneously. How did you prioritize and delegate effectively?
  • Describe a time when you had to solve a complex problem. What steps did you take to identify the problem, develop a solution, and implement it successfully?
  • Tell me about a time when you had to build a relationship with someone who was difficult to work with. How did you overcome the challenges and build a productive relationship?
  • Give me an example of a time when you had to adapt to change quickly. What steps did you take to adjust to the new situation and achieve your goals?
  • Tell me about a time when you had to think strategically and develop a plan to achieve a goal. What steps did you take to develop the plan, implement it, and measure its success?

In addition to these general questions, you may also want to ask more specific questions about the candidate’s experience working with executives, their knowledge of the industry, and their understanding of the role of a chief of staff.

Here are some examples of more specific interview questions:

  • What is your experience working with executives? Can you tell me about a time when you had to manage the expectations of a demanding executive?
  • What is your knowledge of the industry? Can you tell me about a time when you used your industry knowledge to help your executive make a better decision (or made it for them)?
  • What is your understanding of the role of a chief of staff? Can you describe the key responsibilities of a chief of staff in your own words?

By asking a combination of general and specific questions, you can get a good sense of the candidate’s skills, experience, industry knowledge, and fit for the role.

Without a doubt, many of the best executive assistants of the past did all of these things and more. I have had equal or greater success in my career by reaching out to executive assistants than to the executives themselves. Remember this, take a breath, read it again, take another breath.

There will be many more hires for a Chief of Staff in the future, it’s a limited opportunity as there is usually but one. That said, it’s an experience that forges leaders, and executive certificate that cannot be bought and pay range well in excess of $250,000.

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