Elevating your leadership: Why every CEO needs a Chief of Staff

Imagine looking up from your office desk and seeing a stranger in the doorway wielding a baseball bat.

Think it would be a little jarring?

That’s exactly what Robert “Cujo” Teschner wanted. Teschner, a former fighter pilot, served as director of staff for the 49th Wing at Holloman Air Force Base in New Mexico. In that role, he helped oversee roughly 2,000 people. With no experience working with colleagues in departments like human relations or public affairs, he needed to get to know the people he was now leading. So every day, he grabbed his St. Louis Cardinals championship bat and strolled to a different office.

“The baseball bat was a way of breaking the ice,” says Teschner, who today is founder and CEO of VMax Group, an international leadership training company based in St. Louis. “I needed to understand and be integrated with the folks who were getting the mission done.”

That integration was critical to his role as director of staff — a position more commonly known and understood as Chief of Staff. A Chief of Staff is a leader’s “right hand.” They bring a leader’s vision to life and manage all the resources to allow that vision to become a reality, Teschner says.

The Chief of Staff role originated in the military. President Harry S. Truman appointed the first presidential Chief of Staff in 1946. Today, countless CEOs around the world view it as one of the most critical positions in their organizations.

“Every business is doing battle, it just happens that our battle space is in the business battle space, a rapidly changing, chaotic, uncertain, complex, ambiguous environment,” Teschner says. “A good Chief of Staff is going to help us navigate that battle space and make sure that the entire team is equipped, confident, ready and willing to take action to bring the Commander’s vision to life.”

The role of a Chief of Staff

The exact responsibilities of Chiefs of Staff vary from business to business, but what is consistent about the role is that it is a senior-level confidant of the CEO. This person can be charged with everything from being a sounding board for the CEO and overseeing confidential projects to collaborating with other executives and representing the CEO at a board meeting. Many times, the responsibilities can include all of those items, plus dozens more.

“A Chief of Staff needs the ability to make order out of chaos because the CEO’s world is inherently chaotic,” says Heather Stone, founder of Practical PhD, a professional training and coaching company that teaches corporate leaders how to manage the right-hand relationship. “The CEO is chasing ideas or opportunities, so the Chief of Staff is somebody who can help them organize and make sense of (the chaos) in a systematic way.”

Stone says she believes many CEOs have become more open to the idea of a Chief of Staff because of the Entrepreneurship Operating System (EOS). EOS promotes the concept of two distinct roles atop businesses: a visionary leader and a visionary integrator.

Often, the CEO is the visionary leader, the person who has big ideas and thoughts about how to move the company forward. The visionary integrator is the person who gets in the weeds to figure out how to make the CEO’s dreams come true.

Chiefs of Staff are visionary integrators.

“That model really was less familiar in business 20 years ago than it is now,” Stone says. “EOS made it more ordinary to have a Right-Hand person at a senior level.”

To excel in that senior-level role, Chiefs of Staff must excel at communicating, both with CEOs and with the rest of the organization. Many CEOs reach the top of their business, at least in part because of their ability to communicate. They use their words to persuade others, be it in a new partnership pitch or a product opportunity. Since the Chief of Staff sometimes serves as the CEO’s representative, they, too, need to have a way with words.

“The CEO got where they are in many cases by using their words,” she said. “They’re never going to be comfortable with the Chief of Staff representing them if that Chief of Staff is not as careful or as good with their words as the CEO is.”

Benefits for CEOs

Beyond having someone to represent them, CEOs can benefit from a Chief of Staff in countless ways.

A Chief of Staff is a strategic partner and trusted advisor for a CEO. Without a right hand to turn to, CEOs can often find themselves without an adversary to spitball ideas with and plan for potential changes to their organization.

A Chief of Staff gives them that confidant.

“A lot of times, a CEO is looking for a confidential brain partner,” Stone says. “They’re looking for someone whose whole job is to help the CEO thrive. There are at least two benefits of that. One is that it’s less lonely at the top. You have somebody to help you, who’s always got your back, and that’s worth a lot. The other benefit is you have somebody who has the enterprise wide focus that the CEO has.”

As a partner, the Chief of Staff can support a CEO in decision-making or responsibility delegation. They can also amplify a CEO’s impact and effectiveness.

“The CEO is the big idea generator,” Teschner said. “The Chief of Staff is translating that vision into something actionable and then making sure that the actions take place. That’s huge to the CEO.”

Leveraging a Chief of Staff for success

Hiring a Chief of Staff doesn’t immediately translate into organizational success. Clear roles and expectations need to be established for a CEO and their business to benefit from a Chief of Staff.

Stone teaches her clients this practice through her “R.I.G.H.T.” framework. The elements of the framework are:

• Responsibilities
• Interaction
• Governance
• Heads up
• Time and Place

Establishing those five elements upfront is critical to forming a functional relationship between the CEO and the Chief of Staff.

“You need a well-rounded approach to surfacing your expectations,” she says.

Her biggest piece of advice on forming a successful partnership may be counterintuitive for CEOs. CEOs often ask Stone how they can ensure processes are established so that the relationship between them and their Chief of Staff flourishes.

Her answer is simple. Let the Chief of Staff manage the processes. After all, that’s what they excel at.

“The Chief of Staff certainly should be able to say what they need from the CEO, how they ought to be managed, and how they ought to be measured,” she says. “The right-hand needs to drive that relationship because they’re the ones who are usually good at managing processes and people. It’s a paradigm shift in many ways.”

Of course, it takes two people to make a relationship work, but Stone believes that when it comes to aligning Chief of Staff responsibilities with CEO priorities and objectives, the Chief of Staff can do 90% of the initial work. The two can then work together to formulate the final 10%.

Like any relationship, the key to a successful bond between CEO and Chief of Staff is trust. Trust is what empowers a Chief of Staff to act as a proxy for the CEO when necessary.

“You’ve got to know one another and establish a rapport,” Teschner says. “That requires spending time together and figuring out how to best operate with one another.”

The same can be said for Chiefs of Staff and other organizational leaders. That’s why Teschner carved out multiple hours per day when he was director of staff to take his baseball bat and get to know his colleagues. Sure, he wanted to understand their needs and challenges professionally, but he also wanted to establish relationships with them. He wanted them to know who he was and understand his goals for leading them — and the base — forward.

When those bonds are formed, the Chief of Staff cannot only represent the CEO to their employees but also be the voice of the employees to the CEO.

If the CEO has a plan that will place an enormous burden on the IT department, for example, the Chief of Staff needs to be able to speak up for the IT team and present their concerns and objections. If the CEO still wants to move forward, the Chief of Staff must then be able to rally the IT team and explain that the decision is best for the organization despite the extra time and effort that will need to be put forth.

“Chiefs of Staff need an outstanding sense of politics,” Teschner said. “Not political in the sense of Republican, Democrat, or Independent, but understanding the office politics and how to work with people who, with their tribal mindset, are only thinking about their lane.”

Overcoming common misconceptions

A common misconception about Chiefs of Staff is that they introduce redundancy to an organization. While inserting the role into the organization chart does add to the overall headcount, there should be clear distinctions between a Chief of Staff and other executive roles.

“Other roles are all focused on one lane,” Teschner said. “Chief of marketing, go market the hell out of this thing. Chief of sales, go sell the hell out of this thing. Usually, the lane is really clear. The Chief of Staff has to understand it all and integrate with it all. They don’t have to be an expert in each domain, but they have to be an expert enough to appreciate and advocate.”

Teschner says another misconception is that the job is easy. The reality is far from that.

When Teschner was director of staff, he routinely started work at 4:30 a.m. and sometimes went until 11 p.m. To be aligned with his Commander, he participated in as many meetings and deliberations with him as possible. Add to that the hours he spent building bonds with his colleagues and his days could quickly get away from him, so he needed the extra time to get work done.

That brute force, though, was only sustainable for so long.

There also are mental obstacles that come with being Chief of Staff, Teschner said.

“It can be a brutal thing not to be the one making all the calls,” he said. “You’re the implementer of the things that the CEO has made the call on, so it’s not your vision that you’re executing. The challenge is to understand, be clear on, and be willing to take action on somebody else’s vision to a degree that it becomes your own.”

The position isn’t made for everyone, and it’s not the right solution for all companies. Teschner hasn’t hired a Chief of Staff for VMax Group, which provides leadership development based on the foundational principles of Top Gun schools to small and midsize businesses. Part of the reason is that he doesn’t believe the size of his company warrants the position. He also knows that if he does ultimately need a Chief of Staff, it will take time to find the right person for the job.

“I’m going to be very disciplined in how it is that I go about picking one when the time comes,” he said, “and making sure that we’ve got the right skill sets and the right drive and the right passion and commitment.”

Stone believes that’s the right approach.

“It’s magic when it works, and it is possible to have it work,” she said. “The Chief of Staff can drive the process, and when you surface your expectations for each other and you can build a relationship of trust, that person can do amazing work for you.”

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