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Exploring the Future of the CoS Role

Business is changing–in so many ways and with many different factors influencing change, there is a big, blank canvas for leadership to create the future they want to see. Right now is a really exciting time to be a leader in business. The Chief of Staff role is already a newer construct in most businesses and now, on the heels of a world-changing pandemic and rapid technological transformation, even the age-old CEO position is looking a little different. 

In the midst of how the modern business world is changing, what are the opportunities for the executive office, and how are those of us in the role of a Chief of Staff measuring our successes and failures?

A Day in the Life of a Chief of Staff

For context, let's start with a look at where we're at right now. The Chief of Staff role is still somewhat undefined in many businesses. It's a newer position that brings fluidity to the executive office, filling whatever needs might arise as the business landscape constantly changes from one day to the next. 

But what does it really mean to say that there is no defined job description for the Chief of Staff role? Anne Caprara, the CoS for Illinois Governor JB Pritzker, comes from a traditional political background. She mirrors the same sentiment that many CoS in the business world feel–the CoS role is a demanding job that never ends. Anne compares her typical workday to a high-energy treadmill of challenges to overcome and problems to solve. 

Priya Monga, the CoS at Instacart, agrees as she gestures to the rapid pace of changes that the business world has seen with the pandemic, speed of business, and the complexity of the ecosystems that modern businesses operate in. She recognizes that the role of a CoS in modern business is enormous, but it's also a really unique opportunity to be hands-on with the whole organization.

As many businesses are putting more emphasis on human connections within their workforce, the job of the CEO and CoS is becoming more about people and relationships. When a new initiative is deployed, it's often the CoS that is right in the middle of it figuring it out and then working with Human Resources and other departments to get it staffed and integrated.

When you're the right hand to the CEO, there is no shortage of opportunities to try new things but it can also keep you busy starting long before the rest of the team funnels into the office. Finding time to check emails and look over slide decks for presentations usually comes before the sun comes up. The morning commute turns into a brainstorming session with the CEO to talk about strategies for a new account or opportunity. 

Then the day at the office is filled with meetings and impromptu conversations as everyone wants your glance of approval on their projects and deliverables. Even lunch is a multi-tasking event as many executives are trying to find time to stay on top of industry trends and learn new things. Some days it can feel like there is barely any breathing room–you're always expected to be on your game as you attend client meetings, strategize with the CEO, and keep tabs on the dozens of projects and initiatives that you're overseeing for the company.

And for those of us in the thick of it–we wouldn't have it any other way. The pace is exhilarating. The opportunities are limitless. We get to be a part of the magic that happens in conversations had on foot on the way to a meeting or a quick bit of chatter while we're waiting for a conference call to begin.

Measuring Performance in an Undefined Role

One thing that many leaders in the CoS role are struggling with is knowing when or if they're doing a good job. When things are changing at such a rapid pace, it can be challenging to sit back and take an objective look at your inputs and outcomes. There are often no predecessors to use as a benchmark and the very definition of what it means to be a leader today is very different than it was a decade ago.

So, where does that leave us in the CoS role? How can we tell if we're effective leaders? Priya, who has had CoS experience at two prominent tech companies–Facebook and Instacart, says that it's all about learning to scale your leadership. 

There are a variety of ways to approach leadership and it is important first–that those in a CoS role see themselves as leaders and second, that they take the time to get to know themselves as leaders. Self-awareness is one of the most important aspects of effective leadership. You can be strategic or transformative, or even transactional and be a successful leader. The key is to know yourself, use your strengths, and demonstrate consistency.

As leaders, our success hinges on the intentionality of our actions. The CoS has to be able to stand on their own under significant pressure. In last year's Chief of Staff Summit, Anne pointed out that it's really important to have someone who can speak the truth to an elected official or a CEO. The dynamics between the CEO and the rest of the staff make it challenging for almost anyone else to be the one to be critical of the CEO. But for the CoS, it's a very natural response developed through a close working relationship. And the company is likely better for it. 

Measuring performance as a CoS comes down to two functional roles:

The first is your role as a leader.

You can look at the initiatives that you have spearheaded in your organization and tally up the outcomes of those initiatives. You can assess your relationships with colleagues and subordinates. And you can measure your level of influence across the organization. But the most important indicator of success is a measure of your independence from the CEO. Are you willing and able to productively counter the ideas of the CEO, or are you an ego-boosting prop in the executive's office?

The second measure of CoS performance is the level of collaboration between you and the CEO that you work with.

If the two of you are working together like a well-oiled machine, then you are providing value to the organization by enhancing and supporting the CEO. However, if there is distance in that relationship, leaving you to function like an administrative assistant rather than a leader, then there is an opportunity for improvement.

What's Ahead for the Chief of Staff Role

It's impossible to predict the future. If you had asked anyone in business two years ago what they thought was going to happen in the future, there probably wasn't a lot of votes for a life-altering global pandemic that  permanently changed business and social constructs. Yet, that's exactly what we've seen happen. Our panelist, Anne, talked about how dramatically everything changed in our lives over the last 24 months. On a personal level, we were dealing with a scary disease and, on many levels, our own mortality. And at the same time, we basically had to reinvent the modern business model to keep things going in a world where everyone was afraid to interact with one another.

The sheer scope of change and disruption is exactly what cemented the CoS role in the business world. In many organizations, the CoS became pivotal in helping the organization adapt service models to new norms, effectively realigning the business with a new pandemic-era strategy.

Before the pandemic, a lot of people looked at the CoS role as a very temporary transition or stepping stone to something else. In our panel, Scott Amenta from the Chief of Staff Network, brought up the wide variation that we see in this role. He said that most of the CoS he talks to stay in their positions for anywhere from 18-36 months. More and more often now, they are holding this position even longer.

As we move beyond the pandemic, Scott says that there is an opportunity to bring more permanence to this essential leadership role. The CoS doesn't simply function to help new companies get going, or new CEOs settle into their positions. The CoS is actually proving to be a strong asset to the leadership team, expanding capabilities and improving agility to keep organizations mobile and ready to adapt to change.

We could see a rise in decentralized autonomous organizations.

The migration to remote-first and hybrid work models is just the first step in spreading out. On the upside, it widens the talent pool to a global scale which can alleviate some of the stress of skills shortages. On the downside, these organizations will present a new level of complexity for leadership. Perhaps future CoS positions might focus on building remote teams and bridging those teams with the physical presence of the organization.

The CoS role is likely here to stay. Businesses at all levels are shifting their focus from efficiency to resiliency. They want to make sure they can survive whatever unknown comes next. And it makes great business sense from a resiliency standpoint to redesign the executive office, moving away from relying on one person to creating a small, well-functioning team. Organizations are simply becoming more complex and the CoS role is a good way to build out leadership to scale.

If you're not sure where you stand as a leader today, the future will shape you one way or the other–good or bad. People strategy is emerging as a top priority, right alongside financial strategy or technology in business. We're not just talking about well-timed diversity and inclusion initiatives. The CoS role will become much more hands-on with the people in the organization.

These relationships will be largely dictated by employee expectations and not business strategy as they have been in the past. Another unintended consequence of the pandemic left many front-line workers re-evaluating how much space their jobs took up in their lives. While millions of workers walked away, companies began to feel the stress of labor shortages. Bringing the workers back to these companies will take a humanized approach to leadership. 

For the CoS role, this means helping the CEO connect business strategies to human strategies. It means thinking about people first and business needs second, which can be unfamiliar when running a business. In an article published in Inc., the president of Panasonic System Solutions highlighted how the shift in customer expectations and workforce demands are shaping the way that companies do business.

It will become the job of the Chief of Staff to help the CEO navigate new complexities in the business world. And it will become more important to focus on building a positive workplace culture. The CoS role is no longer just about running the business; it's about shaping the organization to meet the demands of the future of work, aligning with customers and employees.

The Takeaway on the Future of the CoS Role

What was once a novel idea in the world of business and largely served as a transitionary role, the Chief of Staff is becoming fully integrated into the fabric of executive leadership. This means that it's time for CoS to accept their identity as leaders and embrace their unique styles. The CoS position is likely going to become a permanent position for many. The need to move on after eighteen months or two years will diminish as these positions and career paths become more defined. 

If you're looking forward to reaching a CoS position in the future, you should focus on building self-awareness and defining your leadership style now. From there, you can begin to build your authentic brand as a leader, which will help you build better relationships with the people around you. Use your people skills to become excellent at collaboration and problem-solving. But most importantly, remain open to new possibilities. Take opportunities when they come your way and focus on building your network with the right people. When you get the CoS role, you'll be positioned for success.


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In-depth analysis of the compensation data based on CoS Level, experience, gender, and more.

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In-depth analysis of the compensation data based on CoS Level, experience, gender, and more.

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In-depth research of the career paths and opportunities the top Chiefs of Staff pursue.

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