Phoenix Normand, a long-time executive assistant advocate with twenty-eight years of experience asks 'is chief of staff the next step for a top-performing executive assistant?'

As a long-time executive assistant advocate, coach, mentor and career EA with twenty- eight years in the seat, the number one question I get from EAs is, ‘What’s next for us?’

The chief of staff role has exploded in popularity over the past three years. Companies and CEOs are now recognising the insane amount of value a chief of staff brings to the organisation, especially when there’s synergy with the highest-ranking executive assistant in the building. This duo has proven to be the secret weapon for quickly scaling companies and the legacy players looking to modernize their approach to managing their teams effectively. But the question remains: is chief of staff the next step for a top-producing EA?

A Brief History

In years past, companies wouldn’t even consider a candidate for the chief of staff role who didn’t have a certain level of education, typically from a brand-name university, years of experience in the C-suite, even having owned businesses of their own. In addition, the chief of staff role was often misunderstood and misperceived by others as yet another blocker to direct contact with the CEO. However, as C-suites got younger and more flexible, with CEOs who went from engineer to ‘Big Cheese’ seemingly overnight, the chief of staff role began to make more sense and became a conspicuous contributor to younger CEOs and their company’s success.

Similarly, the EA role has suffered from mischaracterization thanks in part to inaccurate and condescending portrayals of executive assistants in film and television for decades. Businesses themselves have largely viewed this role as an accessory instead of an essential role. Worse, EAs have done an extremely poor job of rewriting and owning the narrative about the role vs. accepting the incorrect, pervasive one that still exists today.

What Differentiates an Executive Assistant from a Chief of Staff?

When reading a chief of staff job description, especially as an EA, many feel as if the job description fits a majority of what they do already. There is a perceived overlap in some of the core competencies and daily accountabilities of both roles. Both roles require experience, or specific C-suite exposure, that most top-producing EAs have to some degree, although not to the extent required to become a viable chief of staff candidate. There are often some educational disparities, however, even those lines are beginning to blur as more EAs are showing up with Masters’ degrees from top universities, similar industry exposure, and business acumen that rivals even the best chiefs of staff, with the nuanced advantages of empathy and the relationships they’ve nurtured with virtually everyone in the company.

If I were to explain the core competencies of each role as simply as possible, I’d put it this way: Executive assistants keep the train moving seamlessly down the track while chiefs of staff help plot the course and ensure the train reaches its destination on time.

Handling all-things-administrative is the superpower of a great EA. Overseeing all-things- operational while leveraging those administrative superpowers is what makes the EA/chief of staff relationship a true secret weapon within any organisation. However, when there’s discord among those two entities neither can be effective nor truly perform to their potential.

What’s Next?

There is a new breed of EA emerging who are destroying the old narrative and commanding (and getting) a seat at the table. They have a very clear understanding of the game, the players, the rulebook, and the strategy required to win, just like the executives they support. This has allowed the top-performing EA edge-cases to execute at a similar level as the C-suite, leverage their years in the seat typically in numerous industries, and provide a diverse and much-needed perspective of the business as a whole. Remember, Executive assistants have relationships up and down the chain of command, something rarely achieved by the C-suite. When empowered and leveraged correctly, they truly become that one, reliable resource who can accurately speak about the overall health of the team.

‘There is a new breed of EA emerging who are destroying the old narrative and commanding (and getting) a seat at the table.’

Unfortunately, this specific group of EAs max out professionally at EA to the CEO. While the role is fraught with unparalleled access and opportunity, more than any singular role within the company, it’s still hampered by a glass ceiling that doesn’t exist in other roles. Worse, when Executive assistants seek other roles within the organisation at the senior, director level and above, they are routinely passed over by the company and recruiters even though they have the passion, business acumen, exposure, and innate ability to figure it out and thrive. This has resulted in many high-performing EAs chained to roles below their capabilities while watching their co-workers fill the very seats they sought, with little resistance. It’s incredibly demotivating, unfair and, sadly, all too common.

The sunny side of this is the fact that chiefs of staff have levels. There is no longer a one-size- fits-all narrative about the chief of staff role that often disqualifies a top-performing EA from the jump. Some companies are beginning to hybridize the EA/chief of staff role as a way to provide professional development beyond the EA to the CEO role, benefitting from the core competencies of each.

Additionally, organisations like The Chief of Staff Association have created an actual curriculum that provides the opportunity for top-producing EAs to increase their business acumen, knowledge, and capabilities. At no time in the past was this available or even a consideration. It now provides EAs with a very focused educational track and a definitive career path for those truly looking to excel beyond the role. And, most importantly, it re-instils the hope that may have been lost in the numerous concussions suffered from constant contact with the transparent ceiling above our heads.

A Personal Story

After five years as a CEO of my own business, traveling the world thirty-plus weeks per year teaching workshops to top-producing EAs in numerous industries, and chairing my own global community of EA superstars, I decided to sunset my business and return to the seat. Many would view this as failure to some degree. And, I admit, I had a certain level of anxiety around how I would be perceived by my CEO peers once word got out that I’d bequeathed the title. However, something very specific allowed me to rationalize the decision and take the leap. I’ll explain.

I hosted a webinar with the head of a local chief of staff organisation. It was easily one of my most-viewed online webinars. My goal was to finally dispel the myth around whether or not the chief of staff role was a natural progression for a top-performing, C-suite EA. Having taught, coached, and mentored EAs in numerous industries and several countries for the past five years I thought it was important to finally and definitively answer the question with a top-performing chief of staff brave enough to take it on. To my delight he did exactly that and validated everything I’d counselled EAs, for years, around this question.

As a result, I really wanted to put this theory to the test. And since COVID had essentially neutered my business once international travel was halted, I decided to re-join the EA ranks with the express intent of eventually becoming a chief of staff, thus proving it was, indeed, possible. I recently joined an amazing tech start-up led by an incredible CEO and vowed to learn everything I could about the business in the shortest time possible and contribute at an incredibly high level by leveraging the experience and acumen of running a successful business of my own. This story has no ending since I’m only two months into the role, but I know I’ve already made a conspicuous impact in the C-suite and continue to have an impact throughout the organisation as we rapidly scale.

I’m excited for the opportunity to be a conspicuous example of a top-performing executive assistant who put in the work to eventually become a chief of staff. There’s no better way to prove a point than to roll up your sleeves and actually get it done. And I’m confident I will achieve my ultimate goal: the title of chief of staff. Then, I’ll likely write another book, scrap it all, and start another new company of my own.

In Conclusion

So, to answer the original question: Is chief of staff the next step for top-performing executive assistants? Sure, but with a big caveat. For example, young lawyers must start at a junior level and work their way up the ladder until they achieve their ultimate objective: Partner. Executive assistants eyeing the chief of staff title must do the same. Otherwise, without putting in the work and having long-term commitment, the chief of staff role will continue to be unattainable for many. Fortunately, The Chief of Staff Association has created the perfect roadmap and opportunity to convert a long-time dream into an attainable reality.

Phoenix Normand has been a top-producing, C-suite Executive Assistant for 28 years. He’s a top-rated trainer for EAs and teams, an international keynote speaker, and author of the book “AS I SEE IT, Business: Volume One.” His no nonsense workshops, speeches, and writing style have made him an authority in the Executive Assistant space and an exciting, future addition to the chief of staff community.

Further Reading

Normand, Phoenix, AS I SEE IT: Volume 1: Business (Phoenix Normand, 2019).