Anything in life is possible, if you make it happen.

I'm chronicling my journey from a top producing, 28-year, C-suite Executive Assistant to Chief of Staff.

Admittedly, I'm learning a ton along the way and sharing everything I encounter with hopes it will shed some much needed light on both roles, debunk a few myths, and help the curious figure out if either role is for them, and help companies more thoughtfully recruit, hire, utilize, and empower some of the most versatile and effective professionals in business.

This past week I had a couple of epiphanies I wanted to share. One personal, one a professional observation (read: plea).

Observation 1: The Speed of Execution Expectation Chasm

Executing quickly as an Executive Assistant almost feels like a "nice-to-have" whereas a Chief of Staff it's essential. And the expectations align accordingly. I'll explain.

I built my EA career on executing efficiently. It's what made me a unicorn and stand out from the crowd. However, I always felt like it was a value add of me joining the company vs. something absolutely required of me in position. And when I say "executing efficiently" I mean at light speed. There's a certain mastery you must attain in order to execute at light speed. While skills are a high priority, it's often your relationships and your network you leverage each day that determine your speed of execution. Meaning, if you're a newbie and have no network, you'll struggle to be quick. If you're a complete asshole whom no one likes, you'll likely struggle to get advice, recommendations, and privileged help you need to complete a task or project quickly. But if you've developed real, reciprocal relationships up and down the chain, have highly developed skills, and a high degree of business acumen, you will be among the elite in the EA profession who can get anything done in record time.

However, the elite are few and far between. To build and maintain these relationships, constantly improve your knowledge, skillset, and business acumen requires work far beyond a 9a-6p workday. It requires spending hours after the kids are in bed or a few hours each weekend or waking up hours before everyone in the house to study and absorb everything at your disposal like company reports, metrics, projects, stakeholders, external customers, market trends, and living in the email chains to make sure you're completely aware of everything going on at every stage. Let's be honest, most EAs have no desire to "do all that." And that's fine. But please spare me the hate in my comments when I tell it like it is and say that 75% of EAs in the role trend toward "the middle," meaning mastering the basics and little else. 20% are highly competent, confident in their abilities, and actively continuing to learn and improve. And the remaining 5% have mastered all things administrative, are true strategic partners to their Execs, and are striving to move into a role beyond the EA title, often as a Chief of Staff or some highest-level Administrative or Operations role.

That aforementioned 75% are the majority in the EA role. They keep the train on the tracks, provide assistance across the organization, and create enough consistency for Execs and teams to feel supported. The issue is that Execs see them as providing a service of convenience vs. anything that would classify them as a peer. As an Exec when your calendar is "handled," your coffee is delivered hot, your daughter magically receives her birthday gift on time (because you forgot it was her birthday), and your last-minute dinner meeting went off without a hitch, it's easy to see those wins as a relevant measure of success and aptitude of an EA. Unfortunately, this discounts EA's history and exposure across numerous industries, a pretty healthy network of past bosses and colleagues, and professional aspirations. And, like I mention in the subtitle, it focuses on tasks that may be kinda urgent, but wouldn't topple Rome if they happened a bit later than expected.

Conversely, Chiefs of Staff have a completely different expectation of effectiveness and efficiency because their accountabilities directly correlate to a company's/initiative's/objective's success. Chiefs of Staff have an insane level of accountability because it spans teams, not just individuals. They must see tasks in aggregate and judge them based on execution, not dive into the weeds of why something is a day late because someone wasn't feeling well that day and laid an egg. Waiting around for something isn't really an option. It needs to get done and if it's not, consistently, it gets moved to someone else or handled personally. Time is the most precious commodity for a Chief of Staff. Any loss of time has to be accounted for and explained to the C-suite, often the CEO himself. The last thing a CEO wants to hear is "I was waiting for so-and-so to..." as the excuse for why a target date was missed or a project is delayed. Thus, the insanely high expectation level Chiefs of Staff must navigate and internalize every day.

It's important for EAs wanting to transition into a first-tier Chief of Staff role to understand that a higher level of execution and urgency is essential. Additionally, that higher level of execution is a byproduct of a higher level of knowledge, acumen, research, and access, requiring a whole lot of homework and sidebar conversations. There is no plug-and-play model offered, ad nauseam, by EA advocates far and wide. The work and the drive depends solely on the individual. Do the work, get the spoils. Bitch, moan, whine, and complain (and hate on me in the comments about the work ethic required) and you'll never get there. Upside: you'll have plenty of company and lots of [ridiculously subjective] award opportunities. (Yes, that was shade.)

Observation 2: The CEO's EA Should NEVER Be Rolled Under the Chief of Staff

This might be unpopular. Good! Under no circumstances should the EA to the CEO be rolled into the Chief of Staff's org. Here's my take on why.

EAs to the CEO are a different animal. They've likely done their time, built their kingdoms (read: tight networks), and are administrative beasts. Typically, what they lack at that level is the Operations component. They'll have general knowledge and some exposure, but likely not the day-to-day responsibilities of an Operations whiz like a Chief of Staff. As such, the two, in parallel, are an incredibly efficient and effective team with their own, separate accounts to the CEO. These separate (though connected) relationships are critical to the success of both individual contributors following very different paths to success.

When you roll the EA to the CEO into the Chief of Staff's org, you completely disrupt the flow.

1. EAs to the CEO want "EA to the CEO" on their resumes, not "EA to the Chief of Staff of the CEO." EAs who've devoted their careers to occupying that seat will see this as a demotion and wouldn't think twice about heading for the exits with both perfectly manicured middle fingers extended.
   
   
2. EAs to CEOs rely on a very different kind of relationship and language with the CEOs they support. There is a ton of work that goes into truly learning a CEO...the nuances, the "what they actually mean" language cues, their strengths and deficiencies, their whims, and their very specific, inconspicuous needs. When you sever that level of access by moving an EA to the CEO under a Chief of Staff, you literally cut off one of the most important relationships in the business and insert a conduit into the mix. Sorry, but I see very few instances where this hasn't ended up with the EA to the CEO getting frustrated, back-burnered, "de-commissioned," and eventually forced to leave the company in search of another unencumbered, 1-to-1 relationship with a CEO.
   
   
3. Most Chiefs of Staff have zero people management experience, zero administrative experience, and questionable levels of empathy for the unique needs of a high-level Executive Assistant. Actually, that's kinda true for most CEOs if you think about it. But they sign the checks and their expectation and respect level is different from a Chief of Staff. Chiefs of Staff are executioners. Giving them access to the EA to the CEO is definitely a good move as they, too, will create a language between them and execute based on what they heard/surmised from their individual conversations with the CEO. That's where the magic is created. Weighing those two conversations (likely different) and executing on the delta. But Chiefs of Staff need to stay nimble and not be bogged down with managing other employees unless they are hired specifically to help them execute. This could be a dedicated, more junior Administrative Assistant, but definitely not the EA to the CEO. Additionally, since most Chiefs of Staff burn out in two to three years it puts the EA into a precarious position of potentially having to learn a whole new boss who may or may not have their best interests at heart or understand how to manage/utilize/empower a high-level EA. In short, just don't do it. It pretty much never ends well.

Observation 3: You Need Next Level Confidence and Chops

The Chief of Staff role requires you to know your shit. Any fake it 'til you make it BS will quickly be revealed and revealed. I always say that confidence comes from hyper preparation. When you know your shit, you're naturally confident. When you don't, you stammer, umm, and stumble your way through conversations and lose your listener who is likely judging away with each extended syllable.

In order to gain respect at every level of business you need to be hyper prepared. It's important to understand the unique needs of each business unit and have some context about how they're absorbing and executing on the same information being disseminated from the top that everyone else is. Actively listening, asking relevant (sometimes uncomfortable) questions, and being open to meeting people where they are vs. where you need them to be is paramount to developing the level of trust necessary to manage the aggregate efforts of teams and stay on track. That's part of being hyper prepared and, yes, confident. And, yes, being effective in your role. This is applicable to both the highest-level Executive Assistant and Chief of Staff roles.

Chops are another differentiator. When I worked for a supersonic airplane manufacturer, even as the EA to the CEO, I concluded that I would never really understand the nuances nor be taken 100% seriously without getting my pilot's license or at least going through the process to understand the how more comprehensively. I work at a company that helps people learn to code. And as the EA to the CEO (and eventual Chief of Staff) I'm acutely aware that if I don't learn to code in a language or three I'll never truly understand the unique needs of the team or the business and never truly be accepted as a full-fledged member. I'll never understand (nor excuse) EAs or any professional who works for a company for longer than a year without learning that company's core products and services in finite detail. To me, it truly is the difference between doing a job and being (and being respected as) a real pro. I chose the latter, thanks.

In Conclusion

I'm tracking, but I still have a ton to learn and get familiar with. My speed of execution as a Chief of Staff just isn't there and it's frustrating AF. Sure, it's still next-level as an EA, but I'm definitely still "peeing like a puppy" in Chief of Staff terms. The mindset shift I spoke about in my previous article has definitely taken hold. I understand the how and the why of what I'm doing. And for the most part I'm executing well. But, I still find myself fighting with my old way of thinking and executing, because it's what's most innate. Letting go of what's worked for 28 years is difficult, but necessary in order to make it to my ultimate goal. And I will. Those spurts where everything just clicks are happening more and more frequently so I know I'm onto something.

Truthfully, there's no guarantee I'll make it to the Chief of Staff role. I may bounce and go back to being a CEO and bring to market one of a number of viable ideas I have sidelined. However, I'm really, really enjoying the process and wholly committing to it. It's making me an even better Executive Assistant, shaping me into a kick-ass Chief of Staff, and will definitely make me an incredible, comprehensively prepared CEO. Everything I missed when I ran my previous businesses I'm now learning in abundance. I feel grateful for the opportunity to continue to learn, grow, push myself, and be pushed to heights I never thought I'd be capable of achieving.

In closing, you can teach an old dog new tricks. I'm living proof. As I always say, "Get a little SELFish." Set some painfully lofty goals for YOU...no one else. And absolutely commit to doing the work until you achieve them. No certificate of completion or award needed. Remember, the reward is the journey, not the destination. That's just icing.