From EA to Chief of Staff: Some Key Observations

If you are thinking about making the transition from an Executive Assistant to Chief of Staff, here are some essential things you’ll want to consider before you make the move.

Those who know me or read my articles and posts know that I'm (in)famous for circumventing rules that I see as a barrier to reaching my destination or that I feel are kinda stupid, pointless, and/or created expressly from hubris. Sorry, not sorry...I don't subscribe.

As I make the transition into a Chief of Staff role with my current organization the onus was on me to provide insight to my CEO on where I feel I can have tremendous value both for the organization as well as him, personally. As a member of The Chief of Staff Association for almost a year I've had the opportunity to attend numerous Zoom events and connect with quite a few Chiefs of Staff within the membership to get a read on what value they provide to their Execs and orgs. What I'm finding is that every story is different. Sure, the general structure and some responsibilities match the myriad of CoS job descriptions in the wild but, for the most part, each role has some very important differences and nuance.

As I put my pitch together for my Exec I really thought through the myriad of tasks I do for him and his wife co-Founder both at work and at home. I'm sure I'm about to get roasted for breaching the accepted EA code of not mixing Personal with Company work. And truthfully, in my almost 29 years in the seat I've never crossed this chasm to the degree I have recetnly with my two Execs. And therein lies both my perceived dilemma and what I see as tremendous opportunity.

For clarity, my boss' wife was several months pregnant when I broke the code and started doing Personal Assistant work. I saw it as an opportunity to help her out so that she could focus on her role leading one of the most critical business units at the company. Additionally, given the amount of time I've spent (read: wasted) trying to find a nanny for the family using traditional avenues has been frustrating at best. Now, imagine if I'd launched a search for a Personal Assistant? I would have the same frustrating vetting process, possibly hired someone, and then had to train them up over an extended period of time trusting/hoping that they worked out. Net/net, as I see it, it was better to just suck it up and take on those responsibilities as to not introduce another person into the mix during a very important time. While doing THE WORK is my primary responsibility, I'm an empathic being and truly want to create an environment for my Execs that's as stress-free and seamless as possible, especially with one of them being pregnant. The opportunity to create that seamlessness in their personal and professional lives was one I couldn't pass up, especially since there was a finite end as part of the plan.

I had a fantastic conversation over lunch with my Execs and they feel confident moving me to the next rung in my career. As part of my pitch I insisted on a job req that would give them (hopefully) a mini ME. My goal is to find someone who is not trapezing from every syllable of a job req. Someone who is naturally adaptable, curious, proactive, and who simply gets sh*t done. No prima donnas. No clockwatchers. People who can set boundaries, of course, but aren't afraid to roll up their sleeves in the case of an occasional emergency on a weekend instead of timing-out until Monday. If the latter, I'll likely have already handled it with a healthy amount of side eye.

So herein lies the debate as well as my point of this article. As I've been reading through a number of EA-centric websites, publications, etc. that tout the "difference" between being an EA and a Chief of Staff, I'd like to offer a different perspective and, perhaps, a bit of a #realtalk headsup to those EAs looking to make the transition to Chief of Staff.

Fight the Urge to Conform

After 28+ years as an EA I can assure you that the rather unique, EA route I chose will certainly manifest in the route I take as a Chief of Staff. Meaning, I could care less about a job description, especially since I'm staying at my current company. I purposely took an EA role with the express intent of becoming a Chief of Staff. I voiced it in my interview process so it should be no surprise to anyone. My goal was to truly dig in and develop an understanding of the company, my Execs, watch growth happen and how we reacted, watch mistakes happen and how we reacted, and plant little secret seeds along the way to help us grow up where needed to prepare for scale. I'm pretty proud of the work I've done though, admittedly, that has slowed because of taking on the extra Personal Assistant workload.

There is no job description that I've found in the wild for all I do. My goal is to provide value. Period. Whatever form that takes, especially when I've seen its ROI, is what I will do. I believe we get so wrapped up in the widely-accepted narrative with regard to what we will and won't do as a job requirement that we fail to see the forest for the trees. One our company mottos is "seek pain." As an OG EA it's my default. I like busting up the "normalcy party" and pointing out the ridiculousness it typically touts. I love trying things, breaking them occasionally, but being fearless enough to try again until it works. I don't give a sh*t about a job description except to get an interview so that I can blow people away with all the value I can provide. I got over 30 rejections the year before I joined Replit. And as I get closer and closer to achieving my goal of becoming a Chief of Staff I'm flashing two, perfectly manicured middle fingers at all who didn't see what they had in front of them. It's funny to me now, especially since I've dealt with this my entire working career.

My point: F job descriptions. Use them as a tool to get a general sense of what the expectations are in the wild and then craft your own, unique path to the role you create. Recruiters gives guesstimates. They don't know. So why hand your future over to a guesstimate?

Another thing: EAs who know the company cover-to-cover, their Execs and their Executive team cover-to-cover and, of course, have the core competencies nailed, truly are worthy of a crack at the Chief of Staff role. Let me be clear, here. It's truly only a handful. (see that "core competencies part) But I have no doubt that an EA who is just as passionate about the success of the company as everyone in the C-suite will provide as unique and comprehensive a perspective as any fresh-out-of-Harvard-Business grad. There's a level of comprehensive care that seems to be tacitly missing in the numerous Chief of Staff job descriptions I've read. Top performing, C-suite EAs provide the ultimate "yes, and..." for Execs and teams looking for someone who can hit the ground sprinting but may need a bit of coaching or continued education to iron out a deficiency or two, but certainly nothing that should disqualify them from consideration.

The Test of How You Truly See Yourself

I believe any EA who dares to approach their Exec to jump in the running for a Chief of Staff role is truly what separates those who fantasize and those with a healthy (read: needed) amount of confidence. I don't believe in imposter syndrome. (Long documented) I see it as a lazy excuse and an "out" that most take when sh*t gets real. Sure, I do believe in being petrified when given a responsiccountability that's over your head. But I've always found that I perform best when I'm petrified in that moment, but rely on decades of experience handling that or similar scenarios with a different name.

From what I've observed you cannot be anything but confident as a Chief of Staff otherwise you'll get eaten alive. Chiefs of Staff are often required to make critical decisions in the heat of the moment and (sometimes) pray that it's the right decision. Relying on experience, business acumen, data, previous decision making, etc. are the tools most often used when coming to a hypothesis or conclusion. That ain't happenin' if you're running around headless, asking way too many questions, not making a decision praying that someone else will step in, etc. Which means you must be extremely confident in your abilities and brave enough to make the call, even if it's the wrong one.

We fear too much. We act too little. 

Don't Sugarcoat

This is for my EA advocates out there. Y'all trying mighty hard to normalize this transition and paint a picture that it's somehow easy or in the cards for EAs to transition into the Chief of Staff role. That uproarious laughter you're hearing is from current Chiefs of Staff who have made a mountain of popcorn to watch it allllllll go down. With that, I'll issue two warnings...sorry...considerations. (Trying to be better)

I'm all for EA advocates dispensing information about the differences between the two roles, though as I've said above, every Chief of Staff role is different and should be created vs. complied with. Please be sure to let EAs know that similar to the fight for a seat at the Boardroom table as an EA, this fight will be even harder. Going the traditional route of applying and waiting is foolish. Instead, those who have the aforementioned core competencies, time in the seat, and most importantly, respect of the org, should really pitch the role that creates tremendous value for all involved. Two words: TREMENDOUS VALUE. That can take shape in a number of ways and it's up to the EA solve the riddle and paint a picture so compelling it's worth a shot.

For current Chiefs of Staff who are rolling their eyes or feeling some kinda way about the flood of EAs in their sacred channels I'd say, RELAX. No one is gunning for your spot. I truly believe top-performing EAs will create their own spot, mostly in startups, and grow their careers and CoS acumen there. Me applying for Chief of Staff at Google would be silly, though if they gave me the interview I'd rock it and make them truly think. But I have zero desire to be a Chief of Staff at Google. (no shade) I'd much rather craft a role at my current company and with my Execs and teams that allows me to provide tremendous value, even more in fact, than I currently provide as the EA to the Founders. My plate will be full of many of the responsibilities I handled as CEO of my own companies, renewed energy, and oversight of projects that will have a tangible effect on the company's bottom line.

Yep, there may be an EA task or two sliding into my DMs, but that will be by choice as confidentiality needs to be maintained in certain instances or, for posterity, I refuse to give them up. Most importantly, it will be a role that isn't a complete departure from what I've done for almost 29 years...it will be an enhancement. And that is where my excitement is lies.

In Conclusion

My respect for Chiefs of Staff grows by the minute. Similar to EAs there is a lot that goes on in the shadows that goes unrecognized and unrewarded. After mastering the EA game I've realized that those shadow wins are for me, not the general public. And, like I taught for 5 years, they end up on a "brag sheet" that is my ultimate resource to successfully renegotiate my salary at annual review time and remind those with the bag that I'm worth every penny, and then some.

EA advocates let's be careful to push a narrative that provides hope, but is wholly truthful about the .0x percentage of EAs who will actually transition into the Chief of Staff role. It is my firm commitment to help level up the top of the top EAs, those who are supremely confident, have high levels of business acumen, are curious and proactive by nature, and who clear a spot at the table for themselves vs. wait for one to be handed to them. Not saying this is only archetype. But from what I've observed so far, it kinda is.

Current Chiefs of Staff, stop reeling. We need you. We need your partnership. We need your expectation leveling. We need your tutelage. And, truthfully, it's your karmic responsibility to pay it forward. Those who do reap the benefit of helping someone like me achieve a years-long dream. I'm grateful to my squad of Chiefs of Staff who have taken me under their wing and shown me the light. Sure, my role will be waaaaaaay different than theirs, but the spirit of getting sh*t done is woven throughout all of our roles, including EAs.