The TRUTH About the EA-to-Chief of Staff Transition: A RE-Telling.

An amazing EA recently brought to my attention the low key "fleecing" going on about the EA-to-Chief of Staff transition. Specifically, the narrative is now about how "easy" and "natural" a transition it is, even intimating that it's an entitlement in some way. Have y'all gone Fn crazy since I stepped away?

I sent a quick ChatGPT4o query to make sure I wasn't the one going insane. Here's what I got:

Prompt:

What are the top skills required of a Chief of Staff that Executive Assistants traditionally lack?

Answer:

The transition from Executive Assistant (EA) to Chief of Staff (CoS) requires a broader, more strategic skill set. While both roles involve supporting executive leadership, the Chief of Staff position focuses more on high-level strategy, operations, and decision-making. Here are some top skills that are often required of a Chief of Staff but are traditionally less emphasized in an Executive Assistant role:

1. Strategic Thinking and Planning

Chief of Staff Role: CoS is responsible for aligning daily operations with long-term organizational goals, developing strategies to drive business initiatives, and helping executives make data-driven decisions.

EA Gap: EAs tend to focus more on tactical tasks and immediate problem-solving rather than big-picture strategy and long-term planning.

2. Leadership and Team Management

Chief of Staff Role: A CoS often manages cross-functional teams, leads major projects, and acts as a key liaison between the executive and other departments. This role involves overseeing operations and ensuring alignment across the organization.

EA Gap: EAs typically manage projects, but may not be tasked with leading teams or overseeing large-scale initiatives that impact multiple departments.

3. Business Acumen and Financial Literacy

Chief of Staff Role: A CoS must understand the company’s financials, business models, and key performance metrics. They often help with budgeting, resource allocation, and interpreting financial data to make strategic recommendations.

EA Gap: While EAs manage budgets and expenses on a smaller scale, they may lack deeper involvement in high-level business decisions or financial strategy.

4. Decision-Making Authority

Chief of Staff Role: CoS is often empowered to make decisions on behalf of the executive, particularly when it comes to operational and strategic matters. They are trusted to act as a proxy in meetings or negotiations.

EA Gap: EAs typically support decision-making processes but are less likely to have the authority to make critical decisions autonomously.

5. Stakeholder Management and Influence

Chief of Staff Role: The CoS must manage complex relationships with senior leadership, board members, external partners, and other high-level stakeholders. They must also be adept at influencing without direct authority to align the organization’s interests.

EA Gap: EAs frequently interact with stakeholders, but their role is more service-oriented rather than one of influence and strategic negotiation.

6. Operational Oversight

Chief of Staff Role: CoS manages the organization’s daily operations, ensuring the smooth implementation of the executive’s vision. They might be responsible for operational workflows, ensuring that goals are met, and addressing inefficiencies.

EA Gap: While EAs handle logistical and administrative tasks, they typically don’t have oversight of the broader operational functions or processes of the organization.

7. Crisis Management

Chief of Staff Role: CoS is expected to handle high-stakes crises, mitigating risks and guiding the executive through complex situations that may impact the entire organization.

EA Gap: EAs generally focus on mitigating smaller-scale issues that directly affect the executive’s day-to-day tasks but may not be involved in organizational-level crisis management.

8. Change Management

Chief of Staff Role: A CoS often plays a central role in implementing organizational changes, ensuring smooth transitions and communication across teams, and mitigating resistance.

EA Gap: While EAs may help manage change on a smaller scale (e.g., adapting processes for the executive), they are less likely to lead or manage organization-wide change initiatives.

9. Executive Communication and Diplomacy

Chief of Staff Role: The CoS often serves as a spokesperson or representative for the executive team, communicating with high-level stakeholders, board members, or the media. This role requires strong diplomatic skills and executive presence.

EA Gap: EAs are skilled communicators but usually operate behind the scenes rather than acting as the face of the executive team.

10. Data Analysis and Interpretation

Chief of Staff Role: CoS is expected to analyze data to identify trends, evaluate performance, and inform strategic decisions. They may use this information to make recommendations and drive business initiatives.

EA Gap: EAs generally work more on data collection and reporting but may not be tasked with high-level analysis or interpretation for strategic purposes.

My TL;DR

As I mentioned previously, the Chief of Staff role requires everything a top EA already knows and a bunch of information, knowledge, access, and execution opportunities only a subset of EAs will ever be privy to. When I made the transition, I had already run several successful small businesses of my own, replete with all of the bumps, bruises, and boots-on-the-ground education that come with it. I had also worked for some heavyweight CEOs in finance, retail, tech, and even aerospace, providing a unique breadth of exposure and experience across numerous industries to pull from once I made the transition. Most importantly, I had aligned with a CEO from whom I'd garnered full trust and confidence. He endorsed the transition, jacked my salary, and empowered and challenged me harder than he ever had while serving as his Executive Assistant.

I joined a global Chief of Staff community, got "certified" during a beautiful week in Oxford, England, and got tapped for a new role while there as the CoS to the CEO of a national mental health organization. If I had one regret in my professional career, it would be this "clout chase" I'd embarked on leaving Tech and taking the role with the mental health non-profit which, ironically, was the only role in my career where I seriously contemplated jumping off a bridge. Chile...it's in my upcoming book. Stay tuned. #karmagotthatasstho #theremayhavebeenavoodoodollortwocreated #actuallyaboutfive

My Chief of Staff Journey: A Cautionary Tale

Let me be clear here, and as outlined in the ChatGPT query above, the Chief of Staff role required a completely different "me." The hardest transitions were my mindset and innate style of execution. There's quite a bit of a safety being able to "chill in the cut" as an Executive Assistant. Sure, you're executing your ass off if you're at the highest level, but rarely are you responsible for a decision or action that could literally bring down the company, impact market standing, tank morale, or risk the credibility of the CEO you support. Where you could make a mistake as an EA and rationalize how you'd navigate the temporary irritation and disappointment of your CEO, mistakes as a Chief of Staff can literally cost you your job, cost the CEO their credibility, cause whole departments to mutiny, and even cause a Board to start asking questions.

I had no clue how much pressure being a Chief of Staff to a CEO of a national, government- and donor-funded, legacy organization could have. Worse, I was this Silicon Valley smart-ass specifically hired to help bring a legacy organization into the now (read: change management). Not only did I sleuth within a month everyone on the leadership team who, bluntly, needed to go, but I was also dealing with a CEO whose passion was in direct conflict with their execution, ability to lead a flagging leadership team in turmoil, and garner the respect of the Board. After decades spent in investment banking bullpens and Tech C-suites, and running businesses of my own, my style is more "bull in a china shop" than "nurturing right hand." When I see inefficiency, ineffectiveness, and actual harm being done by ineffective employees and processes, I call it out and put plans in place to fix it. That's, ironically, what made me indispensable as an EA to my CEOs. They knew I rarely gave AF about people's feelings (especially if they or their work sucked), that my job was to ensure that BUSINESS was the priority in the building. Everything else was "icing" or distraction.

There were numerous busted processes that were causing tremendous pain for the boots-on-the-ground employees that created such obvious inefficiencies, unnecessary spending, and even attrition that members of the leadership team kept kicking down the road because it would require a complete overhaul of their busted-yet-trusted processes. Coming from Silicon Valley, my approach was, "F*** it, let's get to work! Here's the solution, what it will cost, how long it will likely take, and how much time/money/jobs we'll save once implemented." Sadly, what I encountered was typical of legacy organizations and "mature" leadership teams: agenda, suspicion, intimidation responses, even sabotage because "rocking the boat" at that level for people who were extremely comfortable and well-compensated underperforming will have people clamoring for your ouster. And ousted I was. Thank GOD. It literally saved my life.

There's so much to unpack about that entire experience that it required a full chapter in my new book. (dropping January 2025) But let me toss out a few truth bombs so that we can, hopefully, reel in some of the bullshit I'm witnessing on this platform about the EA-to-Chief of Staff transition.

MMA vs. "Boxing Class"

The Chief of Staff role is like MMA. That may sound a little extreme, but in my experience, it's pretty accurate when comparing the role and the experience of being a CoS vs. a C-suite EA. Being a CoS is full-contact combat. You are orchestrating efforts of the entire organization, not just the tasks of the CEO you support. You have to employ a number of different moves, strategies, psychology, and yes, manipulation in order to get people to align and execute quickly, always under pressure and time constraints, and still maintain respect, credibility, and "non-biased/got-our-back" status each entity expects of you. This requires constant monitoring of metrics, hard data, information queries, water cooler conversations, decoding body language and Slack/email tone, fielding/flipping constant microaggressions, blah blah blah. I'm sorry, but I don't believe a majority of EAs have the resilience, skill, aptitude, exposure, "street techniques," and confidence to be effective Chiefs of Staff. Remember, I've educated, coached, and mentored top 1% EAs for over a decade worldwide...I know what of I speak. The EA role is "Boxing Class." It puts you in the gloves, provides access to the core principles of boxing, and even gives the braver ones the chance to suit up, step in the ring, and spar for a few rounds every now and then. But if you truly want to become a boxer or MMA professional, you'll need to actually train to top fitness, get knocked on your ass a few times (and get back up), learn how to anticipate that left hook next time, and confidently step back in the ring prepared to win. Rinse and repeat.

As Mike Tyson said, "Everyone's got a plan until they get punched in the face." I see this transition as no different. That shit looks great on paper and in these cute little online communities popping up with "experts" allowing you to bypass getting knocked on your ass. Sorry, kids. Gotta call bullshit. #iykyk

"New" vs. "Old Guard" Chief of Staff

I'd like to publicly apologize to all "old guard" Chiefs of Staff. Man, did I speak out of my ass when I originally advocated for the EA to Chief of Staff transition. Until I really immersed myself into the Chief of Staff role, I never realized how comprehensive knowledge of data analysis, change management, preemptive strategy, operational nuance, and C-suite dynamics were required to be an effective Chief of Staff. It was so far beyond even my 30 years in the C-suite EA seat, the decade-plus of small business ownership, and even my own level of "C-suite MMA training." I'm convinced (and now understand) that the best Chiefs of Staff in the world probably emanated from management consulting. If I had the desire to do it all over, I wouldn't have transitioned from C-suite EA to Chief of Staff. Instead, I would have humbly sought a role at a McKinsey, Bain, or BCG. I remember there were some very specific strategies, approaches, and knowledge I was oblivious to when I got the 200+ page McKinsey handoff deck on Day 1 of my shiny new Chief of Staff role. A good year or two at a management consulting firm would have made me an absolute BEAST in the Chief of Staff role instead of a cautionary tale of sprinting before learning to walk competently.

The "New" Chief of Staff role, in my honest opinion, is filled with "peeing puppies." Every puppy dreams of eventually becoming a big dog. But it's an evolution, not an "entitlement." Puppies who wander blithely into traffic get hit by cars. Those who stay within the confines of the yard get the opportunity to learn, grow, emulate, and become big dogs. Truly, I'm kinda bummed being associated with what I see as the devaluing of the title "Chief of Staff." I read some of these CoS job descriptions and get physically ill. The majority are clearly a placation to the EA community and are nothing more than an elevated EA role, which, ironically, could actually be remedied by entrusting current, baller EAs with more responsibility, autonomy, support, and compensation. No need for a vanity title and requiring your Chief of Staff to do administrative tasks as part of the role. Dafuq?!

But, if you must, please realize that the role STILL requires a different skillset, mindset, exposure, and execution level beyond that of even the most highly experienced Executive Assistant. If you've never run a business, you'll not be as effective out the gate as those who have. If you didn't graduate with a Business or Finance degree of some sort, you won't be as effective out the gate as those who did. And most importantly, if you don't have the business acumen, intuition, and "balls" to stand on the hypotheses you're feeding to your CEO and leadership teams, daily, you won't cut it. Period.

Dayum, Debbie Downer! Now What?

Here's the thing, kids, and why I'm stepping back into EA advocacy. One of the biggest epiphanies I had throughout this entire past 3 years of my life was that being a career EA is kinda Fn fantastic, especially if you can get to the absolute pinnacle...EA to CEO. While there should still be gobs more "respect on the EA name," I was able to carve out decades of amazing experiences in the role, support CEOs who became personal heroes to me, create numerous successful businesses and side hustles, amass a SICK network and tremendous social cred, and have more influence than I could ever have imagined from a "support role."

This boils down to perspective, I guess. EAs have been fighting so hard for a new title, respect, compensation, etc., that we've allowed detractors to craft the narrative about us because we got distracted with pomp and circumstance, popularity awards, fake experts who were mediocre-at-best EAs, and these cliques filled with mediocre-at-best business professionals happy to profit off EAs' lack of followthrough, confidence, and their company's healthy continuing education budgets. (An actual quote from one of them, btw.)

I'm not here to discourage anyone from following their dream. I wanted to become a Chief of Staff more than anything to prove it could be done from the EA seat. So I put in the work. I positioned myself perfectly for the opportunity taking a rather non-traditional route. It was very calculated, and I executed it to perfection. And it Fn sucked once I got there. I was ready. But I wasn't "prepared." Does that make sense? Despite all of the work I'd done, new skills I'd learned and honed, and even the aggregate decades in the EA-to-CEO seat, I was not prepared for the amount of pressure, resistance, sabotage, shadow bans by ineffective C-suite "fat cats," daily preparation, constant lack of context, stress to always get it right, decoding lies and "hiding," and constant levels of self-doubt and second-guessing knowing that an entire organization and the reputation of the CEO I supported hung on every syllable of anything with my name on it going live in the public domain.

It's true; the burnout rate for a dope Chief of Staff is about 18 months. If you've done your job well, that's all you can truly last physically and mentally. I'll say it: The Chief of Staff role is a stepping stone, not a destination. It's the perfect role to prepare you for a role with some actual permanence and verifiable prominence or the perfect training ground to launch your own business. Any more than a couple of tours as a Chief of Staff is a one-way ticket to a straightjacket or a premature grave. I said what I said.

In Conclusion

I'm gonna say something a little controversial here and maybe a bit antithetical to my previous stance: There's absolutely nothing wrong with being an Executive Assistant...title and all. However, strive to be the very best one in the world. Develop Chief of Staff-level knowledge and execution. Learn business like an MBA. Start a side hustle that gives you the hands-on experience (and pressures) of being a CEO, even at a small scale. And work/finagle/scheme your way into a seat at the table so that you can get the information straight from the horse's mouth and employ all your magical powers to decode body language, tone, and help your CEO know exactly what's up from a perspective that's wholly unbiased and solidly DGAF. Get really good at negotiation, specifically when advocating for yourself. Watch, learn, and master the game, the players, and the plays. I can tell you from experience, that this is how I built an unparalleled EA career that continues to pay me and pay forward everything I've learned for decades so that others can have an easier go at it than I did.

I repeat. If you're an EA and want to become a Chief of Staff, DO IT! Shit, hit me up for any advice you need. But be prepared to not like what I have to say or to hear some hard truths that will either discourage you or light an even bigger fire under your ass. I don't sugarcoat. Those who know me know. But I always want the best for those who come to me seeking counsel. If you join my communities, prepare to work and contribute. I'm old and grumpy and don't allow my time to be wasted.

Yes, I'm back advocating for Executive Assistants and the role. The shakeout you're seeing has been long overdue. But I know CEOs and C-suites better than most. As much as they obsess over growth, market position, and headcount they still need and not-so-secretly enjoy the very human presence and nuance of having a trusted partner in their corner. They want someone with ambition, but not too ambitious. They enjoy (and highly compensate) EAs who innately provide "that magic" and who anticipate needs and execute steps ahead without much fanfare. If you really deconstruct the professional relationships of the tippy top CEO/EA pairings, it's actually based in mutual respect. Roles and expectations are clearly defined and understood. Both know their lanes. None feels any abject disrespect or underlying tension. And should that occur, it's usually an indication that it's time to move on. There's always opportunity to level up, learn, grow, take on more responsibility. But when ambition gets in the way of execution and the previously agreed-upon (comfort) level, trust and "ease" are eroded.

I can say, unequivocally, as a business owner, I crave "ease." Sure, I want competence, passion, pedigree, and all the things from an EA. But the one thing that will always supersede anything on my wish list is someone who can bring ease to my life and do it on repeat. When I was an EA to CEOs, this was my North Star. How can I make every day, every interaction, every business trip, every Board meeting, every funding series, every painful-but-necessary employee RIFF...easy? My ability to do this allowed me to become a BEAST in the role, command the highest salaries, and score some of the top CEOs in history as bosses and mentors, even if for a short time in some cases. My move from the EA seat to advocacy allows me to continue to be a massive supporter of the role and help those in it get to the highest levels in business. I can't (and won't) help everyone. But that subset who "get it" and who are passionate about maxing out what they already have are my peeps. And if/when they are ready for more, I'm happy to help in that transition...including the Chief of Staff role. But they'll definitely be comprehensively prepared for that role and armed with everything they need to know from someone who got there. Though I tapped out because the role actually wasn't everything I had hoped, I have no doubt that a small but mighty subset of seasoned C-suite EAs could absolutely crush the Chief of Staff role...with the right CEO...in the right organization...at the right time in that organization's journey. Yep, that part.