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The Pilot and the Navigator – My Experience as an Executive Assistant and Chief of Staff

Writer's picture: Meg SteinschauerMeg Steinschauer

If you’ve ever wondered what it’s like to be an Executive Assistant or a Chief of Staff , allow me to introduce you to a tale of turbulence, triumph, and transformation. Having done time in both roles, I like to think of the EA as the trusty, by-the-book pilot, and the CoS as the navigator—both essential for taking an organisation to new heights, but with very different flight styles.


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All clear for takeoff—because every leader needs a strong EA and CoS in the cockpit. 🎯🚀 #StrategicLeadership


While the EA ensures everything is securely fastened, scheduled, and running on time, the CoS is gazing at the horizon, asking, “But what if we flew over there instead?” Both roles are important, and both are demanding—trust me, I’ve worn each of those metaphorical hats (or flight helmets, if we’re committing to the analogy).


The Steady Hand on the Controls – My Life as an EA

When I first stepped into the cockpit as an Executive Assistant, my mission was crystal clear—don’t crash the plane. No, really. Every meeting scheduled. Every email triaged. Every minor detail triple-checked. The boss’s day, week, and sometimes life, depended on my ability to keep everything in smooth formation.


I took pride in being the calm in the organisational storm—the sort of pilot who could guide a plane through a storm cloud without spilling anyone’s tea. There was something satisfying about bringing order to chaos, whether it was mapping out a packed schedule or ensuring tricky conversations happened at “optimal times”.


If the CoS is busy plotting where the plane should go, the EA is the one making sure the thing actually takes off. Once, for example, I spotted a double-booked afternoon involving an irate client and an impending board meeting. Through sheer logistical acrobatics, I managed to relocate one to the morning and morph the other into a virtual call. To the exec, it looked seamless. To me, it felt like performing aerial stunts with a blindfold on.


The Thrill-Seeking Navigator – Life as a CoS

Fast-forward a few years, and I found myself ditching the captain’s seat to join the ranks of navigators—Chief of Staff territory. This was less about ensuring turbulence-free flights and more about dreaming up bold new destinations. Gone were the days of reviewing daily itineraries. I was now tasked with reshaping the strategic landscape of where we were headed—and convincing others we’d get there in one piece.


If the EA in me was methodical and risk-averse, my CoS self was positively audacious. I remember being in a strategy meeting, realising mid-discussion that what we really needed wasn’t polishing the current plan but ripping it up entirely. It didn’t win me many fans amongst the spreadsheet brigade, but the new approach worked out in the end. That’s the thing about being a navigator—you can’t worry about ruffling feathers; you’re too busy spotting new horizons.


Yes, it’s thrilling—but it’s also messy. When you’re guiding the organisation’s “plane” into unknown skies, there are a lot of moving parts to coordinate. Departments miscommunicate, egos flare, and organisational trust is sometimes as thin as an economy-class pillow. It requires diplomacy, persuasion, and, occasionally, distraction techniques worthy of a magician. “Look, over there! A bold new opportunity!”


Risks and Rewards – Flying Styles in Action

The biggest difference between flying as EA and CoS? The approach to risk. The EA me wanted everything grounded in predictability. Neat, clear, actionable decisions. Need to decide between three overlapping meetings? I’d pull out my spreadsheet wizardry and find a solution so smooth it was practically aerodynamic.


The CoS me, however, traded calculated control for bold bets. Making a decision as a CoS often felt like switching off autopilot mid-flight, trusting the instruments, and hoping for a clear landing strip. Once, I championed a partnership with a high-risk start-up when the safer option was to stick with a tried-and-tested supplier. Sure, I lost sleep over it, but the start-up came through, bringing innovation that helped reshape our approach.


Motivation – Cockpit Dynamics

The dynamic between EAs and CoS can be summed up as structure versus inspiration. Picture the EA handing out pre-flight safety instructions, with a smile and on time. Practical, grounded, and precise. The CoS, meanwhile, is in the cockpit, saying, “We’re not just flying to Madrid. We’re reimagining air travel. This flight could redefine what journeys mean!” It’s dramatic, admittedly, but necessary to keep the big picture in focus.


When I was an EA, my motivation toolkit revolved around ticking things off to-do lists. It was all about deadlines and deliverables. When I stepped into the CoS role, however, I realised motivation required emotional buy-in. I wasn’t just asking teams to action tasks; I was asking them to believe in the why behind the work. “Why?” is far harder to sell than “When?”.


The Best of Both Skies

Here’s the thing about these roles—they’re vastly different but beautifully complementary. Organisations that thrive need both steady piloting and adventurous navigation. During my time as an EA, I learned the power of discipline, execution, and forethought. These skills served me well, even as a CoS, particularly on days when visionary thinking needed a grounding in practical realities.


Likewise, my stint as CoS taught me to dream bigger, challenge assumptions, and see further down the horizon—all skills I wish I’d embraced earlier in my EA days. Together, these roles create a perfect balance—one manages the present; the other builds the future. Without the EA’s steady hand, the CoS’s bold ideas risk chaos. Without the CoS’s vision, the EA’s meticulous efficiency loses direction.


Final Call

Having served both as a pilot and a navigator in my career, I truly appreciate the need for both roles in any organisation. They’re not competing forces—they’re complementary, like wings on a plane. One propels forward while keeping things stable, and the other charts the path into the unknown.


If you’re lucky enough to have an EA and a CoS working together, you’ve got a powerhouse team.


Now, if you’ll excuse me, I need to adjust today’s flight path—my EA brain says “finish emails,” but my CoS side insists on planning world domination. Decisions, decisions.


Have a safe flight ya beauties ✌️✈️

Meg


PS If you've worked in either role, I'd love to hear—what’s been your biggest EA or CoS challenge?



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