Zoe Hill takes us on her journey from Executive Assistant to Chief of Staff and back again
Executive Assistants are often on the hunt for the next big career move, and many are eyeing the Chief of Staff (CoS) role. I, on the other hand, transitioned in â and then transitioned back out. Let me take you through my journey and share some things I learned along the way.
The Reality Check
The Chief of Staff role is rapidly becoming a popular path for Executive Assistants to slide into. Businesses are hiring Chiefs of Staff like there is no tomorrow. And the role is growing, like ivy around a house: if you nurture it, understand how it moves, and give it what it needs, it can be the most rewarding role. But let it grow wild, and things might spiral out of control.
I had 15 years of experience as an Assistant before I moved into the Chief of Staff role. After managing nearly 40 EAs, handling project management, and executing strategic plans, it seemed to my eyes that the Chief of Staff role would be a step in the right direction for my career. And, initially, it was the right step for me â just one that would be short-lived to help put me onto the correct step.
What I didnât expect was how much of a change it truly was, and I was essentially saying goodbye to my EA life.
Yes, my previous skills were transferrable, but those skills had to be completely adapted and transitioned to a whole new path completely separate to what I was used to.
It was no longer a case of âCan you set up a meeting with this potential start-up? Here is the name and email address.â It was a case of âCan you research and come up with the top potential Series A start-ups that we could look to reach out to and partner with?â A small example.
My usual âAbsolutely, no problem!â attitude was tested daily. It felt like trying to keep a swan-like posture while navigating a whole new landscape.
It was time to learn.
The Learning Curve
I dove into books, podcasts, and LinkedIn deep-dives to figure out what exactly it meant to be a Chief of Staff. (Side note: LinkedIn never stood a chance against my search history during that time!) What I discovered was both fascinating and a bit overwhelming; every business defines its Chief of Staff role differently. Sure, thereâs a shared core of responsibilities, such as aligning teams with executive goals, managing cross-functional projects, and serving as a strategic advisor. But the nuances vary greatly depending on the company, the CEO, and even the industry.
In short, I realised I was on my own.
While there are brilliant resources out there helping EAs transition into this role, nothing can fully prepare you for the reality that no two Chief of Staff roles are the same.
My Time Spent as Chief of Staff
I wonât deny that I loved the role, I truly did. However, what was missing was fulfilment. I couldnât and didnât want to let go of my EA duties. But if I didnât, it wouldnât have left room to be able to learn about the role that I was in.
I asked questions which were completely welcomed by my leaders; however, their time was scarce, and so I had to do my best to seek out the answers on my own. A very normal part of this role, from what I now know! And in fairness, EAs experience the same here.
I was never completely connected to one person or to a team of people. They were wonderful and we had an excellent relationship, but I was cross-functional. Not to mention I had to have a change in mindset and priorities. So, I dabbled a bit here and a bit there across different areas and projects.
I had a voice at the table, but it wasnât exactly in the seat I expected it to be in. I found myself pushing out deadlines, ensuring that strategic goals were met, and doing my best to manage the expectations of leadership. But I wasnât deeply connected to any one team or person, which left me feeling a bit lost at times.
The Roleâs Complexity
Letâs be clear: the Chief of Staff role is complex. According to a survey, about 70% of Chiefs of Staff are involved in high-level decision-making processes, and over 60% are responsible for leading cross-functional teams. This demands a blend of skills: strategic thinking, project management, and executive communication â that EAs often excel at completely, but in a whole new context.
But not every business truly understands what they need â another curveball. Iâve had conversations with business owners who thought they needed a Chief of Staff, only to realise what they really needed was an Executive Assistant with a strategic edge. EAs often see this role as the natural next step, and in some cases, it is. EAs independently turn their roles into a CoS role. But for those with just a couple of years of EA experience, this leap may feel more like jumping into shark-infested waters with no life vest.
Donât Forget the Other Paths
Here is something that genuinely makes me sad: we are forgetting about all of the other amazing career paths open to us. For example, what about Business Management, Project Management, HR, Event Management, and PR? The EA skillset is incredibly transferable to all of these roles. So why are we suddenly limiting ourselves to just one title?
The Chief of Staff title is shiny, for sure, but itâs not the only way forward.
My Outcome
Even on the best days, I still didnât feel the excitement, joy, passion, and drive that I once had. I was proud of what I was learning and doing, but deep down, I felt lost, fake, and ultimately on the wrong path.
However, I did enjoy it enough to stick it through for 18 months. But I needed to step back into what I love: being an Executive Assistant. I walked away with a wealth of knowledge that Iâve since poured into building my own Executive Assistant business â Premier Admin Services.
I donât regret the move to the role at all, but it is not for everyone.
But just because I am no longer in this role, does not mean that you wonât absolutely fall in love with it. I liked it, just didnât want to marry it. đ
So, here are my top tips if youâre considering making the transition:
Before You Become a Chief of Staff
- Read Chief of Staff by Tyler Parris.
- Donât spend hundreds or thousands on training unless youâre absolutely sure this is the role for you.
- Network with other CoS, engage with them, and learn from them.
- Look at your current EA duties and think about how theyâd be different in a Chief of Staff role.
Once Youâre a Chief of Staff
- Learn the top goals and objectives of the business.
- Start building relationships with the executive team early.
- Understand how processes work and where improvements can be made.
- Be confident in suggesting changes, but donât rush; relationships come first.
- Observe EVERYTHING. Be the fly on the wall.
Conclusion
After nearly 18 years as an Executive Assistant (all except those 18 months as a Chief of Staff), I can honestly say my true passion lies in helping others. Thatâs why I never had a clear answer to âWhat do you want to be when you grow up?â â I didnât want to be any âthing,â I just wanted to help.
The administrative community is full of guidance and support, and Iâm here for it. Thatâs why I love being an Executive Assistant, and now a business owner. Thereâs simply nothing like it.
