How Being An Executive Assistant Made Me The CEO Of My Own Life

By Kali Hill, an Executive Assistant at Waypoint Residential in Stamford Connecticut.

A year ago (almost exactly to the day), I found myself sitting in my new apartment filling out job applications in a new state, after leaving behind my childhood home all my friends and family, contemplating if I had just made the biggest mistake of my life. In my job search, I landed on finding something I thought would be temporary. One year later, and I am still in that role, but now with invaluable knowledge that will serve me well, no matter what’s next.

Today, I’m spilling my secrets on how being an Executive Assistant made me the CEO (Chief Everything Officer) of my own life. From my profession, I’ve come up with a foolproof guide to success in any job or life task.


Over the past year as an Executive Assistant, I have figured out how to set myself up for success. Or, as I like to call it, “successorizing” because being prepared is always a good look. There are really five key takeaways that are the difference between being the CEO of your life and working for the CEO.

1) To-do lists:

There is a difference between those who actively to-do list and those who don’t. I am here to tell you, even if you are in the latter (like I once was) something as simple as making a list can take you leaps and bounds towards looking and being successful in your job and life.

Toss out the idea of one boring long list and embrace a variety of lists for everything from work to personal. I have one on my work computer, in my notes on my phone, written on a pad of paper. The beauty of to-do lists is that they are an amazing way to feel accomplished no matter how small the task. Plus, keeping a record of the things you do is a great way to show your boss how valuable you are.

Make sure to keep at least one list of fun things you want to do, places you want to go or just things that make you happy!

2) Scheduling: 

One of the things I first learned as an EA was how important it is to make a schedule and try your best to stick to it – and encourage your boss and others to do so as well! I found a few ways to make it as painless(ish) as possible.

First, use that to-do list to make a schedule to plan ahead and don’t be afraid to make it clear when something is a priority on your schedule. When you have a schedule, you no longer have to ask yourself what you do and don’t have time for –  you have it all down on the calendar.

This combo makes personal/work-life balance possible with some planning and prioritization. Don’t be afraid to schedule yourself in. If you have a doctor’s appointment or need to do some self-care, schedule that in without risking important work tasks.

3) Start at the Bottom to Get to the Top…of the List:

To be candid, I am not a morning person but I know for certain getting the worst part of the day done with first, is the best way to have a better day. The task you loathe the most might not even be that terrible (relatively speaking) – it might be the pile of dishes in the sink or an overdue expense report. Making the worst part of your day a priority on the to-do list makes everything else you do later seem that much easier.

And while we’re talking about making your day easier – voice to text on my phone is so helpful in terms of things that I can’t take down quickly. But find the method that works best for you. Don’t rule out old-school sticky notes and notebooks. There’s just something about having a physical paper or a tangible item that embeds information into your memory. Plus, technology and apps could let you down but having physical copies of things won’t.

4) Mind Reading:

This may be the best-kept secret in history but mind reading is, in fact, a skill that can be taught and learned as an EA and professional.

Some may call it “foresight” but anticipating not only your boss’ needs, but what others might need, makes you feel like a magician. It’s as easy as embracing the task at hand as well as putting those ‘Where in the World is Carmen Sandiego’ skills to work. The secret is: you already know what to do. Listen when your boss or coworkers talk and observe their body language and non-verbal cues. Something as simple as noticing your boss always picks off the bleu cheese from their salads can go a long way. This is my favorite new found skill because it feels great to know what someone wants before they ask and it makes you look great at your job.

5) Putting the Relate in Relationships:

Thanks to the screen revolution, we are more hesitant to initiate face to face contact, but as a professional, cultivating relationships is so important. The best part is a lot of these relationships start out over the phone or via email, which is already in our skill set. We know that accomplishing anything in life is arguably half skill and half who you know. When you know who can help you achieve certain tasks it becomes a lot easier to ask for help, which (in case no one has reminded you lately) is definitely okay to do.

A year ago if you would have asked me if I would love being an EA or if I would be writing an article about how much I have learned, I would have laughed. What I know now is that I have learned more in the past 12 months about myself and what I am capable of than at any other time in my life.

With a little organization and a few good tips, we see we already know what it takes to be the CEO of our own lives.

Kali Hill is an Executive Assistant to the Chief Acquisition Officer and team at a vertically integrated Real Estate Investment company out of Stamford Connecticut. She supports about 12 people in total from the Acquisition/Disposition group. She somehow manages to only have 1 cup of coffee a day and originally comes from a background in politics which she believes is actually not all that different from the corporate world. A recent work highlight was the installation of her new standing desk which makes it easier to run from her cube to her bosses office.

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