How to Be Your Own Best Executive Assistant


For many small business owners and entrepreneurs, it’s fun to romanticize the idea of having an executive assistant who makes your personal and professional life seamless, comfortable, and organized. You know, like what you see in Hollywood movies where the CEO has someone who brings their preferred morning beverage to the office without having to be asked, who drops off dry cleaning, schedules meetings, and exists to be your set of legs and arms so you can be the brain. And there’s a reason why that’s Hollywood. It’s not reality, nor in my opinion even necessary. I mean, I can handle making myself a cup of green tea in the morning, and with a super casual workspace what even is drycleaning anymore?

But the point I really want to drive home is that the idea of an executive assistant is often better than the reality of it. Sure, there are certain positions that warrant such a person to help with an influx of phone calls, emails, appointments, and requests. But really that’s reserved for the 1% of entrepreneurs and executives who have a complicated work and office model, one where they’re in high demand (or at least believe they are). For the rest of us, I want you to know that you can handle these tasks for yourself. And there are some pretty significant benefits to be gained from training yourself to do so. Don’t you want to be a sharp, efficient, and organized business owner for your clients? Then surely you can be all these things for yourself. And moreover, tasks like invoicing, returning phone calls, responding to emails, and scheduling meetings don’t have to be nearly as complicated as many make them out to be, especially with the tools and technology at our fingertips.

Keep reading to learn how I’ve spent the last decade growing my business, while fully managing my administrative tasks with ease. Along the way many would ask, “Why don’t you hire someone to do that?” and my gut response was always “Just because I can, doesn’t mean I should.” Here are my secrets to becoming more efficient and organized than any executive assistant I could have hired.

Identify the processes that work best for you.

Leading up to starting my professional career, I had many opportunities to learn what organizational processes work best for me. From high school jobs and internships to managing a full college course load, being organized wasn’t optional if you wanted to be successful. Though the tools and technology I rely upon have changed greatly from handwritten to-do lists to now using digital solutions, I learned early on that I like to resolve open action items as quickly as possible. If there’s a meeting I need to schedule, I want a confirmation of the date and time that day so I can add it to my calendar. If there’s an email sitting in my inbox, I view that as a to-do that needs to at a minimum an acknowledgment that same business day. I know intimately well the processes I prefer. What works for me may not work for someone else, and the likelihood of me finding and then training someone to align with my processes is slim. So I’d likely have to settle for a compromise of work styles, and knowing my personality, that would cause more time and tension than if I just managed my own processes with the efficiency I’ve already learned.

Training clients versus training staff.

Consider this. Have you trained your clients to follow your preferred communications and organizational style, or have they trained you to follow theirs? I’d argue that many of the business owners who feel that they need an executive assistant to manage their client communications is because the clients are dictating how and when they make requests of that business owner. Emails at all hours of the day? Requesting meetings that could be an email? You can eliminate living inside this chaos bubble by proactively (and subtly) training your clients to respect both your time and your processes. During the onboarding process be sure they understand your expectations for how projects will be managed. And you can offer the same for them. When you begin with a foundation of understanding for one another’s time and know their preferred processes, you’ll require less of each other because there will be trust in what’s taking place day-to-day.

Understand real versus perceived needs.

I thought about saying this another way, but feel it’s best to tell it like it is. A lot of business owners are needy. We (myself included from time-to-time) feel we need a lot more support and handholding to run the daily operations of our businesses than what is actually necessary. I’m not claiming you can automate everything and phone the rest in, but there are some very obvious “needs” a business owner places on their executive assistant that are hardly “needs” at all. I mentioned some in the introduction of this article. Rather, I urge you to first focus on identifying what are your real needs as a business owner. Especially in the beginning, you can build a business without all the luxuries (and what can eventually become complications) or having an executive assistant. If you write a laundry list of what you think you need someone to do for you in a day, you might be surprised by how much you can simplify that to just your true needs. In doing so you’re likely to realize you’re fully capable and tackling these items yourself, likely with more efficiency and less overhead.

Don’t overthink tasks.

And finally, don’t turn molehills into mountains when it comes to your task list. If you’re a list-maker like me, you might write out absolutely everything you hope to accomplish in a day in painstaking detail. But must those tasks really be that complicated? If you’re convinced they are, you’re likely to procrastinate which only adds to your to-do list the next day. This can then leave you feeling like you absolutely need someone else to manage this list for you. Combat this bad habit by keeping things high level and only adding a realistic amount of tasks to your list for any given day. Start with what’s urgent and important and work from there. When you can get down to only needing to tackle that single most important tasks on any given day (and moving around other tasks to other days) it makes setting goals and accomplishing them so much easier – and all without needing an executive assistant!

Have you had a positive experience with an executive assistant? I’d love to learn your tips for successfully training and managing someone who makes your life easier. In contrast, if you’re someone who thinks they may need an executive assistant to help run the business, I urge you to consider my points above. And as always, I welcome comments to spark a discussion on this topic!