Being an executive assistant is one of those jobs that will always test your temperaments, personality, and character sections every time.

Your patience, tolerance, perseverance, ability to cope up with difficult situations and the courage to stand up and speak for yourself will always be tested on the job.

Being an executive assistant, especially to a high profile personality, can be a daunting task but also it has its highlights too. You just have to know which lines to cross and what to do when walking on thin ice.

I have been compelled to write this piece, especially after the resignation of Trump’s Day 1 assistant who was said to have indiscreetly shared top details during a recent off-the-record dinner with journalists in Bedminster, New Jersey.

Despite how many people feel about Trump, this was a NO – NO. A breach of trust, especially of a high profile personnel, is just as good as committing career suicide. You break the bond of their trust, who will bother to employ you and put their life in your hands?

To make sure you don’t follow in the footsteps of our beloved Ms. Madeleine Westerhout, (whether intentional or accidental), I have formulated a bunch of Do’s and Don’ts that will guide you on your journey right next to, or behind the highs and mighty in the society.


Ok. First of all, I think it’s pretty clear that thou shall not talketh to journalists about your boss’s family or his dealings in the office, bathroom or wherever, whatsoever. That’s the first commandment for a great executive assistant. Now that we are done with that part, let’s begin;


As the old saying goes, there are many ways of killing a rat. Although one person may rise up the ranks from office administrator/administrative assistant doing clerical work to personal/executive assistant of the C.E.O/Company Owner/High Profile personality, the best way to increase your leverage as a professional executive assistant is to study for it just as any other professional career requires you to.

At a minimum, executive assistants usually have a 4-year degree or receive a certificate from a 2-year program. Although you’ll learn a lot of things from the job itself compared to what you were taught in school, having the basic foundations of operating as a professional executive assistant puts you at a better place when it comes to getting an interview for the job.


For this, I am specifically talking about soft skills that will make you a badass at your job.

Communication Skills, Time Management Skills, Organization, Multitasking Abilities, Problem Solving, Independence at Work, Proactive, Detail-Oriented, Leadership and Tech Savvy skills are some of the skills that will help you have a “smooth” run in your job.

If you’re looking around and seeing none of these in your Book of skills, please consider taking classes for them. There are multiple certificate classes both for free and affordable tuition fees happening all over the internet. Ever heard of Khan Academy, Codecademy, Udemy, Oxford, Cambridge, or The Open University? These are just but a few of the numerous online learning centers that offer such courses and more with accessible reading materials, plus the sessions are flexible as per your schedule. Being competent in your job is always a plus for future referrals.


Keeping up with your boss’s calendar is a very important task. Usually, you will be responsible for scheduling meetings and other appointments for your boss, and it could cause a whole lot of problems if you schedule an important meeting without realizing that it clashes with a prior arrangement that your boss needs to attend.

Updating your boss about their schedule will ensure there are no clashes between what you know and what they think you know about their schedules. Better yet, always let your boss know about the schedule you have for them and compare it with the one they have for themselves. You never know the calls he/she made from their own personal phone and what meeting he crossed out to attend to an urgent family/personal matter without your knowledge.


You will be functioning as a filter in your high profile boss’s life. This means that you’ll be the first point of contact for your boss’s clients, colleagues, co-workers or their boss a lot of times.

Always using “I am not good with names” as an excuse won’t really help you here.

Learning about your boss’s circle’s names and something extra about them will reflect well on your boss, his colleagues, clients, and acquaintances. It also shows how good a people-person you are. Plus it’s really annoying to both parties when one of them is constantly asking to be reminded of the other’s name whenever they come into contact. The best way of memorizing names could be rhyming the person’s name with their profession or relating their names with something unique about them that makes them stand out or something popular/famous or common. Some things like creating a professional connection with your boss’s client take time. Accept that and tread carefully.


As an executive assistant, you are bound to effing up a little every now and then at work. Even if your previous and current employers are equal in terms of stature or profession, they are two totally different people. There will always be a day when you slip, make a mistake and mess up a little but there is nothing more mature and professional than owning your mistakes to your boss. This leads us to the next point;


Assumption is the mother of all F ups. As previously mentioned, regardless of the fact that your former boss and current one have the same occupation or are in the same level professionally, it will be a colossal mistake to think that they operate the same. It is foolish to not acknowledge that all humans are different at all levels. In this case, devote yourself to knowing your boss as best as you can. After all, it is your job to know them and anticipate moves for & from them as an expert Chess player would in a game of Chess. Executives are specifically called mind-readers for this reason. Knowledge is power my friend. Know thine boss.



Don’t fall into the trap of being the “boss’s pet.” The best executive assistants are the ones who make their job look easy and natural. Running around like a frenzied animal all-day and working yourself to exhaustion is unsustainable, unhealthy, and not effective when trying to be noticed. The best thing you can do to gain an appreciation for your work is to simply be yourself. Chances are, people will come to like the authentic you. And whether you’re angling for a big promotion or a raise, your boss will be more inclined to grant it if they like you as a person, not as a person who works for them.


Just like any other job, your boss should state to you your job description at the beginning of your work as an executive assistant. It should be on your contract/agreement should state clearly what your roles are. In the field of executive “assistant-ship” however, lines tend to be blurry sometimes. If your boss expects you to do office and home errands for them, make and fetch coffee and serve them lunch even though it wasn’t part of the deal and you feel like that is too much, address the issue immediately it pops up before it becomes a routine.

Remember communication is the most common denominator in forming meaningful relationships professionally and socially. Use this tool to clearly and professionally express your concerns to your boss. But if you’re okay with partaking in such activities, let them know of the extra effort you are putting in and ask for a raise too.

What speaks most about your job as an executive assistant is your ability to surpass expectations and transcend the stereotypical views that accompany the job. What matters most is who you are as a person and what you’ll need to do in sculpting the job for yourself.

It is more of a calling to serve than just a profession under the wings of a celebrity.

Always be ready to learn.