Answering Reader Mail: What questions should I ask an interviewer when applying for an Executive Assistant position?

"I'm an avid reader. Your blog is fabulous! I hope more posts are on the way!

What questions should I ask an interviewer when applying for an Executive Assistant position? I do come prepared with questions. However, sometimes during an interview, the interviewer answers all of my questions during the conversation without me even asking. Then at the end of the interview, I'm stumped on what else to ask regarding the Executive Assistant position or their company. I feel as though if I don't ask, I'm not showing interest!"

Your Emotions Hold You Back

It’s always interesting how standing on the outside of a situation gives a vastly different perspective than to be inside or within that given situation. Upon reading and reflection, the defining element is one’s emotional investment or lack thereof to said scenario.
Even in life or death situations, people hold back from doing the right or best thing because an emotion - guilt, pride, sorrow, embarrassment, anger - is holding them back. If you’ve read Malcolm Gladwell’s book where he talks about the pilot communication problem and the resulting crashes, you will know what I mean. Whenever you are confronted with a problem and have to act or change something, when you are not eager to jump in, there’s an emotional barrier you have to overcome.

Be Your Boss For a Day

One of the best ways to become a better assistant is to be your boss for a day. What I mean by this is hire someone to take care of a task for you or be your assistant for a day with anything you need help with. It’s not until you are paying someone money, to help make your life easier, do you realize the challenges of finding someone good, eager. You will learn how time-consuming and difficult it is to train them or communicate to them how you want a task done to your liking and specifications. You essentially want a mini-you. If only there could be two of you! Something that seems so simple and obvious to you, second nature even, will be hard to translate to someone else.

Remember in grade school when you got that assignment to write directions or an essay explaining how to do something step by step, like making a sandwich or whatever you chose? You had to start by saying, “First, open the bag of bread. Second, pull out two slices, not that yucky first end piece, then cut off the crusts. Third, don't forget to close the bread bag or the bread gets stale. Then, get the peanut butter and jelly jars....” You had to explain every little detail as if you were instructing a 5 year old so it taught you to be mindful of sequential order and specifics. Be your boss for a day is the grown up version of that.

What do I have in mind? Hire someone to do any of the following:

Wash, dry, fold and put away your laundry
Clean your room or apartment
Run to the store for you to grocery shop
Help you find a restaurant
Wash your car

The amount of critical thinking, judging what’s important/not, and understanding that people are not mind readers will blow your mind away. Your expectations and what you envision will be vastly different from what is delivered, and not because they are dumb or didn’t pay attention or anything else. It’s more, without specific instruction and constantly changing variables, everyone’s idea of X is different.

For example, let’s take something as basic as getting help finding a restaurant. This is what typically happens.

You ask someone to help you find a restaurant for a birthday celebration and you say something along the lines of something special, but not too expensive and nearby. When your assistant for the day goes off and does some research and comes back with 3 options, you will probably negate them for the following reasons:

-You don’t like X cuisine they chose.
-It’s either too casual or too inexpensive.
-You’ve already been there so it’s not special enough.
-You hate that restaurant.
-The place is too loud or too trendy.
-Parking is difficult or $20 for valet.
-You’ve never heard of the place or it doesn’t have a good reputation.
-The place is closed on Mondays or X day.
-They don’t have a great dessert menu and you can’t bring your own cake.
-You know X goes there a lot and don’t want to run into them.

As someone’s boss, you have to walk the fine line of not coming across as being scatter brained, picky, or indecisive. You have to provide the right amount of encouragement, praise, and feedback so your assistant has high morale and gets what you need in as little as time as possible. You have to be aware how long certain tasks take although to you it seems rather simple.

Practicing this exercise will make you a better assistant, but it will also make you a better boss to your interns, 2nd assistants, and other colleagues. People make the best decision they could at the time with the information they had THEN. However, life is constantly changing and what you know now, most often, wasn’t knowable earlier.