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!"

Dear T,

Thank you for being an avid reader and for submitting a question! :) I hope my blogs have been helpful to you! Please also feel free to ask more questions and suggest topics. If you are on Twitter, I would love to follow you there as well!

The easy way to answer this question is to have you Google interview questions online. You can find a trove of them.

However, one of the best ways to approach forming questions is to ask yourself, "Is this the best fit for me?" Does the role align with your career goals, work/life balance needs, and your values? Not all roles are created equal and it's your job to approach each opportunity to vet them yourself. Your goal is to find out as much information as possible so there are few surprises and to have a sense of what the role is before you take it. Some good questions to ask might be:

-What is the breakdown of the role? Is it 50% event planning, 10% personal assistant work, and 40% executive assistant/admin work?

-Is this a position that I can receive more responsibilities after a year or two or get promoted within the department?

-With my background, what are some challenges I might face?

When you start brainstorming, you can also ask questions to help showcase your talents and skills better too. On the other hand, you can also lead into talking about projects or programs you may want to learn more about and get more experience with. An approach I use is to ask the question and then explain why I asked it. This way it becomes a dialogue instead of just and Q and A session. Here are two examples.

-Is the executive tech savvy? How tech savvy is the executive?
(They answer.)
The reason why I ask is because I’ve worked for a couple of older executives who were not as tech savvy. Some didn’t know how to type, some liked to write out their speeches by hand which I had to type, etc. So I’m open to “handholding” and understand how each executive works differently.

-Will I be using Excel a lot?
(They answer.)
The reason why I ask is because I am proficient in Word and Powerpoint, but I have the most experience with Excel and really enjoy doing spreadsheets and formulas.

-Are there any industry-specific programs I will need to learn?
(They answer.)
I’m always very eager to learn a new skill or become an expert in the programs I already know.

Finally, ask peripheral questions that are nonetheless important - about training, culture, and challenges with adapting. Since you should be taking notes during an interview, any new information you learn, you can ask questions for clarification or a more in-depth answer.

One type of question you may have overlooked are the “closer” questions.

-What is your hiring timeline?
-What are the next steps?
-May I have your business card before I go?

When I interview, I have a set of 15-20 questions ready, knowing I won’t get to them all or some of them may be answered along the way. I always bring a copy of the actual job description with me. I highlight certain things I didn’t understand or compare it to what they are telling me versus what HR wrote up. I bring notes of research I did on the company from wikipedia, current news, and visiting their website. I look for upcoming projects, their senior management org chart, industry news, and I research what sort of company culture they have. On average, it takes me about 2 hours to prepare for an interview.

Always remember to end the interview on a positive note by asking why they enjoy working at the company and to send a thank you card!

T, I hope this helps and thank you for being a loyal reader! :)

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.

At first, you may not know what it is. There is just an uncomfortable, nagging feeling that something isn’t quite right. And as you talk to your friends, whatever advice or suggestion they give, you shoot it down. Logically all their solutions make perfect sense and will, in fact, solve your problem. However, what you need isn’t a solution - it’s an emotional breakthrough to come to terms with whatever thought, feeling, or misperception you carry about the problem you have.

Until you can be okay with where you are, you won’t be okay with getting to where you need to be. You will allow excuses and laziness to justify not doing anything because you are hoping the problem will magically go away or with enough denial, perhaps you’ll learn to deal with it.

Often, facing the world and seeing reality for what it is, is really difficult. It’s great to walk the line of optimism, hope, and perhaps things changing in a split second, if you are patient just a little bit longer. You wonder if you misunderstood or could have said or done the wrong thing to contribute to the problem.

Life is short. Every day you live that you aren’t actively pursuing your goals or happiness, is another day wasted. Waiting for the right time or person becomes just that - a waiting game.
So whatever it is that you are mulling about, figure out what it is you really want, then figure out how to get there in the smartest, shortest time possible. Life is already hard enough, and will throw challenges your way, so you will already lose time, energy, and money. Waiting only doubles that deficit.

I was taught at a young age to carpe diem. L, I hope you will too. Although it may sound selfish to put yourself first, if you aren’t happy and cared for, you can’t contribute to those around you - be it at work, at home, or in the community. Sometimes, solving other people’s problems should not be your concerns or your burdens to bear. It doesn’t make you a bad person to want a life of your own. I sense that you are trying to grasp that concept and I know it isn’t easy. Everyone has a choice and at times they are all hard, difficult, lesser of the two evil “choices.” However, they are choices that do, in fact, exist. What will you choose, when, and more importantly, for what reasons? And if you don’t look out yourself, who will? This is my way, through invisible, magical osmosis... I am thinking of you. :)

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.