10 Tips to be a Better Executive Assistant - Part 1

Here are 10 random tips I’ve culled over the years on how to be a better assistant. This is part 1.

1. Yes, No Boxes

Since I’ve worked for so many Fortune 500 CEO’s, I’ve actually been coincidentally groomed the same way in all the offices.

Whenever my boss would receive snail mail or an invitation, we had a pile or folder that either needed his signatures or we needed an answer from him. This is where the Yes, No Boxes come in handy.

For example, if my boss was invited to a movie premiere, I would take a post-it note and write:

You are free this evening. Would you like to attend?
____ Yes ____ No

This way it would take my boss 2 seconds to mark his decision. Easy. Sometimes the CEO would add a note underneath like, “See if I can also bring my children.” We would ask for +3 guests instead of just +1.

2. Only give a max of 3 choices.

This is probably pretty self explanatory. Whenever presenting any options, give no more than 3 choices. Presenting too many options just overwhelms and confuses people and makes them indecisive. It would be good to make the choices inexpensive, medium, or very expensive or whatever spread of variety is possible. If asked for restaurants, choose one seafood/sushi, one steak, and one general/American cuisine.

3. Money/gifts contributions etiquette

When it comes to donating money to causes, gifts, or anything else where a lot of people are also pitching in, don’t be shy to ask how much everyone else is contributing. The person to ask would be the other assistants or discreetly ask the person collecting the money. The goal is to solicit enough information so your boss or CEO either contributes the same amount as everyone on his level or slightly more, whatever is appropriate. The goal is to make sure he doesn’t contribute less than everyone else.

4. Answer the phone so the caller only needs to say yes or no.

Whenever I answer the phone and I know who it is or know it’s not a cold call, I try to make it easiest on the caller. Instead of this conversation happening:

Me: ______’s office.
Caller: It’s Jim. Is _________ there?

I say this:

Me: ________’s office. Hey Jim. Let me see if I can find ________. Hold on.

5. Bake cookies, cupcakes, or any homemade gift during the holidays if you can’t afford at $10-$15 gift card from iTunes, Starbucks, or Jamba Juice.

In the past, one of my executives would burn a CD of holiday music and gave those out.

6. Print out your boss’ daily schedule and put in by your desk.

This helps immensely so your boss doesn’t have to check their schedule via their smartphone or walk back to their desk. It also helps when discussing with colleagues when they should stop by again to see your boss. If you’re like me, you always have about 10 different screens open on your computer which makes it a hassle to find the right one showing the calendar and then resuming your task.

7. Meet other assistants from other companies that you work with over lunch or coffee.

Every now and then, if I find myself working a lot with a particular assistant, I ask them if they’d be open to meeting for lunch. Sometimes I go to their office or they come to mine. It’s always nice to get to know them as people and it makes for a better working relationship since you can understand their role, their boss, and how they as clients fit into the bigger picture.

8. If you need to interrupt your boss in an important meeting or when they are on the phone, pass them a note.

In all the offices I’ve worked at, passing a Post-it note with large legible writing is the best way to get your boss information or to ask a question. The reason why writing it down is better is for confidentiality reasons and to not interrupt the meeting/call by talking. You will find that most often, the meeting will continue on around you or the meeting will stall only for 5 secs.

Before you enter the room, knock, then walk straight to your boss. Show them the note and wait for them to nod or shake their head, say they’ll call back, answer yes or no, or follow you out of the office. Then exit as quietly as you entered.

9. Answer every email/request right away even if only to say you got it and keep you posted on answer.

It’s helpful to give them an ETA on your answer and encourage them to check back with you frequently if they so desire.

10. When someone is asking for your help or has a request, write down everything they say and repeat back the information.

Escape the Vicious Cycle By Giving Yourself Permission

Whatever your current problem or vicious cycle, give yourself permission to do whatever it is that isn’t allowing you to breathe, relax or face your deepest fear. Whatever action that you fail to do or keep repeating even though it’s not the best answer - stop, listen, and ask yourself, “What am I really running away from?”

Whenever I seek out solace and validation, it’s really to listen for an answer that will reinforce what I already believe or really want to do. You have to realize that being the Type A person that I am, I hate asking for advice, help, or not being independent. I’m all about self-awareness. Since I was a teen, friends told me to become a philosopher because I constantly grilled them through questioning on what they wanted, who they were, and that knowing yourself was the key to life whenever they came to me with the problem. I would elicit answers and peel away their excuses, justifications, and logic until the only thing left was their unabashed truth.

However, despite all this self-knowledge, of course there would be a gnawing question or major dilemma that I would need to consult my circle of friends every now and then, no matter how self-sufficient I wanted to be. Even though I know the answer, I refuse to implement it because I have not yet given myself the permission to do whatever it is I really should or want, for fear of X, Y, or Z. Or sometimes I wouldn’t be able to see that holding back or not taking any action was the thing to do. It wouldn’t be until my trusted friend or confidante would give me the solution that I wanted that I would allow myself to do it by justifying is as, “They know me really well. They are also very smart, fair, and have my best interest at heart. Since they are an objective party to my dilemma their reasoning and advice must have value.”

If we could only have enough insight into ourselves and unwavering confidence in our loved ones to tell them, “This is my dilemma. This is what I want to do. I know you may not agree with my choice at all, but I really need your support.” Instead we poll all of our friends, find the ones that agree with us, do what we wanted to do all along, and know we can go back to them for more advice or update them on the outcome knowing they are on our side.

One of my biggest eye openers this year is that it took two people to finally get through to me that I didn’t HAVE to do anything if I didn’t want to or if I simply just wasn’t ready. For whatever reason, not being ready that wasn’t even an option in my eyes. My faulty line of thinking was: I must do this, I’m scared, I’ll do it to get it over with because it seems the right thing to do. I didn’t pause to examine if my reason for being scared was one that would push me forward and help me grow or one that hold me back and cause harm. It wasn’t until I spoke to my friends that I realized it was the latter. I knew that I would have to eventually go through with the action that I was scared of, but it didn’t have to be today or even tomorrow. Instead, I waited three weeks. And during those three weeks, I mentally prepared and practiced.

What was I scared of? Everything everyone is also scared of - the truth and what is means, reality, what it might say about me as a person, being rejected, doing or saying it incorrectly or imperfectly, having a difference of opinion or perspective, or not being validated.

Stop, think, and listen to that truth you hide even yourself, especially from yourself. This shall be my new motto.

The Art of Being Lost

When I was in 5th grade, one of my favorite teachers taught me that, “I don’t know,” was an acceptable answer and to not be afraid to say it. This basic lesson had to be explained to us after repeated terrified expressions of the deer-in-the-headlights variety whenever she called on us that rendered victims mute, especially since we didn’t raise our hand. Later on we learned the better thing to do would be to go find the answer, but lesson number one was there should be no shame in admitting when you don’t know something. She said it takes a strong person to admit they are weak, or have a fault, and don’t know everything. Afterall, nobody is perfect. 

So I proclaim I don’t know anymore. And I’m still getting used to the idea that it’s okay to not know all the time where I’m going, where I want to be, or how to get there. This is the difficulty of too much self-awareness, living without distractions, and living a life free of self-medicating reflexes. Where do you go from here when your life has always been lived so happily, pragmatically with such a goal-oriented focus? 

Also in elementary school, my best friend was a straight A student. Her sister was a very average student. While her sister got tons of praise for bringing her C average up to a B average, my friend constantly got straight A’s and her parents never batted an eye. My friend almost secretly wished she was her sister. Maybe she would even go so far to let her grades drop and bring them back up again, just so her parents would appreciate all her hard work, although it is admittedly foolish. I could understand the sentiment and desperation though.

Everything is good, but not great. I’m not unhappy. I am also not overly happy for no reason like I usually am. The great news is, my closest friends couldn’t tell unless I mentioned it, so it’s obviously not that bad. I was spiritually tired, emotionally exhausted, and now in an improvement, I am etching toward just being plain bored - only a tad, a smidge - of being lost. Some days I feel fairly normal and other days maybe stretched a little thin. 

Elizabeth Gilbert said that sometimes just waiting and seeing is often underestimated as a strategy. I decided to take that route - to NOT muse about how to fix feeling lost. I sit with it and accept I don’t have the answer now and may not for a couple weeks. In my quest to improve my life, the constant focus became a source of mild annoyance in and of itself. So begrudgingly I learned to accept it. I’m not sure where this will lead, but at least the burden isn’t looming over me. 

The internal voice that constantly monitored if I had a solution to my woes no longer drones. My attitude now is,"So, I’m lost. Okay. Who cares? Now what? What’s next?" I finally got to this place because I eventually got fed up with myself. I always do. The pressure to be living my best life every single second is gone. In a small way, I gave myself permission - permission to not care, not stress, not fret, and not know the answer right this very second. I’m giving myself permission to say I don’t know. Maybe next month I’ll know, or at least have more perspective on how to find the answer...   For now, admitting I don’t know is all I need to know. It is the answer.