It’s 47 browser tabs. All playing different music at once.
But somehow, it all makes sense to me.

Here’s what the internal monologue actually sounds like:

I opened my laptop to send one email.
Why am I now researching summer camps - acting camp, fencing camp, church camp, AI camp? Am I signing up for too much? But the other option is the kids will stay home. And that’s not an option.

If I don’t write this down immediately it will disappear forever.
Where is a pen.
Why are there no pens in this house.
We have 4,000 pens. Oh here’s that special mechanical pencil I’ve been looking for forever. Shit what did I need to write down?

Where is my phone?
It’s in my back pocket.

I need 12 uninterrupted minutes to solve my entire life.
During these 12 minutes, I have to call AT&T, schedule my hair appointment, oh yes can’t forget botox and the laser appointments, order the cabinet hardware, return the Amazon packages, buy my son’s friend’s birthday present, go grocery shopping, get gas, can I squeeze in a massage?

Did I respond to that email in my head, my dream, or in real life?

I deserve a Haagen-Dazs mini coffee almond toffee crunch for surviving this morning. My diet can start tomorrow, right?

Oh speaking of food. Lunch. It’s 3pm.
I forgot I also eat.

I cannot possibly take on one more thing.
Immediately takes on one more thing. Because I can handle it obvi (ugh why do I do this to myself).

Why is planning for spirit days just as stressful as planning events for work? Neon day? Look like a grandparent day? Wild west? Favorite decade? Twin day? No. No more.

I was just doing something very important.
What was it?

Oh can’t forget to send the meeting invites, but need Comms Team’s greenlight.
Need to also book flight, hotel, car. Reconfirm conference speaking slot.

CEO left ipad on the plane. Ok don’t freak out…
Investor meetings last minute for today? But the day is full of back to back meetings, all of which are, of course, important and hi-pri. Ok no big deal… breathe.

I thrive under pressure.
Creates the pressure.

I need a system.
Spends 45 minutes building a new Notion dashboard instead of doing the task.

I need to learn AI. Let me ask Claude Cowork to help me with something.
Spends next hour prompting and re-prompting and yelling at and apologizing to Claude. I should call her Claudette. Since I call ChatGPT Chad, he’s my homie.

I should be more present.
Brain: Let’s replay that mildly awkward thing from 2014.

Everyone needs something from me.
I also need something from me. Omg look at these white hairs, when’s my next hair appointment?

________________________________

The wild part?

Most working moms with ADHD are high-functioning.

We hit deadlines. Piece of cake.
We show up to meetings prepared. No brainer.
We remember everyone’s snack preferences and dietary restrictions. Easy peasy lemon squeezy.
We manage homes like COO-level operators. I could moonlight as a property manager.

But internally it’s:

“Please do not talk to me while I’m thinking because the thought is fragile and will evaporate.”

It’s loving your career.
It’s loving your partner and your kids.
And also wanting to sit in your car in silence doom scrolling Instagram for 30 minutes before walking inside.
Or hiding in the house somewhere catching up on a Korean drama because I absolutely cannot function and do anything else in that moment (this is where you’ll find me late Friday evenings).

It’s brilliance and exhaustion living in the same body.

And here’s what I’ve learned:

The chaos isn’t a character flaw.
It’s a brain that’s fast. Pattern-seeing. Hyper-creative. High-output.

It just doesn’t always run in a straight line. And that’s ok.

You’re not broken. I’m not broken.

We’re probably just running a very powerful operating system… without a pause button.

And honestly?

We’re still kind of crushing it.

After school in junior high and high school, and even on the weekends, I had to head over there and man the register, peel pounds and pounds of boiled potatoes, scrub and clean sticky, crusty ketchup bottles that never felt clean enough, and refill salt shakers with grains stuck to my hands.

I didn’t understand. Where was my freedom? I was a teen! I wanted to have fun, hang with friends, have sleepovers, talk about boys. I rarely got to watch movies at a movie theater back when that was a cool and fun thing to do with friends. I knew zero pop-culture references (including the ones about Friends!!!). And I basically had the social life of an excel spreadsheet. I was always working (and studying) while everyone was just being a kid.

But you know what? Sometimes, I wish I ran a coffee shop or small restaurant right now where I could have my kids work there a few hours a day. Why? Because the experience at my mom’s restaurant is where I learned the skills no one teaches you in school.

I hated it at the time, but in retrospect, I’m so glad I went through that experience. It built me. So much of who I am now is because of the things I’ve done and experienced in the past, and this was a huge part.

Cleaning ketchup bottles and salt shakers and refilling them seemed tedious and dumb at the time, but the devil is in the details. Everything about the customer experience at a restaurant comes down to the details. Imagine eating your meal, grabbing for the ketchup, the bottle is oily, and there’s old ketchup crust around the rim. You’d lose your appetite. You’d think, if a restaurant can’t keep little things like these clean, what else are they not keeping clean?

Interacting with so many different types of customers (nice, mean, generous, funny) at the register helped me learn about people. It taught me how to anticipate needs, remember names and orders, make people feel seen, and solve problems before they even asked. It also made me realize that everyone is so very different from each other. And even the same person can be different on a day to day basis!

Peeling potatoes taught me about patience and prepping properly before executing. The end result for anything and everything we do requires preparation and setting up the scene and carefully thought out methods.

Plating the food and making it “pretty” helped me learn about presentation. My mom always said people eat with their eyes first, and we must always have red, green, and yellow/orange on the plate to make it look appetizing.

And funny enough, these are all things I still do now as an EA.

When making a salad for Condoleezza Rice for our board meeting, I had to think about colors, variety, presentation, flavor combinations.

When dealing with frustrated or angry executives, I know how to keep my cool and know when to talk, when to stay quiet, and how to read the room. I also know how to listen first, de-escalate, and solve the problem without adding fuel to the fire. The customer is always right, so how do you deal with it and have them leaving happy?

When putting together an event, I know that the little details and preparation are what matter. So depending on the type of event and purpose, I focus on florals, food choices, lighting, colors of linen, types of chairs, ambience, room, views, etc. No one really notices the details when they’re there, they think that’s just how the room came or that’s just how the tables look, but they do notice when they’re not there.

At the time, it felt like I was stuck in a restaurant.

Turns out… I was in training.

Training for reading people.
Training for anticipating needs.
Training for handling chaos with a smile.
Training for a career built entirely on details.

I didn’t know it then, but my first EA job started behind a cash register at the ripe old age of 12… 32 years ago today! :)

ohi!

ok, love the question, and here are my thoughts.

do not try to implement change in your first three months. heck, first six months. no one wants to hear the new EA coming in hot with all these ideas on how to change processes and structures that have been in place. you may absolutely be right in noticing what needs to be fixed. but now is not the time, my friend.

flip the table for some perspective. if you’ve been at a company for a few years, and a new person comes in during their first week telling you why something is broken and how they used to do things or what worked at their old company and why things need to be changed or fixed, you’d be like “umm thanks, but who are you?” right?

the first few months you’re at a company is a time when you need to be studying and observing and learning. you don’t know anyone. you don’t know who your allies are. you don’t know who to trust. you don’t know who’s good at their job. you don’t know how things operate here. you don’t know what the priorities of your executive are. and you don’t know the culture of the company.

take this time to do the tasks that are given to you, and be observant. watch the way people talk to each other in person and on slack. what are qualities they seem to value? what’s the internal company tone? what does your executive’s calendar look like? who and what do they seem to prioritize?

if you take the time to observe and learn, then over time, you will understand what can be fixed, what needs your involvement, and what you don’t need to prioritize. and maybe what you thought needed fixing actually doesn’t need fixing because this company does things differently than your last.

ultimately, no one wants to hear about changes from someone they don’t trust or someone who hasn’t built a good track record for themselves.

so take your time.

now go get shit done,

<3 janet

p.s. i’m starting a new AMA / Dear Janet series. send me your questions if you so choose :) janet@thatexecasstlife.com

p.p.s. thank you for pushing me, j. i hope one day i will be forced to owe you that shirt.

That is too vague and high level of a question to ask. I know a lot of EAs who are looking, but are they looking for someone like you to support or a company like yours to work for?

The right question to ask is “I’m the founder of XYZ company. We are 35 people, series A, based in San Francisco. We work 5 days in office and are now looking for an Executive Assistant who can help us support two founders and potentially manage the office. We are scrappy, culture focused, and hard working, and need someone with ABC qualities. Do you know anyone in your network who is looking for a role like this?” Even better would be if you already have a job description ready. :)

This shows that you’ve thought about this thoroughly, you’ve spent the time to put together a JD, you have a good idea of what type of EA you need and want, and you’re ready to devote time into finding one of the most important hires in your company.

Here are some common misconceptions I see when executives or internal recruiters are hiring for this role:

• They assume all EAs do the same thing - Wow, if only. Every single EA I know is a different EA to their executives. Why? Because their executives are all different. EAs know how to adapt to their execs. Yes, we have overlap in our work, but we focus on different tasks, we have different strengths, different things motivate us, we approach our work differently, our execs ask different things of us.

• They think number of years of experience as an EA equates to whether the EA is good or not - And let me just tell you this is absolutely not true. Hiring an EA is one of the most important decisions you can make. If you hire the wrong one, it’ll be a huge time suck. It will be emotionally and mentally draining trying to push them out. If you hire the right one, your life can be changed. Don’t hire solely based on what the resume says.

• They don’t realize that “fit” is CRUCIAL - Sure, you want to make sure your EA candidates can do the foundational work. You want to vet for intelligence, work ethic, likability. But what’s most important is how they gel with you. You will be talking to them everyday, they will become your closest work friend, you will rely on them and trust them. So you want to make sure they’re a good fit and that you like them. Don’t hire someone who can do the job, but who you don’t really mesh well with. No, no, no.

• They think our job is easy - LOL. In reality, the role requires constant context-switching, good judgment, intuition, constant juggling, empathy, anticipating needs, proactivity, and emotional intelligence while doing all the tasks we’re being asked to do and getting pinged by everyone in the company.

• They think being an EA, a PA, and an Office Manager can and should all be done by one person - also lol

• They think an EA can support 4-6 people - Ugh this kills me every time. “Oh but we’re not that busy, an EA can support all 6 of us” - NO THEY CANNOT! And also, you THINK you’re all not that busy, but combine it all with the context switching, the different personalities, all sorts of tasks, and personal preferences, and there’s no sign of success on the horizon. At this point, the EA is just a machine booking conference rooms, scheduling, rescheduling, canceling meetings, rebooking trips, and barely surviving being thrown in the ocean, and with AI tools now, this is totally not necessary. You don’t need a human EA if you just need them to be a scheduling master and grab you all lunch.

• They’re not clear with the expectations - This is typically because the executives don’t know what they want and need in an EA. They assume the EA will know what to do. Some EAs might, if you’re willing to pay a pretty penny. But most need some sort of guidance.

• They underestimate the importance of the soft skills - Hard skills can be learned. Soft skills are harder to learn. No one puts soft skills on their resume. So interview for these skills. It is so important that an EA have strong soft skills - ability to build relationships, having integrity and good judgment, having high EQ and empathy, being likable, caring deeply about their exec, customer service, etc.

Here’s what to do when looking for an EA:

• Be prepared - If you are prepared to hire for this role, it will show through in interviews. You will attract the type of person you need and want as your EA.

• Have some expectations and share them - Being able to speak confidently about some of the things you’ll want this EA to help you with and work on will also help you find the right type of EA. Obviously, our role is ever changing, but having some sort of structure is helpful.

• Be honest about your culture and your personality - I’m looking for the right match for you as a recruiter. This means the EA needs to be a culture fit but also complement your personality and working style. You know you and your company best, so be honest with your internal recruiter or an external recruiter if you’re working with one so they can help you find the right match.

• Be patient - After you hire an EA, do not expect them to do well on day 1, even if they have a lot of experience. They are learning a brand new company, executive, working style, culture, work, etc. Give them some grace, give them the time to learn, observe, ask questions, grow. When you make new friends, you don’t know everything about them on day 1. It takes time, trial and error, mistakes are made, miscommunication happens, disagreements happen, certain situations and environments create different memories. Have some grace.

• Respect the candidate experience - I introduced a candidate to a role, and she was in this interview process for 6 months. 6 months of stringing a candidate along. That is extreme and unacceptable. If you don’t know what you want, then you’re not ready to hire. If you don’t respect this role and don’t understand the value of this role, you’re not ready to hire. If you string someone along for that long, you’re clearly looking for someone “better”, so do the candidate a favor and just let them go while you continue your search.

All in all, executives can find great EAs if they attract great EAs.

Some of the best executives I know continue to “get lucky” and find incredible EAs who stay on with them for 5+ years. This is not a coincidence. It’s because they understand how much of a powerhouse a great EA can be. They’re willing to devote the time to unofficially train by providing immediate feedback, they have their EA’s back, and they show how much they value their EAs whether it’s through verbal acknowledgment, public praise, monetary gifts, remembering things about them, saying Happy Birthday, listening to their opinions, etc.

I wish all executives good luck in their searches for an EA. I’ve had the pleasure of supporting some incredible executives and working with some amazing executive clients who truly value their EAs and understand how crucial the role is to the company. Treat this role like you would any executive hire (yeah, it’s that important), and you will find a gem who will hopefully stick with you as long as possible and become a huge asset to you and the company.

Godspeed!

“You can kill a tree in seconds but it takes years for the tree to grow.”

(I read this somewhere, but I don’t remember where now -_-)

Whenever I get approached by an Executive Assistant asking me for advice on any sort of question, my answer to them always involves “building relationships”.

“How can I get my executive to trust me?”
“I am drowning, what should I be doing to take things off my plate?”
“I feel more like a task do-er than a partner. How do I shift that dynamic?”
“How do I push back without seeming disrespectful?”
“I have two execs with conflicting priorities. How do I prioritize their asks?”
“How do I get a seat at the table in leadership meetings?”
“How can I develop my own ‘brand’ as an EA?”
“How do I set healthy boundaries?”

The answer to all of these questions and more is “build relationships”.

And this is not everyone’s favorite answer because building relationships takes a lot of time - years even - and usually everyone wants a quick solution.

The best way to look at this is to personalize the situation. Think about your own life and the relationships you have: there are people you trust, people you don’t, people you’d drop everything to help, and people you wouldn’t even text back. Why is that? What about those individuals makes you feel this way about them?

For the people you trust and vouch for, the ones you’d go to bat for, what qualities do they have? How long did it take for that relationship to get there? What made you like them, rely on them, respect them?

Now apply that perspective to your EA/Executive relationship.

Your strongest relationships didn’t happen overnight.
They didn’t happen because you had a scheduled recurring 1:1 on the calendar.
They didn’t happen because every conversation was about work.
They didn’t happen because you forced it.

They happened in the little, unplanned moments - the quick hallway chat before a big meeting, the shared laugh over a travel mishap, the late-night Slack message where you showed empathy instead of just logistics, the team dinner you didn’t want to go to.

Relationship building is the slow accumulation of trust, earned by showing up authentically and consistently over time.

That’s why I don’t believe relationships are built in weekly 1:1s. 1:1s are for alignment. Relationships are for connection. They happen in the in-between spaces: saying hello to the people around you, remembering people’s names and things about them, grabbing lunch, asking thoughtful questions during a project, noticing when someone seems off and checking in, being open enough that your executive (or your teammate) feels safe enough to be open back.

Relationships are the invisible currency of your career.
They’re why someone will vouch for you ten years from now.
They’re why you might get a job you never applied for.
They’re why a former exec or teammate will jump in to help you solve a crisis.

In our world as EAs, being good at the job isn’t just about calendars, decks, or workflows. Those things matter, but they’re transactional. Relationships are transformational.

So how do you actually build relationships?

There’s no one playbook, and I don’t have the perfect answer for you because people connect in different ways, and the best relationships are built when you lean into your own natural style instead of forcing yourself to be someone you’re not.

Some people build rapport over a quick hallway chat or grabbing coffee. Some spark connection through funny slack memes or sending a perfectly timed GIF (it me!). Some thrive in longer in-person conversations, others in thoughtful follow-up notes after a meeting. Some shine during the shared stress of a big project launch, kinda like the “we survived this together” kind of bonding.

What matters isn’t how you connect; it’s that it’s real.

A few things I’ve learned along the way:

Be curious. Ask questions to understand and because you actually care, not just to fill the silence.
Show up consistently. Trust grows when people see you follow through over and over again.
Find shared moments. Humor, stories, even a shared late-night deck deadline - these things create glue.
Meet them where they are. If they’re introverted or prefer slack over coffee chats, go with it.
Chat can be powerful. I’ve built some of my closest work relationships with coworkers solely over gchat back in the day and slack. Throw in some customized emojis, send those gifs, react to people’s comments, be responsive, have fun!
Be human. People can spot performative. Be yourself. Be kind. Be empathetic. Be understanding. Be patient.
And most importantly, do your work well. You can build relationships without ever meeting someone. Your reputation is always in the room, even when you’re not. People notice how you respond, follow through, treat others, and own mistakes.

Relationships aren’t built with grand gestures. They’re built in hundreds of small, genuine interactions over time.

Play The Long Game - starting now

So, if you’re feeling stuck - like you’re “just” a task-doer, or that your exec doesn’t trust you yet or if you’re asking yourself any of the questions at the start of this post - start with building relationships. Play the long game. It’s less about what you say in a 1:1 and more about who you consistently show up as over time.

And don’t just build relationships with your executive. Build relationships with everyone around you.

Grow your tree. Water it. Nurture it. Feed it. You won’t notice the day to day changes, but one day your relationships will blossom.

And not to be dramatic or anything, but remember that it takes years to grow a tree but just a few seconds to kill it. So be mindful of your actions and how you treat others. Would be wasteful to screw it all up because you gossiped with others, associated yourself with the wrong people, treated others badly, didn’t own up to your mistakes or actions, etc. N’ah mean?

One year, on my 30th birthday, I walked into the cafeteria in the morning, and Tilak handed me a bowl of miyeok-guk — Korean seaweed soup.

If you grew up Korean, you know that soup. You eat it on your birthday. It’s a tradition, something a loved one typically makes you. It’s simple but meaningful and def not something you find in a tech startup cafeteria.

He didn’t make a big pot for everyone, and it wasn’t on the menu for the day. He made a single pot just for me, in the middle of his packed morning, prepping for the day’s food, for a company of around 400 people. Because he knew I was Korean. Because he remembered it was my birthday. Because he cared.

And I’ll never forget it.

That moment stuck with me because it wasn’t big or loud. It was personal. Quiet. Intentional. He saw me, and he went out of his way to do something special for me.

That’s the kind of care that can’t be taught in an onboarding doc or at school.

As Executive Assistants, we move fast, but we need to always lead with this kind of care. Our jobs are messy and unpredictable, and no one is handing out gold stars for going above and beyond. In fact, some people might say “you’re doing too much”, “you’re being extra”, “that’s not in your job description”. But the best people in this role (the ones who get brought into rooms early, who get trusted with the real stuff, who won’t get replaced by AI) are the ones who see the people behind the calendar invites and titles, and the ones who remember the little things and act on them.

It’s not about overextending yourself or being a hero. It’s about care and awareness. It’s about quietly choosing to go beyond the job description — not for recognition, but because it’s who you are, you notice it, and you want to.

What Tilak did wasn’t flashy. It was just soup.

But here’s the thing: it’s never just soup. It’s the gesture. The timing. The intention. The thoughtfulness. It’s going above and beyond what’s expected of you, not because someone asked, but because you noticed. Because you cared.

And people notice when you care. They notice when you take the time to remember their birthday, or how they take their coffee, or that they had a hard week and might need a quiet morning. They feel it when you go out of your way to add that extra touch of delight and when you anticipate instead of react.

That level of thoughtfulness, empathy, and emotional intelligence? That’s what sets great EAs apart. It’s what builds trust. It’s what makes people feel safe and supported. Those are things that can’t be automated.

AI can schedule meetings. It can take notes. It can even summarize conversations better than most humans. But what it can’t do is feel what someone needs. It can’t walk into a room and sense the energy shift. It can’t read the subtext, adjust the tone, hold space, or bring the kind of care that makes someone truly feel seen.

That’s the work. That’s the part of this job that isn’t in the job description, but it’s the part that matters most over the long run. And it’s what will separate you from all the other EAs who just do their job.

So yes, I still think about that bowl of seaweed soup. Not because it was extravagant, but because it was human.

And in a world that’s moving faster and becoming more automated by the day, being deeply human in your work is no longer a “nice to have”. It’s the whole point.

If my calendar was packed, my inbox was overflowing, a few different events were in progress, and I was triple-tasking while eating lunch at my desk (spoiler: skipping lunch entirely), I thought this meant I was crushing it. I equated being in constant motion with being a high performer. The more I did, and the more I could handle, the better I must be… right?

Wrong.

The more I did, and the more I could handle, the better equipped I must be to handle a C-level executive, right?

Also wrong.

Over time - and through many hard lessons - I learned that being busy isn't a badge of honor. It's often just a sign that something’s broken. Maybe it’s a lack of delegation. Maybe it’s poor boundaries. Maybe it’s just that I was doing too much of the wrong work.

The better I got at my job, the more intentional my work became. It’s not that I cared less or did less - it’s that I got smarter about where to focus my energy. I learned to say “no” (professionally, of course), and to prioritize the tasks that truly move the needle versus the ones that just fill up time. I also got really good at anticipating my exec’s needs before they even said a word, so my efforts were sharper, faster, and way more impactful.

Here’s the secret no one really tells you: A seasoned EA doesn’t just execute. We observe. We pattern-match. We notice the little things. We anticipate. And that’s where the real magic happens.

Early in my career, I’d jump the second my exec handed me a task. No questions, no hesitation - I was on it. Now? I pause. I give it a beat. Why? Because I’ve learned that nine times out of ten, they’re going to change their mind.

That email draft I just spent 20 minutes perfecting? Useless, because now they want to go in a different direction. The calendar we just finalized? Nope, now they want to meet in person, not virtual, which means we have to buffer in travel time, which means we have to move the other meetings that now conflict. That “urgent” deck? They don’t need it anymore. That flight they said they wanted you to book? It’s going to change.

With experience, you realize that not everything requires instant action or any action at all. Sometimes, the smartest move is to wait. To observe. To anticipate the pivot before it happens. It’s also important to understand the “why’s” so you know how to execute and plan in the future and get into your exec’s mind.

EAs also need to be “on” 24/7, but that doesn’t mean we should be working 24/7. There’s a huge difference. Being available doesn’t mean being busy. It means we’ve set up systems. We’ve planned ahead. We’ve created breathing room, both for our execs and for ourselves.

Our jobs are high-stakes, high-speed, high-pressure. But the goal isn’t to burn out or be in a constant state of motion. Busy doesn’t mean better. The goal is to be effective, strategic, and calm in the chaos. To be the eye of the storm. And that doesn’t happen when you’re running yourself ragged trying to do everything for everyone all the time.

So to the newer EAs out there: I see you. I’ve been you. I used to think supporting 3-4 execs and having a 200-tab Chrome window meant I was killing it. Turns out, the real flex is knowing what not to do. Knowing when to pause, when to wait, when to pivot, when to speak up.

As you grow in this career, you don’t stop working hard - you just stop wasting time and energy. You still show up, stay sharp, and stay on. But now you learn when to act, when to wait, and when to let your exec change their mind before you’ve built the deck, booked the travel, ordered the sushi that they no longer want, and printed agendas or taken meeting notes that no one will read.

Now your time is spent on the things that actually matter. Not performative productivity. Not frantic scrambling. Real work. Thoughtful work. Work that moves the needle.

So yes, you should still work hard. But also work smart. And work with intention.

Master the pause. Own your boundaries (after you’ve built trust). Lead with strategy, not chaos. That’s how you level up. And remember: just because you can do everything, doesn’t mean you should.

And please, no more “quick favors” for people that turn into three hour detours.

Why? Because a lot of EA work is incredibly task-heavy: calendars, travel, emails, expenses, reminders, meeting notes, follow-ups. That’s exactly the kind of stuff AI loves. And it’s getting really, really good at it. Fast.

So yes, if your role is built entirely on scheduling meetings and booking travel, you should be paying attention. Because AI can (and soon will) do that faster, cheaper, and with fewer errors.

But here’s the thing: great EAs were never just doing that anyway.

The Executive Assistants who will not only survive this shift, but actually thrive in it, are the ones who bring something AI can’t touch (for now…):

• Intuition and critical thinking

• Emotional intelligence and empathy

• Strategic insight

• Political savvy and navigation within the office

• Genuine care for people

These EAs are the ones who anticipate what their exec needs before it’s asked. They are the ones who manage up, manage sideways, and often times manage the entire company’s energy. They can read the room, and they can read people’s body language and eye twitches and facial expressions. They can build relationships. They can handle the drama and tactfully deal with office politics. And they can catch the things that don’t live in an inbox.

AI can do logistics. But it can’t do judgment. It can automate a task. But it can’t build trust. It can make quick decisions. But it can’t be strategic.

So yeah, AI is going to force a shift in our industry soon… and honestly? It’s about time. Because this job has always been about more than being an EA. It’s about being a strategic partner, a stabilizing force, and a behind-the-scenes operator who makes the chaos somehow work.

EAs who are willing to evolve - who embrace AI as a tool, not a threat - are going to be incredibly powerful in the years to come. But that’s only half the equation.

Because even if you do learn how to use AI, it won’t matter if you haven’t mastered the human elements of this role.

• The ability to build trust

• To read a room

• To understand when to speak up and when to just know

• To move with grace, empathy, and emotional intelligence - even in chaos

AI can help you be faster. More efficient. Maybe even sharper. But it will never replace your ability to truly take care of people.

If you want to stay relevant in this new era, you have to bring both:

• Tech fluency and human fluency

You have to be someone who can run a company’s calendar and its emotional weather.

Because in the end, executives won’t remember who booked the flight fastest. They’ll remember who had their back.

But there is one constant.

The universal human desire to be taken care of.

If you lead with that, everything else about your job becomes a little clearer. Most EAs can figure out a calendar. Plenty can book international travel or plan a polished offsite. But not everyone wants to take care of their executive. Not everyone knows how to either. And not everyone sees that as the heart of the role.

It’s funny because you’ll never see “take care of your executive” on a job description. It doesn’t quite fit under “core responsibilities” even though that’s like the most important responsibility. To me, it’s the difference between a good EA and a great one.

Over the past decade, I’ve interviewed hundreds of EAs - probably around 170 in the last seven months alone. The ones who stand out? They all lead with care. It’s in their tone, their language, the way they speak about their work, the way they describe their relationship with their past and current executives.

They aren’t just looking for a job - they’re looking to make someone’s life run better, smoother, easier, they’re looking to take things off of their exec’s plate, and they’re looking to learn how to adapt to their exec in order to be the best EA for them.

When you approach your work with the intention to care, everything shifts. You begin to think differently. You take initiative, remove friction, and look around corners. You want to make sure your executive is prepped for their meeting, has something to eat between calls, and feels supported before a big company announcement.

You learn to calendar in a way that mirrors your exec’s energy, not just their availability. You learn how to protect their time and know how to push back on folks. You draft emails and manage inboxes with their voice in mind. You grab coffee because you know they need it. You make sure no meetings go past a certain time so they make it to their kid’s soccer game. You do your very best to learn your executive.

It’s not about being nice. It’s about being intentional, working with purpose, being strategic.

These aren’t just tasks. They’re care in action. You can only do these things well if you care and know how to observe and pay attention.

I started reading Unreasonable Hospitality by Will Guidara, and while I haven’t finished it yet, the ideas resonate deeply in our EA world. Guidara talks about creating extraordinary experiences by going above and beyond - being “unreasonably” generous with your time, energy, and thoughtfulness. That mindset? It’s exactly what separates standout EAs from the rest.

Ask any EA who loves what they do, and they’ll tell you: they care. Deeply. About their executive, their team, the company, the work. And this care translates into making people feel taken care of.

Ask any executive who has had an incredible EA, and they’ll tell you their EA took care of them and the team, was on top of everything, and was responsible, reliable, trustworthy, adaptable, and proactive.

One thing I know for sure is that more so than it being about the work you do, it’s how you make people feel and how you make them feel taken care of. But also, you can’t do a bad job if you start out with a mindset of taking care of people. I feel like it would be a contradiction, no? Like how would you even let yourself do a bad job if you cared about taking care of those around you?

On the flip side, if you care only about yourself and your growth, it will show. You may end up focusing on the wrong things, potentially burning bridges, making bad executive decisions, not understanding your executive. Of course, you do have to care about you and your well being, I’m not saying don’t focus on you. But only focusing on you is what can lead to a negative outcome, if not in the near-term, then definitely in the long-term.

When you can make your executive and team feel taken care of, that reputation is what’s long lasting. That is what makes way for more opportunities. That is what people remember you for even after you part ways. That is where all the positive backchannels about you will come from. That is what gives you your bonuses and raises and promotions.

So wherever you are, whoever you support, always remember that people have a natural human desire to want to be taken care of. It may be to varying degrees (I know some execs are a hard nut to crack), but deep down inside, I think we all have that want in us.

Lead with that mindset, act accordingly, and everything else will follow.

I enjoyed all the different rotations they put me on, but there was one that my shift lead refused to assign me - the barista line. Why? Because I couldn’t make coffee. Well, actually, scratch that. I couldn’t make foam.

(Did you know there’s an actual technique to making the perfect foam? If you know, you know.)

Anyway, I’m not here to talk about foam or my inability to perfect it :)

I’m here to talk about how there are way too many ways to make and enjoy coffee. Like, okay, there’s your regular black Coffee and Café au Lait (coffee w/ milk). Makes sense. An Americano? Fine. A Latte? Great. Cappuccino? I get it (even though I could never make one properly for the life of me). But now we’ve got Einspanner? Flat White? Cortado? Lungo? Dalgona? Ristretto? Red Eye? Cold Brew? Nitro? Breve? Con Panna? Vienna? Romano? Sparkling Espresso? Affogato? Macchiato? Doppio?! Does the list ever end?

I saw a coffee shop menu today that had a bunch of these, and I laughed. It reminded me of all the different types of executives I’ve supported over the years.

At Dropbox, I had the privilege of supporting over 45 executives. I covered maternity leaves, emergency leaves, and new VP/C-suite coverage over the course of seven years. I built a lot of relationships. And let me tell you… it blew my mind how wildly different every exec was.

Just when I thought I had seen it all and figured out how to work with different personalities, someone new would come along and completely surprise me. After about seven execs, I realized the best way to approach the next executive I’d be in charge of supporting was to throw out everything I thought I knew and start fresh.

Just like this coffee menu...

• Some execs are like classic Coffees, Americanos, and Lattes - what you see is what you get. Straightforward. No surprises.

• Some are like Cold Brew and Nitro - not my favorite, but I’ll make it work, and I’ll absolutely still give them my best.

• Some are like Affogato and Sparkling Espresso (or in Korea, they have Peach Iced Tea w/ an Add Shot, sooooo good!!) - fun, quirky, exciting, but sometimes too much fun can be distracting and take you off track.

• Some are like an Einspanner - fascinating, intriguing, and makes you go, WTF is this? But you learn a ton from working with them.

• Some are like the Red Eye - high energy, keeps you on your toes 24/7, but for some reason, it’s kind of fun, and you’re up for the challenge.

• Some are like a Dalgona - a little too sweet, but it’s a nice change of pace. The warmth and care and gratitude is kinda nice.

• And then there are the high maintenance ones - think Romano (coffee with lemon, delicious or nah??) or what I imagine Con Panna and Vienna to be like. But their high maintenance is somehow endearing, and you’re ok rolling with it because you like them as people.

If you’re an Executive Assistant, I highly encourage you to support different executives throughout your career, whether it’s long-term or interim support (don’t job hop, that’s not what I’m saying). Volunteer to help out when and if you have the bandwidth. The things you’ll learn, the relationships you’ll build, and the skills you’ll develop will be invaluable and only continue to help you as you grow.

I’ve been fortunate to have enjoyed supporting every executive I’ve ever worked with - yes, even the Cold Brews and Nitros. They all taught me something of value. No two were ever alike, and each one, in their own way, made me a better EA. Even if they didn’t realize it.

Recently, I came across a reel from a Division 1 coach sharing her secret to recruiting top-tier athletes. Her approach, I realized, is exactly how executives should think about recruiting their EAs—and it’s also a perspective every EA should keep in mind, since we are the athlete in this scenario.

Here’s the gist: when scouting highly ranked athletes, she doesn’t just watch how they play—if they’re ranked, their skills are already proven. Instead, she focuses on who they are as individuals. She observes where they sit on the bench, how they interact with their coach, whether they cheer for their teammates, how seriously they take warm-ups, and how they treat their family after the game.

If you’re an Executive or EA hiring manager, don’t forget to ask questions that will help you learn more about who the candidate is as a person and how they’ll connect with you, your team, and your company. Also, backchannel where you can—ask your network about them so you can learn more. You’d be surprised at how connected we all are.

Ask thoughtful questions to uncover their character and mindset, and think about some of these things as you’re interviewing:

• Are they someone you’ll genuinely enjoy working with? Are they someone who could be well liked?

• Can they represent you, your values, and your company effectively? Do you trust them to?

• How will they treat the team? How will they show up for their team?

• What do they value as an EA, and why have they chosen this career?

If you’re an Executive Assistant reading this, keep these pointers in mind:

• The world is small. Someone knows someone who knows you or has worked with you. If backchanneling is done on you, will people or past co-workers have good things to say about you?

• Be kind. Treat everyone well, not just the people above you or the people you think will benefit you.

• Everyone is watching. Your work ethic, personality, character, work output, and how you treat others are being noticed by more people than you realize.

• Your reputation is everything. How you make people feel, and what you do and say will either build or tarnish your reputation. And your reputation follows you.

• Act with integrity. Do the right thing, even when no one is watching.

Like the D1 coach in the reel, people are paying attention to more than just your skills and your ability to do the job. They’re observing how you show up in every situation.

A D1 athlete is the best of the best. They have exceptional talent and incredible work ethic. They are resilient, can handle pressure, and have high expectations for themselves. They understand the importance of supporting their teammates on and off the field. They are coachable, take feedback seriously, and always strive to improve. They know how to stay disciplined and manage their time. And they serve as leaders who have influence and set the tone for their team. All while being extremely good at their sport.

These are also the qualities that make exceptional EA candidates stand out from the rest of the crowd.

Are you a D1 Executive Assistant?

If the shape of my nails were off or I wanted my nails shorter, I would think, “should I tell them, should I not”, and by the time I mustered the courage to say something, it was too late to even bring it up because the time had passed. I would end up telling myself “it’s fine, I’ll fix it when I get home”.

Last week, I took my 9-year-old daughter for a mommy-daughter nail date. And despite my own inability to speak up at a nail salon, every time we walk into one, I emphasize how important it is that she learn to speak up for herself if her nails are not to her liking.

I sat in the massage chair, while my daughter sat across the way at the manicure table. I watched her chat with the manicurist, even making her laugh (thank goodness she didn’t inherit my social anxiety gene). When she was done, she came to me and showed me her nails and told me that she spoke up and asked the manicurist to change the color and adjust the placement of the stickers because they weren’t to her liking.

As a mom, I was so proud, and then it made me reflect on my own struggles.

Voicing my opinion growing up was considered “talking back”. I would get scolded for it at home. I also remember speaking up in class and feeling stupid or embarrassed because people with stronger opinions would disagree or I wouldn’t know how to back my opinions if questioned.

Eventually, any thoughts and opinions I had were locked in a box and stored away. It allowed me to just put my head down and stay quiet. I learned not to bother others, not to be rude, and not to be an inconvenience. And the only way I felt I could truly show my value was by studying hard, getting straight A’s and a higher than 4.0 GPA, executing really well, and keeping to myself.

It makes sense why I was a very good Administrative Assistant and Office Manager early on. Those roles require hustle, hard work, and execution… and not necessarily my opinions.

Early on in my career, I was an excellent do-er - an executive or team member would ask me to get something done, and I would do it (of course within reason). I still execute very well today and do many of the things execs and teammates ask of me, but now I speak up, I set boundaries, I let someone know if I don’t think the task is a good use of my time, and I say no if I don’t have time (or don’t want to do it). :)

But back then, I didn’t speak up if I was burning out. I didn’t tell my manager that 5 executives was too many. I never told anyone I needed help. I never gave my opinion about work related requests and tasks. I felt it was my job to put my head down and work harder than anyone else, pushing my own feelings and thoughts and opinions aside.

It wasn’t until I supported this one executive who had a habit of asking me for my thoughts, which made me very uncomfortable at the start. I distinctly remember one conversation (during a time when back to back meetings were unfortunately the norm and he was probably burning out) where he said “You know my calendar better than anyone in this company, what should I change about it? It’s not sustainable.”

I realized, at some point, I had worked hard enough and proven my worth enough to become someone he valued and someone he recognized as being really good at their job. I really was the only person in the company who knew his calendar best. So he was genuinely asking me for my thoughts - whether it was about meeting cadences, whom to meet with, what conferences, events or dinners he should attend, etc.

Learning to voice my opinions and share my thoughts taught me how to handle rejection and push back, how to be tactful, and how to be concise. It taught me that sometimes I was right and sometimes I was wrong, but it wasn’t always about being right and wrong. Sometimes, people just wanted to hear other people’s thoughts to make better decisions.

It also taught me to play devil’s advocate, see things from different sides, and empathize. And it also taught me to start asking other people for their thoughts.

But I also had to work really hard to get to that point. No one will ask you for your opinion if you don’t add value in some way.

I am forever grateful to him, for pushing me out of my comfort zone, for showing me that I actually had something to offer other than hard work, and for teaching me that if you become really great at what you do, your opinions will be valued and considered (even if not always right). This was the beginning of me becoming a much more efficient EA for him and everyone thereafter.

Thank you DW :)

“Your character and your reputation are things you can build, which will let you take advantage of opportunities other people may characterize as lucky, but you know it wasn’t luck.”

Naval Ravikant

My husband is a top-producing mortgage loan originator, and every now and then, people will comment to others that he became an “overnight success”. We’ll chuckle at this because what they think is “overnight” is actually 15+ years in the making. It’s been a journey filled with hard work, late nights, calls and emails during weekends and vacations, learning from mistakes, and building and nurturing valuable relationships.

This is the reality for most people who seem like "overnight successes." The truth is, success doesn’t happen overnight. It’s built from years of training, dedication, and hustle, often beginning with our very first jobs in high school or college. Every decision you make, every path you follow, the people you connect with, and the mindset you cultivate all contribute to your growth and eventual success.

This is equally true for Executive Assistants. What you do in the early stages of your career will matter significantly later on.

So here’s my take on how you, too, can become an “overnight success”, especially if you’re just starting out in this role. :)

• Work hard even when no one is watching

  • Hard working people stand out. Even when you walk into a coffee shop, it’s easy to spot those who genuinely enjoy their work and take pride in serving others. Never underestimate the impact your hard work can have on others. You never know, someone might be looking to hire someone like you. That’s how I got my job at Nihon Whiskey Lounge and then at Dropbox.

  • Your hard work will also be something that people remember later on. When you’re interviewing somewhere, and the executive is doing some backchannel references on you, you want those people to say positive things about you. So work hard even when no one is watching, because people are always watching.

• Remember your actions speak loudly

  • You’ve probably heard the saying that you can tell a lot about someone by how they treat restaurant staff. At Dropbox, we applied a similar philosophy to our interview process: the interview began the moment candidates entered the building and interacted with the front desk. This helped us understand how they treated people who weren’t an obvious part of the interview panel.

  • Also, as Executive Assistants, we are the face of our executive and the company. Every interaction counts. How we stay calm under pressure, manage chaos, treat others, balance firmness and kindness, and make people feel heard and respected - all of this leaves an impression. Be mindful of your actions because they speak volumes.

• The relationships you build now will matter later

  • So many of my past relationships have proven invaluable in my career.

  • The reason I was able to start my consulting business after Dropbox was because of all the relationships I built over the 7 years I was there. Many of the people I directly worked for went on to start their own companies or became C-level executives at larger organizations. I like to believe that if I didn’t work hard for them or learn to be adaptable or make an impact, they wouldn’t have reached out to me for help.

  • Even the relationships I’ve built with catering companies, event stylists, event vendors, swag companies, have all come in handy over time. Because of the relationships I built with them over the last 15 years when we were all younger and starting out in our separate careers, I’m able to pull last minute favors and we know how to work really well with each other.

• Have the right mindset and mentality about your work

  • I talk to EAs all the time whether it’s through interviewing or at networking events or just catch ups with people who reach out. And surprisingly, there are a lot of EAs who want the benefits and salary of supporting someone with a C-level title, but don’t want to put in the work or years or time.

  • If you have the mentality of “that’s not in my job description” or “I don’t want to work past 5pm”, that’s fine, I mean to each his own I guess. But that will stunt your growth as an EA. People will notice. When backchannelling is done on you, that will be mentioned. So remember that what you do now and how you act now and how you treat people now will matter a lot later whether you like it or not.

• Don’t try to rush things

  • “Good things take time, better things take a little longer.”

  • So is the case as an Executive Assistant. Don’t expect to become great at your job as an EA immediately. Even for someone who has 15+ years of experience in this industry, for every new executive I support, I have to take 6-12 months to really get to know them. Growth takes time. Building trust takes time. Getting good at your job takes time. Being impactful to a new executive and team takes time.

  • Don’t be in such a rush to get better. Your day to day experiences will get you there. Your mentality and attitude will help you learn. The mistakes you make will make you better. And the time and effort and care you put into the role, the executive, and the company, will help make you a great EA.

• Don’t discount the experiences from your jobs early on

  • So much of what I’ve learned or who I’ve become can be attributed to the things I learned while starting to work at the age of 12 at my mom’s restaurant. While I hated the fact that I had to clean ketchup bottles, refill salt and pepper shakers, refill napkins, peel potatoes, and do dishes, it’s those very same tasks that have made me more aware and observant in my career.

  • Just like with our day to day work as EAs, no one ever really notices if things are going very well, but everyone notices when things aren’t going well. No one notices if the ketchup bottles are nice and clean and salt and pepper are regularly filled. But if they’re dirty or empty, boy will you get complaints.

  • Everything you learn from any job you have, is something that will help you later on in life. So wherever you are working now, think of that experience as a positive one that you can learn from.

And ten years down the road (yes ten years sounds like a long time, but it will go by fast), you’ll look back on your journey and remember how different you are now than you were on day 1 as an EA.

You will have life experience and work experience. You will have relationships both in and out of work that will help you. You will be the EA that junior EAs come to for advice and mentorship because they see what you’ve gone through and how you are now.

People might look at you and think “Wow, they were lucky they got in at the right company at the right time!” or “They’re lucky they supported great executives.”

But you’ll know it wasn’t luck, it wasn’t being at the right place at the right time, and it wasn’t that your executives were all magically great bosses. It’s everything that you did that got you to where you are. All the hard work, the mentality shifts, the late nights, the care/empathy/high EQ, the lessons you learned from the mistakes you made, the relationships you built, your character, your willingness to adapt - those are what will set you apart.

Those are what will make you an “overnight success”.

There is no skill called “business.”

Avoid business magazines and business classes. Study microeconomics, game theory, psychology, persuasion, ethics, mathematics, and computers.

- Naval Ravikant

This concept, in relation to our work, is something that I try to relay to Executive Assistants almost every chance I get.

The path to becoming an EA is not a straight, obvious path. There are no two EAs who have had the exact same experience or trajectory. And that’s because we support human beings, and every single human being on earth is different.

Sure, the concept of what we all do is similar. We schedule and calendar, email with others, book travel, do expenses, plan events, deal with board meetings, etc. But beyond that, the experiences we have and everything else we do for our executives are deeply personal and therefore unique.

Because of this, the best way to grow in your role as an EA is simply by doing the job. And by putting in the years. You’re not going to become a rockstar EA overnight, or through certifications and formal trainings, or going to school for it. The only way to really level up is to do the job.

By doing the job, you learn how to build relationships, become adaptable, gain and earn trust from others, become quicker in your problem solving abilities, and make better executive decisions.

By doing the job, you get better at observing and listening to patterns and behaviors. You start to understand human behavior, you can read your executive’s body language, you know how to provide enough context or prep your executive where it matters, and you learn about human psychology by watching the interactions of everyone around you.

By doing the job, you’ll inevitably make mistakes, but be thankful for them. Mistakes are what help you get better at what you do and help you understand yourself better. By making mistakes, you (hopefully) learn from them, you do your best not to make them again, you start to understand why your executive wants things done a particular way, you know what to expect, and you become great at anticipating needs and being proactive.

By doing the job, you also feel all the emotions. Anger, frustration, pride, embarrassment - it’s all part of the job. You’ll reflect on what you could’ve done differently, feel great about the wins, and laugh at how petty you can get (not proud of it, but I’ve been there!). Through it all, you’ll learn more about yourself - what pushes your buttons, what you’re capable of, and how to handle situations with grace.

There is no skill called “Executive Assistance”.

Avoid spending time and money getting certifications and trainings. Or at least don’t put them at the forefront of your priorities.

No amount of hours studying or taking courses that imply that they can teach you “how to be a great Executive Assistant” will make you a great EA.

Instead (and on top of simply doing the job)…

…Read books (fun NYT bestseller books) about human psychology, organizational psychology (Adam Grant is awesome), human behavior, negotiation, stoicism (Ryan Holiday makes this easy to understand), self-awareness, and communication. You are in the people business, so take time to learn about people.

…Watch and study the people around you - how they operate, what gets them energized, what makes them tick, how they interact with others. What’s the difference between people you want to be like and people you don’t? Why do you trust some people or rely on some folks, but not others? Why does someone have a great reputation, but not others?

…And most importantly, look inward. Learn your limits, your bandwidth, how to say no, and how to let things go. Learn what motivates you, what rubs you the wrong way, what pushes you to do well. Learn about the environment that you thrive in and the one that drains your soul. And figure out how to get what you need to do your job well. You’ll only be able to learn these things if you are in the thick of the role.

Everyday is a learning opportunity. Become more self-aware. Exercise empathy. And watch how far basic values like kindness, trustworthiness, and hard work can take you.

The next time you ask yourself “how can I grow in this role?” remember that it takes a lot more than taking courses and getting certifications. Our role is unique. You can’t be taught how to be an EA. You have to be an EA.

Understanding this and how it can and should affect the way you work could be the difference in your ability to grow and be a great or mediocre EA.

I have an EA friend, Shelley Trask, who told a story once about how she was helping her executive prepare for their company’s conference. He was scheduled to be demoing their product soon in front of a live audience, but the product went down! She was running up and down the aisles, making phone calls to people who could help bring their product back up. And amidst the chaos, another EA stopped her, and said “Shelley… don’t run”. She reminded her that her running was making people anxious.

I also heard another story from Chynna Clayton at the most recent eaRISE conference I was at. She was the Special Assistant to the First Lady Michelle Obama. She emphasized how important it was to watch, observe, listen, and learn, and also carry yourself with a presence that represents your executive well. She shared several fun stories where things went wrong in the White House, all of them last minute of course, and she had to handle them with grace and composure because she knew everyone around her was watching her.

Even in our day to day life, if you are a parent, and your child falls and gets hurt, typically depending on how you react, that’s how your child will react. Or when you’re on a plane and there’s bad turbulence, as long as the flight attendants seem to be calm and collected, it keeps your omg-I’m-freaking-the-f-out-right-now emotions at bay.

I remember early on in my career (in hospitality, but also as an EA), all I knew how to do was walk extremely fast, be short and quick on email and chat responses, and freak out. Things always went wrong. We were always busy. So the obvious thing for me to do, and let’s be real, the only thing I actually knew how to do in these situations, was panic lol :)

And naturally, because of the executives I supported, people associated my behavior with what was happening with my executive and in the company. They would look at my calendar to search for clues. They would watch how I operated. They would be curious as to why I was frantically walking to and from one place to another. They would pick up on my nervousness.

I eventually even had to cancel all my 1:1s because I didn’t want to get caught revealing any sort of emotion or reaction on my face when people would ask me questions. Sometimes, as EAs, we know things months before the rest of the company finds out. I’d be damned if a slight facial twitch revealed to others that I knew some shit was about to go down.

I remember needing to be careful of how I said things because they could easily be misinterpreted. I also had to be mindful of what I wrote on chat and email, as well, and I had to be conscious of what I put on my calendar.

Our quick-to-react actions and emotions during chaos is a sign of lacking experience - this is not a bad thing, just a tenure thing. This is why someone who has been an EA for one year will react much differently than someone who has been an EA for ten years.

More experienced EAs have already been put through the ringer :) We have more years under our belt, we’ve been there done that, we’ve seen so many things go wrong that nothing phases us anymore, and we can now solve problems with our eyes closed.

We also know that things work out in the end, or it’s not really AS big of a deal as we thought it was, or that sometimes laughing about the situation is better than panicking. And we also know how to take a breather. I should add that we also have resources, a network, and people we know we can go to who can help us (this is why building relationships is so important).

Eventually, knowing how to solve problems, responding and reacting with kindness, and walking gracefully, with class, amongst the chaos and the fires that surround you becomes second nature.

Know the role you play as an Executive Assistant whether you work at a small company or a large one. Know that even when it doesn’t seem like it because you’re just a mere employee in a sea of 3,000+ people, everyone is watching you because of your role and because of who you support.

They see what you do, they watch how you act, they interpret what you write, and they judge you and your executive and the company based on all that.

Represent yourself and your executive well.

“Wisdom is knowing the long-term consequences of your actions.”

I got out of my comfort zone the other day and went to dinner with 4 people I didn’t know, but who all knew each other. I was invited by one of them, but even her, I only met irl once, so I didn’t really know her well.

This was a big deal for me because I never go out, let alone with people I don’t know.

But that’s beside the point. Story about my social anxiety and ADHD for another day :)

This dinner was very interesting because it turns out, the number of people I had in common with each of them (found out through checking social media, of course) was surprising. I even went to UCLA with one of them during the same years, and we found out, she was my close friend’s roommate for a little while. I was literally two degrees of separation away from each of the 4 “strangers” I had dinner with.

I cannot count the number of times in my life (like at this dinner) where I’ve said to myself “wow, what a small fucking world”. Like thank goodness I was nice to someone or thank goodness I helped this person or thank goodness I worked hard at XYZ company.

One time I helped someone at work who was in a bind, someone I did not support and who wasn’t even my executive’s direct report or on their team. Long story short, they later left the company, started their own company, and asked me to be their EA.

Another time, I worked with a vendor who was just starting to build out his business. I took a chance on him even though he was new because I saw his passion and drive, and I knew the product would be good. 10 years later, his business became huge, and when I needed a last minute vendor for a holiday party because I had someone back out, he came to my rescue and hooked it up because he remembered how I took a chance on him 10 years back (his words, not mine).

Or sorry one more story - essentially a story of how I became an EA. I worked at Nihon Whiskey Lounge in San Francisco, and I got to know so many of my regular customers pretty well. When I applied to interview at Dropbox, I mentioned this to one of my customers, and he happened to be the best friend (from childhood) of the executive I would be supporting. He put in a good word for me because he knew I worked hard, and he was willing to vouch for me.

It’s important to remember that how you behave/act/work/talk/treat others/etc. will affect what people think of you and what they remember you for, even years and decades later. It’s also important to note that people are always watching and noticing what you do, too.

People also tend to remember how you make them feel. They will remember when you helped them when they needed help. They will remember when you were kind. They will remember your work ethic and your drive. And they will remember when you had their back.

It may not seem like it matters now in the moment, but you will reap the benefits from it in the future (or it will work against you if you don’t understand or you disagree about why it matters now, which I’ve also seen happen with other people). Like the quote at the beginning of this post says, “wisdom is knowing the long-term consequences of your actions”.

I’ve found that even as an Executive Assistant, this holds very true. It’s not about networking and getting to know as many people as you can, because that’s all about one’s ability to talk. You can be a great talker and know 100 people, but if your work doesn’t speak highly of you, it doesn’t matter that you know all those people. It’s about letting your actions speak louder than your words.

How hard working you are, how much you help others, how much value you add to your executive, how well you work with other EAs, how trustworthy you are, all of that will matter even 10+ years from now.

It’s what will help you get a job in the future, what will make it easy to schedule a difficult meeting, what will determine whether a vendor will bend over backwards for you or not, and what will make an executive or other EAs and past coworkers give glowing backchannel references about you.

As an EA, it’s important to build positive relationships with not only your executive, but the people around you. And even if you’re not actively building a relationship (because we certainly can’t build relationships with everyone we work with), it’s important to build your reputation. Your reputation, assuming it is a positive one, will speak for itself and is what will help you move forward in life.

The EA world in general is small. Be kind to other EAs. Help each other out. Make things (like scheduling and communicating) easier for each other. Be empathetic. Put yourself in each other’s shoes. And if you have a big EA team, represent and lead your EA team well, especially if you support the CEO.

You’ve worked with EAs in the past who you appreciate and will do favors for, and you’ve worked with EAs who make you roll your eyes or who you’d never provide a good backchannel reference for.

We need to work hard not to be the latter.

Anyway, then a few moments later, she says “I needed WiFi so I’m working from Chanel this morning”. And this made me chuckle. (Also, look at how cute this Chanel store in the Hamptons looks… so demure… is that how I’m supposed to use that word? ugh TikTok)

How often do we, Executive Assistants, find ourselves doing what we can, wherever we are, to make sure we’re able to log online and get shit done?

I wonder if our executives even know that. I wonder if they know what we do behind the scenes to make things appear so seamless, to make ourselves seem so responsive, and how much we stress when we don’t have wifi connection.

Do they know that we pull over on the street or get off the freeway so we could respond to their text right away? Do they know we take our eyes off our kids competing in a soccer game while we respond to their email? Do they know we burned dinner because we got distracted by an urgent question they sent us on Slack at 7pm?

I mean, don’t get me wrong, none of my executives have ever expected me to be responsive at all hours of the day everyday with no breaks. So I’m not mad that they (or anyone else who has never been an EA) don’t know what we do to make their lives easier.

It’s clear that the problem is me :)

I want to be responsive. This is my job after all, I am grateful for it, I enjoy my work, I want to be available and reliable, and I want to stay on top of it. I also want to show them what I am capable of and to prove that they made a good decision in hiring me (holy mother of goodness, this childhood trauma thing keeps popping up in all my writing lol).

Anyway, I don’t know what the point of me bringing this up was. I just thought it was so typical and funny of my EA friend, and EAs in general, to say she was working from Chanel in the Hamptons because that was the only place she could get good wifi, and she needed to work at that moment. When someone says they’re at Chanel, you’re not picturing an EA with her laptop, hunched over, borrowing wifi, typing away, trying to work.

We really do do whatever we can to get shit done, don’t we? Finding wifi so we can work is just the tip of the iceberg. The rest of the iceberg is loaded with innumerable stories that will blow people’s minds when they hear them.

Like has your executive ever flown from San Francisco to New York to spend a few days for work, and then planned on leaving for London from New York for a slew of business and customer meetings, only to realize, very late the night before they were supposed to leave for an evening flight to London, that they had forgotten their passport?

And then did you have to drive an hour to their house in SF at 5am, let yourself in because you know the code obviously, search for this passport that was in a nightstand drawer in their room where their brother happened to be sleeping because he was house sitting, and quietly without waking him, grab the passport and secretly leave the house like you’re some sort of stealth ninja thief in the night sky leaving no traces behind?

And then, did you have to drive to the San Francisco Airport, get to the United desk so you could purchase whatever flight left for New York the soonest (this was before it was very easy to purchase flights online) so that you could get on it yourself with his passport and hand deliver it to him upon landing in New York? And then plan to fly back on the next available flight?

Yes, it would have been an absolutely ridiculous story if I ended up on that plane. Actually, it’s still a pretty memorable story for me. I was ready and prepped to get on that first flight out, but lucky for me, the United attendant at the desk let me know (after I vented about my predicament) that they actually had a courier plane that could take the passport with them and deliver it to the United desk at JFK within a couple hours of landing.

I filled out all the forms and crossed my fingers and prayed to God that all would go well. And long story short, it did. My exec got to go to London on his 8pm flight that evening. And I went to the office before it even hit 8am.

Our execs (and again, anyone who has never been an EA) will never know the hoops we jump through or the things we are willing to do in order to make their lives easier. But that’s ok. We don’t need to tell the world about it. It’s just what we do. It’s what makes us good at what we do. It’s what separates us from the rest of the company. It’s why they trust us and rely on us.

Hopefully, they feel it and see it and appreciate it. I do think they may not always see or know the details, but deep down they know we take care of them and do what we can to help make them successful.

If you’re an executive reading this, remember that when things are going very smoothly, the event is going off without a hitch, everyone with their 20,000 dietary restrictions is happy with the food and drink options, your calendar looks fabulous, everyone comes to your meetings prepared, you’re able to make it to your kids’ sports games, etc. it’s because a ton of work, thought, collaboration, creative problem solving, and favor pulling went into it in the background. It’s never just smooth by accident.

Aaaanddd… if you’re an EA reading this, I see you :) Go on with your bad self!

Back in the day, this cost $2.95. Then it went up to $3.25. Then $3.95. And then suddenly in the last few months, I noticed it’s at $4.95. A $1 increase in what I feel like was less than a year.

The coffee was delicious at $2.95. I enjoyed it thoroughly everyday, and the Starbucks workers knew me :)

At $3.25 it was fine. At $3.95 it was annoying but bearable.

At $4.95, the coffee, though it was the same exact coffee, suddenly tasted like shit.

I just couldn’t get myself to pay the nearly $5 for my Starbucks coffee everyday anymore because it wasn’t even a special coffee - they didn’t do anything to change it.

It’s not really about the money though. It’s about what I’m getting for the money. If it was an Iced Small Tesora Black Coffee from Philz, I will gladly pay the $5 it costs because what I’m getting for that $5 is high quality and pretty damn good tasting coffee.

My Starbucks coffee no longer added value. And it was no longer worth the cost.

And it made me wonder if that’s how our roles as Executive Assistants are looked at sometimes. There’s a certain expectation executives have depending on what you’re getting paid. Heck even I have that expectation when I’m interviewing EAs. If you’re asking for $175k a year, you better be damn good.

I talk to a lot of EAs, and I always wondered why the discrepancy in salary was so enormous. I’ve spoken to EAs who get paid $22K a year all the way to $275K a year. What differentiates them to warrant such a huge difference in pay?

I think it’s how much value these individuals add.

If you’re starting out at a lower salary, your EA role is probably a more junior role. Not much experience is needed, the tasks could be pretty menial, and the people you support just need someone who can “do” the things they ask.

I was in this position getting paid $45K at my first job as an Admin Assistant / Office Manager. And it was a job where I could easily be replaced at any moment.

With hard work, time, strategic thinking, learning to watch and observe patterns and behaviors, making mistakes and learning from them, and being thrown into the deep waters of the ocean and having no choice but to survive, I eventually rose up the salary ranks.

Over time, and unlike the Starbucks coffee which tastes the same whether it’s $2.95 or $4.95, I grew and became a better EA. I learned to read cues, body language, emails, tone of voice, behaviors, relationships, etc. I strengthened my people skills, learned to be more strategic, built trust, and made better executive decisions. I also built a reputation, I worked hard, I learned to anticipate needs and be proactive. I knew how to quickly put out fires, I could problem solve instantly, and I always wanted to be helpful and never disappoint anyone (Yes, I know. There’s another childhood trauma cue here, which I totally should write about soon).

I think once you get to a level where you can do all that and more (and trust me, I haven’t reached my max, I still have so much to learn), you start to become invaluable. Your executives don’t want you to leave, they offer you more money every chance they get, they don’t bat an eye when you ask for something, and they want to take you with them to their next role, company, or venture.

Think about your own life and what you spend good money on. Don’t you spend a little extra for better quality things, to be more comfortable, to feel safer, for higher quality food, and to have peace of mind?

In the same way, an executive who truly understands the value of an amazing EA will want to pay on the higher end for the same reasons because they know a valuable EA can help make them so much more of a productive and successful executive and lift so much stress off their shoulders.

If you’re not happy with your pay right now or perhaps it’s on the lower side, think about what you can do as an EA to add tremendous value to your executive in all that you do. With value will come more money, whether you get it because it’s given to you through a performance review or you get it by asking for it or you get it by moving on to a different role.

And when you continue to get more money, stay humble, remember what you bring to the table, and continue to seek out growth.

Don’t be a $2.95 iced black coffee trying to charge people $4.95 unless you’re going to change, add value, become special and different, and be worth it.

What can YOU do to be an iced coffee worth spending $4.95 on?

I know. I have to work on my analogies. But you get the gist of what I’m trying to say. :)

He said “She (the client) wants a Lioness at the gate who can take care of people even when saying "No", and those people love her.”

After reading this, it made me realize that there’s a lot that I do as an EA that I can’t put on a resume or articulate in a way that makes non-EAs understand - like saying “no” but still being liked and why that’s important, or knowing how to anticipate my exec’s needs and why that matters, or knowing how to make good executive decisions on my exec’s behalf and how impactful that could be.

Being able to say “no” requires skill. You can’t say “no” to someone’s request in a tactful way that yields a positive outcome if you don’t have the right relationships built, if you don’t have a track record of making good decisions, if you aren’t trustworthy and reliable, if you aren’t respected, if you don’t have empathy, and if you don’t have a good reputation. All of that takes time and experience.

As an Executive Assistant, we have to say “no” all the time. How do you do it in such a way where the recipient of that “no” is not offended, doesn’t think you’re being rude or condescending, accepts the “no”, and still likes you (and respects you, appreciates you, speaks highly of you, etc.)?

I think it comes down to the way you say it (like your tone of voice), the words you choose to speak, your choice of words in texts, having empathy, and humanizing yourself. Every situation and person you’re dealing with is going to be unique, so there’s no one right answer to this. But being mindful of the situation at hand, understanding why you have to say “no” to this person, and knowing who you’re talking to and how to talk to them can help you make the right decisions.

Also, there are a million different ways to say “no”. Sometimes, the word “no” might not even be included in your response. Sometimes, you have to offer alternative solutions, politely decline and provide a reason, or suggest they meet with someone else sooner.

Being tactful and helpful in your reply is important not only because it makes you likable and approachable but because you represent your executive and it’s important to represent our executives in a positive light.

This recruiter’s email lit a lightbulb in my head by reminding me that there are a lot of intangible things we do and qualities we have as EAs. We don’t just schedule and calendar and plan events. We don’t just “work our magic” and snap a finger and make shit happen.

There’s a lot of coordination, strategy, skill, and experience that goes into what we do. And though I personally have a difficult time explaining to people what I do as an Executive Assistant in a way that perfectly paints all the nuances of our role, there are a handful of people out there who get it, and that is sufficient for me.

Yesterday, during one of his classes where part of the homework was to turn in a self-tape by 5pm PT the Friday prior, the coach asked everyone in class “if we have 10 people in this class, how many people do you think submitted their self-tape?”

The answer was 5.

She went on to say that if there is an audition available and 100 actors choose to audition, only 50% of them will actually submit the tape on time. Of the 50%, 99% of the folks who send something in will either have unprofessional tapes due to technical, noise, or background issues or they will submit something that looks and sounds like everyone else’s.

Only 1-2% of the submitted tapes will actually be worthy of considering for the role because they are different, not distracting, special, and stand out.

The point of this was to let the kids know that though acting and auditions are competitive and overwhelming, it’s not AS super competitive as we all think it is.

This is probably true of all industries, but it’s also very true for the Executive Assistant world.

Not all Executive Assistants are good.

If I interview 100 EAs for a role, only 5-10 will really stand out as being amazing, 70-75 will be fine and the same as everyone else in that group, and 20-25 will be a strong no.

So the competition, though it exists and is intimidating, is not as bad as we think it is. You just have to stand out in some way. I’m not talking about dressing outlandishly or being overly enthusiastic or physically standing out.

I’m talking about things like bringing your authentic self in your answers. Showing the interviewers what you’re capable of through stories and examples. Talking about your mindset and how you think about the role. Matching the energy of the interviewer. Talking about what you’re looking for and what you want in your next role. Practicing your story over and over again. Overcoming your nerves (I know, this is a tough one).

For example, if an interviewer says “tell me about yourself”, how would you answer that?

Do you talk about the type of EA you are, the characteristics and attributes you have, your work history? Or do you talk about YOU (in relation to the role), who you are as a person, what you enjoy doing, why you like being an EA?

You can certainly talk about your relevant experience, skills, and education, and why you’d be a good fit for the role. But if you can’t do it in a way that makes you memorable and stand out from everyone else who is also answering in the same way, then it might be time to spruce your answer up a bit.

Bring humor into your answer. Bring some vulnerability, honesty, humility. Tell a short story of why you became an EA or why what you do everyday makes you such a great EA. Make your answers unique but relevant to the EA role. Be you, be genuine, be authentic.

Honestly, I’d hire a likable, memorable EA with a few years of experience who seems like they value work ethic and will be able to learn quickly and adjust to situations and people, over an EA with 5-10 years of experience who name drops, isn’t humble, and answers the questions like everyone else.

I look for people who genuinely enjoy being an EA. When someone likes what they do, you can see it in their eyes and you can hear it in their answers. And sometimes, when you’re looking to hire an EA for a CEO, you need to hire someone who actually likes their line of work, not someone who is just looking for a paycheck, even if they could probably do the job. The long term results of the latter (ie. the Exec/EA relationship) never end up working out well.

Anyway, all this to say, it’s competitive out there. But not AS competitive as we might think it is. Interviewing is a numbers game. The more you do it, the better you get at it. Rejection is hard, but the right role will come when it’s the right time, so keep at it.

In the meantime, practice your story.