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?

“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”.

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.

Things are going well. Questions are being answered. Rapport is being built. You got this.

And then the interviewer throws a question at you out of left field: “What would you do if there was a zombie apocalypse right now and we are here (in the office)?”

How would YOU answer that question?

The company I used to work at would ask this question to all candidates, including Executive Assistants, back in the day.

What is the right answer? Why are they asking me this? What do they want me to say? What are they testing for? Those are the thoughts that would’ve gone through my head if I were asked that question. I would’ve crumbled under pressure trying to come up with the “perfect” answer thinking that’s what I was supposed to do lol.

A couple of my really good friends are the ones who used to ask this question in interviews. I’ve chatted with both of them in the past about this on separate occasions. And I asked them “What was the right answer to that question? You know, I would’ve totally failed the interview if you had asked me that.”

It turns out, there IS no right answer. And the answer actually isn’t as important. The thought process and how the question is answered are what they were looking for.

Are you a brainstormer? Can you problem solve? Are you a creative problem solver? Can you collaborate? Can you delegate? Can you work autonomously? If you aren’t sure of the answer, do you say so? Do you take the question seriously? Do you get into the nitty gritty details or are you care free about it? How do you react?

With that said, obviously, your answer to this question isn’t what gets you hired or not. But it does give the interviewer an insight into what you might be like as a person and potential employee/coworker.

To be honest, this is actually a perfect (and dare I say reasonable?) question to ask an EA in an interview because we deal with so much weird shit on a daily basis. If you’re an EA (with several years of experience) reading this, I know you can remember at least 5 ridiculous, near impossible requests that you were able to somehow successfully complete. A zombie apocalypse? Pfft… no big deal compared to what you’ve accomplished lol.

Next time you’re interviewing an EA, don’t ask only direct, obvious, google-able questions. Ask the off kilter ones that give you a glimpse into their personality, sense of humor, problem solving ability, sense of urgency, adaptability, etc.

Instead of “tell me a time when you made a mistake and how you overcame it” (my least favorite interview question btw), ask them something memorable and different that they won’t be able to google in advance and practice answering!

I have over two decades worth of work experience. I’ve worked in coffee shops, restaurants, retail stores, law firms, accounting firms, and tech companies. No matter where I worked, it was never a good thing when someone left or quit when things were bad.

On the flip side, I also witnessed many folks who left companies when they were at their high, ie. when things were great - they were making change at the company, they had an excellent reputation, they seemed happy in their role, they were making progress. Whether they purposely meant to leave at that point or it was just happenstance, it seemed like a good choice that only benefited them after.

We are human. Over time, we lose momentum and inspiration. We become complacent. We lose a little bit of that spark to grow and push further. We are less challenged over time. Things become routine at work - they’re on autopilot. We get bored. And eventually, people around us see our indifference and lack of enthusiasm. That’s the moment where we’ve tipped over our high (over the peak) and started to head downhill.

I remember working at Starbucks (eons ago). We had this amazing store manager who you could tell was really good at their job. One day, he let us know he’d be leaving in two weeks to manage a different store - but things were great at our store, why leave? He moved on to manage a couple more stores, and last I heard, he became the district manager, and then eventually the regional manager. People recognized his work ethic and reputation.

I also remember working with a shift lead at Starbucks. He was great, but eventually must’ve got tired of it. He still clung to the job, but you could see his energy levels dwindle. One day something happened, and he ended up rage quitting. I can vaguely remember how great of a shift lead he was, but I distinctly and vividly remember his last few weeks of work where he was always annoyed and a pain in the ass to be around.

Leaving a company when you hit the bottom of that hill is no fun for anyone. You’re constantly in a negative emotion state. You’ve lost your umph. And you’ve tainted your otherwise positive reputation. When you leave, those last few months are what your coworkers will remember of you. People remember your exit, not your entrance.

Let me be clear… working somewhere is not always uphill. You’ll have good days, and you’ll have bad days. You’ll have days when you’re grateful to be there, and you’ll have days where you’re like “that’s it, I’m done!” Most of the time, the latter is a phase, and you’re able to work it out and move on from it, still heading upwards towards your highest point. It’s only when that phase, anger, unhappiness is constant that you’ll start to quickly roll down the hill.

If you’re thinking of when the right time to leave your company is, think about where you are mentally and emotionally. Do you still have a few more months or years in you to push through and help make change and progress? Are you still happy and excited about work, your coworkers, the culture, your projects? Or are you constantly burning out and unhappy or indifferent at work? At what point do you think you’ll tip over that peak? Or have you already?

Your reputation is all you have. Don’t taint it.

That’s probably not the answer she wanted to hear. Though, maybe that’s what she needed to hear? But also, there are so many factors at play here, so how really does one answer this question?

Personally, I stand my ground on my answer (I’m not saying everyone should agree, but more so that this is how I operate and it has worked for me over a long period of time so I wanted to share my opinion and perspective) - to me, working hard and being good at my job is the best path to gaining other people’s respect, though whether they give it to you or not, even after all that, is not in your control.

Work hard, make smart decisions, get shit done, and build your reputation. With that reputation you’ll be able to say “no” to tasks you shouldn’t be doing, you’ll be able to work on projects you want to, you’ll gain the trust from your executive, you will be able to grow, and you’ll build confidence. Respect comes over time, with consistency and hard work.

I realized though, “you have to be good at your job” means something different to everyone. And sometimes getting respect from people is, again, outside of your control, no matter how “good” you might be (in which case, if it’s your exec who undermines your role and disrespects you then maybe it’s time to leave them (they’re probably like that to everyone and it’s not a great environment to work in), or if it’s a coworker who looks down on you, do you really need to spend time and waste emotional energy and space caring about what they think (they’re probably the ones who are insecure and suck at their job lol, but I digress…))

Anyway, “good” is subjective. “Work hard” is subjective. My level of “good” is different than someone else’s. Even “respect” is subjective. And work product or decisions that are considered “good” to me could be very different from someone else’s “good”. How we all perceive our own value and worth and what we base it on is different.

It’s like when someone says “omg it’s freezing” and it’s 50ºF. I’m from Los Angeles, and for someone who never saw real snow falling from the sky until their mid 30s, that is very, very cold to me, and I am extremely likely to say something like that, albeit facetiously. But for someone who is going through negative degree weather and currently in an ice storm in Portland, Oregon, they are wishing for the warmth of 50ºF weather. Just like how “freezing weather” is subjective, so is “good”.

Because of this realization, I thought it would be good to expand on my original answer that “you have to be good at your job” to gain respect. Here are my thoughts (in no particular order, and by no means an exhaustive list).

• Be Consistent

  • People, not just your executive, should know what to expect from you based on your history working at the company. This is why it takes time to build your reputation - because no one can know how good or bad you are based on one project, one interaction, one chat thread, one presentation. If you consistently produce good work, if you are consistently reliable and trustworthy, if you consistently make the right decisions, then people start to understand the type of person and employee and EA you are.

• Be Results Oriented

  • When your executive gives you a task (assuming it’s a reasonable and achievable request), do it to the best of your ability - figure out what you need in order to get it done, know who to go to in order to find out the information you need, be resourceful, finish the task on time, and keep them updated so they don’t have to micromanage you.

• Know How, When, & What to Communicate

  • Know how to communicate with your executive - Adapt your style to theirs. If you notice they don’t ever respond to your emails, but they’re quick on texts, then switch to texts. If they need regular standup time with you everyday, make yourself available and ready. If they want straight to the point information, answers, and solutions, then throw out all the fluff, don’t give excuses, and keep your communication concise and results oriented. Understand their personality so that you know what style of communication will resonate best with them.

  • Know when and what to communicate with them. Sometimes they should know something immediately, other times, it won’t be helpful if they know. Timing and knowing what information you should share are both equally as important.

• Observe Their Habits, Behaviors, and Patterns

  • Executives are people. They have particular ways of doing things. They ask the same questions all the time. They’re curious about the same things every time. They have favorite cuisines, and preferred hotels, airlines, and seat preferences. They like their meetings a certain way - maybe max 30 min., zoom preferred, agenda/context for every meeting otherwise don’t schedule, no meeting Wednesdays, done by 430pm, etc. If you can observe the way they operate and understand their why, you can make better decisions, you can be proactive, you can provide quick solutions, and you can become an asset to your executive, which in turn makes you “good at your job”.

• Work Hard & Smart

  • I’m traditional (is that the right word?) in this sense. If I have to work late hours to get something done, I will. If I need to be available and check emails/slacks on my computer or phone all day, I will. This doesn’t mean I work all day, it means that I make myself flexible and available while also setting expectations. If I have to say no to projects, requests, people, I will. Working in this fashion allows you to build the reputation that you need in order to get better at your job in the future. Prove your worth now so no one can say shit to you later.

All of this will take a lot of time, but that’s how respect is gained, isn’t it (regardless of whether you’re an EA or not)? Over time? Naturally? Based on your consistent output and reputation? It won’t be achievable in a day or month or half a year. You will make mistakes, which is ok and expected. But you’ll learn from these mistakes and know how to avoid them in the future.

Like with everything in life, practice makes perfect. Eventually, you get better and better at what you do and how you do it. And then, slowly, over time, the respect will come.

The executives I’ve worked with in the past who were new to working with an EA or didn’t have luck working with recruiters always wondered what they were supposed to look for, how they should be able to tell if an EA would be great for them, and what questions they should be asking in interviews.

And my number one bit of advice always came down to: Don’t hire an EA purely based on resume or whom they supported, where they worked, or how many years of experience they have.

Though those may all be great baselines to help you understand an EA’s foundation and experience, they don’t equate to “oh this must mean this EA will be great for me!”

Instead, spend time with the EA to understand if you both are a good fit and personality match. Think about what qualities are important to you to have in your EA, and if you’ve never worked with one, think about why you need an EA right now in this moment in your career, what you need help with, what style of EA you want, how you want them to represent you, and what type of person and executive you are.

Ask yourself questions like…

• Does your working style or hours of operation seem to match? - If you’re a bachelor, tech CEO of a startup, who starts work at 12pm and goes until midnight, and I’m a mother of two elementary school aged children, our hours of operation may not align

• What about personalities? - If you’re introverted and like to work on your own undisturbed, but you have an EA who constantly has to ask you questions, this may not work. If this is your first time having an EA, you may need someone who has some experience and can help train you, but then do you find someone who tells you how to do things or do you find an EA who is malleable and adaptable to your needs and working style. It really depends on who you are.

• Is this person someone you’d want to have representing you? - Maybe you want an enneagram 7, extroverted EA to be the face for you. Maybe you want a behind-the-scenes EA. Maybe you want someone “fun”. Maybe you want someone “chill”. Whatever it is, people will look at and interact with this EA and make assumptions on how YOU are as an exec, so this is something important to think about

• Do they seem honest and capable? - It’s hard to tell if someone is honest or capable in an interview. So I rely on gut and backchanneling for this one :)

• Is this someone you’d want to chat with regularly? - This EA will be someone you have to work with and interact with frequently. If there’s something about who they are or their personality or style that rubs you the wrong way in the interview, trust that instinct

• Do your values (or things you both find to be important) align? - Not everything has to align of course, but being on the same wavelength can be extremely beneficial and helpful in building this relationship.

• Do they seem trustworthy? - This is another “gut” thing, but being able to trust your EA is extremely important. Ask questions in the interview process that will help you determine whether this person seems trustworthy.

Also, be direct in your interview. Tell the candidate what you need, what you expect, what immediate tasks you’ll give them, and be as clear as you can or if you don’t know, then let them know that you don’t know. In which case, find an EA who can be autonomous and work with minimal guidance.

It’s important to try to find as best a match as possible because hiring a bad EA for you will make your work life more stressful than it may already be. Take your time in this search, and don’t just rush to hire a body because you need the help.

Also, fun fact (or at least my experience tells me it’s a fact). EAs are always the last to get hired. Companies start looking for EAs when shit has already hit the fan.

Instead, hire someone sooner, even if you feel like you don’t have enough full time work to give them. This will give you an opportunity to ramp them up properly and help them grow with you and the company. Once you hire them, you’ll realize you have loads of work for them (especially if they’re good), and you will be prepared when things get extremely busy and chaotic!