Why Most Executives Fail at Hiring the Right Assistant (and How to Succeed)

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Hello, everyone, and welcome back to the show. Today, we have a absolutely tremendous conversation for you with Monique Hellstrom.
Monique cut her teeth as the executive assistant to Simon Sinek. Yes, that Simon Sinek, the guy that wrote Start With Why, Leaders Eat Last, incredible thought leader.
And for more than a decade, Monique was the power behind Simon, making sure that he got where he needed to be, that he got things done, that he was on task, that he was focused. And we have a conversation about not just how do you find or write an executive assistant, how do you be an incredible executive assistant, the dynamic between that role, that responsibility, the power of really leveraging an executive assistant.
We focus in on the communication that happens between these individuals and the human side. As Monique describes far too often, executives who are looking for an assistant focus on

the tasks, and that is most commonly the number one pitfall for why these relationships don't

work out.

Monique defines what we need to think about, how we need to think about an executive assistant,

and how we put ourselves as leaders, as executives, in the right mindset to work with an executive assistant and add somewhere between 30 to 50% more productivity into our day-to-day work by leveraging the executive assistant effectively. This is an incredible conversation.
Monique has so much to offer. I know you're going to love this.
Before we get to Monique, I will have a simple ask for you. It's the same ask I have every episode.
If you are enjoying this content, if you enjoy this show, wherever you listen or watch, whether it's on YouTube, Spotify, Apple, or wherever you consume the Ryan Hanley show, I appreciate you. And even beyond that, I appreciate how much you share the show.
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to share with us her expertise

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leave me that feedback, let me know

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with all that said

Thank you. of leave me that feedback let me know and I will go out and find more of those individuals this show is as much yours as it is mine and I just love you so that we can go whenever, but you're, no, it's not live.
So yeah, you're good. You know, self-awareness and communication.
These are the two most important things we have. and these are the two things we have never been taught how to do.
There's no school. You don't get taught in fifth grade how to have conflict or have a conversation with someone who doesn't agree with you or how to understand your skills.
Like, why aren't we taught this as children? I don't get it. And then we're supposed to do it every day.
So that's my hot button. You know what I find very interesting? Like there's the cliche around boys in particular, right? Like we could be arch enemies and then we have this physical altercation and then we come out of it and we're best friends.
And my best friend in high school happened that exact way. So I'm from this tiny little town in the middle of nowhere.
The fact that our town was even part of this big, huge school district was like a bone of contention and a point of people making fun of me my entire high school life. And this other kid was like the most popular kid in school from the best part of town and all this kind of shit.
So it's like – and we just constantly butted heads because I was good at sports. So I'm like unpopular, poor, wrong side of the tracks, but I'm good at sports.
And here's the opposite. It's like literally like out of like a – it's like out of like one of those 60s movies.
You'd expect us to start like snapping at each other in the halls or whatever right we so we literally hated each other and we played every sport the same for whatever reason and we're constantly butting heads and our sophomore year of high school um I went up for a layup in basketball and he kind of like followed me hard and something broke in my brain and I just had enough and I literally tackled him

and we're on the floor full out fighting now again this is almost 30 years ago so like the coach is just standing there watching you know just there's you know he's probably smoking a cigarette at the same time and so we go through this whole thing and we're like literally bleeding, punching, kicking, get up, look at each other.

He goes, are you guys done?

Slap, bro hug, best friends from that point on. Thank you.
It's like. Tell that story.
Right? Like it just, I, I, it blows my mind. And this is where I want to bring it all the way back to you.
So that very long story, all to tell you that when you said

self-awareness and communication are the two most important skills that we're never taught, I completely agree with you because we had no ability, no mechanism to communicate with each other. Now, I don't know that we could.
I guess here's my question for you, and this is maybe an odd place to start.

But, like, I think what I just described would horrify most parents of similar age kids today.

Today.

And honestly, it's one of the moments in my life I'm the most proud of.

Amen.

Amen.

And I wish more people heard that.

You know, we're humans and we're messy and we have emotions and they come out and they make us think weird things. But can't we just be honest with that and go up to someone and be like, you hurt my feelings.
Or I don't like the way you looked at me. Can't we just come to a place where we could just be honest human beings and then listen to each other and work it out or have a fight and work it out but then when you're done shake hands and be like we're all good we're moving on because these days it's like my way or the highway and if i disagree with you you're gone you're dismissed you're no longer useful to me and that is a disgusting habit that is that is a new thing that has come along where know, the conflict is the end of the friendship as opposed to the thing that holds it together.
Yeah. I think, I think a big part of this was when words became violence, right? When words are violence, now me disagreeing with you, now I'm being violent towards you because I'm just being disagreeable.
Right. You know, one of the, one of and this is going to I don't know.
This may make sense. Maybe it doesn't.
The most listened to single episode of this podcast that I ever did was last January with a buddy of mine who's a Democrat. I'm a I'm a Republican.
Well, yes, I am. In today's version of that, which means I'm like moderate, slightly left during probably like the 20 years ago.
And we had this conversation. The title of the podcast was How to Disagree with a Friend About Politics and Still Love Each Other.
And we had this conversation. We're literally disagreeing, but we're talking about it, being respectful to each other.
And over the course of an hour and a half, we discussed like three or four of the more hot-button political topics at the time from where we were coming from. And I love the guy to death.
I take a bullet for him. Right.
He's amazing human being. You know, his life is based in faith.
But that episode, like what my point in sharing that with you is it's like people are dying for this, for constructive, disagreeable conversation where I can say, I hear you. I appreciate your vantage point, but here's where I'm coming from and not have that person immediately tell me I'm some ist, right.
And we can go both ways with the ist, but like, you know, it's like people are dying for that, but no one, no one has the, the, the guts to give it to them today. Does that make sense? Absolutely.
Absolutely. And I mean it's a combination of a lot of political figures fighting dirty and using – I don't care what political side you're on as long as you're talking about the truth.
And one thing I won't argue with someone on is when they dispel the truth like yeah that to me is is is um it's it's more of a values thing where i don't share the same values with you if you're not representing the actual truth that's happening in the world but yeah um you know the the other side of it is yeah yeah, words, a simple word.

You said something about somebody or somebody looked at you funny, especially with women.

You know, we're just, you say something funny and then you ghost. I've had two friends in the last four years that just ghosted because they didn't want to have a hard conversation with me that I, you know, may have hurt their teeny, teeny little boo-boo feelings.

And I'm like, really?

You can't just sit down and be like, Monique, what you said was hurtful.

I can take it.

Also, who doesn't want to live in a world where occasionally your feelings get

hurt? Like, right? Like that's no fun.

Everybody, your feelings are going to get hurt.

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visit masteroftheclothes.com today close twice as many deals this time next week visit masteroftheclothes.com to learn how like um you know i i have been you know i'm starting to be invited back in but for the last eight years or so i've been ostracized from many of my left-leaning friend friend groups just because they're like they just have all these assumptions on what I believe because I voted for one president versus another. And what I find interesting about those communities, as well as the ones like I also get invited to mail mail groups that are like, you know, let's just fire all our guns in the air and, you know, drive without seatbelts and shit.
And I'm like, what, how can it be fun to only hear the same shit? That's exactly what you agree with over and over and over again. Like I, that to me is the most uninteresting conversation to have.
Like, it's fun to like bust chops and be in those groups and all look at those crazy this or that, you know what I mean? It's all funny. It's funny.
But like really when you're trying to understand a topic, don't you want someone who is willing to push back on you a little bit and question your assumptions? And like you said the truth. I think one of the biggest issues we have today, and this is not just politics.
This goes all the way to leaders and managers and individuals inside of companies, et cetera, organizations.

We've like lost our grip on how to define what truth is.

Do you think that's the case? And I guess my question for you is like, how do we how do we have a conversation with someone either up or down the chain in an organization? Let's take it out of politics., talking inside a company, with someone who literally is viewing the world with a different set of facts than we might have? How do we broach that topic? How do we start to talk to those people, communicate with those people in a way that is productive? Sure, sure. Well, the first thing you need is two willing parties, you know, I can be as willing as I want to be in order to have a really productive and intelligent conversation with you.
But if you're not willing to reciprocate that with me, we're not going to go anywhere. So the first requirement is having two open minded and willing parties that do want to have a discussion because otherwise it's just moot and it's not going to go anywhere.
Um, you know, and the other thing is what is,

what is, what is the goal? You know, is the goal, is my goal to inform and give information? Is my goal to help you be a better version of yourself? So I'm giving you some constructive criticism on things that you can do better. Or am I saying this because I want to be right? There's differences there.
So again, you all have to be working on the same terms, knowing that there's an open-mindedness to the discussion. And then, you know, something that I always tell my coaches, my coaches and clients is find that shared pool of meaning.
Especially in an organization, what are you working towards? What's the goal? What's the thing? You're all working towards something. You just have different routes to take to get there.
So what's the middle ground? Not middle ground. The shared pool of meaning.
What do you all want? Because we can align on what we want. It's just, you know, you want the walls red and I want the walls blue.
Either way, we still want a more beautiful house. So let's agree on where we can agree.

I love that. I think, uh, I had some, I had a leadership coach guy who now I'm forgetting his

name. Cause I've done way too many podcasts and I'm a terrible host and I should have this.

If I were Chris Williamson, I'd have the episode number right at my fingertips right now. But we were having a similar but different conversation and he's like, imagine a Venn diagram where just a tiny portion of the Venn diagram actually overlaps.
And he said what's happening in our country today is on all conversations, not just political conversations. It can come down to parenting.
It can come down to value structure. It can come down to religion, et cetera.
We are taking all the stuff outside of where we cross, and we never focus, and this is what I hear you saying, we never focus on that stuff in the middle because you could have one common shared value that brings you together and allows you to push forward. But we don't even try to get to that point.
We just say, well, you put a blue sign out in front of your house and you put a red sign or you're for public schools and you're for private schools or whatever your topic of disagreement is. And we focus on all these areas of disagreement when we could have really strong intersections and we don't even take the time to figure out what those are.
And I feel like it's very sad that we can't have those conversations – or we aren't. I shouldn't say we can't.
We aren't having those conversations. We aren't having those conversations.
Yeah, that's exactly right. And I think we went sideways in a few different ways.
You know, I'll be the first person to say, I think computers and social media have destroyed our ability to communicate in, I, we don't even have enough time on this podcast to talk about how social media has destroyed communication and conflict. Um, but I think that's had a lot to do with it.
Not only the ability to say ignorant, horrible things about people and not show your face and not actually get into that fight in the middle of the basketball court and have a tough conversation and do that. But there's also an immediacy to everything we do in our world right now.
Everything is immediate. You want something, you go online, you hit buy, it comes the next day.
You want to do, everything is immediate.

So we think that communication and trust and friendship and passion for one another should be immediate.

You did something, I'm done.

You didn't do something, I'm done.

I'm for you, I'm against you.

And it's not this, humans don't work like that.

Humans, we're here, you know, let's – why are we only talking about the ends of the bell curve constantly? Constantly. And the newfound issue of people confusing opinions with facts, you know, because I think it.
It's true. And that's not true.
Yeah. I hate the term.
I hate the term lived truth. I know where it comes from and I'm aware of its origins and what its original meanings were, but I feel like it's been completely bastardized to exactly what you just said.
My feeling, I misrepresent my quote unquote lived truth with a feeling that I have about a topic and it's like just because you feel that or you might think it doesn't mean it's right and it's one of the biggest issues that I have about the free speech argument is I'm I'm a open free speacher I just because I want to know if you're going to say some crazy shit I want to know what you think and like I get the argument of, and I think this goes back to your point about social media, that everything is in such bite-sized chunks and it's so anonymized that we don't have a chance to dig into the nuance. And I'm not a Kamala Harris apologist in any regard, in any regard.
But in that town hall with Anderson Cooper, where he asked her about what would she do differently etc her response was well I take her response was correct in that moment she probably needed to do a better job articulating it but her response was correct which is I take in things that come to me I get with people who know what the topic is about and I make a decision I don't often often agree with her decisions, which is why I didn't vote for her. However, I think that response is accurate.
And the part that I thought was unfair to her was that only in a social media world does the response of, I listened to all the facts, surround myself with people who understand the topic and then make a decision. Only in a media world.
Is that an improper response? Because ultimately, isn't that what we want our leaders to do? Like, do we expect now Donald Trump or any of the people he appoints or, you know, do we expect these people to just have every answer to every question at their fingertips? Like they're, you know, it's impossible for any human to know all the nuances of every topic in, you know, bite-sized social media chunk. And I think it's very unfair to people who are trying to articulate deeper and nuanced opinions.
Yeah. Yeah.
I mean – So that was a big diatribe with no question. Again, I told you I'm not a good podcaster.
For some reason, people listen to the show, which is awesome, but I'm not very good at this. So I want to swing back and put this really into tactical sense.
So your work, you were Simon Sinek's executive assistant and worked with him and did a ton of stuff. And now you coach people on how to be great executive assistants.
So taking this communication issue to that level. So if I am in one of probably the most important roles in an organization, which is support of leadership.
How do I, coming from that position where there is an obvious hierarchical role, maybe relative to how it's positioned, but there is an obvious hierarchy, this is your boss, you are supporting this person. How do you communicate, how do you be disagreeable in a productive way? Because I think a lot of people in these hierarchical situations, they feel like, well, I can't say that to my boss because then they're not going to like me or I won't get promoted.
Yeah. We obviously don't want that.
Good leaders don't want that. They want you to push back on them.
How do we do that in a productive way? How do we give ourselves the confidence to do that in a productive way? Sure. Well, I'll push back on you, though.
Most leaders do not want that information. Working in the world that I live in, and I operate in for the last 24 years, leaders do not want to hear.
They do not want pushback for the majority. I find a very small percentage of leaders these days, or I'll say executives, because I don't even want to bucket them in leaders.
Leaders are everywhere. They don't want to know.
They don't want that, especially coming from an administrative staff person, where we're seen as not being very important. We're seen as doing all the end work, but the business wouldn't go without administrators.
The business doesn't move. You don't sell anything if you don't have anyone putting the things on your calendar.
So, you know, for those executives out there, well, let me start here. I work within the relationship between an executive and their assistant.
I help both sides of the equation. So I help assistants become better assistants and I help executives work with their assistants better.
Because I know for a fact, when this partnership works, the business is unstoppable. I did it with Simon.
I've lived through it. When there is a good partnership.
So, you know, and an executive's productivity can increase between 20% and 50% when they have a good partnership. So think about if you could get 50% more work done in a day, in a week, in a month, in a year.
How can we make that partnership work? So I train both sides because it's not just about the administrative side. For the administrative side, we have to understand what we're doing here, that we have a role, that our role is important, that we have information and skill sets, and we have an ability to do things that not many people do.
We can take big,

huge buckets of scary information and break it down in the little bite-sized nuggets and color code it for crying out loud. So it's a skill set that we don't have.
So for the assistants, you know, when you're, when you need to say something, it's not come with facts. Why, Who? Where? When? Give a solution.
Come with an answer. Come prepared.
You know, it's one of my favorite things that Simon used to say to me, and I hope this doesn't offend your people, but he used to say, don't come in my office and dump a bag of shit on my table. Like when I would come with him with problems.
You're just coming to me with a problem. Come to me with a solution.
I don't need the problem. So for that and for the executive side, you know, be open to the things that this group of people see.
You know, we see things differently. We're, you know, the executives are flying over the forest to make sure that everything's working.
We're the ones walking through the forest and we know every trail and every river and every port-a-potty in that whole forest.

So ask their opinion.

What do they see that you don't see? What do you know that I don't know? And just in general communication, I think that would just help everyone. Like, what do you know that you can put in my brain that can help me be better? Tell me more.
Give me more information. I hate your first comment that executives don't appreciate or respect assistants because – so I exited last November in 2023 from a company that I had founded.
And the only person that I brought with me to my new venture was my head admin. She's the best.
like I tell her all the time, like I find, I found someone who can like put up with me and like is okay with the way that I like communicate and operate. And for some reason can like decipher my craziness into like things that actually get done.
Like you're coming with me forever. Like you will have a job for the rest of your life until I can, until I am no longer an executive.
You will, I will make sure that you are always employed. You're, you're, you're coming with me.
Cause I, I, I'm like the exact opposite. I believe you.
And I, I a hundred percent believe you. And I, I just think it's so short sighted.
What is, what are the primary things? Is it ego? Is it insecurity? Like, like I know I do a lot of crazy shit. Like as an executive, I, I, you know, she says you're, you're full fire hose all the time.
Like she's like, I, I, I never get anything in chunks. It's, you know, I do like, and I, you know, you talk about offending the audience.
I do like the Donald Trump weave with the way that I speak, which is probably obvious in my responses to you thus far, where, you know, I kind of like take stories and I move back and forth. And she's like, you know what? She she's like, I just listen for all the shit in the middle.
She's like, when you go off over there, she's like, I kind of stop listening. And then I wait for you to come back and then I catch the stuff in the middle and then I let you go off again.
And I'm like, that's amazing. Like, oh, my God, like I would never be able to do shit.
So is it, are you dealing with ego? Are you dealing with insecurity? Is it like, this is my first time leading? Like what, or being in an executive position? Like what are the reasons that, and what I'm hoping for is the audience picks up on maybe some of their own personal characteristics that they might be missing on. So like, what are some of those things that someone should be self-aware about to, to maybe understand how they're playing a role in not optimizing the relationship with their assistant? Sure.
Okay. Well, I'll give you two, two ones that I hope it's not.
And I'll give you the one that I hope everyone fits into. Absolutely.
It could be ego. You know, there's a big history with our profession dating back to when we were secretaries in the Mad Men days.
And there certainly wasn't a lot of respect for that role back then. And that has continued on because a lot of those executives are still in business at the ripe old age of 85 years old and trying to tell us what is happening.
We love you, but move on. It's ego and it's a disrespect of the profession.
But what I really hope it is, is it is a misunderstanding of the profession. You know, I don't know.
I have no clue what a CFO does every day. I'm not a finance person.
I don't know their day-to-day actions, but I don't disrespect what they do because I don't understand it. I don't know how it happens and I can't do it.
There's, for whatever reason in the support and administrative profession, it's like, it's got to be easy because it sounds easy. It's got to be easy.
So it's easy. Well, it's not easy.
It's one of the most difficult roles you can hold because we don't support, we support a human and all humans are different and we have to support the human in the way the human needs. So we have to mold our personalities constantly.
And so I think it's just a real, it's a misunderstanding of the role. It's a misunderstanding of the type of person you need to accomplish the goals that you want to accomplish in your business.
As a recruiter, I do a lot of recruiting for executives, helping them find assistance. The heavy majority, and I'm going to go as far as saying 75% of my executives will explain to me that they want a C-suite executive assistant who can roll with the punches, who's got strategy, who can forward think and really become that sort of chief of staff mentality and operate in a C-suite and operate with the board of directors.
And I say, great. How much money do you have for them? I don't know, 50,000, 60,000.
Is that okay? 60,000? I'm like, would you pay a CFO? It's the difference between a CFO and a bookkeeper. Yeah.
You want a bookkeeper? That's what you're going to get. So there just has to be a bigger understanding of what the profession is for, what it's required, and the difficulty that it requires and to be paid appropriately or to at least be acknowledged appropriately.
I had a friend who I was talking to him about how to get the most out of my admin team. This is early in my business.
And he said, understand that you can miss three sales, hit on the fourth and still make your numbers for the month. They have to be 100 percent on everything there's no miss if you have a meeting that gets miss scheduled they get in trouble if they mistake a note they get in trouble if if that you have an event in the office planned and it doesn't happen or the food's not there or something like whatever you've tasked them with they don't get to miss and he's like appreciation for that.
And that really, that really opened my eyes. I felt blessed that he gave me that advice so early in my career.
But it was like, all of a sudden I was like, oh my gosh, like they literally don't get to miss. Like, cause.
And we get blamed for things that don't even, that we don't even do. I have to cancel a meeting with somebody else's executive because my executive is too busy.
They're yelling at me for that. Yeah.
I'm the one getting called names for that. You know, anything that our executive does, you know, your executive promises that you'll get something done by Friday.
And then somebody is asking you, well, where's the thing that your executive promised? I said, well, I don't have it. He's not done it yet.
I'm the one getting yelled at. So we get yelled at for your mistakes too.
How personal should that relationship get? Because I have a hard time. I have definitely had a hard time disconnecting.
This is someone I work with and works for our organization, works for me, et cetera, if I'm the top. And like the getting to know them as a person, their family, like that, that if to me, it feels important, but at the same time, there's, there's obvious there's, there's obstacles and triples or trip wires there.
Like how do you navigate that professional and kind of personal nature that ends up developing with an assistant? Sure. It really will depend on your organization and, and who you are, I guess, as an executive, you know, I tend, this is a generalization, but, you know, in the larger corporate arenas, everyone sort of has their job.
Everyone sort of has their box. The admin support has their box.
And so it's not really a personal relationship. They're not doing personal tasks for you.
Everything has to do and revolve around the professional world. So some of that may be not as necessary and maybe you don't want to, that's fine.
But if you're in a situation like you are with your assistant or I was with Simon, I mean, you're together all the time. It's constant, it's constant communication.
And if, you know, at the end of the day, this person likely knows your social security number and your bank account number and when you're fighting with your wife and when you slept on the couch the night before. And we know everything anyway.
So let's just make it a real personal relationship. You know, it's not a relationship unlike dating.
You got to go through it. You got to go through some of these like things.
And what are they like? What do I like? And how do I say that better so that they understand me and do what I'm going to say? And, you know, you got to kind of work out all that mushy stuff in the middle and then you're dating and then you're in it. Yeah, it's funny.
I had a moment where early in my in my business, in my relationship with this particular individual, I got divorced. I've been married for 13 years and whatever life happens.
but what was funny is like, you know, you go through like the, there wasn't much of a mourning period, but you know, we get past that period and then you start dating again. And now all of a sudden I'm like my coworker and, and then another co-worker, they're like giving me dating advice.
And I'm like sitting there going, I'm happy for this. At the same point, I'm like, I'm not, I'm really glad like there's not like an HR person on the phone right now.
I'm like, I don't know how much of this we're supposed to be talking to each other about. It's your company.
It's how, it's how comfortable you are and how comfortable they are. Yeah.
It's all about that. It's, you know, as long as you're not sexually harassing, sexually abusing, calling somebody names, you know, HR, to give someone dating advice.
It's like, I don't know if I, if, and when I have my assistant, I want them to know about my life because guess what? Those people care about you enough to give you advice. If they didn't give a crap about you, they wouldn't give you any advice.
They care about you going on these dates. They want you to be happy.
They want to encourage you because they want you to feel good. That's what happens when you have a good relationship with your assistant.
They take care of you. Yeah, I completely agree with that.
The other thing, too, that I think gets lost on some of my peers that I've talked to about this particular topic is that person, and correct me if I'm wrong in this assumption, but a lot of times your assistant attaches their professional success to your professional success. And they see like, as you move up the ladder, as you maybe move to another company, as you grow in your career, they're going to be brought along.
There's more opportunities for them to make money, to go on go to cool places or whatever, whatever the perks are of that particular job. And you know, there's like this, there's like this disconnect between like, like, dude, you need to do a good job so that, cause that person is like piggybacking you to a certain extent.
You know what I mean? Like they want you to be successful. You should use them.
Cause I got buddies that will get assistance and they won't even use them. Like they like give them like you know menial tasks and i'm like i'm like she's really smart or he's really smart like you sure they can't be doing other stuff for you like helping you i'm sure they want to no one likes sitting around down their hands yeah i equate this to i often say to my executives you know let's let's talk about I just gave you the most beautiful brand new MacBook computer.

It's got all the bells and whistles, huge RAM, all the things, every program you've ever imagined. And you're using it to play Solitaire.
Now that's fine. Solitaire is fun.
And maybe that does it for you. And maybe that fills your bucket.
And if you want to waste $3,000 on a really beautiful computer or sometimes more to play solitaire, go for it. You're the one not getting the benefits out of that.
But just know that there is a million, almost a million other things that your assistant could be doing and could be helping you. And you're the barrier to your success at that point.
So let's flip the conversation to how we find a good assistant. And by good, I mean, relative to that particular individual, I don't necessarily mean good in general.
I have a lot, a lot of the conversations that I'm in, in different, in different groups is they can't find somebody that to me. I always see as a cop cop out.
And I always that's why I don't get invited back to a lot of these groups is my responsibility. Well, that's, that seems more like a you problem, because I know there's plenty of smart people out there that would love a good job that pays well, that's exciting and interesting and engaging.
So what are they missing? Where do they go? How do we start this search? How do we make sure that we find the right person? Okay. So, uh, you know, I've, I've a million opinions on this, but I think one of the biggest things is that people hire for the skill, not for the human.
And this is a very human role. You know, we've been talking about it the entire time.
This is just a, it's a human profession because it comes with empathy and understanding and consideration and, uh, you know, understanding a human's life and how they operate. So, you know, it's, it's something that, um, it can't just be put in the skills bucket.
You know, when I see these resume, the job descriptions that go out, it's like, they need to know how calendar is one bullet and, um, expense reports is a bullet and, um, travel. And there's like four things on there.
And then they're like, I don't know why I can't find the perfect assistant. It's like, because you're looking for Lassie.
I mean, I don't, there's four bullet points on there. I don't, I don't know who you need, you know, so I'm, I'm just going to apply because this tells me nothing.
So in all the job descriptions that I make, I talk more about the human that is needed for this role. Is this executive? I have one executive right now who's from New York and he's high powered and high talking, fast talking and fast moving.
He needs a certain type of executive assistant who can keep up with that, who understands that East coast mentality. You're from New York.
I'm from Philly. We understand that it's not personal.
If I tell you to do something and it ends with a period instead of an exclamation point, it's just because I wanted to give you the information. And so he needs a certain type.
That's going to be okay with that little tougher skin, little East coast mentality, as opposed to another executive that may need something slight, very different, you know? So who is the human that is going to get along with the executive enough that the executive is going to want to pick up the phone and go, hey, how are you? That's the trick. Do I want to talk to her? Do I want to talk to this person? So please, please, please don't just put on your job descriptions, four bullet points of the tactical needs that you need.
Put on there who the human has to be to put up with the other human or to put up with the industry or what skills do they need? Fast learner. Do you need to be quiet? You know, I'm a particular personality.
If not everyone wants me, I'm loud and I'm ballsy and I'm, you know, I say what's on my mind and that's not okay for everyone. So I want to be able to read in the job description that that's not okay for me.
Yeah. So ask for the human that you need.
Yeah. I, yeah, that's right on the mark to me because it, a lot of the things, what I find what I find interesting to your point is the things that – the actual things that the executive wants the person to do, pretty much anybody can pick up and learn if they don't already have that thing.
If you're a skilled DA, if you've been an executive assistant for five years, you know how to do a calendar. Yeah.
do it. The complaints are never he or she isn't managing my calendar properly.
It's they, you know, I'd really like them to be there at eight, eight, log in at eight every day. And they log in at eight 30 because they have a kit and it's like, well, did you say that it was like a hard line that they had to be there at Did you say it in it in words in your mouth? Because if you didn't, then you didn't set the expectation.
And I talk about this a lot in my world, which is the insurance industry, is we're just so bad at setting expectations for people. We're so bad at setting expectations.
Like your expectation and people are like, well, what

does that mean? And it's like, like you just said, like, I'm going to write emails to you

and I'm not going to put a smiley face emoji at the end. Is that okay? Like, are you going to

survive or is that going to be okay? Cause I'm not going to do that. Like, I'm just not going

to slow down enough to do that. Is that okay? Like, do you need that in your emails and, or,

you know, whatever. And, and it's like some people, you know, you want the person to come back and be like, you know, I really need to have a head pat once in a while.
Like, I just need that. OK, great.
Or I'm not going to do that. Sorry.
And now we know. But it's like the bitches are always the human stuff.
It's never the actual tasks. Yeah.
And it's all the stuff that nobody ever actually scanned for in the beginning anyway. And, you know, never actually asked the question, do you have kids? What time can you come in in the morning? Or do you need constant reinforcement? They don't ask those questions.
And then you hire them and you come in and then they're like, this girl needs constant reinforcement. How dare she? I'm like, don't blame her.
She is who she is. And the fact that she needs constant reinforcement has nothing to do with you and doesn't make her wrong yeah it's your problem that you didn't ask her yeah or you didn't say i'm not the type of person that's going to give you a smiley face all the time if you can work in that world and if this person accepts the job and still needs a pat on the back that is their fault but if you don't screen for it you know i need someone who who uh can can you know drop everything at a dime if i'm gonna call them at midnight well then say that in the job description yeah i often call my assistants at midnight put it in there yeah because some of us love that yeah some yeah People are going to be okay.
And, you know, I think, you know, it's funny, you know, the conversation often does not,

it's like, what do I need?

I'm the one hiring you.

It's what I need.

Right.

So I, what can people say in the interview?

I've had friends say to me, like, I don't know how to screen for the human stuff because I'm afraid I'm going to offend somebody or they're going to sue my company if I ask them the wrong question because, you know, it does feel like the last 10 years or so, some of the things that you're talking about have become a little taboo. Maybe this might not be accurate, but at least from a belief standpoint, I think a lot of executives feel like they can't actually ask some of those questions.

They can't dig into some of those things because they don't want to discriminate or they don't want to, in a very shallow way, they just don't want to get in trouble for saying certain things. So what can they say? How do they approach some of these topics in a way that, you know, I hate offensive because being offended is a choice.
but like how do we not be – how do we be accurate in our speech and our expectations while still maintaining whatever the proper HR is that we can talk to them about, I guess? Sure, sure. Well, you know, what comes out of our mouth is 100 percent under our control.
So if what you're saying is ignorant and rude, that's how it's going to come across. So if you're being obnoxious and offensive, it's going to be offensive.
But there's a thousand ways to say things, so maybe come up with a different way. And this is where the learning about how to communicate is really helpful because there's other ways to say certain things.
One of the things an executive can do is talk about themselves. I am the type of person.
I'm a very hard worker. I am someone who I'm in here at 7 a.m.
I've already worked out. I've done the thing.
I come here. I'm working until 5, and then I go home, and I'm a bulldog the whole time.
Talk about yourself. This is how I am.
I don't need you to be like that, but what I do need you to do is be okay with someone who's like that.

You know, I tend to not give everyone directions because I forget. And it's just not because of malice.
It's because I have ADD and I can't get all my thoughts out. So one of the things you're going to have to do is decipher my ADD language.
How do you feel about that? You know, it's not, are, it's not, are, are, are you gonna, um, uh, can you, can you deal with my personality? It's like, no, this, here's what I do. Here's how I operate.
Here's the things that I don't know about. Uh, and, and how can we work together on that? So talk about yourself, talk about your needs, talk about your personality.
You know, I always tell my executives, bring the poop, bring the poop because they're going to see the poop. They're going to see you in 48 hours after they take that job without a doubt.
They're going to see all the poop. So just give it up front.
Who are you? What are the type of person you are? What are the type of people you get along with? Like, just be a real human instead of a robot. Yeah.
It's so hard for people to do that. It's so hard for people.
And again, I'll take this back to the communication. It's because we're not really taught how to do it.
And, you know, for nobody's fault somewhere over time, having an opinion or disagreeing became an insult. You know, and it became an insult to somebody else.
And that sort of developed over a time period. But it developed the same way that we can undevelop it.
And that's by talking about ourselves and not assuming you're like this. You do that.
And talk about more facts. Yeah.
It's yeah, it's this. It's such an intriguing thing because now – I mean the other interesting part is you can take literally the conversation we've had about an executive assistant, replace executive assistant with any other person in your organization and all of this – hiring – in the insurance industry in particular, there's a lot of conversations around it's very hard to find good help and i hate hate that line of thought because there's how do you really feel right there's so many amazing people out there and like i'll give you an example um we hired a lot of single moms and moms of young kids because in our industry uh tends to be very regimented and it's very like old fat white guy ish and great people but they're just just imagine every old fat white guy you've ever met and that's like a lot of the insurance industry and yeah they're very they're very regimented in this and anybody with not just, but anybody with young kids understands the dynamic nature of their schedules, particularly the moms, because they get oftentimes the lion's share of dealing with all the random shit that comes up from your kids.
So we've essentially established this like when I would hire people, I'd say, look, I don't care when you log in. If your kid, if it takes, if your kid's bus is late and you don't log in for 15 minutes past when you're supposed to be there, I don't care.
I was like, here's what it is though. We're a results-based organization.
We have X number of sales, tasks, whatever your job is that you have to get done, that we need you to get done. And I don't care if you work two hours or ten hours.

If you get these things done, I'm going to be happy.

Obviously, if you can get it done in two and you work two more, you're doing more.

That's great, and that's what I would prefer.

But here's what I need you to get done and whatever.

And what's funny is I got handwritten notes in the mail from some of my team.

And I feel like I'm bragging.

I don't mean to be. I did this one thing right, so I'm going to to take a minute of all the stuff that I messed up.
You know, this one thing I did right from these women that'd be like, I've never worked at a place where I didn't feel like I was going to lose my job because my kid barfed at school. That was one of the letters I got.
And I was like, why you're fucking awesome. Like, why would I let you go? Cause your kid barfed at school? Like that's stupid.
But so many people I feel like are measuring that. And this goes back to our conversation.
We're as exact, we're measuring the wrong things in the relationship, right? And every relationship with every employee is a different, but like particularly this executive assistant role, like if all your meetings are on time, your notes have been given back to you, whatever the tasks are you need. If those things are in your hand and at your disposal, the way they should be, if he or she has to run out for an hour and be incommunicado because their kid's barfing at school, who's the asshole? It's not the person going to pick up their kid.
Yeah, it's not. Well, this is, you know, this is this old, old school mentality of thinking, you know, it's the command and control.
It's the command and control executives of the 80s and 90s that came up, and it was you do what I say because I told you to. I got heard that from a lot of my ex-bosses and my father.
You do it because I told you to. That's that good old boy's mentality.
That's the good old generation, and it just keeps going, you know, it's, if they're command and control with all their staff, they're going to be command and control with their assistants too. So it's, it's a matter of, do you want to, you know, you're trying to tell people what to do or do you want people to get the job done? Pick, pick which one you want.
And, and hopefully this is the last surge of baby boomers making decisions. You know, that command and control structure only worked when the people who were in the control bucket of that scenario could believe, and it was true, that they were going to be taken care of by that company.
And the thing that I tell all these guys today when I run into into it, I'm getting the, I pay them. Why don't they do their job argument, which is another one that makes smoke come out of my ears is we have over the last 20 years, whether it's your organization or just society in general, corporations have taught employees that, that they are no longer loyal to them.
Why do you expect that person to be loyal to you? That's the part that drives me nuts. I'm like, you want to know why your team isn't fully vested in your company? Because they believe at any given moment, if they do something wrong, they're out the door and that you will just punt them with not a second thought.
So who would, I mean, think about any type of romantic relationship you've had. If you're all in and the other person's only halfway in, that doesn't work.
So yeah. All right.
We've beat that up a lot. I want to finish.
I have one more question that I want to hit you with and we can wrap this up and be respectful of your time and the audience's time. This is fun.

How is AI impacting the executive assistant space?

Sure.

You know, as with many industries, everyone freaks out when AI came out thinking it was going to take over a lot of things. And frankly, it has in many professions everywhere.

I mean, if I was a copywriter at the moment, I'd be shaking in my boots with chat GPT. So it's happening everywhere.
And it's just because it's new and nobody understands that. I mean, when we got the computers, you know, when we got a cell phone, everyone was like, what about answering machines? Nobody's going to have a, we're not going to voicemail.
And like, so, but it has impacted in that the job is no longer solely tactical. You know, there are those executives and companies that really do only want a tactical administrator and fine.
But that's dying. That's a dying profession.
It's not just about the tactical work. It's not just about the calendar.
It's not just about travel. It's about the forward thought.
It's about, you know what, he's been in meetings back to back to back all day and he needs to get home at this time and he hasn't had any food. What if I do this and this and that? It's forward thought.
It's strategy. It's, you know, I heard this in the meeting the other day, but she said that the other day in the other meeting.
What if I put those two together? It's not just tactical and And AI is taking the tactical work away, or at least it's making it easier for us to do our

jobs, let me be honest with you. So use it.
Get on the surfboard and ride it rather than

be pissed off that the waves keep hitting your shore. You have to jump on these bandwagons

because AI is not going away. Yeah.
I also think that this particular technology, more than, say, cell phones or VoIP for phones or the internet in general, this seems to be taking hold much faster. It doesn't seem like we can sleep on this one like we could on the internet or having a cell phone or whatever.
Like this, this feels to me like something in general, we have to be digging our toes in a little bit. We got to be playing with it.
And I think, I think you make a really good point that trying to pretend like it doesn't exist or fighting it is not protecting your job. It's absolutely making you more expendable.
Yeah. And to your point earlier, being a really good executive assistant has to do a bit with how you do your job, but it has a lot to do with how you care and how, uh, how empathetic you are and how, you know, being really good at this job sometimes isn't about the tactical work.
So, you know, we, we have to too. It's, it's a different profession.
You know, it's not, it's not like your CFO. It's different.
Moni, this has been an incredible conversation. People who are listening that want to, maybe they need advice.
They need, where do they go? How do they work with you? How do they start to dig into your world? And if they already have an executive assistant become better, if they are an executive assistant can become better or find that person, find their person who's going to help them and whether it's up or down the chain, how do they, how do they connect with you? Yep. So, you know, for anyone out there, who's in that dynamic of an executive and assistant for again, for assistance, as well as executives, I do coaching, I do, and I do recruiting.
So those are my three big buckets. I coach assistants on how to be better technically, emotionally, better versions of themselves.
I teach them communication skills and self-awareness skills. And then I teach the executives the same thing on how to work with your assistants.
On the executive side, I'm not a leadership coach. I'm not a work biz dev coach.
I work specifically within the relationship of how you can operate better with your team, the humans on your team. And how to find me, it's my name everywhere.
I'm not hard to find. You can stalk me as often as you need to.
MoniqueHellstrom.com. It's all my socials.
It's all my website. And you can just reach out.
I'm a very human person. My phone is phone numbers, unfortunately everywhere.
So you can also just pick up the phone and call me.

I love it. And guys, we'll all have links to everything in the show notes, whether you're

watching or listening, just scroll down and you'll be able to find links. Um, if this is a point of

pain for you, I highly recommend you reach out to Monique. I think your work is incredible.
I dug

through all of it and, uh, just so happy to have you on the show. Thank you so much.

Thank you. I hope, uh, your team can understand there is a way to be more productive.
It's using the SMEs around you. As you said that Kamala said, find the SMEs that know what they're doing and hold on to them tightly.
Thank you. Let's go.
Yeah, make it look, make it look, make it look easy.

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