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 Helstrom. Monique cut her teeth as the executive assistant to Simon Sinek. Yes, that Simon Sinek, uh, 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 m- how do you find the right 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. Uh, we focus in on the communication that happens between these individuals and the human side. As Monique describes, far too often, uh, 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 gonna love this. Uh, before we get to Monique, I 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, uh, you consume The Ryan Hanley Show, I appreciate you.

And even beyond that, I appreciate how much you share the show. We don't do advertising for the show. We don't push this out in Instagram ads to try to grow our audience. It happens 100% by word of mouth, by you, the listeners, sharing with friends, sharing on social media. And if you're feeling super froggy and you really wanna go the next level, leave a rating and review or a comment on YouTube, Apple, Spotify.

Uh, that tells those algorithms that this is a show worthwhile, and that they should send more people to our community, to this content. It'd mean the world to me, and ultimately, guys, it, you know, and this is the reality of doing a podcast, your numbers matter when it comes to getting great guests. Like, Monique is a, a, a busy individual, and you know, very appreciative of her taking time out of her day to share with us her expertise. And to get great guests like Monique, we need to have numbers, and we need to keep growing. And, uh, you know, leave me feedback.

If there's a certain type of person you wanna hear, if there's a certain vein of content that you wanna hear more 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, uh, I just love you for being here. With all that said, let's get on to Monique Helstrom. In a crude laboratory in the basement of his home.

Uh, it's ... Oh, do you want me to wait? Sorry. No, you're good. I, I don't, it's not live.

Oh, okay. I just started it so that we can go whenever, but you're- Oh, okay, okay ... no, it's not live. Well, uh- So yeah, you're good. You know, it's 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.

Mm-hmm. 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.

Yeah. So that's my hot button. You know, you know what I find very interesting, um, like, there's a, the cliche around, uh, uh, boys in particular, right? Like, where 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, uh, this tiny little town in the middle of nowhere. You know, the fact that our town was even part of this big, huge school district was like a, a bone of contention and a, and a, uh, a, a, a point of people making fun of me my entire, like, high school life. And th- 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. Yeah.

So I'm, like, unpopular, poor, you know, wrong side of the tracks, but I'm good at sports. Yeah. And he was the o- the opposite. It's, like, literally, like, out of, like, a, like a ... It's, like, out of, like, one of those '60s movies.

You'd expect us- Yeah ... to start, like, snapping at each other- Yeah ... in the halls or whatever, right? We, 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 kinda, like, fouled me hard, and something broke in my brain and I had just had enough, and I literally tackled him. And we're on the floor- Full out fighting. Now, again, this is tw- almost 30 years ago, so like- Yeah ... the coach is just standing there watching, you know, just- Yep ... there's, you know, he's probably smoking a cigarette at the same time.

Definitely. 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, and this is where I wanna bring it all the way back to you. So that, that very long story, uh, 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. Like, I guess my, 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, this, the, we're, we're humans, and we're messy, and we have emotions, and they come out, and they, they, they make us think weird things, but can't we just be honest with that, and, 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, 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. Yeah.

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, you 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. Oh, yes.

Right? When words are violence, now me disagreeing with you, now I'm being violent towards you- Right ... 'cause I'm just being disagreeable. It- Right ... I, you know, one of the, one of the, and this is gonna, 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. Ugh. Yes, I am. Um, in today's version of that, which means I'm, like, moderate, slightly left during probably, like, the 20 years ago. But, um, 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, 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'd take a bullet for him, right? He's amazing human being.

Uh, uh, you know, his life is based in faith. But that episode, like, what, what, my point in sharing that with you is it's like people are dying for this- Mm-hmm ... for, for, for constructive, disagreeable conversation where I can say, "I hear you. I appreciate your vantage point, but here's where I'm coming from." Right. And not have that person immediately tell me I'm some ist, right?

And we can go both ways with the ism, 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. Mm-hmm. Yeah. Does it make, does that make sense? Absolutely.

And I mean, it's a combination of, um, a lot of political figures fighting dirty, and, and using... You know, I, I don't care what political side you're on as long as you're talking about the truth. Yep. 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- it's more of a values thing, where I don't share the same values with you if, 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, a, a, words, a simple word, uh, uh, uh, um, 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 we, and then you ghost. I've had two friends in the last four years that just ghosted because they didn't wanna have a hard conversation with me that I, you know, may have hurt their teeny weeny little booboo feelings. Mm-hmm. 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- Grow up ... wanna live in a world where occasionally your feelings get hurt? Like- No doubt ... right? Like, that's no fun.

Grow up, everybody. Your feelings are gonna get hurt. That's, that's the part that I don't understand. Are you tired of endless follow-ups and missed opportunities in your sales process? Chasing leads is a losing game.

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Ready to stop chasing leads and start closing? Visit masteroftheclose.com today. Close twice as many deals this time next week. Visit masteroftheclose.com to learn how. Like, um, you know, I, I have been, you know, I'm, I'm starting to be invited back in, but for the last eight years or so I've been ostracized from mem- many of my left-leaning friend groups just because- Mm-hmm ... they're like, they just, 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 male, male groups that are like, you know, "Let's just fire all our guns in the air and, you know, drive without seat belts 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 oh, look at those crazy this or that.

You know what I mean? Yeah. It's all funny. It- 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, like you said, the truth?

I think one of the biggest issues we have today, and this is not just, this is not just politics, this goes all the way to leaders and managers- Mm ... and individuals inside of companies, et cetera, organizations. We, we've, like, lost our grip on how to define what truth is. Do, do you think that's the case? And, 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 now- Okay ... talking inside a company, with someone who literally is viewing the world with a different set of facts than we might have? How, how do we, how do we broach that topic?

How do we start to, uh, uh, talk to those people, communicate with those people in a way that, uh, is productive? Sure, sure. Uh, well, you know, the, the first thing you need is two willing parties, you know? Uh, 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 gonna go anywhere. So the first requirement is having two open-minded and willing parties that do wanna have a discussion, because otherwise it's just moot and it's not gonna go anywhere.

Yeah, yeah. Um, you know, and the other thing is w- what i- what is the goal, you know? Is the goal, is my goal to, um, inform and give information? Is my goal to help you be a better version of yourself, so I'm giving you some con- some constructive criticism on things that you can do better? Um, or am I saying this because I wanna be right?

Th- there's differences there. Yeah. So again, you all have to be working on the same terms, uh, knowing that there's an open-mindedness to the discussion. Um, and then, you know, something that I always tell, uh, my coache- my coachees and, and clients is find that shared pool of meaning, where, especially in an organization, what are you working towards? What's, 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? What- not middle ground, the shared pool of meaning. What do you, what do you all want? 'Cause we can align on what we want.

It's just- Mm-hmm ... you know, you want the walls red and I want the walls blue, either way we still want a more beautiful house. Yeah. So let's agree on where we can agree. I, I love that. I think, uh, I had some- I had a, a leadership coach guy who now I'm forgetting his name because I've done way too many podcasts and I'm a terrible host, and I should have this, if I were, if I were Chris Williamson, I'd have the episode number right at my fingertips right now.

Um, but the, he was, he was ha- we were having a, a, a similar but different conversation and he's, 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 could come down to parenting, it could come down to value structure, it could come down to religion, et cetera. We are taking all the stuff outside of where we cross and, and we n- 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, we don't even try to get to that point. We just say, "Well, you know, 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, we don't even take the time to figure out what those are.

Yeah. And I feel like that's, it's very s- it's very sad that we can't have those convers- or we, 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.

Yeah. You know, and I think, I think we went sideways in a few different ways, you know? I'll, I'll be the first person to say I think computers and social media have destroyed our ability to communicate in, I, I, I, we don't even have enough time on this podcast to talk about how social media has destroyed communication- Yeah ... 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 a basketball court- Yeah ... and have the tough conversation, um, 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 wanna da-da-da, everything is immediate, so we think that communication and trust and friendship and, 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, it's not this, humans don't work like that. Humans- Yeah ... we, we're, we're here, you know? Let's, why, why are we, um, only talking about the ends of the, the bell curve constantly?

Yeah. Constantly. Um, and, and the, the, 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- That's not the case ... 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, I misrepresent my, quote-unquote, "lived truth" with a feeling that I have about a topic. Yeah.

And it's like, just because you feel that or- Yeah ... you might think it, doesn't mean it's right. And it, it's one of the biggest issues that I have about the free speech argument is I'm a h- I'm a open free speecher. I just ... 'Cause I wanna know, if you're gonna say some crazy shit, I wanna know what you think. And, like, I, I get the argument of, and I think this goes back to your, 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, a Kamala Harris apologist in, in any regard, in any regard.

But in that town hall with Anderson Cooper where he asked her about, uh, uh, what would she do differently, et cetera, her response was, "Well, I take it..." 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." She is. I don't often agree with her decisions, which is why I didn't vote for her, however, I think that response is accurate.

I- And the, the part that I thought was unfair to her was that only in a social media world does the response of, "I listen to all the facts, surround myself with people who understand the topic, and then make a decision," only in a social media world is that an improper response. 'Cause 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, it's impossible for any human- Yeah ... to know all the nuances of every topic in- Yeah ... in a 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, 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. Um, so I wanna, I wanna swing back and, and put this really into tactical sense.

So your work, um, you were, uh, 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. Mm-hmm. So if I am in a, one of probably the most important roles in an organization, which is support of leadership, um, how, how do I, coming from that position where there is, there is an obvious hierarchical role, you know, maybe relative to how it's positioned, but there is an obvious hierarchy. Mm-hmm.

This is your boss. You are supporting this person. Mm-hmm. How do you communicate, how do you be disagreeable in a productive way? Because I, I think a lot of people in these hierarchical situations, they feel like, "Well, I can't say that to my boss 'cause then they're not gonna like me or I won't get promoted."

Yeah. We, 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. Uh, 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 operated in for the last 24 years- Yeah ... 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, 'cause I don't even wanna bucket them in leaders. Leaders are everywhere. Yes. Um, they don't, they don't wanna know.

They don't want that. Um, especially coming from an administrative staff person, uh, where we're seen as not being very important, we're seen as doing all the, the end work, you know? But, um, the business wouldn't go without administrators. The business doesn't move. Mm-hmm.

You don't sell anything if you don't have anyone putting the things on your calendar. So, um, 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.

Okay. So I help ex- assistants become better assistants, and I help executives work with their assistants better. Mm. Because I know for a fact when this partnership works, the business is unstoppable. I did it with Simon.

I've lived through it, um, when there is a good partnership. So, um, you know, and an, 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, uh, how can we make that partnership work? So I train both sides, 'cause it's not just about the administrative side. Yeah.

Um, for the administrative side, we have to understand, um, what we're doing here, that we have a role, that our role is important, that we have information and skillsets, 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 into little bite-sized nuggets and color-code it, for crying out loud. So it's a skillset that we don't have. So for the assistants, you know, when you're, when you need to say something, it's not, "Mah, mah, mah, mah." Come with facts.

Why? Who? Where? When? Give, give a solution.

Come with an answer. Come prepared. Uh, 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 end, 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, 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. Um, so ask our opinion. What do they see that you don't see? How- what do you know that I don't know? Um, and just in general communication, I think that would just help everyone.

Like, what, what do you know that you could put in my brain that can help me be better? Tell me more. Yeah. Give me more information. I hate, I hate your first comment that executives don't, don't appreciate or respect assistants because, uh ...

So I re- I exited last November, uh, in, in 2023 from a company that I had founded, and the only person that I brought with me to my new venture was, uh, my head admin. She's the best. Like, I, I tell her all the time, like, "I fi- I found someone who can, like, put up with me, and, like, is, 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- Yeah ... till I am no longer an executive, you will Right ...

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, I believe you, and I, I 100% believe you, and I, I just think it's so shortsighted. W- 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- Mm-hmm ... I, you know, she says, "You're, you're full fire hose all the time." Like, she's like, I, I, I d- I never get anything in chunks.

It's, you know- Yeah ... I do like, and, and I ... Again, I'm, you know, you talk about offending the, 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- No, no ... you know, I kinda, like, take stories and I'm moving back and forth, and she's like, I ... You know what she, she's like, "I just listen for all the shit in the middle."

She's like- Yeah ... "When you go off over there," she's like, "I'm I kinda 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- It- ... oh, my God, like I would never be able to do this shit. So is it, are you dealing with ego?

Are you dealing with insecurity? Is it like, this is my first time leading? Like, I, what ... Or being in executive position. Like, what are the reasons that ...

And, and, and what I'm hoping for is the audience picks up on maybe some of their own personal characteristics that they- Mm-hmm ... might be missing on. So, like, what are some of those things that someone should be self-aware about to- Sure ... to maybe understand how they're playing a role in not optimizing the relationship with their assistant? Sure. Okay. Um, well, I'll give you, um, two, two ones that I, I hope it's not, and I'll give you the, the one that I hope everyone fits into.

Um, absolutely could be ego. You know, there's, there's a big history with our profession dating back to when we were secretaries in the Mad Men days, and, uh, there certainly wasn't a lot of respect for that role back then, and that has continued on because a lot of those, um, executives are still in business at the ripe old age of 85 years old and trying to tell us 40-year-olds- Please, boomers, move on ... what is happening. Move on. Um, so- We love you, but move on, boomers ... it's ego. It's ego, and it's a disrespect of the profession.

Um, but what I really hope it is is a, is a, is a misunderstanding of the profession, you know? I, 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 gotta be easy because it sounds easy. It's gotta be easy, so it's, it's easy." Well, it's not easy. It's one of the most difficult roles you can hold because we don't support ... Uh, 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.

Um, and so I think it's just a real, it's a misunderstanding of the role. It's a misunderstanding of, uh, the, the type of person you need to accomplish the goals that you want to accomplish in your business. Um, as a recruiter, I do a lot of recruiting for executives, helping them find assistants. The heavy majority, and I'm gonna 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, and really become that sort of chief of staff mentality and, 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. 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 gonna get. So there just has to be a bigger understanding of what the profession is for, what it's required, and, um, the, the difficulty that it requires, and to be paid appropriately, or to at least be acknowledged appropriately.

I had a friend who, uh, I was talking to him about how to get the most out of my admin team. This is early in my business. Mm-hmm. 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% on everything.

There's no miss. If you have a meeting that gets misscheduled, they get in trouble. If they mistake a note, they get in trouble. If, if they, 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." Mm-hmm.

And he's like, "Just have 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- No, and we get blamed for things that don't even, that we don't even do. Yeah.

I have to cancel a meeting with somebody else's executive because my executive's 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's 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. Yeah.

How, 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, if I'm the top. A- and, like, the getting to know them as a person, their family, like, that, that, it, to me it feels important, but at the same time there's, there's obvious- there's, there's obstacles and trip holes or, uh- Sure ... trip wires there. Like- Yeah ... how do you navigate that professional and kinda 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, in the larger corporate arenas, um, 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, some of that may be not as necessary, and maybe you don't want to. That's fine. Um, but if you're in a situation like you are with your assistant or I was with Simon, I mean, you're together a- 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, uh, 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? Yeah. It's, it's not a relationship unlike dating. Yeah.

You gotta go through it. You gotta go through some of these, like, things and what do they like and what do I like and how do I say that better so that they understand me and do what I'm gonna say? And, you know, you gotta 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, it's funny.

I had a moment where, uh, ear- early in my, in my business, in my relationship with this particular individual, um, I, I got divorced. I had 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 coworker, 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, 'cause 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, it's, it's how, it's how comfortable you are and how comfortable they are. Yeah. It, it's all about that.

It's, you know, i- i- as long as you're not sexually harassing, sexually abusing, calling somebody names, you know, HR, t- 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. Mm-hmm. If they didn't give a crap about you, they wouldn't give you any advice.

Yeah. They care about you going on these dates. They want you to be happy. They want to encourage you 'cause 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, I, I completely agree with that. I think, you know, the other thing, too, that some- I think gets lost on some of my peers that I've, that I've talked to about this particular topic is, like, that person, and, and correct me if I'm wrong in this assumption, but a lotta 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 gonna 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.

Yeah. 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? Yeah. Like, they want you to be successful.

You should use them. Yeah. 'Cause I got buddies that will get assistants, and they won't even use them. Like, they'll, they'll 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?" Yeah.

I'm sure they want to. No one likes sitting around on 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's fun, and maybe that does it for you, and maybe that fills your bucket. And if you wanna waste $3,000 on a really beautiful computer, or sometimes more, to play Solitaire, go for it. The, you're the one, you're the one not getting the benefits out of that. But just know that there's 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- Yeah ... success at that point.

So let's flip the conversation to how we find, uh, a good assistant, and by good, I mean relative to that particular individual. I don't necessarily- Yep ... mean good in general. Um, I have a lot, a, a lot of the conversations that I'm in in different, in different groups is they can't find somebody. That, to me, um, I always see as a cop-out, and I always, that's why I don't get invited back to a lot of these groups is my response will be- ... "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 how- Yeah ... 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 have, I have a, 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, u- understanding a human's life and how they operate. So, you know, it's, it's something that, um, it, it can't just be put in the skills bucket.

You know, when I see these resume, uh, job descriptions that go out, it's like they need to know how, uh, 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 gonna apply because this tells me nothing. Um, so in all the job descriptions that I make, I talk more about the human that is needed for this role. Is this executive ... Uh, 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- Yeah ... 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.

Yeah. Um, and so he needs a certain type that's gonna be okay with that, a little tougher skin, a 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 gonna wanna pick up the phone and go, "Hey, how are you?" That's the, that's the trick. Do I wanna talk to her?

Do I wanna talk to this person? Um, 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, or do you need to be quiet? You know, I'm a particular personality.

If, uh, p- so 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. That's a really good point.

So ask for the human that you need. Yeah. I, I ... Oof. Yeah, that's, uh, that feels right on the mark to me, 'cause it, a lot of the things ...

W- what I find interesting to, to what, to your point is the things that the, 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. Like, manage my calendar- If you're a skilled EA- Yeah ... if you have been an executive assistant for five years, you know how to do a calendar. Yeah. But- You do ... it, the, the complaints are never he or she isn't managing my calendar properly. It's they, uh ...

You know, I'd really like them to be there at 8:00, 8:00, log in at 8:00 every day, and they log in at 8:30 'cause they have a kid. Oh. And it's like, well, did you say that it was like a hard line that they had to be there at 8:00? 'Cause- Did you say it in words- Yeah ... out of your mouth? 'Cause if you didn't, then you didn't set the expectation. And, and I talk about this a lot, um, in my world, which is the insurance industry, is we're just so bad at setting expectations for people. Yeah.

Yeah. We're so bad at setting expectations. Like, your expectation, y- and, and people are like, "Well, what does that mean?" And it's like, like you just said, like, I'm gonna write emails to you, and I'm not gonna put a smiley face emoji at the end. Is that okay?

Like, are you gonna survive, or is that gonna be okay? 'Cause I'm not gonna do that. Like, I'm just not gonna slow down enough to do that. Is that okay? Like, do you need that in your emails? Yeah.

And, or, you know, whatever. And, and it's like some people sh- 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." Okay, great. Or, "I'm not gonna do that.

Sorry." And now we know. But- Right ... it's, 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 qual- 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, uh, "Do you need constant reinforcement?" They don't ask those questions. Yeah. 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 gonna 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. Yeah. 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. 'Cause some of us love that. Yeah. Some of ... Yeah, people are gonna be okay. And, you know, I think, um ...

You know, it, it, it's funny. You know, the, the, the conversation often does not ... It's, it's like, what do I need? I'm the one hiring you. It's what I need, right?

So I, 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, 'cause I'm afraid I'm gonna offend somebody, or they're gonna sue my company if I ask them the wrong question," because, you know, I, it does feel like the last 10 years or so, some of the things that you're talking about have become a little taboo. May- maybe, and maybe this might not be accurate, but at least from a, a belief standpoint, I think a lot of executives feel like they can't actually ask some of those questions, right? They can't dig into some of those things 'cause they don't wanna discriminate or they don't wanna- You know, in a, in a very shallow way.

They just don't wanna get in trouble for saying certain things. Yeah. So what can they say? How do they approach some of these topics in a way that, um, you know, I, I hate, I hate offensive because of- of being offended is a choice, but like how do we not be ... How do we, how do we be accurate in our speech and our expectations while still maintaining whatever the, whatever the proper HR is that we can, that we can talk to them about, I guess?

Sure. Sure. Um, well, you know, what comes out of our mouth is 100% under our control. Yeah. So if what you're saying is ignorant and rude, uh, that's how it's gonna come across.

So if you're being obnoxious and offensive, it's gonna be offensive. But there's a thousand way to say things, so maybe come up with a different way, and this is where the, the, the learning about how to communicate is really helpful, because there's other ways to say certain things. Um, 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 7:00 AM, I've already worked out, I've done the thing, I come here, I'm working until 5:00, 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 'cause 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 gonna have to do is just like for my ADD language. How do you feel about that? You know? It's, it's, 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. Yeah. 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," 'cause they're gonna see the poop. They're gonna see you in, in 48 hours after they take that job, without a doubt. They're gonna 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- Yeah ... be a real human instead of a robot. Yeah. So hard for people to do that.

It's so hard for people. And again, I, you know, I'll take this back to the communication is 'cause we're not really taught how to do it, and- Mm-hmm ... you know, for, for no, for nobody's fault, somewhere over the, over time, um, 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 w- it developed the same way that we can undevelop it, and that's about, that's by talking about ourselves, and not assuming you're like this, you do that. Um, and, and talk about more facts. Yeah.

It's, yeah, it's, this is ... It's such an intriguing thing, because now y- I mean, and then the o- the other interesting part is you can take literally the conversation we've had about an executive assistant, and replace executive assistant with any other person in your organization and all of this ... You know, hiring, uh, in, in the insurance industry in particular, there's a lot of conversations around it's very hard to find good help, and I- Yeah ... fucking hate, hate that line of thought, because there's so- How do you really feel, Ryan? ... there's so many amazing people out there. Yeah. And like, I'll give, I'll give you a- an example.

Um, we hired a lot of single moms and moms of young kids, because in our industry, uh, it 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- Okay ... they're v- yeah, they're very, they're very regimented, and this ... And anybody with, not just moms, but anybody with young kids understands the dynamic nature of their schedules, particularly the moms, 'cause they get oftentimes the lion's share of dealing with all the random shit that comes up from your kids.

Yeah. So we've essentially established this like, like when I would hire people, I'd say, "Look, like I don't ca- I don't care when you log in. If your kid, i- 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." Yeah. I was like, "Here's what it is, though.

We're a results-based organization." Exactly. "You have X number of sales, tasks, whatever your job is that you have to get done that we n- that we need you to get done. And as l- I don't care if you work two hours or 10 hours. If you get these things done, I'm gonna 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." Yeah. "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 just, I did this one thing right, so I'm gonna take a minute. Uh, of all the sh- stuff that I messed up, you know, this is 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 gonna lose my job 'cause 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." Yeah.

But so many people I feel like are measuring, a- and this goes back to our conversation, we're, as exec- we're measuring the wrong things in the relationship, right? Yeah. And every relationship with every employee is 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, you know, of the '80s and '90s that came up, and it was, "You do what I say not, not, because I, because I told you to." You know, I got heard that from a lot of my ex-bosses and a lot of my- Yeah ... and, and my father.

"You do it because I told you to." That's that good old boys mentality. That's, that's the good old generation, and, and it just keeps going on. So, you know, it's, if they're command and control with all their staff, they're gonna be command and control with their assistants too. Yeah.

So it's, it's a matter of do you wanna, you know, you trying to tell people what to do, or do you want people to get the job done? Pick. Yeah. I completely- Pick which one you want. Um, and, and hopefully, uh, this is the last surge of baby boomers- Yeah ... 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 gonna be taken care of by that company. Sure. And the thing that I tell all these guys today when I run into them and I'm getting the, "I pay them, why don't they do their job?" argument, which is another one- Ugh ... that makes smoke come out of my ears, is- Yeah ... 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. Yeah. Why do you expect that person to be loyal to you?

Right? Like that- Yeah ... that's the part that drives me nuts. I'm like, you wanna 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 without a second thought. Yeah.

So who would... I mean, think about any type of, uh, romantic relationship you've had. If the oth- if you're all in and the other person's only halfway in, that doesn't, that doesn't work. Yeah. So, um, I, yeah.

I, all right. I, we can, we've beat that up a lot. I wanna finish. I have one more question that I wanna hit you with and, um- Sure ... and we can wrap this up and, and be respectful of your time and the, and the audience's time. No, no, this is fun.

Um, how is AI impacting the executive assistant space? Sure. Sure. Uh, you know, a- as, as with many industries, everyone freaks out when, when AI came out, thinking it was gonna take over a lot of things. And frankly, it has in, in, in many professions everywhere.

I mean, if I was a copywriter at the moment, I'd be shaking in my boots with ChatGPT. So it's happening everywhere. Um, and it's just 'cause it's new and nobody understands it. I mean, when we got the computers, you know, uh, uh, uh, when, when we got a cell phone, everyone was like, "What about, what about, um, answering machines? Nobody's gonna have a, we're not gonna have voicemail."

And like, so, ugh. Um, but it has impacted in that, um, the job is no longer solely tactical. You know? There, there are those, um, 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, uh, 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, it's not just tactical, 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. Uh, so use it, you know? Get on the surfboard and ride it rather than be pissed off that the waves keep hitting your shore. You know?

We, you have to jump on these, these bandwagons 'cause it's, AI's not going away. Yeah. You know? I also think that this te- this particular technology more than, say, cell phones or VoIP, uh, for phones, uh, or, or the internet in general, this seems to be taking hold much faster. Oh.

It doesn't seem like we can sleep on this one like we could on the internet or having a cell phone or whatever. No. Like this, this feels to me like something in general, we have to be digging our, our toes in a little bit. Yeah. We gotta be playing with it and, um, I think, I think you make a really good point that, uh, trying to pretend like it doesn't exist or fighting it is not protecting your job.

Yeah. 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, y- 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 remember that too. It's, it's a different profession.

Yeah. You know? It's not, it's not like you're a CFO. It's different. Monique, this has been an incredible conversation.

People who are listening that want to, uh, maybe they need advice, they need gui- where do they go? How do they work with you? Sure. Um, how do they start to dig into your world and, uh, 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- Yeah ... who's gonna 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 assistants, um, as well as executives, I do coaching, I do speaking, 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. Um, on the executive side, I'm not a leadership coach.

I'm not a word, biz dev coach. I work specifically within the relationship of how you can operate better with your team, the humans on your team. Um, and then 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.

Um, moniquehelstrom.com. It's all my socials. It's all my, uh, website. Um, and you can just reach out. I'm a very human person.

My phone is, phone number is 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, using this, the SMEs around you.

You know, as you said that, that Kamala said, you find the SM- find the SMEs- ... that know what they're doing and, and hold onto them tightly. Thank you. Let's go. Yeah. Make it look, make it look, make it look easy.

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