--:-- Ryan Hanley: Hello everyone and welcome back to the show. Today we have an 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. 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.
--:-- Ryan Hanley: We have a conversation about not just how to find or hire an executive assistant, but how to be an incredible executive assistant, the dynamic between that role, that responsibility, and the power of really leveraging an executive assistant. We focus 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.
--:-- Ryan Hanley: 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.
--:-- Ryan Hanley: 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 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.
--:-- Ryan Hanley: If you're feeling super froggy and you really want to go to the next level, leave a rating and review or a comment on YouTube, Apple, Spotify. That tells those algorithms that this is a show worthwhile and that they should send more people to our community, to this content. It would mean the world to me. Ultimately, guys, and this is the reality of doing a podcast, your numbers matter when it comes to getting great guests. Monique is a busy individual, and I'm very appreciative of her taking time out of her day to share her expertise. To get great guests like Monique, we need to have numbers and we need to keep growing. Leave me feedback. If there's a certain type of person you want to hear, if there's a certain vein of content that you want to 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 I just love you for being here.
--:-- Ryan Hanley: With all that said, let's get on to Monique Hellstrom.
--:-- [Sound of a door or a lab setting, then a pause]
--:-- Monique Hellstrom: In a crude laboratory in the basement of his home. Oh, do you want me to wait?
--:-- Ryan Hanley: Sorry.
--:-- Monique Hellstrom: No, you're good.
--:-- Ryan Hanley: It's not live. I just started it so that we can go whenever, but you're good. It's not live.
--:-- Monique Hellstrom: 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. 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.
--:-- Ryan Hanley: You know what I find very interesting? There's the cliche around boys in particular. We could be arch enemies and then we have this physical altercation and then we come out of it and we're best friends. My best friend in high school happened that exact way. 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. This other kid was the most popular kid in school from the best part of town. We constantly butted heads because I was good at sports. I'm unpopular, poor, wrong side of the tracks, but I'm good at sports. And here's the opposite. It's like out of one of those 60s movies. You'd expect us to start snapping at each other in the halls. We literally hated each other.
--:-- Ryan Hanley: We played every sport the same for whatever reason, and we were constantly butting heads. Our sophomore year of high school, I went up for a layup in basketball and he followed me hard. Something broke in my brain and I just had enough. I literally tackled him and we're on the floor full out fighting. This is almost 30 years ago, so the coach is just standing there watching, probably smoking a cigarette at the same time. We go through this whole thing, bleeding, punching, kicking. We get up, look at each other. The coach goes, "Are you guys done?" Slap, bro hug. Best friends from that point on.
--:-- Ryan Hanley: It blows my mind. I want to bring it all the way back to you. That very long story tells 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. I guess my question for you, and this is maybe an odd place to start, but what I just described would horrify most parents of similar age kids today. Honestly, it's one of the moments in my life I'm the most proud of.
--:-- Monique Hellstrom: Amen. Amen. And I wish more people heard that. We're humans and we're messy and we have emotions and they come out and they make us think weird things. 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 my way or the highway. If I disagree with you, you're gone. You're dismissed. You're no longer useful to me. That is a disgusting habit. That is a new thing that has come along where the conflict is the end of the friendship as opposed to the thing that holds it together.
--:-- Ryan Hanley: I think a big part of this was when words became violence. When words are violence, me disagreeing with you means I'm being violent towards you because I'm just being disagreeable. One of the most listened to single episodes of this podcast that I ever did was last January with a buddy of mine who's a Democrat. I'm a Republican. In today's version of that, that means I'm moderate, slightly left during probably like 20 years ago. We had this conversation. The title of the podcast was "How to Disagree with a Friend About Politics and Still Love Each Other." We were literally disagreeing, but we were talking about it, being respectful to each other. Over the course of an hour and a half, we discussed three or four of the more hot button political topics at the time from where we were coming from. I love the guy to death. I'd take a bullet for him. He's an amazing human being. His life is based in faith.
--:-- Ryan Hanley: My point in sharing that with you is that people are dying 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. We can go both ways with the -ist. People are dying for that, but no one has the guts to give it to them today. Does that make sense?
--:-- Monique Hellstrom: Absolutely. 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. One thing I won't argue with someone on is when they dispel the truth. That to me is 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. The other side of it is, a simple word, you say something about somebody or somebody looked at you funny, especially with women. 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. I may have hurt their teeny, teeny little boo-boo feelings. I'm like, really? You can't just sit down and be like, "Monique, what you said was hurtful." I can take it. Who doesn't want to live in a world where occasionally your feelings get hurt? That's no fun.
--:-- Ryan Hanley: Hold up, everybody. Your feelings are going to get hurt. That's the part that I don't understand.
--:-- Ryan Hanley: I've been ostracized from many of my left leaning friend groups for the last eight years or so just because they have all these assumptions on what I believe because I voted for one president versus another. What I find interesting about those communities, as well as the ones where I get invited to mail groups that are like, "Let's just fire all our guns in the air and drive without seatbelts," I'm like, how can it be fun to only hear the same shit that's exactly what you agree with over and over and over again? That to me is the most uninteresting conversation to have. It's fun to bust chops and be in those groups and say, "Oh, look at those crazy this or that." It's all funny. But 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.
--:-- Ryan Hanley: 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 and organizations. We've lost our grip on how to define what truth is. Do you think that's the case? My question for you is, how do we have a conversation with someone either up or down the chain in an organization? Let's take it out of politics. We're talking inside a company with someone who 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?
--:-- Monique Hellstrom: Sure. The first thing you need is two willing parties. 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. The first requirement is having two open minded and willing parties that do want to have a discussion, because otherwise it's moot and it's not going to go anywhere. The other thing is, what 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 are differences there. You all have to be working on the same terms, knowing that there's an open-mindedness to the discussion.
--:-- Monique Hellstrom: Something that I always tell my coaches and clients is find that shared pool of meaning. Especially in an organization, what are you working towards? What's the goal? You're all working towards something. You just have different routes to take to get there. 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. 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.
--:-- Ryan Hanley: I love that. I had a leadership coach, and I'm forgetting his name because I've done way too many podcasts and I'm a terrible host. If I were Chris Williamson, I'd have the episode number right at my fingertips. We were having a similar but different conversation and he said, "Imagine a Venn diagram where just a tiny portion of the Venn diagram actually overlaps." He said what's happening in our country today, on all conversations, not just political conversations, it could come down to parenting, value structure, religion, et cetera. We are taking all the stuff outside of where we cross, and we never focus on that stuff in the middle. 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, "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," whatever your topic of disagreement is. 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. I feel like it's very sad that we can't have those conversations, or we aren't having those conversations.
--:-- Monique Hellstrom: Yeah, that's exactly right. I think we went sideways in a few different ways. I'll be the first person to say I think computers and social media have destroyed our ability to communicate. We don't even have enough time on this podcast to talk about how social media has destroyed communication and conflict. 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, 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. 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. Humans don't work like that. Why are we only talking about the ends of the bell curve? Constantly.
--:-- Monique Hellstrom: And the newfound issue of people confusing opinions with facts. 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 "lived truth" with a feeling that I have about a topic. Just because you feel that or you might think it doesn't mean it's right. It's one of the biggest issues that I have about the free speech argument. I'm an open free speecher because I want to know what you think. If you're going to say some crazy shit, I want to know what you think.
--:-- Ryan Hanley: I get the argument, 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. I'm not a Kamala Harris apologist in any regard. In that town hall with Anderson Cooper where he asked her about what would she do differently, her response was correct. In that moment, she probably needed to do a better job articulating it, but her response was correct: "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 agree with her decisions, which is why I didn't vote for her. However, I think that response is accurate. 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" become an improper response. Isn't that what we want our leaders to do? Do we expect Donald Trump or any of the people he appoints to just have every answer to every question at their fingertips? It's impossible for any human to know all the nuances of every topic in bite-sized social media chunks. I think it's very unfair to people who are trying to articulate deeper and nuanced opinions.
--:-- Monique Hellstrom: Yeah.
--:-- Ryan Hanley: That was a big diatribe with no question. 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. I want to swing back and put this into tactical sense. Your work, you were Simon Sinek's executive assistant and worked with him and did a ton of stuff. Now you coach people on how to be great executive assistants. Taking this communication issue to that level, 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 hierarchy, this is your boss, you are supporting this person, how do you communicate? How do you be disagreeable in a productive way? I think a lot of people in these hierarchical situations feel like, "I can't say that to my boss because then they're not going to like me or I won't get promoted." 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?
--:-- Monique Hellstrom: Sure. I'll push back on you, though. Most leaders do not want that information. Working in the world that I live in and operate in for the last 24 years, leaders do not want to hear 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 as leaders. Leaders are everywhere. 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.
--:-- Monique Hellstrom: I work within the relationship between an executive and their assistant. I help both sides of the equation. I help assistants become better assistants and I help executives work with their assistants better. 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. An executive's productivity can increase between 20 and 50 percent when they have a good partnership. Think about if you could get 50 percent more work done in a day, in a week, in a month, in a year. How can we make that partnership work? 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 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. It's a skill set that we have.
--:-- Monique Hellstrom: For the assistants, when you need to say something, come with facts: why, who, where, when. Give a solution. Come with an answer. Come prepared. 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." When I would come to him with problems, he'd say, "You're just coming to me with a problem. Come to me with a solution. I don't need the problem." For the executive side, be open to the things that this group of people see. We see things differently. 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. Ask their opinion. What do they see that you don't see? What do you know that I don't know? In general communication, I think that would just help everyone. "What do you know that you can put in my brain that can help me be better? Tell me more. Give me more information."
--:-- Ryan Hanley: I hate your first comment that executives don't appreciate or respect assistants. 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. I tell her all the time, "I found someone who can put up with me and is okay with the way that I communicate and operate and for some reason can decipher my craziness into things that actually get done. You're coming with me forever. You will have a job for the rest of your life. Until I am no longer an executive, I will make sure that you are always employed. You're coming with me." I believe you 100%.
--:-- Ryan Hanley: What are the primary things? Is it ego? Is it insecurity? I do a lot of crazy shit as an executive. She says I'm full fire hose all the time. She says, "I never get anything in chunks." I do the Donald Trump weave with the way that I speak, which is probably obvious in my responses to you thus far. I take stories and I move back and forth. She says, "I just listen for all the shit in the middle. When you go off over there, I kind of stop listening. Then I wait for you to come back. Then I catch the stuff in the middle and then I let you go off again." I'm like, "That's amazing. I would never be able to do this shit."
--:-- Ryan Hanley: So is it ego? Is it insecurity? Is it "this is my first time leading"? What are the reasons that... and what I'm hoping is the audience picks up on some of their own personal characteristics that they might be missing. What are some of those things that someone should be self-aware about to understand how they're playing a role in not optimizing the relationship with their assistant?
--:-- Monique Hellstrom: Sure. I'll give you two ones that I hope it's not, and I'll give you the one that I hope everyone fits into.
--:-- Ryan Hanley: Absolutely.
--:-- Monique Hellstrom: It could be ego. There's a big history with our profession dating back to when we were secretaries in the Mad Men days. There certainly wasn't a lot of respect for that role back then. 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. Please, boomers, what is happening? We love you. It's ego and it's a disrespect of the profession. But what I really hope it is is a misunderstanding of the profession. 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. For whatever reason in the support and administrative profession, it's like, "It's got to be easy because it sounds easy." Well, it's not easy. It's one of the most difficult roles you can hold because we support a human, and all humans are different. We have to support the human in the way the human needs. We have to mold our personalities constantly. I think it's just 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.
--:-- Monique Hellstrom: As a recruiter, I do a lot of recruiting for executives, helping them find assistants. The heavy majority, and I want 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. I say, "Great. How much money do you have for them?" "I don't know, $50,000, $60,000. Is that okay?" I'm like, "Would you pay a CFO that?" It's the difference between a CFO and a bookkeeper. You want a bookkeeper, that's what you're going to get. There just has to be a bigger understanding of what the profession is for, what it's required, and the difficulty that it requires to be paid appropriately, or to at least be acknowledged appropriately.
--:-- Ryan Hanley: I had a friend who I was talking to about how to get the most out of my admin team. This was early in my business. 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 you have an event in the office planned and it doesn't happen or the food's not there, whatever you've tasked them with, they don't get to miss." He said, "Just have appreciation for that." That really opened my eyes. I felt blessed that he gave me that advice so early in my career.
--:-- Monique Hellstrom: They literally don't get to miss. And we get blamed for things 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. I'm the one getting called names for that. Anything that our executive does, your executive promises that you'll get something done by Friday, and then somebody is asking you, "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.
--:-- Ryan Hanley: How personal should that relationship get? I have 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. Getting to know them as a person, their family, that feels important, but at the same time, there are obstacles and tripwires there. How do you navigate that professional and kind of personal nature that ends up developing with an assistant?
--:-- Ryan Hanley: It really will depend on your organization and who you are, I guess, as an executive. I tend—this is a generalization—but in the larger corporate arenas, everyone sort of has their job. Everyone has their box. The admin support has their box. So it's not really a personal relationship. They're not doing personal tasks for you. Everything has to revolve around the professional world. So some of that may not be necessary, and maybe you don't want that. That's fine.
--:-- Ryan Hanley: But if you're in a situation like you are with your assistant, or I was with Simon, you're together all the time. It's constant communication. 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. We know everything anyway, so let's just make it a real personal relationship.
--:-- Ryan Hanley: It's not unlike dating. You have to go through it. You have to go through some of these things. What do I like? How do I say that better so they understand me and do what I'm going to say? You have to work out all that mushy stuff in the middle. Then you're dating, and then you're in it.
--:-- Ryan Hanley: It's funny. I had a moment early in my business, in my relationship with this particular individual. I got divorced. I was married for 13 years, and life happens. What was funny was, you go through the mourning period, and then you start dating again. Now all of a sudden, my coworker and another coworker are giving me dating advice. I'm sitting there thinking, I'm happy for this, but at the same time, I'm really glad there's not an HR person on the phone right now. I don't know how much of this we're supposed to be talking to each other about.
--:-- Ryan Hanley: It's your company. It's how comfortable you are and how comfortable they are. As long as you're not sexually harassing, sexually abusing, or calling somebody names, HR-wise, giving someone dating advice... I don't know. When I have my assistant, I want them to know about my life. Because 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.
--:-- Monique Hellstrom: Yeah, I completely agree with that. I think the other thing that is lost on some of my peers that I've talked to about this topic is that person—and correct me if I'm wrong in this assumption—a lot of times your assistant attaches their professional success to your professional success. They see that as you move up the ladder, as you move to another company, as you grow in your career, they're going to be brought along. There are more opportunities for them to make money, go to cool places, whatever the perks are of that particular job.
--:-- Monique Hellstrom: There's a disconnect. You need to do a good job because that person is piggybacking you to a certain extent. They want you to be successful. You should use them. I have buddies that will get an assistant and they won't even use them. They'll give them menial tasks. I'm like, she's really smart, or he's really smart. 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 on their hands.
--:-- Monique Hellstrom: I equate this to something I often say to my executives. Let's talk about this. I just gave you the most beautiful brand new MacBook computer. It's got all the bells and whistles, huge RAM, every program you've ever imagined. And you're using it to play Solitaire. That's fine. Solitaire is fun. Maybe that fills your bucket. If you want to waste $3,000 on a really beautiful computer to play solitaire, go for it. You're the one not getting the benefits out of that. But just know that there are a million other things your assistant could be doing and could be helping you with. You are the barrier to your success at that point.
--:-- Ryan Hanley: Let's flip the conversation to how we find a good assistant. By good, I mean relative to that particular individual. I have a lot of conversations in different groups where people say they can't find somebody. To me, I always see that as a cop-out. That's why I don't get invited back to a lot of these groups. That seems more like a you problem, because I know there are plenty of smart people out there who would love a good job that pays well, that's exciting, interesting, and engaging. So what are they missing? Where do they go? How do we start this search? How do we make sure we find the right person?
--:-- Monique Hellstrom: I have a million opinions on this. I think one of the biggest things is that people hire for the skill, not for the human. This is a very human role. We've been talking about it the entire time. This is a human profession because it comes with empathy, understanding, consideration, and understanding a human's life and how they operate. It can't just be put in the skills bucket.
--:-- Monique Hellstrom: When I see the job descriptions that go out, it's like, they need to know how to do calendar, one bullet; expense reports, a bullet; travel. There are like four things on there. Then they're like, "I don't know why I can't find the perfect assistant." It's because you're looking for Lassie. There are four bullet points on there. I don't know who you need. So I'm just going to apply because this tells me nothing.
--:-- Monique Hellstrom: In all the job descriptions 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. He's high-powered, 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. He needs a certain type that's going to be okay with that—a little tougher skin, East Coast mentality—as opposed to another executive who may need something very different.
--:-- Monique Hellstrom: 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? Please, please, please don't just put on your job descriptions four bullet points of the tactical needs. Put on there who the human has to be to put up with the other human, or to put up with the industry. What skills do they need? Fast learner. Do they need to be quiet? I'm a particular personality. Not everyone wants me. I'm loud, I'm ballsy, and I say what's on my mind. That's not okay for everyone. I want to be able to read in the job description that that's not okay for me. So ask for the human that you need.
--:-- Ryan Hanley: That feels right on the mark to me. 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. Manage my calendar. If you've been an executive assistant for five years, you know how to do a calendar. But the complaints are never, "He or she isn't managing my calendar properly." It's, "I'd really like them to log in at 8 every day, and they log in at 8:30 because they have a kid." Did you say that it was a hard line that they had to be there at 8? Did you say it in words with your mouth? If you didn't, then you didn't set the expectation.
--:-- Ryan Hanley: I talk about this a lot in my world, the insurance industry. We are just so bad at setting expectations for people. Your expectation... people are like, "What does that mean?" Like you just said, 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? Are you going to survive? Is that going to be okay? Because I'm not going to do that. I'm not going to slow down enough to do that. Is that okay? Do you need that in your emails?
--:-- Ryan Hanley: Some people want the person to come back and be like, "I really need to have a head pat once in a while. I just need that." Okay, great. Or I'm not going to do that. Sorry. Now we know. But the bitches are always the human stuff. It's never the actual tasks.
--:-- Monique Hellstrom: It's all the stuff that nobody ever actually screened for in the beginning. Nobody ever actually asked the question: Do you have kids? What time can you come in in the morning? Do you need constant reinforcement? They don't ask those questions, and then you hire them, and you come in and they're like, "This girl needs constant reinforcement. How dare she?" Don't blame her. She is who she is. The fact that she needs constant reinforcement has nothing to do with you and doesn't make her wrong. It's your problem that you didn't ask her, or you didn't say, "I'm not the type of person that's going to give you a smiley face all the time. Can you work in that world?" 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... I need someone who can drop everything at a dime. If I'm going to call them at midnight, well then say that in the job description.
--:-- Ryan Hanley: I often call my assistants at midnight. Put it in there.
--:-- Monique Hellstrom: Some of us love that. Some people are going to be okay with it.
--:-- Ryan Hanley: The conversation often does not go to what I need. I'm the one hiring you. It's what I need. So what can people say in the interview? I've had friends say to me, "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." It feels like the last 10 years or so, some of the things you're talking about have become a little taboo. Maybe this isn't accurate, but from a belief standpoint, I think a lot of executives feel like they can't ask some of those questions. They can't dig into some of those things because they don't want to discriminate, or in a very shallow way, they 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... I hate the word "offensive" because being offended is a choice. But how do we be accurate in our speech and our expectations while still maintaining whatever the proper HR guidelines are?
--:-- Monique Hellstrom: What comes out of our mouth is 100% under our control. If what you're saying is ignorant and rude, that's how it's going to come across. If you're being obnoxious and offensive, it's going to be offensive. But there are a thousand ways to say things. Come up with a different way. This is where learning how to communicate is really helpful, because there are other ways to say certain things.
--:-- Monique Hellstrom: 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'm someone who is in here at 7 a.m. I've already worked out. I come here, I'm working until five, and then I go home. 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. I tend to not give everyone directions because I forget. It's 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?"
--:-- Monique Hellstrom: It's not, "Can you deal with my personality?" It's, "Here's what I do. Here's how I operate. Here are the things that I don't know about. How can we work together on that?" Talk about yourself, talk about your needs, talk about your personality. 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 type of person are you? What type of people do you get along with? Just be a real human instead of a robot.
--:-- Ryan Hanley: It's so hard for people to do that. I'll take this back to communication. We're not really taught how to do it. For nobody's fault, somewhere over time, having an opinion or disagreeing became an insult. It became an insult to somebody else. That developed over a time period, but it developed the same way that we can undevelop it. That's by talking about ourselves and not assuming, "You do that." Talk about more facts.
--:-- Ryan Hanley: This is such an intriguing thing. 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. All of this applies. In the insurance industry in particular, there are a lot of conversations around, "It's very hard to find good help." I fucking hate that line of thought. There are so many amazing people out there.
--:-- Ryan Hanley: I'll give you an example. We hired a lot of single moms and moms of young kids, because in our industry, it tends to be very regimented. It's very "old fat white guy" ish. Great people, but just imagine every old fat white guy you've ever met. That's a lot of the insurance industry. They're very regimented. Anybody with young kids understands the dynamic nature of their schedules, particularly the moms, because they get the lion's share of dealing with all the random shit that comes up from your kids.
--:-- Ryan Hanley: We established this. When I would hire people, I'd say, "Look, I don't care when you log in. 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. 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. 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. But here's what I need you to get done."
--:-- Ryan Hanley: What's funny is I got handwritten notes in the mail from some of my team. I feel like I'm bragging. I don't mean to. Of all the stuff that I messed up, this one thing I did right. From these women, they'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. I was like, "Why? You're fucking awesome. Why would I let you go because your kid barfed at school? That's stupid."
--:-- Ryan Hanley: But so many people are measuring the wrong things in the relationship. Every relationship with every employee is different, but particularly this executive assistant role. 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, and 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.
--:-- Monique Hellstrom: It's not. This is the old school mentality of thinking. It's the command and control executives of the eighties and nineties that came up. It was, "You do what I say because I told you to." I heard that from a lot of my ex-bosses and my father. "You do it because I told you to." That's the good old boys mentality. That's the good old generation. It just keeps going on. If they're command and control with all their staff, they're going to be command and control with their assistants too. It's a matter of, do you want to tell people what to do, or do you want people to get the job done? Pick which one you want.
--:-- Monique Hellstrom: Hopefully this is the last surge of baby boomers making decisions. That command and control structure only worked when the people 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.
--:-- Ryan Hanley: The thing that I tell all these guys today when I run 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. Over the last 20 years, whether it's your organization or just society in general, corporations have taught employees 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. 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 without a second thought. 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.
--:-- Ryan Hanley: We've beat that up a lot. I want to finish. I have one more question 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?
--:-- Monique Hellstrom: As with many industries, everyone freaked out when AI came out, thinking it was going to take over a lot of things. Frankly, it has in many professions everywhere. If I was a copywriter at the moment, I'd be shaking in my boots with ChatGPT. It's happening everywhere. It's just because it's new and nobody understands it. When we got computers, when we got a cell phone, everyone was like, "What about answering machines? We're not going to have voicemail."
--:-- Monique Hellstrom: It has impacted the job in that the job is no longer solely tactical. 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, "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, "I heard this in the meeting the other day, but she said that in the other meeting. What if I put those two together?" 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. 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.
--:-- Ryan Hanley: I also think that this particular technology, more than say cell phones or VoIP for phones or the internet in general, 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. This feels like something in general we have to be digging our toes into. We have to be playing with it. Trying to pretend like it doesn't exist or fighting it is not protecting your job. It's absolutely making you more expendable.
--:-- Monique Hellstrom: 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, how empathetic you are. Being really good at this job sometimes isn't about the tactical work. We have to remember that too. It's a different profession. It's not like your CFO. It's different.
--:-- Ryan Hanley: Moni, this has been an incredible conversation. People who are listening that want to maybe get advice, where do they go? How do they work with you? How do they start to dig into your world? If they already have an executive assistant and want to become better, if they are an executive assistant and want to become better or find that person, find their person who's going to help them, whether it's up or down the chain, how do they connect with you?
--:-- Monique Hellstrom: For anyone out there who is in that dynamic of an executive and assistant, for assistants as well as executives, I do coaching, I do speaking, and I do recruiting. 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. 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 biz dev coach. I work specifically within the relationship of how you can operate better with your team, the humans on your team.
--:-- Monique Hellstrom: 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. You can just reach out. I'm a very human person. My phone number is unfortunately everywhere, so you can also just pick up the phone and call me.
--:-- Ryan Hanley: I love it. Guys, we'll 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. 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. I'm so happy to have you on the show. Thank you so much.
--:-- Monique Hellstrom: Thank you. I hope your team can understand there is a way to be more productive. It's using the SMEs around you. As you said, find the SMEs that know what they're doing and hold on to them tightly.
--:-- Ryan Hanley: Thank you.
--:-- Monique Hellstrom: Let's go.
--:-- Ryan Hanley: Make it look good.
--:-- Ryan Hanley: Thank you for listening to The Ryan Hanley Show. Be sure to subscribe and leave us a comment or review wherever you listen to podcasts.
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