I had the honor of speaking with Monique Helstrom about what it means to lead as an assistant, what executives should look for in assistants, how the EA role provides so many unique opportunities to learn, and that time she got a voicemail from Will Smith. 🙂

Monique Helstrom episode 16 podcast

Monique served as Executive Assistant to Simon Sinek – New York Times Best-Selling author and TED celebrity. Though her official title ended up becoming, “Chief of Simon.”

She now speaks and trains executives and assistants on how to build confidence within their partnership.

I learned so much from my conversation with Monique, so whether you’re an executive or an assistant, I know you’ll benefit from this episode.

P.S. – Monique and Bonnie Low-Kramen are hosting an event in NYC in October. Be sure to check it out here.


If you always do what you’ve always done, you’ll always get what you’ve always got.

– Henry Ford

About Monique Helstrom

After serving for nearly a decade as the Chief of Simon Sinek, Monique has had unparalleled opportunities, unique experiences, and perspective shifts. With the tools she’s accumulated in her own successful career as the primary support person for one of the most influential thought leaders of our time, Monique helps people decipher and disentangle the common, yet rarely discussed issues plaguing this indispensable partnership.

Monique helps both Executives and Assistants build confidence within their relationship by focusing on their own innate strengths and natural abilities.

In addition, Monique helps startups and new businesses grow.


monique helstrom headshot


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Monique Helstrom 0:00
Hello, I’m Monique Helstrom and today’s leadership quote is from Henry Ford. If you always do what you’ve always done, you’ll always get what you’ve always got.

Podcast Intro 0:14
The Leader Assistant Podcast exists to encourage and challenge assistance to become irreplaceable, Game Changing leader assistants.

Please review on iTunes, you’re listening to Episode 16.

Jeremy Burrows 0:29
After serving for nearly a decade as chief of Simon Sinek, New York Times bestselling author and Ted celebrity, Monique Helstrom has had unparalleled opportunities, unique experiences, and perspective shifts with the tools she’s accumulated in her own successful career as the primary support person for one of the most influential thought leaders of our time. Monique helps people decipher and disentangle the common yet rarely discussed issues plaguing this indispensable partnership. Monique helps both executives and assistants build confidence within their relationship by focusing on their innate strengths and natural abilities. In addition to speaking and training, Monique offers her organizational experience to new businesses and startups looking to grow and evolve. I’m very excited to have Monique on today’s episode, we have a great conversation. Let’s jump right in. Hey, everyone. Thanks for tuning in to The Leader Assistant Podcast. Today I have a special guest Monique Helstrom. Monique, thanks for joining me.

Monique Helstrom 1:38
Thanks for having me, Jeremy.

Jeremy Burrows 1:40
So let’s talk a little bit, go back in time a little bit and talk about your very first job. Maybe your first you know where you had to pay taxes job.

Monique Helstrom 1:51
That’s funny because I actually read on there was it my first first job like working with my father and construction, which I started when I was somewhere between the ages of six and eight, my father built houses. So during weekends and nights and summers, we always worked with him and did lots of manual labor. But think my first job, I was a bagger at a grocery store in Philadelphia and I actually lied to make myself are older. Because I really wanted a job I knew at even at the age of 13, I knew I had to save for college. So I lied and told them that I was 15, which was the legal age to work so that I could start making wages. So that tells you anything about me. But yeah, it was a bagger in a grocery store.

Jeremy Burrows 2:39
So what did you learn from that role? Maybe from how you got the role that you applied in your career.

Monique Helstrom 2:50
You know, it was a very service oriented job. And I was very young. So I was lucky enough to understand the value of living and working in service to others and just something small, and what seemingly could feel meaningless to you might change someone’s day. So I always really tried to specifically watch the customer see what their needs were and see if there’s any just little thing that I could do to help brighten their day. Definitely was the start of my service career.

Jeremy Burrows 3:23
So when did you become an assistant and why?

Monique Helstrom 3:29
Well, I became an assistant, I’ve always had some sort of logistically minded job. The official time of when I became an EA is questionable because my my first big job as an event planner, was sort of assisting the director of the department where I was kind of helping her out. And my title didn’t say as much, but that’s pretty much what I was doing. Then I went on to owning my own company. I was a professional organizer. And that’s actually where I met Simon. And so officially my first executive assistant job was in 2011 with him where I actually had the title. But I started off as I said, As an event planner, assisting the director of the department in tourism and hospitality association.

Jeremy Burrows 4:16
So was there when you were doing that, And you said you that’s how you met Simon, did you run an event for for him or something?

Monique Helstrom 4:25
I did. Yeah, this was way back in 2007, I want to say or 2008. I was both running the professional organizing company as well as planning some events on the side just because I knew how to do it. And I had a girlfriend of mine who was in need of some help with planning some events and I met Simon he was on you know, speech number six or something like that. He had really just started out there publicly speaking. And so I was the event planner, and he was the speaker. And we you know, I really I loved what he had to say I love his movement, I loved his vision of the world. I love the world that he was trying to build. And so after the event, we started talking and, you know, I told him, I’m in your tribe, I don’t even know what that means. But I’m a part of your tribe. And we just became very good friends for years and years and years. Whenever he would come into LA, we would hang out, or if I went back to Philadelphia, go up to New York. And, you know, his celebrity name was growing. And his experience was growing, as was mine. And so back in 2011, when I did eventually move back to Philadelphia, from Los Angeles, him and I connected on a project. And actually, I was moving him since I endedup up organizing a moving company, I was actually moving him from one location to another in New York, which I don’t recommend that anyone do ever. I think, if you live in New York, just you have to stay in the same apartment, because moving is, is the church’s thing to do. But yeah, I moved him. And so by the end of the first day, he sort of looked at me as like, I had four heads and asked me if I was always like this. And I said, What do you mean, and he was like, you know, all organized. And you know, and I think I had color coded post it notes with me or something really just bizarro. And he hired me that day, and said he wanted me to help him organize his whole life. So that’s how I got started.

Jeremy Burrows 6:21
So did you ever during your career doing event planning and all that kind of stuff, did you ever envision having this sort of chief of staff executive assistant role?

Monique Helstrom 6:34
You know, I did, I was always logistically oriented, and always in a role where I felt that I could build something. And so in every position that I’ve ever had, and I’m a rarity in that I’ve, I haven’t had that many jobs, I’ve mostly stayed at all of my positions for I think the shortest time I’ve ever spent at a job was five years. So I tend to stay for a long period of time. And, you know, as we grow up, it’s it’s not an a profession that is widely known. It’s not like going through college, there was a specific wing that I could take to be the best executive assistant possible. As you will know, there’s not a whole lot of education out there. But once I learned about it, I knew I was always going to fit in that spot pretty nicely, just because that’s where my strengths that lies, and I always thought it was such a cool job. So I was really excited when I got the opportunity.

Jeremy Burrows 7:28
So what’s the number one struggle you had as an assistant?

Monique Helstrom 7:34
Um, I would probably say it had a lot to do with me and my worthiness, my value, I had for a long time felt very bad that I wasn’t at the center of the decision making process, you know that I wasn’t the Wizard of Oz, I was only asked for drugs behind the curtain. And that took a toll on me. And I think I looked up to those in the visionary position in the strategic position in an executive position. And I sort of envied what they had, they had this power that I didn’t have, or they had this way of words that I didn’t have. And I always sort of felt like I was second best. And so for my my first four years in this career, working with Simon, I think that’s, that’s what plagued me more than anything was my own value and what I thought I was worth. And once I really got to understand what my value actually was, and how nothing in that association got done without me and like most executive assistants, or just assistants in general, nothing in their office gets done without them. It really changed my viewpoint and changed my perspective on really what my skills were worth, and how I could help the large organization.

Jeremy Burrows 8:49
You struggle with your value. You said, so was part of that the maybe dehumanizing interactions that you might have had with people who also kind of had this, you know, put people like Simon Sinek on a pedestal or the visionaries are the ones that are important. And, you know, did people try to get close to just to get close to Simon? And did that play a part of your personal struggle with kind of where you placed your value?

Monique Helstrom 9:20
It didn’t necessarily affect the bringing up of my struggles and my issues with value. I think I’ve had those since I was young, as most people do. And for the first couple of years within the organization, I certainly struggled with it. I think the the humanizing or devaluing from the external sources was, was just icing on that cake. Really. Certainly people tried to get close to Simon by getting close to me it happened more times than I care to talk about. But you know, when when you’re in a position of feeling devalued as it is, and then when that sort of incident happens It definitely can affect you and bring, you know, sadness, and what am I worth and all those sorts of things. I think once I realized what my own value was having those sorts of interactions changed a lot. And I, I mostly used humor. And I mostly understood that it wasn’t necessarily had anything to do with me whatsoever, that it really had to do with them and who they were and what they were going through at the moment and, and their need or want to get through to someone else. So I tended to, again, just I use humor, or I would just ask them, you know, why would why did you do that? Why did you go through me? What is it that you really need, and just try to help them actually get what they need to survive, as opposed to blocking them? You know, because they treated me in such a way.

Jeremy Burrows 10:51
So if there are assistants, which I’m sure there are, no, this is common, I’ve experienced that before as well. But if there are assistants listening, who kind of deal with that issue of everybody wants to, you know, comes up to me and says, Hey, you know, how’s it going? And then the next the next 10? Questions are about, you know, their boss, and how their bosses? What would you what would you say to assistants that are struggling with those types of interactions?

Monique Helstrom 11:18
Well, I mean, it’s human nature, right, I would first say, you know, people have to understand that it’s human nature. And for someone to want to access, you know, if you wanted to access someone, you would find any means necessary in order to access them. That’s one of the things that assisted still, you know, we, we are the spies that go and try to find a way to find that magical Person that our boss wants us to talk to. So I always kind of kept that in my head thinking, well, that’s something in a way that I do, I would never go about it in that manner, necessarily. But I certainly go by any means necessary to get the job done. So first and foremost, I would say just just understand that this is slightly human nature, and it might not be a malicious intent. I was trying to find the the best of our people and not expect the worst. But then I would, I would say, you know, communication, communication, that’s my real soapboxes, how people speak to one another, and the communication behind it. And I personally would just say, you know, this is how I feel, I feel as if you’re trying to get through me in order to get through my CEO, is that actually the case? Because if it is, then we can, I’m happy to help you in any way that I can. So please let me know what you’re actually looking for, like, cut through the chase, you know, actually ask the question that you want to know. And then move forward.

Jeremy Burrows 12:44
That’s great. So do you have any crazy stories or times when you save the day, or maybe both from your career as an assistant?

Monique Helstrom 12:55
I mean, I think we all have those experiences of some crazy days where you just never thought anything was going to get done. And then how you save the day, I think assistants on a regular basis, save the day, every single day. I mean, there is little innocuous things that you catch, the address isn’t in the calendar, or the flight time isn’t in there. And those teeny weeny little wins actually are very life changing and very day saving for your executive. So I think you know, the more we can pat, pat ourselves on the back and say we do do these things every day. But I certainly have crazy stories of fans and people bum rushing the stage to try and get to Simon and having to walk through security to get out that actually happened in Sweden, which was very interesting. Somebody rushed on stage to presumably tackle him. I’m not entirely sure what was happening. But there’s lots of fun stories about bands and things that they did to get close to him that are funny and strange all at the same time.

Jeremy Burrows 14:01
So did you ever have to physically tackle somebody?

Monique Helstrom 14:05
Not yet, but I definitely did used to use the title that I was I was both his executive assistant or chief of Simon and slash bodyguard. There are certainly a lot of interesting fans who would wait in line to have you know, Simon sign their book or whatever, and would bring various items from their house to get him to sign or, you know, some whatever it may be, or just, you know, girl fans that really wanted to spend their time and talk this time and I definitely had to block and tackle quite a bit. Not literally tackle but sort of just the blocking and tackling. And, you know, just to make sure that we could get what we needed to get accomplished at the event.

Jeremy Burrows 14:46
I mean, be honest, was it fun to do that? Was it fun to kind of like keep your eyes out and open at all times and like, you know, where where do I have to jump in and kind of handle the situation

Monique Helstrom 14:59
Oh, completely. I mean, that is so my wheelhouse. I’m a I’m an Army kid, my father was Army. So we got lots of training like an army battalion as a child. And so I think I was in a former life, I was probably some sort of a gladiator or spy or 007 or something, because I really did enjoy it. To be able to, you know, keep your eyes on the door, and where is everything? And, you know, where’s the exits? Who do I need in case of emergency, so on and so forth? All those kinds of things. Where’s the signal? I love it.

Jeremy Burrows 15:31
It’s funny, because I always dreamed of being in the FBI. I was a big X Files fan. So I was, yeah. And I always tell my wife, if I, if I wasn’t an assistant, I’d probably be like, you know, cop or FBI or something.

Monique Helstrom 15:47
I mean, hey, this skill set isn’t there are many skill sets that are not exactly the same. But what we do is really uncovering, uncovering history and covering how you get something done. So I can totally see that. And, and that just sounds fun.

Jeremy Burrows 16:03
Right? So what was the biggest mistake you made as an assistant? And what did you learn from it?

Monique Helstrom 16:10
I mean, I’ve certainly sent him to the wrong airport. And then all of a you know, not had car services show up, because I booked it for the wrong day, sort of all the things that all of us assistants go through on a daily basis and run into. But I think, for the most part, communication was an issue for me, I I realized, you know, in year two or year three through through this job that my communication was very one sided, like my side, basically not one sided, my sided. And when I was communicating with Simon a, I was taking all of the emotion out of it, it was just task task tasks. It wasn’t, I didn’t feel like I was communicating with a human, I felt like I was communicating with a task or a taskmaster. And that was all my doing. And I just, I just didn’t pay the relationship, enough attention to really work on my communication. So Simon and I, and this is a story that I’ve told before we were in the Chicago airport, after a very long week we had done, I want to say it was four cities in five days. And we were just both plumb exhausted, I don’t even know how we were standing up right at this moment. And I was feeling a nag that I had a lot of work that needed to be done that week, because while we were on the road, and on airplanes, I wasn’t getting as much done. And I knew I had to get some information from Simon. And instead of actually observing the situation, and understanding that both of us were exhausted. All I thought to myself was I need to get this done. So I need to get this done in any means any means necessary. So I pull out my notebook, and I start hounding him while we’re in line, question this did you do this? Did you do that? Did you do this? And this, he was just so exhausted. He looked at me with these just tired eyes. And he just said not now Monique. And he didn’t mean that in any sort of way. He just couldn’t answer these questions right now. And I was in such a way that I did not take that comment. Well, and we just started to have a big ol argument right in the middle of the TSA, precheck line and Chicago O’Hare Airport, screaming at each other and I mean sceaming at each other, it was very embarrassing. We had the security had to come over to us the whole nine yards. And we finally got through security to the other side. And I kept on barking because all he wanted to do was be right. I just wanted to be right. And I wanted to get my job done. And I wanted to prove to him that I was worthy. And so when we finally did get to the other side and actually sat down and had a conversation, he explained like, look, I’m I’m just tired. That was really it. I didn’t, I wanted to show up for you, but I just couldn’t. And that instance, changed me in so many ways. I sort of it held up a mirror to the insecurities that I had. And it held up a mirror to the ways that I was expressing these insecurities. So I did lots of work on my communication from that point forward and really listened to not only what they were saying, but spoke in a manner that other people could understand me. I realized how rigid I was, I you know how I needed to work on my adaptability. There was just a lot that came out of that one seemingly small incident, but I still think we might be on the Chicago airports do not fly list. So that was probably my biggest mistake that I had was was that incident.

Jeremy Burrows 19:37
Let’s talk a little bit about the opportunity to work on different types of projects. And I was you know, my previous boss was an author. So I was given the opportunity to work very closely with literary agents, publishers, editors, just very behind the scenes. I have a, you know, a book and I’d never even had any idea of what goes on behind the scenes of writing a book or publishing a book. And so I kind of got to see, you know, how the sausage was made. And what types of projects did you get to participate in? That gave you insight and exposure to things you maybe never would have been able to see? Or learn from? If you were not an assistant?

Monique Helstrom 20:26
Sure, I mean, that that answer is endless. So almost every project that I was involved in, I don’t know if I would have that opportunity. If I was working another job. I agree with you, you know, working in the literary world, figuring out how a book is published, it’s very interesting, it’s kind of zone world up unto itself. And so having that knowledge, you know, under my belt is something that has definitely helped me in so many ways. So I loved book launches, you know, we did lots of different events for book launches in different cities, and just how each city responded to the message or how each in each area, how they register for events, I mean, even just something as silly as that where, you know, some some different cities, you get people register right away, and sometimes they register for an event, two days before the events happening. So I had lots of different experiences, not only with the book launches, but Simon’s events, I mean, his events were so varied, for all kinds of different audiences. I think the the few that stick out to me was, you know, we had the immense pleasure of working with the military, United States military quite often and international, for that matter. And again, I’m a military kid, and I have nothing but respect and honor for, for what these soldiers do, and our sisters and brothers in the military. So working with with both them as well as law enforcement and, and various organizations like that, I think that was the most rewarding of all of the types of events that I could do, or, and just how I can help that sector of people. I think that’s something that I’ll never forget. And I would never have access to the rank and leadership that I was able to talk to, you know, through this through this event directors and colonels and, you know, people with lots and lots and lots of stars on their shoulders, I would have never had access to people like that had I not been in this organization. So I feel myself very lucky for that.

Jeremy Burrows 22:32
So I had a experience where my former boss was, in some circles was kind of, you know, famous, if you will. And he was the chaplain to the St. Louis Cardinals baseball team. And I grew up in Kansas City, Missouri. So I’m a huge Kansas City Royals, fan baseball is my favorite sport. You know, I’ve just just super diehard fan. And there was one time where he was the Royals were in town in St. Louis, and he was going to lead the chapel for the Cardinals and the Royals. And he’s like, Hey, do you want to come with me? And I was like, Heck, yeah, I do. And he’s like, No, don’t wear any Royals gear, because we’re going to Busch Stadium. But it was, my point is I was I was walking through the literally the locker room of the Kansas City Royals, the team that I, you know, since as long as I can remember, I rooted for, and I just had to be a professional. And so my point is, like, what, what’s a situation like that, where you were kind of maybe starstruck or just, you know, in all the opportunity, whether it was military event, or whatever, where you just, you just kind of had to put your fandom, if you will, aside and just be professional. Did you have any, any experiences like that?

Monique Helstrom 23:48
Sure. I actually funny, funnily enough, we did some work with the Philadelphia Eagles for a brief period of time, and I’m a huge football fan, and I’m from Philadelphia. So that unto itself, was I definitely had to keep keep myself together as we were sitting in the lunchroom. And I’m staring at guys that I have their jersey, like, I had this guy’s Jersey in my closet, and I’m looking at him and I’m watching him eat. I’m like, this is absolutely insane. So there are definitely instances like Dad, I mean, we just got to meet so many amazing people throughout. You know, I was with him almost a decade over over eight years. And so the people that I got to meet it was, it was incomparable. I think if there was one standout for me, at one point, Simon was actually at TED, and he met Will Smith, and I’m a huge real Smith fan, not only because he’s from Philadelphia, but I just really appreciate how he’s navigated his way and in the celebrity world for so long, with integrity and honor, and so I knew he was there and he said, You know, I might be able to meet up with Will Smith tonight, and I was just, I was biting my tongue. I was so jealous. And the next morning I woke up and I had a voicemail from Will Smith as Simon was standing right next to him, called me on his phone, and then handed the phone to Will Smith and I still to this day, have a voicemail from Will Smith, saying, hey, you know, hello Philly friend, and just some funny things and just stuff like that. I could have never imagined anything like that would happen to me.

Jeremy Burrows 25:24
So part of the reason that that happened to you and that I got to experience something like that with the Royals was because our executives were very understanding and empowering and letting letting us kind of see the behind the scenes and in paid attention. So how, what would you tell an executive, who maybe doesn’t let their assistant kind of in on some of these fun experiences like those, or, you know, is considerate and thinks about, you know, your personal affection towards Will Smith and going to spend a few minutes to do something like that, that makes your day or make sure, you know, decade? But then, you know, they think, you know, they’re just to schedule meetings and grabbing coffee. And you know, what, what would you tell an executive Who has not done that yet? Or?

Monique Helstrom 26:21
Well, I mean to this is this is another soapbox of mine is is having executives understand the benefit and the value of us executive assistants of what we have to offer. I think what I would tell an executive is is point blank, you’re missing the boat, you are currently the person who is getting in the way of higher increased productivity, increased efficiency, profits, resources, harmony in the workplace, like it is basically endless on what an assistant can do. And the person standing in the way that usually is the executive. You know, an assistant is someone who’s innately involved in almost everything that an executive does, sometimes even personally involved in what an executive does. And you would think that that would actually be the executives greatest competitive advantage, you would think this would be someone who they would want by their side, you know, an executive tends to sway towards a strategic focus a big picture thinking, no that that in the cloud view, and they shouldn’t be that they they need to be squarely in that position. Whereas an assistant focuses on detail on activation on the pathways through the forest, not over it. Both are important. None are better than the other, neither side of it is better than the other. But to me, wouldn’t, wouldn’t it be advantageous to have someone by your side who sees what you don’t see who knows what you don’t know, who can build what you don’t know how to build this person, when when of course, hired right and in the right spot, can can literally help your business increase in ways that you would never even imagine, give you time back in your day gives you more energy. And that’s that’s the the place that all that executive assistants really want to be in a place that they can affect change.

Jeremy Burrows 28:15
Soon as an executive is listening, and they’re convinced now you just convinced them to, you know, get more out of their assistant, empower their assistant. So what’s a tip that you would give to them to take that next step? And to actually do that?

Monique Helstrom 28:30
So, you know, for the beginning, I always get this question like what can an assistant and an executive do together in order to push forward to becoming this really powerful strategic partnership? And my first suggestion is, again, communication, communication, talk about where you are at the moment? What is the vision of the future? Where did these where does the executive want to go? Like, talk about it as if it is two years from now as if it is four years from now? Where do you want to be? Where is this company going? And where is this person going as a human? And how does this relationship work? You know, what are the what are the benefits of it? Where to where are the areas that you struggle, having these open conversations as one would with a partner like an actual, romantic partner? These conversations are so important, it’s it needs to happen in order for the relationship to grow. Second, I would say through the executive specifically, try and offer not only the content to your assistant, what they need to do and when they need to do it behind, but try to offer more context. Why did you ask for this test can be done? That is something that I think is, was a game changer for me. And my relationship when I was working with Simon was getting the context behind the content really helped me not only perform the task in a better way, but potentially perform 10 other tasks that he didn’t even know he needed. It’s like it If, if an executive tells an assistant, hey, will you go to the library and get a book out about Martin Luther King? Sure an assistant could go get a book out about Martin Luther King, that’s easy enough to do. But if an executive gives the context and says, Listen, I’m about to write a blog, or a book, or an article or something about those in history that have commanded large followings. And I need to get a couple of books about that, could you help me? Well, then the assistant could go to the library and get a book out about Martin Luther King, but also Julius Caesar, Genghis Khan, and Hitler, because all of those people also commanded large volumes of history. So that’s a that’s a pretty, you know, simple answer to that question to what the difference between context and content is, but again, you can see how this would help an assistant not only perform the task, but go beyond go beyond just checking off that box. So beyond just performing the task at hand, context is unbelievably important.

Jeremy Burrows 30:59
That’s great. So if you could snap your fingers and instantly give all assistance more of something, what would it be?

Monique Helstrom 31:06
That’s a great question. I would give them I’m going to cheat and give two

Jeremy Burrows 31:14
snap your fingers, you can get more fingers

Monique Helstrom 31:17
I want, I want another answer. First, you know, again, just because of my struggles with value, I would probably say pride, I would, I would hope to give more assistants, a sense of pride in who they are and their skill set. And then part two of that is the voice. I’ve heard more times than not executive assistants being afraid to speak up afraid to say something, even when they think it would be helpful, even when they think they have a better way of doing a project or a process. I’ve heard so many assistants say but I was just scared to say something, I didn’t want to have my boss, you know, make fun of me or think I was stupid, or raise my hand in that meeting or whatever it may be. I think once we can get our voice back, and knowing that confrontation isn’t always a dirty word, that or just having a communicate, you know, having an experience with someone or communication experience. I think things would change very quickly for us in our profession if we could find our voice.

Jeremy Burrows 32:24
So let’s shift topics just a little bit and talk about something that I don’t think people talk about much. But what would you say to an assistant who becomes romantically or sexually attracted to their executive?

Monique Helstrom 32:43
Interesting, I’ve never had that question before. I mean, you know, when you’re working so closely with someone, it’s it’s, it’s not understandable, I would say, but you’re working very closely with someone day in and day out. So, you know, I think there’s probably something behind this attraction is what I would say, you know, especially if, if an executive is in a situation like they’re married, or they have kids and they have a situation, or both sides are for that matter, I would probably want to help identify what’s behind the attraction for the assistant? Is it you know, is it something that they’ve been dealing with for a long time? Is it is it a part of their need, you know, maybe they lost a parent, maybe they have some sort of a need behind it, maybe there’s something that’s actually pushing the attraction, more so than just actually being attracted to this person. So I would probably work with both sides of it to see if there was any history, anything behind the attraction first. And then figure out how to move forward equitably, so that both teams can feel comfortable working together in that environment. But also understanding sometimes it just wouldn’t be a comfortable environment after that. So probably helping both of them solve the problem that they needed at hand wanting to get another job and the other to fill a spot to fill the hole for the executive assistant.

Jeremy Burrows 34:18
Yeah. Yeah, it’s an interesting can be controversial topic. I’ve had mixed reviews when I’ve when I’ve kind of brought this topic up in EA settings. I think the general thought that I would I would kind of add to that is, when you spend, like you’ve mentioned, when you spend so much time with someone, and you know, executive assistant usually spends, sometimes spends more time with an executive than the executive might spend with their spouse.

Monique Helstrom 34:49

Jeremy Burrows 34:49
So there’s just going to be a natural connection from spending time together with somebody. Sure. And so there’s just certain I think, personally, I think there are certain boundaries And whether it’s emotional, physical, social, even, that you can put in place, especially, particularly like you said, we’ve both parties are married, and our One of them’s married and has kids. Like, I think there’s just some mature character boundaries that you can put in place like maybe, you know, you don’t go to happy hour one on one with your boss, you know, that might be something that some people have to put into place.

Monique Helstrom 35:25
Absolutely. I mean, that’s a given, you need to avoid the, I want to say temptation, I’m not going to use that in a lighter sense, then then that word can can be used. But you have to avoid all the temptation to want to grow that relationship in that manner. You know, avoid personal outings like that avoiding, you know, getting into a position where you could be compromised, not only your job, but somebody’s future could be compromised.

Jeremy Burrows 35:57
Yeah, one of my one of my buddies is always like, I still can’t believe you’ve never been in a fight, like a physical fight. Well, my brother’s he’s like, No, like a real fight. Like, well, maybe because I’m smart enough to not put myself in situations where a fight might happen. Exactly. So I feel you there. Yes. All right. Well, let’s talk a little bit about if you are hiring an assistant, what would you look for? And maybe what’s a question that you would ask in an interview?

Monique Helstrom 36:32
Sure. So my perspective on this is slightly different than than most and what I encourage executives, and if I was ever going to hire an assistant, I, I would hire for values. This is so important that so many people do not do they write a piece of paper with some words on it, that say you need to be proficient in Google Drive and know how to use Slack. Well, it’s more than that. It’s values based, especially this job where you’re working so closely with somebody else, and you need to make sure you guys are in lockstep. So I personally recommend, and I would only hire for values because skills can be taught. For example, you know, if you were, if the executive is a family, man or woman who’s got kids, and you know, the husband, or the wife, or the partner or something, and they hire an executive assistant, let’s say who’s single has never had kids, and has never grown up around kids, now, there’s better or worse, so I’m saying that out loud, now, not dinging on either side of the coin there. But when the executive would say, Hey, I have to be out of here by five o’clock, because I need to go to a little Timmies baseball game. That means something else, if you value family, the way that your executive values family, that is something that they would go above and beyond to make sure that you got to Little Timmy baseball game, as opposed to someone who just doesn’t have that human experience. So I take lots of time, whenever I’m hiring someone, I get to know these people, as humans, what, what makes you tick as a human, what do you value in the world, if integrity is not in your top five values, I’m probably not going to hire you. Because that is one of my top five values. And then again, pass that skills can be taught, you know, whether or not you can load something up on Google Drive is something that can be taught. But having the same values as someone that you’re working so closely closely with, I don’t think is something that that you can get through resume. So I spend a lot of time I take potential training, you know, potential hires out, sit down with them, have a meal with them, talk to them about their history. And it’s not to be done. You know, secretively, but I will ask questions that that will reinforce or give me more information. So if, if I’m interviewing a potential candidate, and I say, you know, one of my biggest values is honesty, and they say, Oh, me too. Me too. One of my biggest values is honesty. 10 questions down the line, I might say something to the effect of, you know, how many times have you had to lie for your job? Isn’t that funny? See what they come back with? Because if they say, oh, yeah, I used to lie all the time for my boss. Well, it’s a data point. It’s incongruent with what that person said before, and that might not be the you know, I might not not hire them because of that, but again, it’s a data point. So once they say their values and I asked for you know, reinforcing stories show me how that how your value did show up in your last job or how didn’t it you know, when were you inconsistent with your values and what did you do to correct that? Those sorts of things.

Jeremy Burrows 39:48
I love it. I not to bring it back to baseball, but I will bring it back to baseball. So the you know, the Royals were terrible, my whole life and then 2014 They finally made the playoffs, made the world series made of the game seven, almost won and 2015 They ended up winning. And they interviewed the general manager Dayton Moore about how it took him like 10 years to get the team to the playoffs. And he’s interviewed about how did he choose players back, you know, 10 years prior. And he said that he looked for two things, one, athleticism, and to character. And he said that those were the two things I would not draft for somebody, I would not trade for somebody, unless they had their athletic, and especially the young, like farm system, was their athletic and had good character. And he said, You can you can teach the skills. So that’s what they did, they got these guys that were super fast, super athletic. And, you know, took 10 years, but, and they had good character. So you didn’t have all these crazy stories in the media about such and such player did this and this. And anyway, so

Monique Helstrom 41:10
it’s so underutilized, and it’s so unbelievably important. We have all had experiences in our jobs, where you work with someone who is really good at the job, and a very bad human. We’ve all had experiences with that one person who makes people’s lives miserable, or is the, you know, that sales guy that people talk about, or that whatever guy, HR person, or whatever it may be. So, you know, when you think about that, and we’ve all had experiences about that, what what could one do in order to take, you know, step over that? Well, you’re talking about your values, what kind of a human Are you and then for the executive, reinforcing the values throughout the and publicly to the staff is something that I highly encourage. So if the executive says, Well, I value integrity and honesty, and then the person that gets promoted and gets the corner office is the person that lies in never does what they say they’re going to do. Well, that’s incongruent. And what you’re showing your team is that you’re going to say you value these things, but what you actually are valuing is the production out of that person is the money that they make is the value that they add, is the sales that they got, whatever, whatever. So, you know, I highly encourage our executives to, you know, feed the Good Wolf and promote the things that you want to see in your, in your, in your team, and instead, promote the person who maybe didn’t make the goal, maybe didn’t make that sales number, maybe didn’t make that, whatever it may be, but who perform in a manner that is congruent with the values of the association? Because that’s your, you’re gonna get what you, you know, you’re gonna get what you promote? Right?

Jeremy Burrows 42:56
Yeah. So let’s talk about your next phase in life. So when did you when did you kind of know it was time to move on from your role? You said, you’ve usually or at companies or at certain roles for quite a while? When did you say it is time to move on and tell us about what’s what’s next?

Monique Helstrom 43:15
Sure. Well, I I know myself, I’m self aware enough to know that I’m, I am wonderful in the building, I’m great at building an idea and making it into a reality and taking a concept and making it something I’ve always been able to do that. Where I do like, the enthusiasm is for when things are sort of stasis when things are just maintaining, and there’s nothing to build or grow or develop. And we were in a point at the company where we were sort of leveling out and going into a bit of a stasis mode. And Simon wasn’t traveling as much. And I knew that my gifts and my talents were were more than that. And I wanted to get back to building and growing something. So I just left at the end of January, and started my own company where I’m helping other people build and grow their dreams. And so I’m now doing the same thing, but I’m just doing it for more people. So my company, it’s called Onpoint. And basically, I’m helping solopreneurs entrepreneurs, small businesses, those that have a vision, those that have such a clear vision in their head that they can taste it, but they what they don’t know how to do is build it. Because that’s, you know, in a small business, sometimes there’s only two or three people who are running the entire organization and they have to be chef cook and bottle washer. But what if you don’t know how to be a bottle washer? What if that’s not your strengths and to be a bottle washer? What if you really just know how to be the chef to cook. So I’m helping small businesses actually build their dreams, build their empires, but in the capacity of the actual build, not the strategy. So it’s slightly different than some other folks.

Jeremy Burrows 44:58
That’s great. If so, any tips for assistants who feel like it’s time for a change, maybe they want to start their own home deal like you’re doing or maybe they just need to move on to a different executive.

Monique Helstrom 45:12
You know, you have being self aware and really asking yourself the tough questions and knowing that any decision that you make is for you and your life and the good of your life. And as long as you’re staying with your your values as who you are as a human, and knowing that there is just some sort of inconsistency we all know when there’s an inconsistency we all know when our gut tells us something, it’s just a matter of you want to listen to it or not. So listen to it is I think my first suggestion and and then figure out why why are you having these feelings? What is it about the company that makes you want to leave? This is helpful for a few reasons, a, you know what to look for, in the future, if you’re being abused, if you’re not being heard, if you’re, you know, if you happen to be in that role, where you where you’re being treated as second best, if that’s the reason that you’re leaving, make sure you know that and make sure that when you’re getting when you are on your next interview, that you bring it up, you know, in my last roll, I was really not heard. And I have plenty of good ideas. And I definitely helped the company in this way, that way, and this way. And I want to be in a role in which I can affect change, I want to be in a role where I can actually make something happen. And that’s very important to me. So you know, that can help you in future future interviews. But getting to the heart of why you want to leave getting like really listening to that gut, what is it? What is it about this current organization that is making me want to go somewhere else, and identify that, I know that there’s nothing wrong with it, there’s nothing wrong, if you do want to leave, there’s nothing wrong with it. If you need to find another job for whatever reason, it may be to make you happy. You know, at the end of the day, if you’re not happy, you’re not performing at your optimal best and your executive is not getting the optimal best out of you. So it may actually be a good thing in order to move on and let somebody else take that role where they can help their executive in better ways.

Jeremy Burrows 47:14
Yeah. Last question, what makes an assistant a leader?

Monique Helstrom 47:18
Wow, I think most assistants already are leaders, whether they say that they are or not, or whether they think they are or not. You know, I’ve had the advantage of learning from the foremost leadership experts. So you’ll probably hear have heard this before, when I say, you know, a leader is not someone who’s at the top of an organization, a leader is someone who chooses to take care of the person at the left of them, the person at the right of them, a leader, someone who takes care of all those around them, regardless of how the executive is showing up, or the sales guy showing up or how the teacher showed up that morning, or anybody else, a leader, someone who just is there to take care of everyone else. And so I’ve met plenty of people at the top of organizations who are not leaders, they have authority, but they are not leaders over us. And I have met even more people at the bottom of organizations who absolutely are absolutely our leaders, because they’ve made the decision to take care of those around them. And so I think, the more you can concentrate on that, again, regardless of how your executive is showing up, if you’re there helping your fellow team members, your fellow tribe members helping those around you. I think that’s what makes the biggest leaders

Jeremy Burrows 48:32
love it. I like how you said that. You’re a leader, whether you like it or not.

Monique Helstrom 48:36

Jeremy Burrows 48:37
because we are no and we all have influence, just what do we do with it?

Monique Helstrom 48:40
Absolutely and people look up to us to know what’s right, what’s wrong, how they’re supposed to act, people look up to the executive assistant a lot more than more than is ever talked about. And, and I think the role of an executive assistant to show that leadership capacity, even though they may not have a see in their title, or whatever version of the title makes them, you know, the at their optimal best, I think, you know, we’re leaders, whether we want to be or not, and we should act as such. And we should continue to try and take care of those around us and help our fellow executive assistant rise. This tribe, this community that we have, unfortunately, we we tend to come from a place of I can do it all, you know, we we’re self sufficient, most of us EAs and I can do everything. Well, maybe you can, but you also have a tribe of people around you that are there to lift you up and help you up and, you know, dust off your knee if you fall down and vice versa for you to be there for somebody else to support and help. Unfortunately, we live in a pretty divided world these days where it’s, you know, it’s a it’s a selfish type of community. It’s divided and selfish and that’s what I need. So the more we can share and the more that we can help help our people under us, I think it’s not only going to make our organizations better, but hopefully make the world

Jeremy Burrows 50:05
Awesome. Well, where can we find you online? And how can people support what you’re doing?

Monique Helstrom 50:10
Sure. My business website is onpoint.expert. Apparently all the dot coms are taken. So they have a new handle now .expert, which I’m a big fan of. So onpoint.expert. And then if you’re interested in hearing me speak, or interested in hiring me to speak at your event, you can just go to Moniquehelstrom.com. My full name Moniquehelstrom.com. Both of those are available.

Jeremy Burrows 50:35
Perfect. Well, I’ll put those on the show notes so that everybody can find it easily. Thanks again for joining The Leader Assistant Podcast and I’m very excited to get this thing published. And we’ll talk to you soon.

Monique Helstrom 50:49
Sounds good. Thank you so much. Thank you for your time and thanks everyone listening.

Jeremy Burrows 50:54
Thanks for listening everyone. check out today’s show notes on leaderassistant.com/16 also join our Facebook community at Facebook.leaderassistant.com Talk to you next time

Podcast Outro 51:17
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