When to hire an executive assistant (and why you keep putting it off...) with Monique Helstrom

Meet Monique Helstrom, former Chief of Simon Sinek’s team, who's now made a career of helping Executives and Assistant's create symbiotic, profit-generating relationships.

In this episode, hear how the right support person can boost productivity in your business by up to 50%, and how to navigate those first (often messy) steps of sharing passwords, delegating tasks, and trusting someone else with the innermost details of your business. 

Monique also shares three unconventional ways to get more clients—from treating employees well to leaning into referrals and focusing on how your company presents itself to the world (a.k.a. “executive presence”). If you’ve been thinking about hiring an assistant—or just need better collaboration with the one you have—this episode is a must-listen.

Some takeaways...

1. It’s Supposed to Be Work (At First): Don’t expect instant relief. Onboarding a great assistant is an intimate process that requires time, clarity, and trust.
2. Female Entrepreneurs, Take Note: You can do everything, but you don’t have to. Let go of the guilt and you'll see the ROI of having support.
3. Sht You Hate vs. Sht That Moves the Needle: Offload tasks that drain your energy or aren’t in your zone of genius—especially those that don’t push your business forward.
4. 3 Ways to Earn More Clients (Unconventionally):
   • Treat Your Employees Well: Happy employees are your best brand ambassadors.
   • Focus on Referrals: Stay top of mind with past clients—you’ll be amazed by how many people they can send your way.
   • Mind Your “Executive Presence” (Business Persona): Align the way you speak and act with the brand you want to convey to potential clients.

Need help bridging that executive–assistant relationship gap?

Connect with Monique at www.MoniqueHelstrom.com. 

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Hosted by Jenna Harding (Warriner), Creator of Magic Marketing Machine

Transcript

As a small business owner, you are strapped for time. Actually, that's why these episodes are so short. You're strapped for time. I'm strapped for time. So let's bring in someone to talk to us today who is an expert in productivity and organizational growth.

 Let me introduce you in just a second to Monique Helstrom. She has over 23 years of experience. She's the former executive assistant and chief of Simon Sinek. So cool. It's like we're one degree of separation from Simon right now. In that organization, she played a key role in launching Best selling books and managing global speaking tours.

She has seen it all and now, as a coach, a speaker, and recruiter, she helps leaders and their assistants, assistants and their leaders, turn their relationship into something that gives them major strategic advantage. And something I thought that was really cool. That was really cool reading up on you, was that a great executive and assistant partnership or business owner assistant partnership can boost productivity by up to 50%. 

That's worth it. Yes. Amen. So, Monique, one of the things that I know my listeners have experienced or will experience is bringing on that friendship. first person to support them in their solopreneurship journey. And realizing that now things feel like more work than they were before.  And they will! Is that sort of par for the course, when you bring in an assistant, would you say?

Sure. And, and frankly it should be. I don't know what to tell the executives that think this should be a really easy entry and that you should not pay attention to this person or spend a lot of time with them or onward them in a really good way or concentrate on this partnership because again, this partnership can completely transform your business in a very short period of time, 20 to 50 percent on average.

So, Get in there, get, get going, figure out what you want to do and, and hire the people that you need to move forward. It's funny. We often have so much resistance to bringing someone into our business. I feel like there's like, there's a bunch of reasons for that one. Cause it feels like it's going to be more work, even just  organizing passwords to share with someone can be really overwhelming.

  Are there other things that, you know, make people resist bringing someone in that we need to kind of get over? Sure, sure. I'd say two things. Exactly what you said, that it's going to be more work on the onset. And again, it should be. This is a very I'll call it an intimate partnership.

You know, at the, at the end of the day, you know, I knew Simon's social security number. I know how much money he had. Like, we know everything about you. We have your bank account numbers. So, it is an incredibly intimate partnership, and if you don't spend the time in the beginning to set it up well, nothing will happen.

You know, this isn't just , , a random person you could just throw into a spot and they'll figure it out.  This partnership doesn't work that way. So you have to spend the time in the beginning. And that's usually one of the things that, that holds people back.  , I will be very, um, what I like to call Philly blunt and say that the most resistance I have found is from female entrepreneurs, female business owners, female, small business owners who, , Convince themselves that they can do everything.

I can do everything, even if I don't know, I can't. And here's the thing you can, but should you. Do you need to? Yes, you could probably do it all, but the fact that you need someone to help you is not a slate on you. It doesn't mean that you can't. It means that you have more important things to do right now than those.

 This is something that Simon always tells me, he's like, I am the best at what I do, but you're the best at what you do. And so don't try to overlap those. I don't want to be you, and you don't want to be me. Let's just stay in our lanes and do what we're good at, and together we'll make magic.

Yeah, you know, I had a social media management agency, and I went from being a social media manager to an agency owner, Um, and then I was like, Oh, I now run a company and then was just hobbling it together as best I could. And we use Asana for task management. And so that's basically, if you're unfamiliar, like, it's like a monday.

com or any sort of  project management software. And , I, I think I hired like three people to try and fix it after I had made a mess of all of our  systems for many years.  It took three tries to get someone to come in and take my brain and translate it into, like I should have done it sooner is what I'm saying.

I held on way too long to doing everything myself. Yeah, I mean, that happens and and it's not out of,  you know, ignorance or anything. It's just as women were kind of built to do everything and be everything and take every role and never say no. And, um, again, , hiring administrative help doesn't mean you can't.

It means that this is an area where you shouldn't be spending a lot of your time or you're not good at it. Give it up.  You know, this is what you just said about that. I have found this so much in my business. I'm a doer. I'm a worker. I'm an executive assistant by trade. So me owning a business is difficult.

I'm not  really good at the strategic thought. I'm not great at high level marketing and thinking. And I'll be totally honest with you. I despise social media. I don't know how to do it. I'm not good at it. I'm really good talker. I don't know how to put it all in teeny weeny little words and make a picture that goes with it.

So I struggled for so many years. I could do it. I could do it. I could do it. And I was like, you know what, Monique, give it up. You're terrible at it and you hate it. Why are you making yourself crazy? So I hired a chief marketing officer to tell me what to do. And my life is so much better. One of the first tasks I did when I signed on with , my first major business coach was,  she called it the shit I hate doing list.

Right. So you like went through all the things and then also you realize all the stuff you're doing. Cause I think another, , barrier to entry to having somebody on your team working there with you is it's hard to even differentiate when you're doing an admin task and when you're doing project work because everything is all jammed together.

Like, at the point where you're hiring someone, you're, you're pretty much cooked, right? Like, you're full to the brim. That's why you need someone. So  how do you choose the first tasks to pass off? , how do you audit your business? , can you speak to that?

Sure. I would say it falls heavily into two different categories. A, the shit you don't like to do. That is absolutely a category. Or that you don't want to do. Or that is not in your skill set. Just admit that , you need help in some area. , we can't be everything. We can't be good at everything. , the things that you don't like, Things that you're not good at, things that you don't want to do.

That's a great list. However, some of those things might still have to be on your list. If you're focused on sales or if you're a CEO, there's some crap that you're not going to like to do that you still have to do being that you're in that position. But the second list is, and I encourage all of my executive staff to do this.

to do this is take like two weeks and break down all the things that you're doing. And if you want to get a pomodoro or a tracker or a timer and write down the list really quickly. Like I just spent an hour on email. I just spent two hours trying to find X Y Z. , ,  without judgment  don't judge yourself on why you're doing it or that you're switching tasks.

Just make a random list and then look at that and say, what should I have been doing?  How many hours did I spend on things that aren't moving the needle forward?  As a business owner, that is your job. What is moving the needle forward? So you have to get rid of the tasks, even if you like doing them, that aren't moving the needle forward.

 Listening to the show love taking away some actionables and Monique did her homework, came with this really good idea of sharing with you three things that you can do that are kind of  unconventional ways to get clients. And we love giving, we love giving listeners homework. 

Great. So, yeah, as I said, you know, marketing is not necessarily my strong suit, but I can tell you from all of my experience, one of the best ways to get clients is to treat your employees well.  And I know that sounds bizarre, but you have happy employees, guess what happy employees do? They talk about you.

They talk about the job. They talk about your services. They're at the counter getting a bagel at the deli and they're like, Oh my goodness, you have a blah, blah, blah, I do blah, blah, blah. This is great. So when you treat your employees well, they are your best marketing asset. Period. Yeah. ,  right now mostly I teach social media to small business owners.

I don't do the agency as much anymore, but I have had writers say to me, I keep telling my friend to hire you. I keep telling my friend to hire you. I'm like, that is such a good sign. And also maybe even rewarding those employees when they do send over a referral.  Absolutely. Absolutely. And reward them in unconventional ways.

Yes, money is always good. And depending on who you want to give, that's fantastic. But,  what if this person wanted to go to a conference one year and learn and get some professional development dollars? Maybe give her 1, 500 to go to a conference to learn, to grow her skills, pay for the hotel and the airfare.

Like, these are things that you can do that are extra that show your team you believe in them. As a human, not what they can do for you. Yeah, and because a lot of people listening, they're like, yeah, okay, that's one day I'll have the money for the airfare. And you will, dear listener. As you will. You will, as you will.

, but another idea, a book. Send them a book, you know, like in that episode of Ted Lasso, where he gives every member of the soccer team a book that he feels like . This is where you need to get to know your assistants and your people that you work with, you know, you know what they like and you send them something that they like.

Yeah. And when you get a specific gift from your executive that is targeted to you, you're like, big hearts, like your heart is just jumping out of your skin. So, , there is no better marketing than having a really great set of employees. Amazing. Okay. Next up. What's your second one? Your second idea. Yeah. 

My number to focus on referrals. You know, happy employees make happy sales. Happy clients make happy sales. I feel like we're in this world of newness and constantly trying to just  every day. There's something new happening and we have to just go out there and find the new clients where where, is if you  connected with the clients that were really happy with you before and maybe caught up with them every once in a while and checked in with them three weeks after you sold them whatever the product was and said, how is it going?

These are very simple ways to tell your clients that they're cared for. And your second best marketing effort is clients who've already paid you and are telling people I've paid her for this. And I was satisfied. That's what people want to know. Did you get your money's worth? Yeah, 100%. Nobody can tell a better story about that than your clients who got their money's worth.

And, , in terms of social media, I won't talk about it for too long because I know you don't like it.  I know it's like the worst thing to say on your, it's, I don't like it because I don't understand it and I don't know how to do it and it intimidates me.  again, it's not my specific skillset. So why am I going to push myself into something that, that I won't do good enough that'll get me the result that I want it to.

Yeah.  Hire experts. I love that. Here's the thing.  And I kind of have of two If I'm just going to segue for a sec. If you came to me and you said all that and you were like, I don't like it. I don't really understand it. It feels overwhelming. It feels like I'm not good. I'm the only person in the world 

that doesn't get it. , but I want to, then I would be like, come into my office. I've got you. I've heard it a million times, but if you're saying  I hate it, I don't want to do it. I actually don't want to do it. Then I'm like, great. Don't. Great. Don't. Yes. Yes. I mean, we, you know, I talk a lot about self awareness and all of my coaching and everything that I do.

And if we're not self aware about it. what our skill set is and where weaknesses lie. And let's just be really honest with all of them and not, it's not a slate on you. Everyone can't be everything. So. Yeah. Yeah. So I do want to give one quick tip for the audience. If you are a person who wants to use social media, , sometimes we think if we have a bunch of followers that are friends and family and our old network and internal clients, and the, and there isn't that element of newness that it's not worth it, but But put the words in those people's mouths that they need to refer you.

If you just started your business yesterday and you only have a personal account, you can still be getting clients from that and you can still be generating referrals from that by telling your audience what you're up to and exactly who to send to you. Absolutely. Same thing with referrals.

You know, when you're talking to your past clients, you know, when I get on with a recruiting client or an executive who I hired a great assistant for, and they're super happy, and we're six months later, I will say something to the effect of, do you know anyone else who was going through the same thing that you were going through?

Do you have any buddies that are, ,  struggling like you were struggling?  And they'll go, yes, I do. I mean, oh, Bob and Steve and Jim and Joe. And they'll, then they'll send them over. , but you have to give them the words. And then sometimes people feel like, okay, but I don't want to ask him for that.

And he's already paid me this client of mine. And like, I don't want to ask him for that. No, dude, you're making him the hero. Cause he's about to go save Bob and Joe and George. Right.  Right. And if you don't ask him, there's a hundred percent chance that he's not going to say anything.  Yeah.  There's a 50 percent chance that I'll say something.

So go with the odds.  Yeah. , okay. And what's our third one?  You know, I talk a lot about executive presence, executive presence is all about how you show yourself into the world. Now, as a human, that's what that's called executive presence, but the business can have that as well.

It is What you say, how you act and how you look. Those are the three things that make up executive presence. And again, that can be done for a human, but of a business. What are you saying? What are the words that are coming out? What are your marketing words? How are you talking about things? What sort of emotionally charged words are you using?

Are they congruent with what you're selling? Does it make sense that your words and your product are congruent? Go together. , and then how you act. If, , I see a business that I really want to get, , attached to and I really want to work with, and then I do some research on social media and I find out that they've posted some really gross things on social or, or whatever.

I'm not taking that. Are you crazy? There's no, I don't care if you have the best product in the world. There is no way that me personally I'm going to work with someone who doesn't act the way that they, that they say they will. Controlling your public image, I would call it if I was in my publicist days.

, having a personality, sharing that with the world, being intentional about how you want to show up and how you want to make people feel.  Yep. Absolutely.  Had a client go through my program and there's  a question near the very beginning  it's like, how do you want to make people feel when they arrive here?

If you had a storefront, how do you want people to feel when you walk in? And somebody was like, that question ,  like transformed how they were thinking about things and how they were writing and how they were taking pictures and how they were doing all the stuff. I'm like, really that question? Like everything in this program, that question,  Absolutely. Something that I teach a lot in communication is communication isn't about what you have to say. It's about what they need to hear so that they understand you and can take action. So this is for employees, friends, family, and clients, and everything. , me saying to you, me telling you something is a very one sided.

I'm gonna tell her blank. That's very kind of aggressive, and it's very, uh, One sided. It's coming from my brain, how I think about things and my perception. But if I just twist it and said, what do they need to hear so that they will act so that they will feel so that they will buy so that they will whatever.

Let's talk about that instead of what I need to say. That's not going to help you. That is so simple, but I feel like that applies to copywriting,   that applies to everything.  Everything. It's, it could apply to how you communicate better with everyone, you know, and this isn't manipulation.

I'm not going to, I'm not saying you turn your personality into someone else. I'm saying, you know, when I, uh, I'll give you a great example. I'm, I'm very loud and boisterous. Stress. I talk a lot. I'm very animated. , and so whenever I talk with people who are more introverted, who are more quiet, who maybe don't have the same level, I keep my level, I keep my voice a little bit lower.

I don't try to raise it as much. I'll go lower, deeper, but I don't take it up high. You know, I just, I just allow myself to talk calmly and clearly and get the message across. It's not manipulation. That's me getting my point across.  That's this actually understanding what I have to say. And isn't that the point?

Yeah.  People often think that by , not using jargon in their copy in the posts and using like simple language, they call it dumbing it down. I'm like, why are we don't, uh, I have a, I have a few things to say about that. We're not dumbing it down. We're just communicating effectively.

Like if someone is. on the bus looking at their phone briefly, they don't have time for you to write an academic caption. They're not absorbing it. So we're not dumbing it down. We're meeting them where they're at and their stop is next. And they're glancing at their phone quickly. Like it's communication,  it's communication.

And frankly, if your tactic is to dumb it down, then get ready for some dumb clients. Like, I'm just going to be real about that. if you're attracting the lowest common denominator. That's what you're going to get. So the, the, the dumber you go, you know, how, how are you going to get people really attracted to it  if you're dumbing it down and now, so that confuses things, I don't, I don't know what you mean sometimes when the words are too simple or too flowery or too colorful or too, you know, up in the air that I don't know what you're like, what is the ask?

What do you want me to do? with this information. Be clear.  Be clear.  , okay, Monique, who should call you and when?  I work within the relationship of an executive and an assistant. Uh, so I work with all types of administrative professionals from office managers to chief of staffs, as well as on the executive side, that could be, you know, Small business owner, solopreneur, , or even a personal assistant all the way up to a c suite executive assistant.

That's, you know, for the CEO. So whatever your needs are on the executive side, I do specialize in first timers. I love my first time. Your executives that have never had support before and they again, they don't really know what to do. It's like this beautiful piece of technology that nobody taught you how to use.

I want to get out there and help people understand what this beautiful piece of machinery that us executive assistants are.  Online, you can find Monique at MoniqueHelstrom. com. That's for the drivers, M O N I Q U E H E L S T R O M, Monique Helstrom, and I'll put it in the show notes and everything as well so everybody can find you.

Thank you so much. This was so fun. Good. Thanks for being here.