I hired an executive assistant, here's what I've learned

Summary

I avoided hiring an executive assistant for years. classic DIY entrepreneur. I finally pulled the trigger and here’s the version I wish someone had given me on day one.

1. an executive assistant is not an administrative assistant. the admin role takes tasks off your list. the executive role manages the flow of decisions, calendars, communications, and projects so you can focus on the two or three things only you can do. price tag is different. so is the impact.

2. you need a real operating system before they can plug in. not a vague mental model. actual documented processes, written priorities, calendar conventions, communication norms. building those for myself before the hire was 80 percent of the value. the EA showed up to a clean engine instead of a junkyard.

3. trust and competence get tested fast. they handle money, schedules, sensitive emails, family logistics. you either trust them quickly or the role doesn’t work. hire slow, interview deep, set the bar high.

the mental shift that finally broke me free: what is my time actually worth per hour? once I wrote that number down, every task I was doing that was not worth that number became a delegation candidate. the DIY mindset is an ego problem. delegation is a math problem.

Transcript

introduction to hiring an executive assistant

The most impactful business is the business that genuinely improves another human, a better human business. And to grow a business like this, you have to continually improve yourself. This podcast is a documentation of that thesis, scaling businesses and also personal growth. My goal is for you to shortcut this journey.

So if you’re ready to try hard, subscribe. If you like what you’re hearing, please share and enjoy. All right. I hired an executive assistant. I’m going to talk about why I made that decision, what I’ve learned so far, and why you may or may not want to consider doing the same. This is the Better Human Business Podcast.

I’m Jerred Moon. And I have been fighting hiring an executive assistant for a long time, like a long time. I’ve always, I’ve always felt like the business revenue for, you know, going, investing back in the business would be better somewhere else, right? Like I would rather spend more on marketing than hire an executive assistant, or I would rather hire this person who does marketing over here than hire an executive assistant for me.

differences between administrative and executive assistants

It was, it seemed like such a selfish thing to me, hiring an executive assistant of, yeah, they just kind of handle me, manage me. And it just seems so extra and unnecessary. To be honest, I’ve struggled, like I said, I’ve struggled with it for years. Like I’ve, I’ve talked to all my kind of mentors and people a little bit further along than me.

They all have executive assistants. They highly recommend it. And I’m just been like, eh, yeah, I don’t know. I feel like I can manage my schedule. I can, I can do these things. So I fought it for a long time, but I finally broke down and I hired an executive assistant. Now, I do want to first clarify the difference between an administrative assistant, a personal assistant, executive assistant, all those kinds of things.

And administrative assistant is someone who, I mean, they really just follow protocol, right? They have some rules set in front of them. They do some clerical work, answer phones, schedule a meeting here and there, data entry maybe, you know, and that’s it. They keep things organized, supplied, and that, I mean, really that’s about it.

my journey from resistance to hiring an executive assistant

They don’t make a lot of decisions other than following the protocols. Sometimes you just need that help. That is not what I hired. An executive assistant is a couple levels above that, in my opinion. So they have, they provide like specialized support for higher level executives. That means they have a good understanding of business.

Typically they have some business experience. Yeah, they still will help with the scheduling and coordinating meetings and all those things, but they can handle incredibly confidential information. They can prepare reports. They can help you in the decision-making process. They can make decisions. Like you can delegate some of your decision-making based off of, you know, kind of some rules for them.

They might be able to make some decisions for you in business and help you work on bigger projects, you know, project management, organization, because again, they understand these things at a higher level. They’re just two different calibers of hiring. So administrative assistant is, yeah, you know what?

I’m just doing a bunch of little clerical tasks I shouldn’t be doing. I need to offload those. Nothing wrong with the administrative hire. Executive assistant is how I look at it, in all honesty, is like having a backup. Someone who’s got my back on like almost anything, and they also have a high level of decision-making and can help with a lot of things.

immediate impacts of hiring an executive assistant

So anyway, that’s kind of the difference between the two. And I hired one primarily because I was getting to a point where it was just too much. The only things that I really want to work on are the things that are growing the business. And the further I’ve gotten into entrepreneurship, the more that is true.

So I don’t want to answer emails. I don’t want to get into project management. I don’t like running business operations. I just don’t like a lot of things. Like I said, the more I do this, the more focused and narrow my work becomes because I just know what I need to do, what my role is. And then once I realize that I’m spending time in all these other areas, yeah, answering all these emails, doing a lot of business operations, and all these things that have some value to them are not the best use of my time, not the best way to leverage my time.

And this has not been more true, like having had the executive assistant now, it hasn’t been very long. So I’ll update you if I change my mind. But my ability to completely focus without having to worry about his communication and some of these other things has increased dramatically. Like I’ve had very focused work knowing that someone else is handling all of my affairs somewhere else.

the necessity of systematization for effective assistant integration

It’s just been a huge, huge impact for me already. And like I said, I’ll continue to update you on this, but that’s why I went that direction because let’s say I spent three hours on some sort of business operations project that might help the business. No doubt team members need it, I’m capable, I could do it, but it’s just not the best use of my time.

Like I really should be focused in the areas of growing the business. So when you actually calculate those things out, okay, three hours spent over here or three hours spent on business growth, business growth could generate this much more revenue for the company. This task is going to save the company a little bit of time and also cost one of the owners a significant portion of his day.

Once you start to calculate that out, even in rough estimates, you realize that an executive assistant is a no brainer. Now here are the things that I’ve learned so far, and it hasn’t been very long, but the first thing is I think that I should have done this way sooner. It’s not because I’m seeing all these results and amazing things.

Like I said, it hasn’t been very long. But what I can tell is I truly feel, like I said earlier, that I have a backup. Like I have somebody who’s got my back on everything. Now I’m not saying my team doesn’t have my back, but my team might have my back in a very specific area. Like the customer success team has my back in customer success, so I can focus a little bit less on that thing, right?

criteria for selecting the right executive assistant

Or I might have someone I hired for marketing, and they have my back in marketing, but that’s the only place they have my back. I feel like an executive assistant kind of has my back everywhere. And just knowing that has freed up so much mental bandwidth. Like the time I used to spend just like checking or dealing with messages and like all these kind of things, I’m just not doing those things at all anymore.

And even when I used to just ignore those things so I could do deep focused work, it’s still in the back of my head. It’s in the back of my head. It’s like, yeah, you can do this deep focused work right now, but at some point you’re going to have to do all this other stuff. Like that was always in the back of my head, and I didn’t even realize it until I hired an executive assistant.

My mental bandwidth has freed up. I feel like I actually have the permission and time to focus very heavily on really big projects, and I can’t wait to see what that produces over the next several months. The second thing I learned is, and this is true of almost any hire, but your level of organization needs to 10x.

So I decided to bring on this individual, and then I was like, you know, I’d never hired for this position before. So I was like, well, you need systems, you need operations, you need some way to onboard this person and have them run all the things that you need them to do. And so at first I was like, ah, this won’t be hard, you know, I’ll just shoot a couple videos.

conclusion and thoughts on the transformative potential of the role

I ended up spending a day and a half, like a full eight hours, and then another four hours like the next day. So 12 hours of work, like putting together systems and processes for making sure this person can fully take care of what I need them to take care of. And it’s still being refined. Like I spent a bunch of time on it, and we’re still going to have to refine it.

What do we talk about in meetings? How do we do these things? All that kind of stuff. And I’ll do another podcast really getting into the weeds of like exactly what they do and all those kinds of things. But for now, I’m just kind of keeping things high level. So my level of organization had to 10x.

And I’m very glad that I did that because it helped me bring him on in a very, you know, ready to hit the ground running capacity. And it’s been great so far. So my level of organization, like my personal level systems, like in a business, I have great operations and great systems. But I would say as a human being, I don’t feel like I had those and I had to create them before this person came on board.

So I guess that’s my main point is having extreme level of organization system and process not just for your businesses, but for you as a human being. Now the third thing is you do need a badass. And I think I’ve I’ve checked that box, you know, he came on and it was basically the first day and I kind of I was like, let’s just, you know, ease into things.

And here are your basic responsibilities. We started with just some easy like schedule management, inbox management. And he finished everything the first day and caught on incredibly quickly to all of my preferences, what I need, how I need it. And I mean, just straight up told me after that, yeah, I’m going to be bored if you don’t give me more.

If you don’t give me more responsibility, more things to do, which is all on the docket. I kind of laid out like all these phases, four phases for him just in working together. And I thought phase one, which is more of the clerical, like easier to handle stuff. I thought that was going to take at least two weeks to manage.

And I think that he nailed it all in about two days, one to two days, in all honesty, like, yep, got it. What else? And so we’re going to move through these phases really quick and then I’m going to get him fully integrated into me and my role, which is going to be scaling companies. So you need a badass.

I can’t tell you exactly how to do that other than have a lot of hires. Don’t think that if you are getting an executive assistant, like you’re just going to nail it. Like I think I do think I got pretty lucky. And you’re also going to have to trust this person. I’ve known this person for a long time.

We’ve worked together and other projects and stuff. And I have a lot of trust there. And I am not a very trusting person. I really am not like letting someone else see my email or use a credit card on my behalf. Those things are not things I typically trust, but I kind of had to let go of all that with this hire and let it happen and realize that, hey, I trust this person.

They’re awesome. And it’s just going to make my life easier. So far, it has been a huge impact and it’s only been a small amount of time here. I’ll update you again as things go through. Typically when an entrepreneur hires somebody, that’s when they’re most excited. I don’t feel like I fall prey to that because I’m normally way more like skeptical about a new hire.

I’m like, yeah, you’re good now, but will you be good in three months? I don’t feel that way about an executive assistant. I think it’s something I should have done a long time ago. It’s going to free up a lot of my bandwidth and I’m really looking forward to seeing what I can create. Now that’s all about me and what I’ve done.

But here’s what I want you to do is just to start thinking about your life in general. You don’t have to jump up to an executive assistant. I don’t know where you’re at in business, but if you’re like me, I had a very DIY mentality about everything, like for a long time, like for a long time, I didn’t want someone to cut my grass or I didn’t want somebody to answer my emails or I didn’t like, I just always, if you ever asked me, I’m like, I can handle it.

I can do it. And it’s true. You’re very capable. You probably can do all those things, but is it what you should be doing? That’s the question I want you to ask yourself. Are you doing what you should be doing or should you hire that thing out? I can keep my books. It’s not hard for me to log into QuickBooks and categorize things and put them there, but why would I want to spend my time on bookkeeping?

Hire a bookkeeper. It’s a pretty minimal fee. So start looking at all of those things and see what you have time for and a budget for and see how much time you could free up and how much it would cost. Now if you can calculate what you feel like your time is really worth, which I’ve done a podcast on, I’ve written articles about.

If you really know what your time is worth, these things become easier to realize. If your time was worth 200 bucks an hour, okay, this person frees up 10 hours a week. Boom. That’s huge, right? That’s a home run. If they could free up 10 hours and you can actually use those 10 hours to focus on business growth activities, that’s easy day.

Now you can do this in all sorts of different areas. You can have someone do your laundry. You can have somebody clean your house. You can have somebody mow your grass. You can have somebody do basic administrative assistance. You can hire an executive level position like an executive assistant. And it just all depends, but I want to urge you to start delegating where you have so you can free up more of your time to focus on what matters most.

And for a lot of people, it’s not a financial thing. It’s not a time thing. It’s really only the mental side that’s holding you back from doing it. That’s what was holding me back for so long from making this hire, and I regret I didn’t do this much, much sooner. So if you’re struggling mentally to offload some tasks and free up your time, try harder.