Episode 242: The Bottom Line - My First EA

In this episode of the Club Capital Leadership Podcast, host Bradley Hamner shares a personal story about hiring his first executive assistant (EA) and the costly mistakes he made due to a lack of preparation. He recounts hiring a full‑time EA for a $50,000 salary without a job description, playbooks, or documented processes, which led to inefficiencies, duplicated work, and loss of institutional knowledge when the assistant left. Hamner explains why an EA is essential for small business and insurance agency owners: to buy back the owner’s time so they can focus on high‑value activities that drive revenue. He advocates starting with a fractional EA—working a few hours a week and scaling up—as a more flexible, cost‑effective approach. He stresses the importance of creating and maintaining playbooks for every recurring task, using tools like ChatGPT to help document processes, ensuring knowledge stays with the business regardless of staff turnover. The episode concludes with actionable advice on hiring, delegating, and building operational systems, framed as a “secret weapon” for scaling businesses.
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So the big question is this: how do small business owners like us grow our leadership, develop our teams, and scale our business in a way that allows us to get our products and services out to the world yet still remain profitable? That is the question, and this podcast will give you the answers. I'm Bradley Hamner, and this is the Club Capital Leadership Podcast. Welcome to The Bottom Line, a new weekly podcast series that we drop every Thursday to complement our weekly Monday podcast interviews with the industry leaders.
These podcasts are going to be designed to give you short, impactful, and value-driven information that you can start using right away in your business.
I value your time and attention and will do my very best not to waste it.
Just get what you need and go.
So with that, let's get into today's episode.
Hey everyone, so I was telling this story to a couple clients and I thought I'd share it with all of you. I don't know if I've actually shared this on the podcast cast. So it was 2014, 2015, and the coach that I had at the time, uh, they were really more focused— it was kind of an executive coaching, but it was really more of an executive sales coaching program as much as anything else. I mean, everything that they taught really kind of had a bend towards sales, which was great. Um, I look back on all the coaches that I had over the period of time helped me at that point in my journey. It's kind of like my son Cooper now, uh, he's, you know, learns obviously basic math. He's in 6th going into 7th grade. He learns, you know, higher levels of math, but if he didn't learn addition, subtraction, division, he wouldn't be prepared for algebra, calculus, etc., moving on down the line. And I kind of think about business coaches, uh, that I had along the way that helped me in different areas. And so that felt the same way with this coach too, but Um, one of the things that they shared, and this is maybe a few months into working with them, they said, you know, you really need to get an executive assistant. And I had never really considered getting an EA and I was so hung up on having an assistant and, you know, why would I need to have an assistant, et cetera. And so anyway, I reluctantly do it, but I hire someone, full-time person, and paying them a $50,000 salary because that's what it was going to take. And of course I was getting an idea from my coach of what it was going to be. What are the chances that I had a playbook, uh, for that executive assistant? None at all. Like, I did not have it at all. Had no idea what they were going to do. I didn't have a job description. I just went, hired the person, and I probably put together some sort of one-pager. But more than anything, I probably just talked to them enough and convinced them that this can be a great opportunity. So they come in, and I remember, uh, giving them over, sort of transferring over, uh, them to help manage my inbox, but but really they had no idea what they were going to be doing. They would— every time an email would come in, they would come and say, what do you want me to do with this email? And it was still kind of filtering through me. Um, but eventually I had them doing something that was, uh, uh, to me made a lot of sense, and it was for appointments. And so then they would get all the customer information, they would contact the customer, they would verify the appointment, they would prepare the paperwork, etc. And then when the person showed up, they would hand me the portfolio, and I would go back and have the conversation and sell them and whatever. All right, that sounds all well and good, right? Well, sort of. Uh, look, this EA was doing the best that she could. I was not prepared for my first executive assistant at all. Like, I had no systems in place, no operating system for the business in any way. I had no playbooks, I had no documentation. And so every single time that I was sharing this with her— pains me to actually talk about this now, really, because it just wasted so much time and so much money— is I would share something with her about like, here's how to handle this email, or here's this one little thing I'd like to do differently with the appointments, etc., just so you begin to iterate. I never documented that. So about a year later, whenever she left, what else left with it? All of that intellectual property. And I felt like I was starting over yet again. That was a terrible place to be. And for the longest, I said, well, screw this EA stuff. This is, this doesn't work for me. No, it wasn't that. It wasn't, I wasn't working. I didn't know how to see it now. And so as I share this, uh, with all of you, some of you have executive assistants, some of you. Have never even considered having an EA. I can tell you any business that I would start now, I would not start any business. Many of you are insurance agency owners. I would not start an insurance agency now without the very first hire being an EA. You may say, an EA, really? An executive assistant? Why is that? Because an EA is helping you to do the thing that matters the most, and that's to buy back your time. So that you can focus on the things, the handful of things that are actually going to move the business forward. A million-dollar business isn't built on a $10 task. A $2 million business isn't built on a $20 task. Managing your inbox, putting things on your calendar, scheduling things on your calendar, running payroll, doing basic administrative things are not the items that are going to move your business forward. There's not. I'll share with you, if you had a client that had $1 million and they wanted to put, uh, they wanted to put it in some sort of product or policy or whatever, and you had interns that were working for you, would you ever even remotely consider handing that client or that prospect off to one of your interns and saying, hey, here's a good opportunity for you, see if you can sell them something? No, of course you wouldn't. You wouldn't even, you wouldn't even think about doing that. Yet we do the opposite all the time. We're doing $10, $12, $15, $20 an hour task, which yes, they have to be done, but not necessarily by you. And yet some of you make $300,000 a year. That's $150 an hour. Some of you make $500,000 a year personally. That's a $200— your time's worth $250 an hour. Use that money to buy back your time so you can focus on the things that are going to really move the business forward. And not only that, but also allow your EA to begin to build playbooks. So the event that— in the event that they were to move on or if it's not the right fit, and this really kind of goes not just for your executive assistant, really goes for any position you have. But I think your EA is the one that can really begin to help you to unlock in building the playbooks for you. Have every single time that you're, um, making tweaks or adding things or adjusting things to be— and make sure that that's put down into a playbook. I mean, the amount of times that I did things thinking that it was going to be a one-off time, but the reality is it came up probably once a month, and I just kept having to say the same thing over and over and over again. Versus, if we're going to build it, we're going to do it once. Let's create a playbook for it. Let's put it down into a Word document. Now, of course, you've got ChatGPT, which can kind of help fill in some of the blanks here and there, etc. I really urge you, learn from my mistakes. Whether you decide to hire an executive assistant or not, I do believe an EA is the key unlock for every single person listening to this. I know some of you where you might be started out, your business may be doing $300,000 a year. No, it doesn't mean you need an executive assistant full-time. Hire somebody that's at 5, 5 hours a week, 1 hour a day, that's just helping manage your calendar. In your inbox and then bump them to 8 and then bump them to 10 and then bump them from there. Start there. It doesn't have to be full-time. Maybe years ago that was a little more foreign to have someone that was going to be fractional. I don't even call the people that work for me, I don't even call it if they're not working 40 hours, I don't call them part-time. It doesn't feel part-time. It feels fractional. And so I don't just, I just don't even use the the word part-time. I call it a fractional team member. So hopefully that serves you along the way about kind of the mistakes. That's just one of the many mistakes that I made with my executive assistant, the very first one, uh, that I have. But they are absolutely, truly your secret weapon. All right, everyone, hope this serves you. Till next episode, lead well.
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