Timestamps:

00:00:00 Introduction and Episode Overview
Josh introduces how he uses AI with his executive assistant to multiply productivity and free up the CEO’s time.

00:02:22 What the Executive Assistant Owns
He describes the assistant’s responsibilities, including inbox triage, calendar, travel, sports schedules, follow-ups, coaching administration, and financial coordination.

00:06:40 The Goal: Own and Delete Work
Delegation should remove responsibilities from the CEO’s mind, not create more approvals, questions, or follow-ups.

00:08:45 The CEO as the Delegation Bottleneck
Trust, onboarding, and sharing enough context are essential to help assistants make decisions independently.

00:10:45 A Five-Step Foundation: Context and Judgment
Josh explains why team members need to understand the reasoning, trade-offs, and criteria behind decisions.

00:12:54 Connecting Business Context to AI
He outlines his AI setup, connecting tools and business information so his assistant can access relevant context.

00:15:13 Capture Thinking with Daily Check-Ins
Short daily meetings, voice dictation, and meeting transcripts capture decisions and help the assistant learn.

00:21:41 Build a Judgment Library with Loom and AI
Josh explains how recording real work and decision-making helps AI turn examples into practical SOPs.

00:27:18 Product Research and Development Example
Hundreds of Loom recordings helped create 273 decision rules and an AI assistant for product research.

00:29:38 Family Travel Planning Example
An Airbnb-search process becomes a repeatable AI workflow, with the executive assistant reviewing and refining options.

00:32:47 Automate Recurring Work
Josh recommends using AI tools such as Claude Code to automate routine tasks rather than having assistants repeat them manually.

00:34:01 Automated Coaching Follow-Up Workflow
Meeting recordings generate email drafts, saved notes, and preparation materials for future coaching calls.

00:38:19 Why Executive Assistants Still Matter
AI supports automation, but leaders and skilled assistants remain essential for growth, judgment, and human connection.

00:40:38 The Six-Month Delegation Ramp
Josh outlines onboarding, calibration, and momentum stages that help assistants gradually take ownership of work.

00:43:53 Closing and Access to Resources
He invites listeners to subscribe, leave a review, and access his slides and AI prompts.

Links and Mentions:

Tools, websites, and platforms

“YouTube“: “00:01:09”
“Email address: Josh@EcomBreakthrough.com”: “00:05:34”
“ChatGPT“: “00:13:00–00:14:08”
“Power BI“: “00:13:00–00:14:08”
“ClickUp“: “00:13:00–00:14:08”
“Email, calendar, and Google Drive”: “00:13:00–00:14:08”
“Fireflies“: “00:13:00–00:14:08”
“Slack“: “00:13:00–00:14:08”
“Calendly“: “00:13:00–00:14:08”
“Claude“: “00:14:08–00:15:13”
“Google Workspace CLI“: “00:14:08–00:15:13”
“Whisper Flow“: “00:15:13–00:16:20”
“Google Drive / Google Docs”: “00:20:36–00:21:41”
“Loom“: “00:23:56–00:25:01”
“Custom GPT / Claude skill”: “00:28:23–00:29:38”
“Airbnb“: “00:29:38–00:31:40”
“Claude Code“: “00:32:47–00:34:01”
“OpenAI Codex“: “00:32:47–00:34:01”
“Podcast platforms“: “00:43:53–00:44:59”

Other resources and items

“Copy-and-paste script/prompt“: “00:14:08–00:15:13”
“QR code and prompts“: “00:29:38–00:30:39”
“Slides and SOP prompts“: “00:43:53–00:44:59”

Transcript:

Josh Hadley 00:00:00  Today, I’m going to share with you exactly how I’m using AI inside of our business, and specifically how I’m using AI with my executive assistant in order to ten x their productivity and get more decisions off of my plate, and freeing up more of my time and how you can do the exact same thing. Welcome to the Ecomm Breakthrough Podcast. I’m Josh Hadley. I’ve scaled my own ecommerce brand from 0 to 8 figures, and I’m actively building towards nine figures in sales. This podcast is where I document that journey and share the systems, the strategies, and the lessons learned in real time so that you can learn what actually matters and scale your own business. My name is Josh Hadley. First and foremost, I’m a man of faith. I’m a husband to a beautiful wife and a father of four children. I’ve been selling in the e-commerce space for the past ten years, and I’ve been doing over $20 million in annual revenue in multi millions on channels such as Amazon, TikTok shop and Shopify. Last but not least, I’m also the host of the number one business strategy podcast for eCommerce entrepreneurs, and that is E-com breakthrough.

Josh Hadley 00:01:09  So let’s dive in today. If you’re just listening to this, make sure you come check this out on YouTube. Because I’m actually sharing slides. I’m going to be sharing very specific examples and how you can apply these exact same setup AI setups and principles into your own business. So let’s dive in. Now when I talk about using AI to train your executive assistant, I don’t mean it allows them to answer ten times as many emails. What I’m referring to is ten x, the amount of work that you’re going to be able to completely remove off of your plate and out of your mind, and ultimately your E becomes the judgment layer that you need in order to get this kind of out of your mind. So let’s dive in into how that is actually set up. Let’s talk about what my EA owns today. So my new executive assistant that I have right now, they joined me December of last year. Okay, so I’m not even a year into working with them quite yet, but man, the amount of progress that we’ve been able to, make in less than 12 months has been incredible.

Josh Hadley 00:02:22  But let’s talk about last December. My executive assistant was just learning how I work. And now today she owns all of these things that I’m about to mention. Okay. And this isn’t just an assistant or a virtual assistant that just goes and does exactly what I tell them to. This is an actual judgment, manager that is actually able to execute decisions not only on my behalf, but on behalf of the business as well. So number one, she is responsible for my email inbox triage. she has done time study after time study and ultimately, like she is in my inbox at least three hours a day right now, and we’ve worked on trying to get that more and more efficient. But like, she still spends three hours a day in that delegating tasks, making sure that the right people are being responded to, following up on things, etc.. That’s at least three hours that I would have to spend per day that is immediately been delegated off my plate. Now that’s the easiest one. Next we have like calendar and priorities.

Josh Hadley 00:03:26  So again, if somebody wants a piece of my time it’s okay. Great. You’re going to have to work with my executive assistant to find a time that works. And I have a very regimented time frame of when I actually take external calls. And so she’s able to plug that in and make sure that it meets, you know, our working guidelines that I’ve already established so that I ensure that I have uninterrupted, deep work time scheduled on my calendar and that random meetings don’t just pop up on occasion, okay? She also manages all of my travel. Okay. Not only just business travel, but also my family travel as well. So whenever we book a, you know, family vacation, she is in there looking for verbose. Getting that set up or Airbnbs and also coordinating all of the flights, the logistics, rental cars, etc.. I coach multiple sports as softball team, a baseball team, a girls basketball team, a boys basketball team. She manages all the communication and the schedule, behind the scenes as she, like, reaches out to the team.

Josh Hadley 00:04:35  Hey, guys, make sure you RSVP. Hey, are we going to have enough players for this weekend? Do we need to find subs? Hey, what tournament should we enter into? Like she is behind the scenes helping me do all of that. And that in and of itself feels like a part time job. she manages all my podcast follow up. So after I have guests on my calls, okay. She is also doing personal follow ups. if there’s somebody that I met at an event or a church event or something like that, she’s the one personally following up with those people. in addition to that, reoccurring reports that need to be automated throughout the team, she’s bringing those in. random founder requests, people that want to ask me questions, etc.. She helps. Kind of like, be that gatekeeper, if you will. she also I do coaching on the side. So I have a couple people, and I only accept three at any given point in time that just want me to kind of like be their coach or mentor or consultant, whatever it is for their business.

Josh Hadley 00:05:34  And, so number one, if you’re listening to this and that’s you, feel free to reach out to me, Josh, at Ecomm Breakthrough Comm. I currently have one available slot if you would like some one on one coaching, you just want to kind of get inside my brain. And, how I would approach your business. That’s an opportunity there. But she manages all of the the billing when it comes to that, the scheduling of those clients or those coaching students that I work with, she manages all of that. So as you can see, this is not just like a VA that’s like, oh, they just do. My email inbox and calendar management, like there are many, many decisions that are being made across the board in here. And again, my purpose today is to show you how she is managing all of this. Last but not least, she also sits between me and also my wealth management team. So whenever I have kind of like a tax planning strategy call with our CPA team, she is receiving all of the transcripts of everything that we talked about, and then she is being able to action a lot of things.

Josh Hadley 00:06:40  We have rental properties that I oversee, and she is the one who is able to oversee kind of the basic administration that needs to happen on a lot of those things. And again, it just completely gets it off my plate and I don’t need to worry about it. That is massive leverage. If there’s anything I want to talk about today, it is how important finding somebody with excellent judgment is. And when you can get them plugged in, you can see like the number of tasks that can begin to get off your plate and allows you, as the CEO, to start focusing on the growth of your organization. So here’s kind of like the wrong goal that most people think about when it comes to, hey, I want to hire an executive assistant. And hey, maybe AI can be my executive assistant. Okay, just delegating the task of, hey, reply to this email or draft this email. That’s not the responsibility of the EA, okay? That’s not the goal. If delegation basically creates more questions, approvals, reminders and follow ups on your side, you haven’t gotten anything off your plate.

Josh Hadley 00:07:43  In fact, like you’re only actually like increasing your workload if you have to review everything. If you have to be the one who is kind of critiquing and giving feedback on every little thing that that assistant is doing. So here’s the main goal. Your goal is to give your executive assistant as much context and as much kind of like reins and freedom as you can possibly give them, so that they can actually do things on your behalf. And we’ll talk about that. All right. So the concept I want you to think about is like own and delete. I want my executive assistant to be able to own something. And once they own it, I can delete it from my mind. So how do you get that set up to where, like, truly, your executive assistant owns something? It’s not it’s not just them checking off boxes. It’s they own it. They feel responsible for it. And they’re going to make sure that it succeeds. Okay. So let’s talk a little bit about that. Because if you’re deleting it from your memory it means you don’t have to remember it.

Josh Hadley 00:08:45  You don’t have to check in and be like, hey, where are we at with this? You don’t have to chase it down, right? It’s like, hey, I told you I needed this do by X, Y, and Z. You don’t need to do that. And last but not least is like, you don’t have to repeat context over and over and over again. So here’s the real bottleneck. The real bottleneck whenever somebody hires an executive assistant. And this applies to any team member, by the way. But in this example we’re talking about an executive assistant. The real bottleneck ultimately becomes the CEO because there are many CEOs, many business owners that have the the premise that nobody can do this as good as I can or I don’t trust people. So, Josh, I don’t know why you give them access to your financial data or your personal like your Social security number or your passport, etc.. I don’t trust people. Cool. I say, if that’s you, you need to learn how to rebuild trust with human beings because there are many ethical people out there.

Josh Hadley 00:09:45  And maybe the first step is you yourself have to ask yourself, are you an ethical person and are you a person of integrity? Because guess what? Integrity and virtue attracts integrity and virtue. So maybe if you’re running up against a lot of unethical individuals and you just find yourself in that perpetual spiral, maybe you should take a look in the mirror first. So let’s assume that you have somebody that you trust and you get them in place. Here, your most important job is to not be the bottleneck. But oftentimes you are the bottleneck because you ask them to do something, but you don’t fully trust them yet. So you ask them just to create the draft, but you’re not unwilling to give them enough context. So they’re always following up and asking you questions. And so while you thought you were hiring an executive assistant to get things off of your plate, you’re realizing like, oh my goodness, Like now I just have more questions to answer. Like, I’ll just do this myself. It’s so much faster.

Josh Hadley 00:10:45  That is the trap that most people fall into when it comes to hiring people. They’re just like, screw it. This isn’t like they don’t just get it. And of course, somebody naturally is not going to just get it on day one. I promise you that. It all depends on how good you are at teaching and coaching that individual and onboarding them. So let’s dive into how do you unleash this kind of like bottleneck. Ultimately it’s kind of like a five step equation. And this again applies to an executive assistant. And it applies to the rest of your team. And again, I promise you AI and how we’re actually utilizing AI in this is coming. So stay tuned. But I’ve got to set this foundation number one context. You’ve got to give the background. You’ve got to give as much understanding and information as you can so that that person does not need to come back to you. They have access to everything that you have access to. Number two judgment. Why do you make the decisions that you make? Period.

Josh Hadley 00:11:47  Okay. Then that’s going to lead to trust greater access and greater ownership. So how do you ultimately give context that builds judgment? Well, ultimately that’s what we’re going to be talking about is like, how do you build this context layer with AI so that your executive assistant or any team member that you hire makes better decisions overall and ultimately is able to express better judgment? And so ultimately, this will come down to how good are you at explaining your own judgment? So don’t just tell your EA or your new team member what you decided you need to tell them. What did you decide or why did you reject it? What trade offs were you making in your mind? Why did you decide it? What mattered most and what would have changed? Your answer? Possibly. Those are like six really good questions to always ask yourself instead of just saying like, hey, go do this. Help explain the context and the reasoning behind the judgment call that you are making, and that makes everything that much better.

Josh Hadley 00:12:54  So we’ll talk about all of the practical, step by step actions that you can take in order to make that come to fruition. All right. So now let’s dive into the juicy part of this presentation, which is all about connecting the context. And when I talk about connecting the context, it’s getting your company’s brain in all the information about your business, what you have access to, and enabling that team member with the exact same amount of context and understanding that you have. So before AI can help make my executive assistant make more decisions on my behalf and remove me from the equation. That executive assistant needs to be able to see exactly what I see. So here’s how I have my ChatGPT account set up. These are all of the plugins that I have. Okay, so it’s plugged into our power BI, which is all of our analytics from all of our sales platforms that we have aggregated. It has our project management system with click up. It has my email, it has my calendar, it has Google Drive, it has fireflies, which records every single one of our company team meetings.

Josh Hadley 00:14:08  It has access to slack, has access to all of the new product ideas that I’m kind of noodling on, and kind of a cloud format. And then it has different, plugins and calendly creations. So those are all the different plugins that I have set up next. Guess what? My EA actually runs on a separate operating system. She runs on cloud. Okay, well guess what? She has the exact same plug in, so she’s connected to my email. She’s connected to my calendar, my drive. so on and so forth. Literally, it’s kind of like a mirrored image. Now, here’s a really important one to call out. If your EA works in a Claude code, make sure you add Google’s open source workspace CLI. That’s the standard Gmail connector, and it has label limitations. The CLI actually covers Gmail, calendar, drive, docs and sheets. So paste this kind of like, there’s a whole little prompt in here. So again, if you’re just listening to this, make sure you come check it out on YouTube.

Josh Hadley 00:15:13  copy and paste this little script into Claude, and it will make sure that you get it all set up properly when you’re connecting Google Drive there. Okay, so now that we’ve done the foundational layer okay, we are now going to move into step number one. How do you actually deliver? Now that you have context, how do you begin delivering judgment and giving freedom to your EA that they are actually taking a load off of your shoulders? So as we begin trying to deliver kind of content, further context as to why you’re making the judgment calls that you are making, here’s the best way to support your executive assistant. Number one, it is through capturing your thinking. And my favorite way to do that is through voice to added context. So two tools that I highly recommend are whisper Flow number one. And number two is going to be fireflies. And we’re going to be talking about how I am specifically using each of these in my meeting rhythms with my executive assistant, and then what they’re doing with that.

Josh Hadley 00:16:20  So again, further stepping into step number one here, which is every day I am going to have a touch base call with my executive assistant. This is going to be a 15 minute call. That’s it. It does not need to be longer, but 15 minutes, 30 minutes if you’ve got a lot to talk about. Now here’s the key thing. In these 15 minutes, this is a time for your EA to say, hey Josh, we’re going to go through your email inbox. Here are the emails that I have questions about. Or I’m not exactly sure how I should be responding to these, because even though you might have had an SOP and a reoccurring pattern, at the end of the day, there’s always going to be some random email that comes in that’s like brand new. And these EA could be like, I have no idea what to do here. So here’s how we’re moving mountains here and how it’s actually increasing the flywheel. And my EA is learning ten times faster because the two tools that I’m referring to, whisper Flow and Fireflies.

Josh Hadley 00:17:21  So let’s talk about this exact setup. All right. So for Whisper Flow My EA has like at the trigger ready to go the double click on at least on a MacBook it is the FN key, right? You double tap it and it begins recording your voice and then turns it into, you know, text for you, like while you’re there on on the call. So here’s what happens. Step number one the EA opens the email or the decision during the touch base. Okay. Then me as the CEO, I read it out loud and then I say what I think out loud. Then Whisper Flow is capturing all of those actual words while I’m already talking, and then it just gets dropped into. So like the draft is created for that email thread, and then it automatically just like drops all of that context that I just like spilled out of my head and voice and it drops it into that email. And then the EA immediately moves to the next email. So it’s like, cool. Got it.

Josh Hadley 00:18:24  We’ve now captured that it is saved in a draft. Onto the next email. Okay. And then what will happen? Step number five. Here is the AI will then polish. It will like so ChatGPT or clod. Whatever you want will come in behind the executive assistant. And then basically read the email, read the, you know, whisper flow kind of like context that I added in the decision that I made. And then it will craft a more beautifully architected email response to that email thread, all without us having to like, sit down and like, actually type out these emails and think through about, like, every word that we are saying. So that’s the overall process. But that’s cool in and of itself. And here’s the kind of the case study on this in general. Here’s what we’ve been able to move through. Oftentimes I would have emails sit in my email inbox for days and weeks. And the reason why is because, like, it wasn’t a very hard conversation to have, but I just I knew it would take like 5 or 10 minutes to really, like, flesh out my mind and the way I wanted to think about it.

Josh Hadley 00:19:36  But instead, because we’re having these 15 minute huddles, we’re able to move through and the goal is one email per minute. And so in general, that’s 15 emails per touch base. And there’s a lot more emails that my EA is handling. But these are 15 kind of like difficult emails that I actually need to think through. And sometimes, you know, one email might take me 2 or 3 minutes to think through, but I’m talking out loud. And while I’m talking out loud about the decisions I am making. Number one, Whisper Flow is documenting it in a written language. And then number two, fireflies is recording the entire zoom call at the same time. And that is one of the most powerful things, because at the end of every touch base. My EA will then take that transcript and then riff with it on clod to say, hey, by the way, Josh also tasked me to do X, Y, and Z, or he needed access to the following emails. Or he wanted context on this.

Josh Hadley 00:20:36  Hey, can you gather all of that? Can you find that in the transcript? Can you also finish drafting up all of those emails that we talked about in that touch base today? And guess what? Claude is then able to go through and go and do that. And then here’s the most powerful thing. It is a virtuous cycle. And it’s a has its own kind of enclosed feedback loop. So as I document more of my knowledge and reasoning, if a similar scenario presents itself, guess what? The AI has that context and it will remind my executive assistant. Like this is how Josh approached the situation in the past. This allows me to spend less time answering questions with my executive assistant because it is documenting and capturing everything. Adding it into a memory vault. And again, all of our transcripts, all of our meeting transcripts are then stored in a Google Doc folder or a Google Drive folder. And then AI is constantly able to review those and see them and bring it into its memory. Okay.

Josh Hadley 00:21:41  So that is step number one is use Whisper Flow and use fireflies to document every single conversation that you are having. I promise you, if you’re doing this on a daily basis, imagine how much context you have about the the business and the decisions and why you make the decisions. After one year of doing this 15 minutes a day with your executive assistant and think about how much more capable your executive assistant will be after following a process like this. Let’s move into step number two, which honestly, this is probably one of my favorite steps here. And I’ve got a really, really fun example that I’ll be sharing with you of like how we’re actually applying AI into this specific step. So we talked already about like how I give more context and more nuance to my emails and just various random things that are coming up inside of the business and how we’ve got that in an operating system. In step number two, we’re going to talk about building an actual judgment library about, you know, whether it’s specific SOPs that you need to create in your business or it’s just kind of processes that you need automated on your behalf.

Josh Hadley 00:22:57  But like the reason why your business is as big as it is today is because you’ve made good decisions and there’s a judgment layer that you have used to be able to make those decisions. If you want your business to be able to scale, you’ve got to help other people understand how you make the decisions you make. So what I’m going to share with you is exactly how I document all of the decisions I’m making, not just on emails, but throughout the entire business and organization that honestly, it ten X’s every team member that this touches. And a really good example that I’ll dive into here is like for product research and development. I always had this kind of like thought process. Nobody could do this as good as me. Nobody knows the intricacies of the business and the way I see things in my mind, and the way I could see it coming to light in the future. But I proved myself wrong, and I did it by following this exact process and these AI tools that I’ll be sharing with you now.

Josh Hadley 00:23:56  So number one, my favorite tool that I’m using here is loom. Okay. This is a Chrome extension. I’m a big fan of loom because here’s what I’m doing. The founder mindset shift is like what I just said, which is hey, nobody can do this as good as me. The actual truth is I have never documented how I make decisions, and that’s why I’ve never been able to get anybody else to do this as well as me. That you have not documented your decision making process. That is why nobody else can do this as good as you. Okay, the problem with normal SOPs is that they fail because they’re just written from memory. And there’s a lot of exceptions that get made here and there. And they try to give an SOP based on the ideal if everything’s working according to plan, follow this process. But we all know there’s always going to be like, but what about if this happens? What about when x, Y, or Z happens? What I’m sharing with you is going to be how to take all of those kind of exceptions and kind of fringe instances into, into its context.

Josh Hadley 00:25:01  So the bad way to use AI is to say, hey, I need to go create an SOP for how to do, you know, personal travel management for my family. Right. I told you that. That’s one of the things my EA handles. A bad way would have been for me to go to chat and say, hey, give me an SOP that I could give over to my EA, because guess what? You’re just asking AI to just randomly make up crap for you. And guess what? It will very confidently make up random crap for you. Here is the ten x ai sop method. Number one, you record the work. So whatever it is, whatever the process is, if it’s me looking for Airbnbs and videos for my family, I’m literally going to record the work. I’m going to do the task while recording a loom, and while I record the loom, I am talking out loud the entire time, and I am explaining why I am making each of these decisions. Then I’m going to feed AI that transcript.

Josh Hadley 00:26:03  Then I’m going to ask AI to interrogate me, repeat it across multiple looms. And then finally I will build out the SOP. So let’s talk a little bit more about this. One of the most important things is don’t just take one little process like let’s say as an example, you want your team members to maybe complete their maybe it’s their receipt, their reimbursement forms in a very particular way. that’s a very basic one like that one you could probably do in one loom video, and there’s an SOP for you. But something that’s a lot more nuanced is, hey, here’s how we should do Amazon pay per click advertising. It’s like, man, that is a can of worms because there’s a lot of nuances based on seasonality, time of the day, weekend, day of the week, etc.. Okay, so if that’s true, what you need to do is I recommend doing at a minimum for different looms. And so the reason why is as you record those different rooms, you’re going to be in different times of the day, different days of the week, and you’re going to have different situations presented in front of you.

Josh Hadley 00:27:18  So again, I mentioned this like one of the best things I’ve been able to get off my plate is product research and development. Originally, I thought, I’m just going to have to own this thing forever. But instead I sat down and every week I made I made sure I would record at least 2 to 3 different loom videos that were about, hey, this particular product, why am I saying yes to this one, but no to that one? Okay, and guess what happened after doing this for six months? I didn’t just have four loom videos. I actually had 100 few loom, a few hundred loom videos. And then I was able to take all of those and the transcripts that were created from those loom videos, feed it into AI and say, can you help me put together an SOP? And like a rule, a decision process for why do I make the decisions I make that somebody else could go replicate? And guess what? It came out with 273 different rules that we should be following for our R&D process.

Josh Hadley 00:28:23  And then it turned it into a custom GPT or a cloud skill that then is able to help be an assistant to the new product research and development manager that we hired for the team. That is how I have been able to get my brain out of, or my knowledge out of my brain into something else that can actually be an assistant. That is the power of AI. So here’s how to record those looms that actually work. Number one, you want to make sure that you’re talking out loud while you do the task. You need to be explaining the trade offs in real time, why you choose speed over quality, or you make an exception, say so explicitly. Okay. And do it while you’re on camera. Record across different scenarios. Right. Doing a very routine case, a tricky case, an exception to the rule, etc. and it will just build your judgment layer for you. So if you like kind of what I’m referring to, there’s very specific prompts that I’ve used in order to, you know, have AI interrogate me so that it fleshes things out into a very, very systemized SOP that you could then turn into a cloud skill or a ChatGPT plugin.

Josh Hadley 00:29:38  aka custom GPT is what they used to be called. Then make sure you scan this QR code and you will get access to those exact prompts. Now, I love to share very specific examples of how this is actually working in our business. So here’s the exact way that we’re doing this in our business. So, you can see, my executive assistant. At the end of one of our touch base calls in the morning, I was like, hey, I need you to go look into, you know, we’re we’re going to Park City, Utah. I need you to go find some places for us to stay with our family. And then my executive assistant was like, cool, I’ll help you build the playbook. For that. You’re going to need to record some loom videos. So this is the exact kind of like conversation that my executive assistant had with Claude. Then Claude came back and helped her format an email saying, okay, Josh, if you want me to do this, here’s what I need from you, and I need you to record it in a loom video.

Josh Hadley 00:30:39  And then when I recorded the loom video, she took that back, added it into AI. AI fleshed it all out into an SOP or a preference as to like how Josh operates, how Josh makes decisions when it comes to Airbnbs and videos for his family, if they’re going on a family vacation and then guess what? She built it one time, and we’ve been able to repeat this and just run it on an ongoing basis. So instead of my executive assistant having to be the one that goes on to Airbnb and looks and finds things and ultimately like wastes hours of time, we now have a cloud skill that just goes, does this, runs it, and then guess what? It’s going to serve up ten different options for my executive assistant. She’s the judgment layer she’s looking at and be like, that’s not quite right. Let me go tweak this or you know, hey, that’s actually pretty darn good. I think we’re 90% of the way there. Let me go bring this across the finish line.

Josh Hadley 00:31:40  Then it’s going to be ready for Josh that way. What I get is always my desired end result. Because my executive assistant sits as the judgment layer in between me and AI. Because if any of you have been using AI, I think you can confidently understand that like AI isn’t perfect, and oftentimes you need to keep giving it feedback and keep, you know, muscling it until it actually gives you the desired output that you are ultimately looking for. And so the judgment layer really resides in the executive assistant. That’s why executive assistants are so important. That’s why I’m still very bullish on hiring and getting leadership level talent in your business, because I think the best ROI always is and always will be people, because they have very specific skills and knowledge that you don’t. So this is ultimately what I got. And you can see like, when I got it back, I was like, yeah, that’s exactly like, these are fantastic places. These are places that are I’ve never even found places as nice as this.

Josh Hadley 00:32:47  And they were all within my budget. You can see it went through 342 listings. It reviewed 44 of them. talked about how close they were to like the kids ski school and things like that for the winter. totally on point. And it included photos. And again, my executive assistant helped bring that across the finish line, and I was able to make the decision very confidently. Now let’s move into our third and final step of exactly how we’re using AI in order to help kind of make my executive assistant ten x more impactful in the business. And again, this applies to every single role that you could be hiring for in your business. Step number three is to turn recurring work into operating systems. AKA best tool for this is cloud Code. There’s obviously Codex with ChatGPT as well. So same principles apply, but my executive assistant prefers cloud code and she is very good at this. So let’s talk about this. If there is a specific thing that needs to get done on a regular reoccurring basis, AI should be doing that.

Josh Hadley 00:34:01  Not an executive assistant and not a virtual assistant. So let’s talk about one of those instances in my business that was very basic, something that I was manually doing. Okay. So I would have a coaching call with somebody okay. And after the call ends, I would need to remember to follow up with like an email or saying, hey, here’s kind of a summary of our call. And, you know, some pleasantries and you know about their personal life. Draft that email, send the email, and then jot down notes. Save those notes so that I’m prepared for the next conversation I need to have, whether it’s a week or two weeks from today. That way I don’t forget like, oh, one in the world did we talk about during our last session? It was there. Well guess what, AI does all of that now without me. And most importantly, without my executive assistant. But the good news is, I wasn’t the one who even had to build that system. My executive assistant is the one who actually built that automated flow so that all of these things just happen on repeat.

Josh Hadley 00:35:08  So I ask my executive assistant every week when we meet. What is something that you see that you have to do on a reoccurring basis? that’s very manual because that needs to be automated and that we’re just looking at like every week, can we just get one thing automated per week? There’s always a mountain of ideas and opportunities in front of us. And so it’s just like, can we just keep chipping away at this thing like one task at a time? All right. So now in that example right now that every call is recorded. So the transcript is captured. It’s saved to Google Drive. Claude finds it in Google Drive, creates an email draft, sends it into my email, puts it in kind of my end of day review folder so that I can go and review it and then actually be the one who actually clicks the send button. If it has my blessing that it is good enough. And maybe there’s a little bit of extra context that I want to add to it. Or another thought that popped into my mind, okay.

Josh Hadley 00:36:07  And then it’s automatically going to capture the notes from the meeting and give me a quick paragraph summary, and then it’s adding it to a new Google doc and saving that in the upcoming calendar invite for that client. All done automatically. But previously that was human intervention. That is the reoccurring work that’s super important. so again, this is how the coaching workflow runs. If you’re watching this right call lens fireflies is recording it get saved. The recap lands in my email inbox in the calendar invite for the next coaching call. A new link gets added there. That is only for me to see. That is the context of here’s what we’ve been talking about, and a whole prep page for the next call that I can get myself prepared with. I can show up five minutes before the call and have all of the context previously. Now you may be asking, well, like Josh, how in the world did your executive assistant, put that together? This is the exact prompt, or I’ll call it a lack of prompt that she used in order to build that out.

Josh Hadley 00:37:15  Hey, Claude. like, she’s just having a conversation with Claude. In the conversation that I had with Josh today, he tasked me with thinking through. How can I automate the manual, outreach that we are doing with anybody that he has is, like a coaching client or something like that. how do I automate the email outreach? How do I save notes about that call and store it on the calendar invite for the next call so that Josh has all the context he needs. And then guess what? Claude gave her the exact step by step steps that she needed to take, and then ran it on a schedule, and she was able to build all of that within cloud code. And so while I’m not sharing, like, well, she did this step, one step, this step to this, like that part’s not important, because what I would encourage you to do is do the exact same thing. The best thing to do is to go to Claude and say, this is what I want done, or give it a loom video, give it everything.

Josh Hadley 00:38:19  all of those SOPs that I talked about building, and then give it to Claude and say, like, how do I automate this? And then follow the step by step instructions? That is exactly how you automate that work. Those of you maybe listening to this or watching this, you may be thinking like, Josh, why in the world do you have an executive assistant? if a lot of this is just like AI running in the background, you have fireflies recording things, that’s creating a bunch of email drafts, etc. and here is my best argument for this. Number one, you as the CEO or the founder of the business, your time is not best spent developing software or automation flows. Period. And I know there’s going to be people that will argue that point with me. And there are certain, you know, founders that are very tech tech savvy and they’re more development oriented. And so they’re going to nerd out on that stuff. So maybe they get a kick out of it that two to everybody their own.

Josh Hadley 00:39:21  But your job as the CEO is to focus on growth of the business, not how do I automate things. How do I make things a little bit more efficient? How do I save five minutes here? Ten minutes there? That’s not your job. That’s my executive assistant’s job. That’s the job of my Director of operations. That is thinking through our bigger architecture for how we’re utilizing AI in the entire business, and how we’re allowing AI to empower all of our team members. My job is not to go build these things out. My job is to hire really smart, individual contributors that have excellent judgment. At the end of the day, you’ve heard that in my recent podcast episodes, the number one skill that I hire for is judgment. I want somebody with excellent judgment. And guess what? Judgment gets built up over time, and that’s the most important thing to take away is like, get out of the details, let an executive assistant like, no matter where we go with AI, I don’t see it being realistic that we have $100 million businesses and everybody’s just solo founders, and we all just work with a bunch of AI bots.

Josh Hadley 00:40:38  I don’t think any of us want that. Like we enjoy that human one on one connection and interaction, right? But most importantly, other humans have different skill sets than you do. So I’m going to deploy some of their skill sets they have. My executive assistant is much better at dotting the eyes and crossing the t’s, whereas like, I’m just going to leave a wake of disaster behind me. Take a look at my office desk right now if you want a good example of that. But let me wrap this up with this look. The first six months are the hardest, and this applies to any team member I know. Today I talked really a lot about like how you could set up AI for your executive assistant, but you could take and repeat this with any different team member at the end of the day. And so the first six months are always the hardest. And the reason why is because you are trying to shift and like, you’re trying to shift all the judgment in the decisions and criteria that you’ve built up in your mind over the whatever number of years that you’ve been working on this, you’re trying to give that to somebody else.

Josh Hadley 00:41:47  It’s going to take you at least six months. But now that my executive assistant is coming up on a year, my goodness, the speed at which we are operating now is like definitely ten ex that what it was that first week of December when I was just trying to give her the lay of the land and explain, number one, what type of products we even sell inside of our business. But here’s the overall principle. It’s number one, month one and two. You’re laying the foundation. It is a heavy investment of your time. Lots of loom videos, lots of zoom calls. Maybe if you’re in person, make sure that you’re meeting in person, but make sure that you are using plod. That’s another kind of like AI note taking tool. Like long story short, is almost every conversation you have with any team member should be recorded at this point. And the reason why is because I want to be able to feed our AI brain inside of the business. That’s one of the best advantages being a remote, forced business for the past decade and recording every single one of our team meetings.

Josh Hadley 00:42:49  I have a massive amount of context, and AI can really help us strategize because it has so much context. So make sure you’re recording every single one of those calls and have calls. Don’t skip over calls. Don’t think I’ll just talk to them via email. I’ll just slack them. I’ll just send them a text message. It doesn’t cut it. Have live either zoom or in-person meetings where you get down to business and you’re explaining things in your mind why things work the way they would do. Month three and four is all about calibration. You’re going to see fewer questions from that team member. Better drafts. Your executive assistant will start pattern matching better. You’re still reviewing everything, but corrections are getting much smaller. Month five and six you’re actually building momentum there, anticipating your needs. Drafts barely need minor edits, and you’re starting to trust the output without having to check every detail. And then month six and beyond. This is all about compounding, really. The investment pays off. Less of your time is required.

Josh Hadley 00:43:53  They own the entire categories and you are no longer the bottleneck. That is what you are ultimately working towards. So if you would like access to these prompts, if you want to be able to take this, basically this presentation, upload it to Claude or ChatGPT and riff with it and say, how do I go emulate exactly what Josh is doing with my own team members? Well, here’s my ethical bribe for you. If you haven’t yet been a follower of the podcast, make sure you hit subscribe. then next, leave me a review on the podcast platform of your choice. That would go a massively long way, and if you do that and share it with your mastermind group or a slack community or another operator who needs to hear this, then make sure you come check this out on YouTube where I’ve got a QR code. This will link you to have access to all of these slides. You’ll also have the prompts that I talked about of how to create those loom videos, and use AI to interrogate you until it turns into a very robust SOP.

Josh Hadley 00:44:59  Like I said, 273 step rule book for how we do product research and development, because that’s what I documented over the course of six months. I hope this gives you a better idea of how you can utilize AI inside of your business, to really harness its power to make you ten times more effective, not ten times busier, but ten times more effective. Getting things out of your brain so that you can focus on the growth and only the growth of your business. Because sales cures all. Till next time, good luck out there.