Add Automation to Your Coaching Business (Without Losing the Personal Touch)

You started your coaching business to help people—not to spend hours scheduling calls, chasing invoices, and managing emails. But somehow, the admin work never stops. You’ve probably thought about automating some of it, but you don’t want your business to feel impersonal or “robotic.”

That’s exactly where Joe Casabona found himself. As a former software engineer turned solopreneur, he thought working harder was the answer—until he nearly burned out. That’s when he discovered that automation isn’t about doing less—it’s about making space for what matters most. In this episode, he shares how to use automation to save time without losing the personal touch.

By the End of This Episode, You’ll Know:

✅ Why automating doesn’t mean losing the personal touch. Most coaches think automation makes things feel robotic—but done right, it actually strengthens client relationships.

✅ The biggest automation mistake coaches make. You’re probably automating the wrong things (or avoiding the things that could save you the most time).

✅ How to know when to automate vs. delegate. If you think you can’t afford automation or a VA, this episode will completely shift your perspective.

✅ The easiest automations to start with—even if you’re not tech-savvy. These simple tweaks will free up hours this week, without complicated software or hiring a team.

About Joe Casabona:

Joe Casabona knows what it’s like to be overwhelmed by the business side of coaching. After leaving his corporate job to work for himself, he quickly realized he was spending more time on admin than his actual work. That’s when he started using automation to cut out the busywork—and everything changed.

Now, Joe helps business owners streamline their processes so they can focus on what actually moves the needle. 

Connect with Joe Casabona:

🌎 Website: casabona.org/unstuck

Next Episode Teaser:

Ever tried to start a Facebook group only to hear crickets? If you’ve been struggling to build a real community—or wondering if it’s even worth your time—you won’t want to miss the next episode. Paul Gowder ha

Chapters

• 3:02 The mistake that kept Joe overworked and overwhelmed (and how he fixed it).
• 7:45 How a single moment forced Joe to start delegating—and why it was life-changing.
• 12:05 The most common automation mistake coaches make (and how to avoid it).
• 17:00 The simple automation that immediately saved Joe hours each week.
• 21:05 How to start automating today (even if you’re not tech-savvy).

Transcript

Stephen Box: 0:00

What if you could free up hours every week in your coaching business without hiring a team or cutting corners? Today's guest, Joe Casabona, has mastered the art of blending content creation with automation, helping solopreneurs reclaim their time without sacrificing results. With a background in software engineering and a knack for making tech feel effortless, Joe's built a system that lets him grow his business, and be fully present with his family. If you've ever felt overwhelmed by all the moving pieces in your coaching business, this episode will completely change how you think about automation, delegation, and getting more done without getting burnt out. Hey guys, welcome to another episode of Coach Smarter brought to you by Unshakable Habits. I am your host Stephen Box and this is the podcast where we help fitness, health, and nutrition coaches, sharpen their coaching skills, stand out in a crowded market and build a sustainable business. Let's dive into my conversation with Joe Casabona. Joe, welcome to coach smarter. Thanks for being here today.

Joe Casabona: 1:06

Thanks for having me. I'm really excited.

Stephen Box: 1:08

Yeah, so I've heard through the grapevine that you perfectly blend content creation and technology like it's the best cup of coffee ever. granted, I heard this directly from you, but tell me a little bit about that.

Joe Casabona: 1:26

I have been starting that rumor. yeah, so I have my master's in software engineering, but I don't write any code anymore. One of the things that I was told is one of my greatest strengths is the ability to take complicated topics. And make them simpler. And it's probably because I spent a lot of time in the classroom. And so I'm in this unique position, I believe, where I deeply understand technology, I'm good at teaching. And I have this kind of like entertainment or edutainment, I hate that word, but, entertainment bend, because I also did drama club and I do podcasting and stuff like that. where I can. Both teach the content and the technology, hopefully in a way that the people I help don't get too overwhelmed.

Stephen Box: 2:21

I think that's going to be really helpful today because I know a lot of coaches out there when it comes to technology. Are not too keen on using it because it can be very overwhelming. so I really want to dive into your story a little bit today, how you got into using automation more and why, and then maybe we'll wrap this up with what are some of the tools that you're using that you would recommend for other coaches out there?

Joe Casabona: 2:47

Yeah, absolutely.

Stephen Box: 2:49

so let's start with your story. tell me a little bit about, once you started coaching. How did you come to this place of realizing that you needed to find this blend of technology and content creation?

Joe Casabona: 3:02

Yeah, so I think my toxic trait is that I over engineer things and a perfect example of that happened I promise you just this morning I can send you a picture if you want to include it in the show notes, but I have this Elgato mounting setup And I just got a new light and I'm recording more short form videos from my phone and I wanted something with perfect lighting that I can mount my phone on and it took me like an hour and a half and I definitely did not need to spend that time doing it, but I had to write. And so I know this thing about me that once I am told a problem. I need to find a solution for it, and I need to, act on it, almost immediately. This is why my wife never tells me about problems during the work day anymore, because she knows it's going to derail me. and if I was going to have a business that worked, where I didn't just keep getting sidetracked, I would need to leverage technology, automation, and delegation so that I could still solve these interesting problems and potentially over engineer them, but still serve my clients and students. And so I think that was, that's always been something embedded in my DNA. Can I make computers do work for me?

Stephen Box: 4:25

Okay. Was there a specific thing that kind of happened for you that made you lean more into it?

Joe Casabona: 4:36

Yeah. having kids there, I think there are two nexus points, for that set me down on this path. when my daughter was first born, my oldest, I have three kids. so when my oldest was first born, I immediately realized that being a web developer at an agency that served fortune 100 companies was not the job for me anymore because I didn't want to have to give up my nights and weekends. To build some website or because a website went down. couple that with the fact that my super supportive wife told me to leave my agency job and make my own business I knew that I had to put systems and automations in place if I was going to run my own business and be a present father because Running your own business is hard It's not just oh, you get to do whatever you want, right? I, there are so many people who are like, when are you going to get a real job? And I'm like, this is a real job, because I make money and I have to do a bunch of different, I have to serve in a bunch of different roles. And so, about six months or so into my, self employment, post kids, a friend told me that I had to take stuff off my plate. And I, what I heard was keep doing the amount, the same amount of stuff, but let robots do some of them. And so I really started automating as many processes as possible. that was the kind of the first point, that hit a wall in March, 2020. which for those of us who are trying to forget, was basically when the pandemic started here in the United States, at least, my wife's a nurse. And so I had one kid at home. Soon to be two kids at home. They couldn't go to school. I was self employed. My wife was working more. So I, the own, not the onus, but the responsibility fell on me to keep my kids at home and watch them because my wife was literally saving people's lives and I was like talking to people. but because of that, my business started to suffer and shortly after my second was born, or a few months after my second was born in July, my wife had gone back to work after her maternity. I was struggling, and in November, I had a panic attack. And I remember this vividly. I'm sitting on the floor of my kitchen. My daughter comes up to me. She is three years old at the time. My son is crying, because he's a baby. And, she just gives me a towel and a bottle of water, and she says, It's okay, Daddy. Everything's going to be okay. And, it was not, that was not okay for me. I'm supposed to be taking care of her. And so I continued the mission I started in 2018, which was to take as much stuff off of my plate as possible until I finally hired a VA. I stripped out anything that I was doing that I didn't need to do. And I automated everything else. and then fast forward a year from that point. our, we welcomed our third into the world on Christmas Eve actually, and I took off an entire month stress free to spend time with my new family, my newest addition to the family. because I had those systems and processes in place.

Stephen Box: 7:45

Cool. When you look at back at that time in your life, what were the first things that you started to automate? I know you said like you automated everything else, but like, where did you prioritize automation?

Joe Casabona: 8:00

So the way that this is the blend, of technology and content that I think about, because I learned somewhere during this journey that I think more like a computer than most people do because I'm a programmer. And so I understand Oh, for a computer to do something, it needs a trigger, right? It needs to say if this happens, then do this thing. and so I made a list of everything I was doing. And I immediately looked at the, okay, what are the things that always happen and always have the same outcome? So one example is with a scheduling link, right? Someone picks a time. On your calendar, and then they get a calendar invite, right? or someone buys a digital course from you, and then they get an email with a login to access the course, right? Stuff like that, I looked at my list and I said, Okay, these two apps talk to each other, or these two apps do something and need the same information, can they talk to each other through Zapier? that's how I started automating. If I want to send information from a Google form to Notion, Or from Calendly to Airtable or whatever, that's the first stuff I really started to automate. and then I looked at everything I was doing and I said, do I actually have to do, do I personally need to do this? And if the answer was no, I either looked at if I could automate it or if I was going to give it to my VA.

Stephen Box: 9:32

When you say that you looked at it and decided, was it something you needed to do yourself? I think this is something that a lot of coaches get caught up on because we want to do everything we feel like we need to have our hands on literally everything that happens in the business, because if we don't something's going to go wrong. How do you help coaches deal with that?

Joe Casabona: 9:57

Yeah, it's a little bit of a harsh truth, right? And I should say, I was like this too. in college, I was, like the chairperson of this planning board at the school that planned events. And one of the things that, my, like faculty or staff, mentor told me to do was delegate more. She's you do too much yourself. So I delegated a couple of things to my co chair and he did them wrong. and that reinforced for me that I, if I want something done right, I have to do it myself. But when you're sitting on the cold kitchen floor and your three year old is it's okay, daddy. that, that's like a, that's like a harsh truth that you need to meet. I can't possibly meet my family obligations and run my business. and do everything for my business, I should say. when I ask, do I personally have to do this, it's really a question of, does it require my brain? Does it require my exact skillset or does it require my voice? If it's one of those three things, then I do it. so like the podcast, I can't outsource the hosting of my podcast because It's my voice, but scheduling a guest, I don't need to do that. I can send them a scheduling link. We don't have to do the time zone dance, or doing research on a guest. I give my VA some light things to look for. Here's a website and a name, find their socials, find the last podcast interviews they did, transcribe them and throw them into chat GPT. I'll take it from there, but I don't need to, I don't need to do that initial stuff. and I usually remind people that the things that you think only you can do, somebody else can probably do better. And that's, that has proved to be true time and time again, right? if it wasn't, we'd have a bunch of solo businesses with one person doing everything, right? But most businesses are not like that.

Stephen Box: 12:05

One of the other things that I think pops up for me is you've mentioned a couple times a VA and I know for a lot of people, especially if they're still in the early stages of that business, or if they're running a one on one coaching business where. Maybe their time is maxed out, but their income really still isn't where they want it to be. The common reframe is I can't afford to hire a VA, right? So I guess the question I would ask you is one, what would you say to someone who feels like they can't afford it? And then two for the person who truly actually can not afford it, what would my recommendation be in terms of how can they use automation to fill that gap a little bit?

Joe Casabona: 12:53

Okay. I'll say I felt this way for a long time. I would ask two questions. Are you willing to invest in your business and do you value your time? Cause if you don't value your time, like I can't, I cannot help you. That is the one prerequisite for me to help people. and I think about this when I think about the first time I hired somebody to mow my lawn. Cause that feels stupid. As a man, I feel like it's my job to mow my lawn. And so every Saturday I would dutifully go out and mow the lawn. And it would take me an hour and a half and I would smoke a cigar and it'd be fine. but again, during the pandemic, a lot of things changed and my wife was working. And so I was working on the weekends to try to make up for the time I missed. And then it rained a lot. And so like on the days I could mow my lawn, it was raining. And then we went on vacation and three and a half weeks of a lot of rain had gone by. And it took me six hours. When I finally got to it, it was a Wednesday. It took me six hours to mow my lawn. And I thought, it just cost me 1, 200 to mow my lawn. Because my, that was, that's my billable time. But, my crappy lawnmower kept getting clogged up. And it needed gas and oil. And my, weed whacker is also crappy. Because I have a small lawn, I don't need the best stuff. and all the grass was wet. So my leaf blower didn't work six hours later. And so I looked into hiring lawnmowers and for 30 a week, I never have to think about mowing my lawn again. And so if you say you can't afford it, I would challenge that. What else are you paying for? that you could divert funds, right? There are people who say, Oh, I can't afford to get new tires for my car, but they buy a 6 coffee every day. Right now, there are people who are maybe just starting and bootstrapping and they really can't afford it. maybe they don't have clients and they're not willing to go into debt. I'm not here to talk about that. If you think that using your credit card is a worthy investment, then fine. I would never tell somebody to go into debt if they don't have to, that said, I have used my credit card to help me out. neither here nor there. If you really can't afford it. what I would do is look, figure out your highest impact time. And optimize for that, right? So if you coach people and you charge, let's just say 100 an hour for the easy math, then you want to try to get as many hour long sessions as possible. And if that means not posting on Instagram, or not logging into Twitter. Or whatever, X, then so be it, right? Think about your highest impact time and spend it there. If you feel like Instagram is the place where you get clients, then fine, be on Instagram. But if you're just like wasting your time posting and scrolling, that's time that you can better spend. Because when you optimize to bring in more money for your business, Then you will be able to afford a VA, or you will be able to pay Zapier, for Zapier, right? Which is 20 bucks a month. I think if you're not willing to, and this is I guess the last harsh truth on me, because I know I've been talking for a long time. If you're not willing to invest 10 to 20 bucks a month, 10 is how much make. com costs, 20 is how much Zapier costs per month to, to get more than just the free stuff. I would question, I'll put it this way. I don't want to sound like a jerk. If I wasn't willing to invest 20 bucks a month into a tool that could save me hours per week, I would question my commitment to the business. Maybe I should just get a full time job then because at least I know I'm just working nine to five and the business will pay for all the tools, right? I would, there are people who say they can't afford a VA, they can't afford the tools. I would strong, I would have you strongly reconsider that position. because there are VAs, offshore VAs, mine, I do, I pay her a living wage for the Philippines, but a living wage for the Philippines is like three to 400 a month, right? and I pay her way more than she told, than she asked for, right? Because she is so crucial to my business and I never want her to leave me. I would really strongly consider that position because as Bill Gates said, time is the only thing. You can't get back, you can make more money, but you cannot make more time.

Stephen Box: 17:50

One thing I want to throw out real quick, and I want to just get your thoughts on this. I think a lot of times when people hear automation, they think that means it's completely hands off. Like you're just, you're putting something in and it's doing all the work for you. And for me personally, I tend to think of automation not just from a software perspective, we use the example of the scheduling link. that's something I go and set up one time and going forward, I'll have to do a send people a link or some places I just have the link posted and people can go click on themselves only have to send it to them. But I also think about things like setting an alarm on my phone is a reminder or things like that is being automation because it reduces my things that I have to remember to do.

Joe Casabona: 18:37

I love that, and I fully subscribe to that, right? My wife one time asked me how I, I, I do have a good memory, right? my brother called me yesterday and they were trying to think of emo bands from our youth and I just rattled off like 20, some of whom I still listen to. I do have a good memory, but my wife one time asked me how I remember all this stuff and I said, I don't. I write all of this down if I have optimized my phone and my Apple watch for quick capture so that whenever, wherever I am, I should be able to shout into the void and record a thought while I'm driving, while I'm in the shower, while I'm on my walk, wherever I am, I should be able to be like, Oh, I need to remember to do this. Let me type it in or say it into my phone. I've been talking to my phone a lot. It feels weird, I gotta get over it. and I fully believe that, right? So I have the iPhone 16 Pro. I don't, I forget which models now have the action button. But that action button, I press it and it brings up a list. Do you want to record a note, a voice note? Do you want to input a task? Great. Those are the two things that I want to do the most, that I want to be the easiest. And so in two taps, I am capturing an idea. The action button on my watch, because I have the Apple Watch Ultra. That just straightly, that straightly, that immediately goes to an app called Whisper Memos. Where as soon as I push it, it just starts recording. And when it's done recording, it transcribes and emails me. I think all of those things are automation. Anything that makes your life easier. That reduces your cognitive load, right? I have a reminder in an app called do because it's like persistent reminders like it'll remind you every five minutes until you tell it not to That reminds me to pick up my kids on Monday, Thursday, and Friday because those are the days that my wife is working and if my father in law picks them up great, but I get the notification at two 30, so I never have to worry after lunch about losing track of time. I can get in the zone and then I get that notification. I go, okay, great. I gotta leave now. Or, oh, Bob's picking them up. I fully subscribe to that. And if you're automation hesitant, do something like that to dip your toes in the water.

Stephen Box: 21:05

Okay. as we wrap up here. I do want to give people something they can really walk away with today. Before we dive into that, I do want to take a second to give you to tell us a little bit about who you help and what you do and how people can get a hold of you.

Joe Casabona: 21:24

Yeah, this is a. thank you. I appreciate that. I help busy solopreneurs create space in their lives by improving their processes. Those busy solopreneurs are probably parents. And they probably have a podcast because that's where a lot of my systems, a lot of my money comes from my podcast. And so that's where my systems are optimized. and if you go to casabona.org/unstuck, you'll see two things there. If I've just like totally sold you like, yes, I need your time. You can just get some of my time right there. but there's also an opt in on the bottom of the page that'll give you access to my automations database, which has 40. Blueprints and templates, but ideas. So if you're like, I don't even know what I could automate, this automation database will give you things that I use on a regular basis to automate my business.

Stephen Box: 22:19

So this is totally unplanned, unscripted here. I was actually going to ask you for a list of things that people should, look at automating, right? Like a high level overview, but you know what? he just told you where to go find it and for free. So go to the link. I'll drop it in the show notes and you will be able to get that information there. Joe, not only an automation specialist, also a mind reader. So Joe, thanks for coming today. I want to give you one final, chance here to share anything with my audience that maybe we didn't get a chance to talk about that you think is really important for them to know.

Joe Casabona: 23:02

Yeah, I want to reinforce this fact because it took me a long time to learn and it was life changing, right? it's like how everyone tells you should niche down in your business, but you don't really see how impactful that is until you actually do it. you don't have to do everything yourself. In fact, you shouldn't do most things. there was one thing that I gave to my VA that was publish my podcast episode. And publishing my podcast episode is a multi step affair because as I mentioned at the top of the show, my toxic trait is over engineering. And when you publish an episode for my podcast, you have to upload it to YouTube because there's a video version. Upload it to Transistor because that's my audio host. you have to mark in the file in Transistor where the dynamic ads should go. And then you have to take all of that and publish it to my WordPress site. Because my website or the show is crucial in its growth, I believe. And I thought, this is too complicated. But, you know what? I recorded myself doing it. I narrated it. I gave my VA the video. And now she does it better than I do. Because I don't follow the steps that she wrote out. I, full of hubris when I have to do it. I'm like, I've been doing this for 12 years. But, there's always one step I miss. Where I'm like, Oh, I forgot to do that. So if you might think a process is too complicated, but if it's, if you can clearly explain it, and you can walk somebody through it, they can do it and they'll probably end up doing it better than you. Okay.

Stephen Box: 24:49

And I'm going to assume that you have some, some suggestions on that download that we're talking about for apps and ways to capture that, that data to give to your VA. Okay.

Joe Casabona: 25:00

Yeah, for sure. There's a bunch of, Zapier templates and things like that. and I do, so I do have a video as well. Maybe I should put this in the email sequence, but I have a video on my YouTube channel, outlining exactly how I work with my VA. and so it's, I showed the notion template for that and how I assign her tasks. And, if you watch that video, there's a link to download that template too. yeah, I, I aggressively give away things for free because I know that, if people. There are a lot of do it yourselfers, but for the people who are ready to accelerate, that's where I can come in and help them with their specific problems. yeah, you can probably find a lot of my notion templates, on my website.

Stephen Box: 25:41

All right. Awesome. Joe, thanks so much for coming today. Appreciate the time and, have a good one.

Joe Casabona: 25:46

My pleasure. Thanks for having me.

Stephen Box: 25:48

Hey guys, that's a wrap on my conversation with Joe. Thank you so much for tuning in today and thank you to Joe for being our guest today. I hope this episode gave you some ideas on how to simplify your coaching business and free up your time. Before you go, I do have two quick things for you. First, if you got value from today's episode, do me a favor and share it with another coach who could use a little more breathing room in their schedules. And if there's a topic that you love for me to cover on the show, there's a link in the show notes where you can send me a message, or you can also send me a message on Instagram. That link is also in the show notes. I would love to hear from you. Before we wrap up, I do want to give you my four key takeaways from today's episode. Number one is automation isn't about replacing you. It's about removing the distractions that pull you away from actually what matters. I know for a lot of people, they think of automation as a way to like remove themselves from the process, but as coaches, it's very important that our clients still feel connected to us even when we're using automation. Number two, the easiest place to start is with anything that you do repeatedly. So if you've sent the same email more than once, things like a calendar invite, stuff that you're doing repeatedly. just go ahead and automate those tasks. Number three, your time is worth more than you think. You wouldn't spend hours mowing your yard just to save a few bucks. So why are you spending time on tasks that software can handle for you at a fraction of the cost? And number four, you don't need to be a text expert. Start small, get one system in place, or hire somebody who can help you set these things up, and then you can always build from there. Coming up on our next episode, we're going to be diving into something that a lot of coaches want, but few know how to build, and that is a thriving community. So if you've ever started a Facebook group only to hear crickets, or you're wondering if community building is even worth the effort, My next guest, Paul Gouder, is going to share how he grew his online community to over a hundred and thirty Thousand members without constantly posting or pushing sales So if you're not already following the show go ahead and hit the follow button So you do not miss that and as always I appreciate you spending time with me today This is Stephen Box reminding you that coaching smarter creates a lasting impact for you and those you serve