Sometimes You Need to Fire Everyone and Start from Scratch with Jordan Eaton

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In a way, the chaotic start to our interview, followed by the calm, cool conversation that followed, is a metaphor for Jordan’s business journey this year. 

See, this isn’t just a story about how to hire good people for your business. It’s a cautionary tale, and proof that running a business is about always learning and adjusting. See, Jordan runs an agency of high-level remote assistants. 

Today, she’s telling us her own trials and tribulations with making what seemed to be the right hiring call but ended up plunging her business into a few chaotic months 

Don’t worry though, through patience and vigilance, she came out on the other side in a much better position. Plus, in the PRO show, we talk about what she’s doing for me…and why she’s contributed to me potentially leaving Airtable for Notion.

Top Takeaways

  • You need to share your mission with your team early on. This ensures that you’re both aligned on the same values – which will form a stronger bond than a paycheck. 
  • Know when to communicate. Jordan saw that through hiring contractors, they were taking on too much, and as a result, the quality of their work slipped. Clear communication could have prevented the worst outcome for her: loss of clients. 
  • Know when to cut ties. Jordan saw that for her agency, a contractor relationship would not work. So she pivoted and decided to hire full-time employees instead. It took several months to find the right fit, but she’s happy she didn’t rush into the decision. 
  • When you do bring on new employees, make sure to have a rock-solid, hands-on training program. This will allow them to start learning and doing, from day 1.

Show Notes


Jordan Eaton: The main one was the clients coming to me and saying, “This person is not doing their work. They’re not checking in. They’re not doing what was promised.” And yeah, we lost a couple of clients. That is not great. I don’t like that.

So after having the conversation with them, they were like, “Yeah, I have a lot of stuff on the go, blah, blah, blah.” And I was like,” Oh, that’s unfortunate. I wish you would have communicated that with me before.” And yeah, it just was not great. So being a business owner, you learn. And, you know, sometimes you make mistakes, but you learn through doing.

Joe Casabona: In a way, the chaotic start to our interview, followed by the calm, cool, collected conversation, is a metaphor for Jordan’s business journey this year. See, this isn’t just a story about how to hire good people for your business. It’s a cautionary tale and proof that running a business is about always learning and adjusting.

See, Jordan runs an agency of high-level remote assistance. She was an administrative assistant herself starting in 2005, gathering a bunch of skills in different areas and honing those skills in organization, communication, and problem-solving before going out on her own and starting BOSS Assistants.

Today she is telling us her own trials and tribulations for what seemed like making the right call in hiring, but actually ended up plunging her and her business into a few chaotic months. Don’t worry, though. Through patience and vigilance, she came out the other side in a much better position. So you’re going to hear that story.

Plus, in the Pro show, we’ll talk about what Jordan is doing for me as I have hired her agency and why she might be contributing to me leaving Airtable for Notion.

Look for these top takeaways. The fact that you need to share your mission with your team early on. This is going to make sure everyone’s aligned on the same values and will form a stronger bond than just a paycheck.

Number two, know when to communicate. Jordan saw that through hiring contractors they were taking on too much, and as a result, the quality of their work slipped. Clear communication could have prevented the worst outcome for her—loss of clients.

Which brings me to number three. Know when to cut ties. Jordan didn’t realize she had to cut ties until she lost those clients. So she saw that, for her agency, a contractor relationship would not work, she pivoted to hire full-time employees instead. And it took several months but she’s happy she didn’t rush the decision.

And finally, a bonus number four top takeaway. When you do bring on new employees, make sure to have a rock-solid hands-on training program.

We’re going to talk about all of that and so much more in this episode. I know you’re going to love it. You can find all of the show notes over at There you’ll also be able to become a member of the podcast Workflow Foundry, where you can get ad-free extended episodes and behind-the-scenes look at how I put this podcast together, as well as so much other stuff.

If you’re an Apple Podcast subscriber, you can subscribe right in the app.

But that’s it. Without delay, let’s get to the intro and then the interview.

[00:03:23] <Music>

Intro: Hey everybody, and welcome to How I Built It, the podcast that helps busy solo producers and creators grow their business without spending too much time on it. I’m your host Joe Casabona, and each week I bring you interviews and case studies on how to build a better business through smarter processes, time management, and effective content creation. It’s like getting free coaching calls from successful solo producers.

By the end of each episode, you’ll have one to three takeaways you can implement today to stop spending time in your business and more time on your business or with your friends, your family, reading, or however you choose to spend your free time.

[00:04:11] <Music>

Joe Casabona: All right, I’m here with Jordan Eaton. And I’m excited because while Jordan and I do work together and while we have done a webinar together on automation and delegation, today we are talking about something that I think is a little scary but needs to be done.

So, Jordan, let’s dive right into it. What do you take into account when you’re building a team of remote assistants or really a team of people to work with you?

Jordan Eaton: When you’re building a team it is so, so important that you find people that are team players and then also that they’re extremely bright and that they’re going to be part of the vision that you’re seeing for your company, and they’re going to help you go forward with what you’re trying to do.

Joe Casabona: Yeah, being part of the vision. That’s really important. Because it’s really the difference between just doing a job or advancing the company as a whole. Like, I always did my own side stuff, but I made it very clear to employers that when I’m here, when I’m on the clock for you, I’m team you.

Even now I’m an evangelist for while still maintaining my business. And when I talk to them, I still say, I’m all about the product and the team. So I feel like being part of the vision is something that might get overlooked because people are looking for either high performers or just people who they know can perform the task well. But it really needs to be the full package, right?

Jordan Eaton: Yeah. I mean, some business owners don’t even let their employees know what their vision is and what their mission is. And that’s crazy to me because if you’re not on the same page, they’re not going to give you their hundred percent. They’re not going to be there for the business in the way that you want them to be showing up for you.

Joe Casabona: I wish I had a stat in front of me that’s like after a certain amount of money, people stop caring. Money is not their driver, right? You know, you need the people who work at like Patagonia, right, who care about the environment. Sounds like it’s dumbing down what they care about. But to put it succinctly,

REI, you know, they make it really important that they’re not going to open on Black Friday because they care about family and their values drive that mission.

If you don’t know that as an employee… Well, first of all, if you don’t know that as a founder, you need to figure it out. Like as a business owner. And then you need to share that with your employees or potential employees because that’s… I think, based on what you’re saying, especially more than anything is the thing that’s going to make them feel part of the team, make them want to do as good a job as they can.

Jordan Eaton: Mm-hmm. For myself, remote work was actually a value of mine. Like, being comfortable and working from a place where you can be creative and you know, maybe you’re sitting in your PJs but at least you feel comfortable and you’re able to work. That shines through because it’s actually… I was reading a study and people are actually more prone to taking a pay cut as long as they can work from home.

Joe Casabona: Wow.

Jordan Eaton: This is kind of crazy. But I’m glad that I was able to build this 100% remote business and let people work in the way that they are most comfortable.

Joe Casabona: I think that’s really important because, I mean, the reason that I quit my only in-office job as an adult, like I had a bunch of internships in office, because I’m an elder millennial and remote work wasn’t the thing for a while. But after I graduated college, I wanted almost exclusively remote jobs.

And one of the reasons I quit my job at the University of Scranton was because they were… my one manager at least was very remote averse. She did not want me to work outside the office. Like sometimes I want to go to a coffee shop, and she’s like, “No, what if someone sees your screen.” And I’m like, “It’s not like we have state secrets. I’m working on the website.” That was very frustrating to me.

So I think really understanding those values, right? If someone wants to be in the office or wants to meet their employees because they feel isolated or whatever, that’s something that they need to know upfront. So knowing your values and communicating them is really important right from the hiring standpoint.

Now, once you hire someone… I guess one of the big scary things about hiring somebody is they can interview great, but then be terrible. What’s your process for after you hire somebody?

Jordan Eaton: You have to make sure that you have a down-packed training program. You want to set them up for success from the get-go. So I have different mediums of training. So there’s hands-on, there’s them watching me do stuff over screen, they’re watching videos, they’re filling out forms, like all that kind of stuff, doing quizzes. There’s different ways that people learn.

And I think that it’s a good idea to get them doing some hands-on stuff from the get-go and then have someone there kind of overseeing and supporting. But yeah, you really need to set them up for success and not just throw them to the wolves. You need to have things that you want to tell them about. Like, have that planned is basically what I’m trying to say.

Joe Casabona: Yeah, I agree. Looking at some of my old job and the training that I went through, I basically was like forced my first week to sit and watch my coworkers do stuff, or sit and have my coworkers word-vomit things at me. And as you can imagine, that did nothing for me.

When I actually started doing the work, I went in and I asked them questions. So the most effective onboarding for me in those jobs was a quick meeting to like show me how to access something. And then as I started to do stuff, I could ask them questions, like you said, doing the hands-on stuff.

And now for you, Boss Assistants is a remote assistance agency where ideally you have a number of people who are working with clients. Do you want those people to be interchangeable? Like if I’m working with you on a Monday, but then, like, you’re out sick on Friday, can someone else take over for you? Or is it more like one person is assigned to a client based on the abilities and the needs of the client?

Jordan Eaton: I try my best to get one person working with them. Because it does take that time to build up the relationship, build up that communication, figure out how you guys work best together. I mean, if there is a time where that person has to take a leave or something like that, then definitely having SOPs and making sure that we’re documenting how we’ve done things is great. We do SOPs. That’s kind of some stuff that we do. But for the most part, we like to just have one person working with that business owner.

Joe Casabona: Gotcha, gotcha. That makes sense. It’s almost like a remote employee for that business, right?

Jordan Eaton: Yeah. Yeah.

Joe Casabona: So with that in mind, do you generally try to hire for the same skill sets or different skill sets? This is very interesting to me. I guess, full disclosure, I’m working with Jordan and Jordan’s agency, and at this point, Jordan is the person I’m working directly with. You’re doing cold outreach for me to try to get more coaching clients and things like that.

When you hire do you look for people who can do those things? Or when you hire, you’re like, I want to offer a new line of service for maybe like graphic design, or whatever? Do you look for somebody who can do that? Does that make sense?

Jordan Eaton: Yeah, I definitely look for people who are multi-skilled. But there is a certain point where people aren’t going to have a huge array of skills. Like, it kind of makes me laugh when I look on websites and virtual assistants are like, We can do everything. We can do 100 different things.” And it’s like, people really aren’t going to be that skilled at 100 different things.

So for the most part, when I’m onboarding people, I am asking them, What do you enjoy doing? What do lights you up? What is your favorite thing? Like if you could just do one thing, what would that be? And then I make sure I pull it out of them, like, “Oh, I really liked doing the social media portion. I really like creating content for blogs. I really like doing email newsletters. Like they let me know, and then I try and match them with a client that is asking for that particular skill.

So, yeah, most of the time, they’re multi-skilled, but there is going to be some things that they really enjoy doing. And I want to put them in a place where they’re actually liking what they’re doing as opposed to doing stuff that doesn’t really.

Joe Casabona: Yeah, stuff that feels like grunt work or something, right?

Jordan Eaton: Yeah.

Joe Casabona: Going back to what you said earlier, it goes both ways, right? You want to know what lights them up, as you said, and they need to know what lights you up as a business owner, so that everybody kind of remains happy, right? Because once someone becomes unhappy, maybe their work starts to suffer.

The term quiet quitting was a thing at this time last year. I don’t even really know what quiet-quitting was. I assumed you just like stopped doing your job, but you’re still on the payroll?

Jordan Eaton: I think from my understanding, it’s you put in the most minimal effort just to make sure that you’re still getting paid, but you’re really like checked out from your position.

Joe Casabona: You definitely, as a business owner, want to prevent that. So you ask, what do you enjoy doing? You look for people that you can align with, with those businesses who need that particular skill set.

I want to touch on what you said about offering a million different things because a VA agency reached out to me and asked if I was interested in hiring. My VA was sick, so I was like, “You know, might be good to have somebody who can step in and fill her shoes in case she’s out for a while.” And they hit me with this crazy long, unnecessary presentation. So I’m like, “Okay, so you want to save me time and you’re wasting time.”

And then they presented like 20 different services that they offer starting at $5 an hour. And I’m like, they’re in the Philippines, so, you know, there’s a currency translation there. But I asked them I’m like, how do you offer this many services? And they’re like, “Well, you know, we hire a lot of people and then we bring in more employees through the mission. And I’m like, What’s the mission?” And it was like very… felt very cult-like. And it was just like a really bad feels.

But the first alarm for me was the fact that they said that they could offer the services that usually cost tens, hundreds of dollars an hour in some cases for $10 an hour or $5 an hour. So that’s an immediate red flag.

So how do you know when it’s a bad fit? The good employees, right, they’re going to… I feel like we are both good at our jobs. We get some autonomy and then we kind of run with it, we run the important things by whoever we’re supposed to report to, you know, client freelancing, or in a full-time job capacity, whatever. How do you know when it’s going bad, though?

Jordan Eaton: I mean, are you asking for my business, like personally when I knew or just in general?

Joe Casabona: I mean, let’s go with your… because this is really subjective, right? When I managed people in my agency job, I could tell when they weren’t doing a good job because I would look at their code, and they weren’t doing a good job. And I had actual reasons for that. For me, I would talk to them and say, like, “Hey, you can’t do it this way.”

And the big thing for me was like, “That would take longer. This was easier.” And I’m like, “Yeah, we don’t get hired to do easy. We get hired to do right.” So that’s how I would know it’s going bad. So I guess, yeah, for you in your business, right? Because you hire people, and then they work with other clients. Like the other client is essentially their direct report, I’d imagine, right? So yeah, how do you know when it’s going bad?

Jordan Eaton: They have to be crazy good at communicating and also have a high EQ, emotional intelligence to know what’s the best way to communicate with the clients they’re working with. Like, if they’re writing long, long emails and the client that they’re working with doesn’t like reading emails, then obviously they’re not communicating with them in the way that they need. If they would rather you just pick up the phone and call them for something, then like, you know, obviously do that.

They really have to pick up on cues. Like, be one step ahead is kind of what I look for, honestly. You have to be just really good at communicating and knowing what the person needs kind of before they even do.

Joe Casabona: Yeah. I mean, in this case, that makes sense, right? People hire you to make their lives easier. I have a VA in the Philippines. She’s great. Hey, Ana. But there’s a little bit more oversight with her, because the things that I have hired her to do are not judgment call things. She doesn’t understand me and my business in such a way that I could say, like, Oh, find me podcasts to be on or find me conferences to speak at. Because that takes a little bit of understanding and autonomy, and understanding the culture of the country I’m living in.

But for you and people who are hiring you, I imagine that they’re hiring what’s close to an online business manager, maybe like below that a little bit, or an actual assistant to take things off of their plate, and then they have to never think about it, right?

Jordan Eaton: Yeah. We want to be helping you be the brains of the operation. Like, if you say, I need to do this, but I’m not sure how, we want to be able to help you take it from your idea to fully finished product. Or say, Hey, I want to, you know, fix my website or this or that. Like just little things to be able to just go and do it. And not sit on things too much. I feel that sometimes business owners they overthink or overcomplicate things. I make sure that the people we have on board are people that are doers, that are wanting to go and just get things done.

Joe Casabona: Yeah. We’ll talk about this more in the pro show, which you can become a member over at Or if you’re listening on Apple Podcasts, you can subscribe directly in Apple Podcasts. But one of the things that I hired you to do is cold outreach because I don’t like doing that. I overthink it. I’m like, “What if they say no? I’m emotionally attached to it in a way that you have high emotional intelligence but you’re not taking it personally. Right?

And some people are straight-up mean. Like there was one lady who didn’t accept… I guess I will tease the full conversation here. But there was one lady who didn’t accept the connection and was just straight up mean to me about the… and I’m like, I was nice. But I was like, God, I wonder how many of these Jordan sees that I don’t see that would ruin my day because I just think about that.

But thanks to your efforts, right, I’ve had multiple discovery calls a week, and a bunch of potential clients. Yeah, right? Like, yeah, Jordan… that I wouldn’t have because I wouldn’t be doing that. I want to focus on creating content.

Jordan Eaton: I think, for the most part, I have removed myself from the outcomes of a lot of things just as a business owner. Even in my business, if I’m outreaching to people… like there are people who are mean or they are having a bad day, but for the most part, you can’t take it personally for anything, really.

People they might treat you a certain way but I just let things roll off my back. I think that’s something that people have to do, in general.

Joe Casabona: Yeah, I definitely agree. I tell my kids hurt people hurt people. So sometimes if I’m having a bad day, especially, it just like… for me, I always have a witty and biting comeback, and I know that that’s not the most constructive thing to do. So, for me, I just think about it later. I’m like, Man, what if I just said that, but I don’t because I’m actually a nice person.

Jordan Eaton: Oh, you are. As an assistant, though, I have worked with people that have been in high-stress positions, or you know, they’re business owner, or they’re VP or they’re CEO. Like, yeah, that’s super stressful. And I have been the direction of their stress sometimes. I know that they don’t mean it. So I’ve like really been able to build up that.

That’s another thing too, that I look for in my assistants. Like, don’t take things personally because if someone’s had… like your client is having a bad day, they might say something a little different than what they wanted to, or how they meant it kind of thing. But you can’t let it, you know, sully your relationship. You just have to, you know, be like, Okay, it was maybe a bad day, and it’ll be better tomorrow.

Joe Casabona: That’s really important. Again, that kind of goes back to having high emotional intelligence. So we’re gonna take a quick break. And when we come back, Jordan is going to tell us why she felt she needed to fire everybody and start from scratch. But that’ll come after a word from our sponsors.


Joe Casabona: And we’re back. All right. Well, that was quite a cliffhanger that I left for people. So I asked how you know if it’s going bad. You said they need to be able to communicate, they need to have high emotional intelligence.

There was a point, I think earlier this year, maybe as people listen to this, where you realized it wasn’t working out, in general, and you want to start back from square one. I’m going to ask you two questions here so you know they’re coming. What led you to that decision? And how did you handle it from an intra-personal relationship thing?

Jordan Eaton: So I guess this is directed towards my business needs and how I envision running my business. So I was using contractors at the start. And I realized that they were working with so many clients and they weren’t being honest with me. That they were taking too much on and pulling their time thin. And they didn’t have enough time to have the quality work that I was expecting from them.

So just by taking on too much, and not communicating with someone that, “Oh, I feel a little stressed out, I’m not having enough time to do all this stuff,” not keeping that communication open, I started realizing that they’re looking more for just the paycheck and not actually helping the business owner and giving them the quality that is expected.

So yeah, I decided that I was going to move from contractors to employees, because I want them to be working with only our clients. And then I have that control over how many people they’re working with and I’m making sure that they’re not stressed out, they’re not working with too many clients.

Like I have a maximum and they’re only allowed to work this many hours or with this many people at once. And I really want to make sure, especially from a mental health standpoint, first and foremost, that you know, they’re not getting stressed out because stressed-out employees is not good for your business. And then from there that the quality and that they’re, you know, delivering, hitting deadlines, and then just doing their best work.

Joe Casabona: Gotcha. Okay, this makes a lot of sense. And this is something that I feel makes me a little unemployable, is that I’ve always… whenever I was hired for a full-time job, I was always like, “I have a side hustle. I’m going to keep doing it. It’s not going to affect my work with you.” But you know, as a younger single guy, that was what I chose to do with my evenings and weekends, right? Would absolutely not be the case.

I mean, one of the reasons I quit my last job was because I knew I couldn’t do my own business, have a family, and be in an agency. So I recognized that and made that choice. But this is something that a lot of freelancers and contractors could fall victim to.

They say that most freelancers won’t starve to death, they’ll overeat. They won’t die of thirst, they’ll drown. I guess the other part of that is having a contractor does make it a little harder to control. You can have in a contractor agreement, but it’s a little bit harder to put certain restrictions in place, like a non-compete agreement, or you know, a nondisclosure agreement, because now you’re not giving that person the salary, and you’re impeding them and their ability to work.

Moving from contractors to employees, means like, Hey, I’m gonna take care of you but you also need to… like, I need your full attention and or clearly communicate.

So they were stretched too thin. How did you find this out? Did you realize it or they realized it and they quit? Like, “Hey, I’m spread too thin. This is not working out. I’m gonna leave.” But worst is your client goes to you and says, Hey, this person that you gave me is being terrible and now I’m going to cut you loose. Which of these scenarios or what combination of these scenarios happened when you were like, everyone needs to go?

Jordan Eaton: So the main one was the clients coming to me and saying, “This person is not doing their work? They’re not checking in. They’re not doing what was promised.” And yeah, we lost a couple clients. And that is not great. I don’t like that.

So, you know, after having the conversation with them, they were like, “Yeah, I have a lot of stuff on the go, blah, blah, blah.” And I was like, “Oh, that’s unfortunate. I wish you would have communicated that with me before.” And yeah, just was not great.

So being a business owner, you learn and you know, sometimes you make mistakes, but you learn through doing. And I realized that I want to take them on as employees for myself so that they would be technically a contractor for our clients. But because I’ve taken on that burden of making sure that they are comfortable, that they’re at an appropriate work level, and that they’re trained properly, that’s what we’ve taken on as supplying them to you.

Joe Casabona: That makes a lot of sense. So I guess I’ll ask you… feel free to be like, I don’t want to answer that. But how many contractors did you have that you ended up letting go?

Jordan Eaton: Yeah, at the start, I had six.

Joe Casabona: And did you let them all go at once? Was it like, cut loose, start from zero?

Jordan Eaton: It was within a month. I explained to them that this was not aligning with my vision and my values of what I was looking for and the client output that I was looking for. And they all understood. It was good. We left on good terms. I mean, sometimes you just gotta do what you got to do.

Joe Casabona: And then how did that affect your relationship with your current clients? I mean, assuming your contractors didn’t cost you all of your clients.

Jordan Eaton: No. But yeah, for the time being while I was doing the transition, I ended up taking on all the client work myself. So it’s been interesting, and a journey. But I have recently hired some employees on where… we’re in it now.

Like I said, it’s learning in progress but I think from my outlook and knowing now what I need from them, and having my training program really set out in stone and communicating with them from the get-go, like, “These are the expectations. This is what I need you to be doing for me to be a part of this team,” and then accepting that saying, Yes, I will, then I think everybody’s on the same page, and it’s a great way to move forward.

Joe Casabona: Awesome. So it sounds like we’re moving into proverbial act three of your story here, which is tips for successful onboarding or for successful hiring clients. I’m really glad to hear that you’ve hired a couple of people because you, like I, are a parent just like I’m a parent. And you know, running your own business and also being a parent is no joke.

So now that you have employees and things are looking up, can you tell us about maybe the success story after going through the storm of cleaning house? What are the things that you’ve learned and how have you implemented those with this new batch of employees?

Jordan Eaton: So when it comes to moving from contractors to employees, of course, there’s a different set of rules, a different set of things that you’ve got to be aware of. But yeah, like I said, I’ve been very clear with my expectations and you know, explain to them this is the vision, this is the mission, this is what we’re going for.

We want to be known as a quality virtual assistant company that is going to be almost like a partner to you. Like, we’re not just going to sit there and say, What’s my next task? What’s my next task? We’re going to actually become part of your business, someone you can depend on, lean on, reliable, those kinds of things.

So the people that I brought on are extremely bright. They have worked in all different kinds of fields such as healthcare, finance. And yeah, I think that they were just a good fit because of how they were go-getters.

Even after we had the interview, they were following up, calling me like, Hey, like… So I could tell that they get stuff done. And then when I asked them, Can I have your references? Like, boom. The same day they’re getting back to me. So I know that they are reliable. And it’s been really good for the most part. So I’m really happy and excited.

Joe Casabona: That’s awesome. I’m really glad to hear that. And I think there’s like a couple of… you know, for those who might be looking for contract work or employment, the interview is the entire time, right? The interview is not just the hour call that you have with somebody. It’s how you communicate, how you act. It’s not just how you answer the questions during the interview. Like, “Oh, where do you see yourself in five years?” That’s a terrible interview. Sorry, if you ask that. That’s a terrible interview question.

But, you know, following up, being quick with responses and things like that, all really, really important stuff. I think a thank-you note probably goes a long way too. Just shows you’re thoughtful. Like, “Hey, thanks for your time. If you need anything else from me, let me know.” Just kind of that stuff.

I also want to point out here, based on conversations we’ve had offline, that you didn’t rush into a decision, right? Like, even though you had clients and things were a little bit stressful for a while, you didn’t want to make the same mistake of just hiring someone who’s gonna do a crappy job. You don’t have to answer how long it took you, but I want to highlight the patience aspect of it.

Jordan Eaton: I definitely did take my time. And I really vetted them because, yeah, I didn’t want to make the same mistake. So during the interview, I was asking mostly personality questions. And I was seeing, like, you know, their confidence when they were answering them or, you know, just little cues of what would tell me that they would make a good assistant. But yeah, I definitely did take my time. And I interviewed a lot of people.

Joe Casabona: And that’s great to hear really important, right? I think, again, sometimes you feel time-crunched, and you just like, whoever. Like, whoever, this person is fine. But you learned a lesson the hard way, right, where like an employee or a contractor cost you a client.

So I want to highlight this year because I learned from our mistakes, right? This is what I tell my podcasting clients too. Like, learn from our mistakes so that you don’t make those mistakes.

Jordan Eaton: I also want to pass on the benefit to our clients as well that I’ve taken that care and that time to thoroughly vet them and make sure that they’re a good fit for my company and also they’ll be a good fit for them.

Joe Casabona: Yeah, right. Because now you can go and say like, Hey, I’m not just hiring some schmuck, right? I’ve put hours days and weeks into making sure these people will represent you the way that I would represent you, but more importantly, the way that you would represent you.

Jordan Eaton: And I do look for people that have experience. I know that a lot of virtual assistant companies are hiring brand-new assistants or brand-new VAs. And that’s really fine. But like I said, for my vision, I wanted it to be quality and that they’re able to just get started working with the client and not take too much time of having to be trained. Not only trained on their business but being trained on how to be an assistant. I don’t want to put that burden on them.

So yeah, I definitely make sure that they have experience. Even having remote work experience. Because that’s a whole nother ballgame. Like yeah, you can be an assistant but to work from home and know how to manage your time and actually get the work done. Because there’s no one there pushing you, there’s no boss looking over your shoulder. Those kinds of people that are reliable and also they’re, you know, just responsible.

Joe Casabona: This is something that’s really interesting to me that I didn’t really learn until the pandemic and not even firsthand. Because my wife’s a nurse, like you can’t nurse remotely. You can’t be an ICU nurse remotely, I’ll say.

So I didn’t even witness it firsthand, but like talking anecdotally to friends who have only had office jobs, they’re like, Working at home is hard and really distracting. And I’m like, “Oh, you need… oh, you probably don’t have a de… Why would you have a dedicated office space if you never work from home? Why would you maybe have really good noise-canceling headphones and a plan for when your kids are home? So yeah, knowing how to work from home.

Something that bothers me… This is tiny soapbox. I talked to people who were like, “I have to have Slack up because my boss wants to see I’m online.” And I’m like, “That’s stupid.” Like, you could just ignore Slack. I’d rather trust that they’re in front of their computer and say, like,”Yeah, just log out of Slack if you’re not…” Like your work is your work. I can tell when you’re getting your work done. I don’t need to see a green dot next to your name to know that you’re constantly available.

Or like the same thing when my brother was doing remote learning, they had this—this is crazy to me—this software where it accessed the camera to make sure the students weren’t cheating on tests. And I would be like a hard pass on that. You don’t get to look into my house or my dorm room or whatever. Like hard pass. Like a giant pain in the neck, though. So finding somebody who can walk that line and understand working from home is not just being at home, right?

Jordan Eaton: Yeah.

Joe Casabona: Having that level of autonomy is really important. So if that’s what you want, great. Some people want a blank slate that they can train in. That’s a totally different type of hire. Right?

Jordan Eaton: Definitely.

Joe Casabona: And again, my VA Ana was like that. She didn’t know anything about my business. She basically gets videos from me showing her how to do the thing I want her to do. But like with you, I mean, we had a conversation recently… well, again, we’ll dive more into this in the pro show over, or you can subscribe on Apple Podcasts. Something wasn’t working, like you know, some text or whatever that we had agreed on wasn’t working and you’re like, “Oh, maybe we can make these tweaks and kind of test it a little bit.” Right?

That’s maybe not something I would have thought of or it would have taken me a lot longer to realize that you were very forthcoming about. So that’s exactly what I hired you for, right, so I don’t ever have to think about it. I’m just like, “Oh, they booked a time on the calendar. Great.”

Jordan Eaton: Yeah. Even looking at those analytics or making sure that what you’re doing is working, those little things it’s like people take for granted because not everyone would think to do that. But I make sure that… The assistants on my team are those kinds of people that would realize, like, Oh, maybe we could do it this way, it would be more efficient, or, You know, we could save money this way.

It’s all about the business owner and making their life easier, making their budget less. Like, you know, Oh, I noticed that you’re spending like $150 on this software and this software does the same and it’s have the praise. Like, you know, those little things. Like you want to help them out. So, yeah, that’s what I’m looking for.

Joe Casabona: I mean, in that exact example, perhaps something that falls under the purview of you or one of your employees is, “Hey, this is cheaper and I can help you switch to it. Because I know one of the things is like, “Oh, maybe that’s cheaper, but it’s gonna take me like forever,” right? We’ll put this in the pro show too. But I’m considering leaving Airtable for Notion, which is wild because I’ve been the biggest Notion advocate ever. We’ll talk about that in the pro show.

Right now, Jordan, this was so great. Thanks for spending some time with us today. If people want to learn more about who you are and what you do, where can they find you?

Jordan Eaton: I hang out on LinkedIn a lot. So you can search me at Jordan Eaton or, you can learn more about our company what we do.

Joe Casabona: I will link to that and everything we talked about in the show notes over at You can go over there to become a member and get ad-free extended versions of this, and every episode as well. That’s it for today. Jordan, thanks so much for joining us.

Jordan Eaton: Thank you, Joe. It was a blast.

Joe Casabona: Likewise. I agree. Thank you for listening. Thanks to our sponsors. And until next time, get out there and build something.

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