One of the biggest challenges most brand owners face is how to effectively scale their business and hire the right people without adding significant overhead.

Join me as I host Connor Gillivan as we discuss opportunities, benefits and best practices to outsourcing freelancers to scale your business on and off Amazon. Connor Gillivan is currently a Founder and Owner of He was an Owner of, which he helped scale and was acquired in 2019 by The HOTH. Connor is an expert in hiring and scaling with virtual assistants and shares his business insights on his own blog, He currently lives in Denver, Colorado.

Webinar Transcript

Shannon: Hey guys, welcome to the webinar. I’m so glad that everybody here is able to join us today. My name is Shannon. I am the founder of Marketplace Seller Courses, online courses, tools and resources for brand owners and product labels starting and building their brands and companies on Amazon.

I have with me today is special guest, Connor Gillivan. He is the CMO of And he has sold over $30 million online. He has hired hundreds of freelancers to help build those companies. He’s a published author and is the owner of He currently lives in Denver, Colorado and lived and worked in areas of South Africa for two summers working to a company focused on social entrepreneurship. So, Connor, thank you so much for joining me today. I’m really glad to have you.

Connor: Yeah, absolutely man. Thanks for having me as well. It should be great.

Shannon: Yeah. So, we’re going to be talking today about outsourcing which is a huge topic in today’s day and age. There are sort of two sides to this topic. And on one side, we have the technical aspect. How do I find good consultants or contractors to outsource to? And then the other side is maybe some of the internal hurdles of – OK, once I have a contractor how do I work with them? How do I communicate? How do I know this person is trustworthy? So, we’re going to be talking about both of those today.

But why don’t we step back a little bit and just tell me how FreeeUp started, how you got involved and what that process looked like a little bit, because I’d love to hear sort of the back story of FreeeUp as a brand and as a company.

Connor: Yeah, of course. I’d love to share. So, like you said, I sold a lot online. I actually started selling online in 2009 so, early on as Amazon was really growing up and the whole world of e-commerce was coming about. I was working with my business partner who is the CEO of FreeeUp today and I continue to work with. We’re building up this Amazon business, working with brands around the United States, helping them to sell their products through the Amazon marketplace. And in the process, we run into a situation where we had to start hiring.

So, we started hiring some part-time people. We had some full-time people in an office. But then we are also exposed to this idea of outsourcing and using websites like Upwork and Fiverr and We spent a couple of years using those and posting jobs and getting applicants and spending time trying to figure out who’s the best for our business. We hired some really great people but we also did run into a lot of turnover in the process. And I’m sure we’ll kind of dive into to some of those frustrations as we talk today.

And so, FreeeUp really came as a solution to those frustrations we’re having. We one day, after a couple of years, kind of said to ourselves, you know, the people we’re networking with, it seems like they’re having similar issues. It’s hard to find good people for Amazon and Shopify and e-commerce in general, what if we created our own marketplace that address some of those frustrations focused on just this whole world of e-commerce and we made sure that we were there to help people along the process. So, that was really the birth of FreeeUp that happened mid 2015, so we’ve been at it for about three and a half years now.

Shannon: Wow. You know, it’s so cool. There are challenges and I think there are two sides – there are two things that come to mind immediately. The first is that I think a lot of people are like me, I like to meet with people in person. That’s just my personality. I love to be able to sit down with them over coffee, had to get a feel for them, get a feel for their character and their personality and that kind of thing if it’s going to be a good fit. And so, the idea of outsourcing to somebody that I might not be able to meet in person face-to-face is really hard for me, self-admittedly.

Connor: Yeah.

Shannon: The other thing that you mentioned that comes up is so many startups specifically, especially solo entrepreneur, solo props, it can be so challenging to find those first people that you need to hire. And I’ve run into more companies that spent so much money, a significant amount of money hiring somebody that wound up not working out and doing little to nothing for them. You know especially when I was doing web design six, seven years ago.

Connor: Sure.

Shannon: That was a huge challenge. And we were like “Hey, I need to, you know get this – get to my Shopify storefront or my Amazon storefront.” And you say, “OK, this is how much it’s going to cost.” And they’re like, “I don’t have any money” and you found out that they did have money at one point but it’s gone now and it’s because they spent them somebody who wound up being totally uncredible.

Connor: Right.

Shannon: That’s a huge challenge especially in that thing, that startup phase when you don’t have a system, you don’t have an HR person who has done this, you don’t have a talent pool that you’re pulling from. So, I think that going through this webinar is going to be really helpful especially if you’re in that stage but also if you’re an emerging business or an established business and looking to grow. There are so many benefits to using somebody who is an outsource freelancer or contractor and we’ll talk about the logistics of it. But not having to have a full-time employee, maybe you don’t have full-time employee work, maybe you don’t you know, you’re looking at the taxes and all the different you know benefits and healthcare and all that stuff that part-time freelancers and subcontractors can be huge, huge benefit to you without all the headaches

Benefits of Outsourcing

So, that being said, let’s start with our first topic which is benefits of outsourcing. And specifically, let’s talk about that in comparison to employee. So, what are some of the biggest benefits in your mind of hiring a freelancer or outsource as opposed to an employee?

Connor: Yeah, absolutely. So, two or three kind of pop in the mind. Like I said, I had experience hiring full-time, part-time employees in an office and then also a lot of experience hiring outsource contractors, freelancers. And for myself, as a business owner, I think one of the biggest benefits is that I more strategically am able to spend my dollars on talent when I’m hiring freelancers. So, as opposed to hiring a full-time employee that come in and handle all of my Amazon operations for a set salary per year, I might go out and hire three or four freelancers that specialize within different areas of Amazon. I hire all of them at a different rate depending on their experience, where they’re located, how much they’re going to be working for the business, and in effect, I’m able to save money by spending my dollars a little bit differently. So, I like that flexibility that you have as a business owner when you’re hiring freelancers over employees. So, I would say that’s my, my first major one.

Second one would be just lower risk. So, bringing on a full-time employee whether you’re a startup or an emerging business, it’s just a lot, right? You had a lot to your overhead. It could be 30,000 plus dollars per year that’s just on your books. And you need to make sure that that employee is being as effective as possible for your business. So, hiring a freelancer, they’re more used to stop and go work. You may have them only on for part-time hours. If your business goes down in a month, you can reallocate your hours and your time there, spend a little bit less money and make more cents for your business. So, you’re a little bit less risky when you’re hiring freelancers.

And then the last one I would just say is something you mentioned it’s the overheard. It’s ­– you don’t need an office. You’re not paying health benefits and you’re not paying retirement benefits. All of those add up when you have employees. So, if you’re hiring freelancers you kind of take those off the table and you can use those towards other things for your business.

Shannon: Yeah. And just to comment on that I think some people look at it as hiring freelancers and outsourcing is a way to skirt those things and not be responsible and that’s actually not true. There are certainly companies that may attempt to sort of manipulate the system and do that. But in many cases that I found working as a contractor or the people that I have hired, it’s a huge benefit to them. They didn’t have time or availability to work a full-time job, they only have the allocations so for them, it’ actually, it can work out really, really well.

So, you know, again, I think that the principle of being able to hire strategically when you need it for somebody who’s specialize in that area, it gets away from this mentality that – or hiring freelancers or outsourcing people that’s only for small startups, “We’re an established company. We can afford to hire people.” But that still might not be the best use of your dollars. You might do only somebody you know a few hours a week or a few hours a month depending on your scenario and the different seasons. We all know that you know come Q4 obviously Amazon and a lot of the platforms pick up and you’re going to need more help, maybe with customer service or different areas, so not having somebody who’s sitting on their hands for a good percentage of the year and only being utilized part-time. People are looking for that extra work so we’ve actually seen it work very well that in some cases, outsourcing and using freelancers can be a very, very responsible aspect of hiring.

Connor: Yeah, for sure. And just to build off that one more time. So, the thing too is you can – even when you’re hiring freelancers and contractors, you can still build a company. You can build a culture. You can have people dedicated to your mission, your vision. They aren’t people that are just so distant and far off from what you’re doing. You can very much find ways to incorporate them and keep them involved and get them interested in what you’re trying to build.

Challenges with Outsourcing

Shannon: Let’s talk about our next topic which is you know challenges with outsourcing. So, these are some of the biggest technical or interpersonal challenges with outsourcing. I’ve got some of my own stories to share as well but let’s start from the technical standpoint. When somebody is going to hire freelancers and outsource, what are some of the biggest challenges that most companies are going to face?

Connor: Yeah, absolutely. So, the first one and these are all challenges we ran into when we are hiring from some of the other larger platforms. The first one and the biggest is I just think the time that it takes to actually post a job, get introduced or have 20, 25, 30 people apply to that job and then you’re responsible for the looking at all their profiles, trying to make a judgment call on who’s telling the truth, who’s actually able to complete the work, setting up interviews with them, talking to each of them and actually making that the end hire. It can take a lot of time to do all that browsing and vetting. So, I think that’s one of the challenges that a lot of entrepreneurs – they get into it because it’s attractive to be able to hire an outsource person. But then they get into that process and it becomes overwhelming. So, I would say that’s one of the first ones for sure.

Shannon: Yeah.

Connor: How about yourself, did you run into that as well?

Shannon: Well, yeah, I mean in fact, it’s so funny. I have a friend of mine who used to work in HR. I was so overwhelmed looking at hiring somebody to be social media and also as an executive assistant that I actually hired them part-time to write and post the jobs to hire for these other people. Like, that’s how much time I knew it was going to take. And it is. It’s incredibly overwhelming to do the posting, go through all the resumes, vet it, setup phone calls and stuff. That alone is a part-time job.

Connor: Right.

Shannon: So, that was the first hurdle and obstacle that I had to overcome just looking at outsourcing in that aspect.

Connor: Yeah, for sure. Another one with us was actually just feeling like we were so much on our own when we were first getting started with some of these larger platforms. They very much operate as software platforms. So, like we are just saying, we post our job, you get applicants, everything is so automated that when you hit a point where you may need help with something or you’re just confused or you’re looking for some sort of advice, it’s hard to come by with some of the larger platforms. So, that was another frustration we run into and something that we’ve really tried to make more of a focus with FreeeUp where, “Hey, you can always get in touch with me. You can get in touch with my business partner. We have a team of support that knows outsourcing well and you can talk with them and ask questions as you’re going through the process and understanding how it can apply to your business.”

How FreeeUp Solves the Problem

Shannon: Yeah, and you services like Upwork and Fiverr before and some of those great platforms and definitely recommend it for certain uses. But you know, in terms of that pairing up, in terms of the HR component, that’s actually something that you guys take out of the process. Talk – so let’s talk a little bit about, specifically about FreeeUp and how you guys solve that problem of pairing somebody up with somebody who’s going to be a good contractor for them and what that looks like, what that process looks like for you guys behind the scenes.

Connor: Yeah, of course. So, the first thing we do is we actually pre-vet all of the freelancers that want to join the platform. So, they go through an application interview and testing process. We only take the top 1% of people that apply. So that initial process, we dealt a lot of people that maybe on the other platforms that aren’t going to be as good of a fit for you, specifically as a business owner. And then when it comes to actually getting introduced, you fill out a simple form, you know almost a job post as if you would on the other places.

But instead of it just getting posted and everyone being able to apply, it actually comes in to us internally. It goes out to the freelancers that are available for the work and then we only match you up with one person at a time based off all your requirements. So, you, as the entrepreneur or the business owner, you get to meet them, have the conversation. If there’s feedback, you can share it with us. We’ll introduce you to someone else. You could hire them, you could ask for another person. It’s very much a one – so, one freelancer at a time process as opposed to being inundated with a lot of requests.

Shannon: Yeah. I mean I think that was the biggest thing for me was, again, from my previous experience, you guys took the HR component out of it, right? I didn’t have to vet all these different ones. And you know, review and manipulation is always a potential I think that people are scared of. You know this person has thousands of reviews, their stars, or they’re all legitimate. But even more so, sometimes it’s challenging because you’re not just looking for somebody who’s really good, you’re looking for somebody who’s going to be a good fit for you. And I think that’s the difference.

So, my experience with this was I was talking to one of my business development, you know business coaches. And he basically looked at it like, “Here’s all the different things I need, what do I need from that?” And you basically broke down and said you need an executive assistant. And so, I have mentioned that you guys reached out to me and had – they even provided some initial credits which was awesome for me to get started. It was like, “That’s a no-brainer, signup for FreeeUp and go ahead and use it for your executive assistant.” So I literally filled it out, exactly what I was looking for, broke down all the tasks that I was looking for, skills and things that they would to need to accomplish those. And I think within 24 hours, I got like the perfect fit profile.

Connor: Yes.

Shannon: And you know I was really, really floored by that and I’ve hired her, my executive assistant, part-time, the schedule works out really well. And one of the cool things that I want to mention and we’ll talk a little more about is that you guys, instead of just sort of making it anomalous, you actually allowed people to select the level that they’re looking for and whether they’re US based or not.

So, that to me was huge because I really needed somebody that was US based for a couple of different reasons and being able to find that that like I was one that pay more for it but it just fit so well, I mean some being the same time zone so that we could talk during day and there was just handful things that really made a good fit. But let’s talk about that aspect. So I think that’s actually very, very critical, makes a huge difference and is a huge differentiator between you and other platforms. Talk about that pricing level structure and also the skill level structure and how that correlates.

Connor: Yeah, of course. So, like you said, we really try to break it down as much as possible when we started the business into these different tiers of where a freelancer could land and also based off of where they’re living. Because we have over 2,000 freelancers in the network today about 40% are in the Philippines, 40% are in the US and the other 20% are scattered around the world. So we really want to try break it down. And so, what we did is we have kind of three tiers to try to make it easy for a business owner to understand.

You have your basic tier, which is usually someone from outside the US. They may be priced $5 to $20 per hour depending on the skill set. But they’re going to be more of a follower. You have your own processes, you know, how to do something you want to take it off your plate. OK, this person is great for that.

You have your mid-tier, more of a specialist. They might come with their own expertise, their own processes, maybe it’s something you’re familiar with and you’re doing within your business but you want someone to take it off your plate so you don’t have to worry about it anymore. That could be someone outside the US or in the US. They’re going to be a little bit more expensive, maybe your $15 to $30 per hour rate.

And then you have your kind of higher level, expert, consultant agency level. They’re going to be $25 plus per hour. They could be US or non-US. But they’re really going to be able to come into your business, setup new processes for you, teach you new things about the business that you may not know and really be there kind of as a partner or an advisor as you’re building the business in different ways.

So, those are kind of the three tiers and the pricing. And we found it to be very helpful to break it up in that way so that business owners can wrap their head around it a little bit more.

Shannon: And what’s nice is you can actually select multiple ones, you’re not required to just select one. So, if I’m open to them being US and non-US based as long as they’re in this range or yeah, maybe I need somebody to be somebody who’s starting out but let’s also get some applicants of people who are a little more experienced.

Let’s talk real quick about that because I think knowing, as a business owner, knowing what you need is so important. Then that’s always the first, most challenging step. So when I was having this conversation with Tyler, we were talking about it and looking at that different aspect of you know social media for example, that’s going to be my next hire. And so, we can look at it from the three levels. So, one is I’ve got a system for social media and all I need is somebody to go in and do the logistical posting kind of thing.

Connor: Sure.

Shannon: The step up would be somebody who you know they know they got a little more experience about it and they’re basically able to take some of those tasks off, they would be proactive. But the highest level would really be somebody that says, OK, you know, you’re bringing your own like you said expertise to the table. So, I think sort of that three levels of like the low level is I’m telling you what to do. The mid-level is like we’re going to collaborate on this and I’m going to assign you tasks. And the higher level is you tell me what to do.

Connor: Yeah.

Shannon: And that was the biggest difference. I hired somebody else previously and they had done a decent job but they weren’t trained in the arena of executive assistant, like it’s very specific in terms of that you need to do.

Connor: Sure.

Shannon: And when I got on-boarded with Jeanne, my current assistant, she was like, “Here’s what we do. Here’s how we communicate. Here’s a system that we’ll use.” It was just like brilliant. Thank – it was like, that’s what I need. I need somebody to tell me what to do and how this works so that you can take the things off my plate. And I think that was the biggest challenge before. I hired interns and I hired different people part-time. And it never worked out because they were just at the delegate level and just where I was at in terms of my business, there were just certain things that I needed where I needed that higher level of productivity, I needed that higher level of experience.

And so, I think as a business owner knowing this is a very simple menial task and it’s repetitive, I just need somebody else to do it, can outsource this easily, I can train them easily. That kind of gives you good levels versus I have no idea what I’m doing. I need somebody else to tell me what to do and I have to pay top dollars for that. But that’s the different level of experience you’re going to get and that’s why that ability to match it with those different levels was so helpful.

Connor: Yeah. And there are tons of opportunities too where you could come in not knowing anything. You spend a little extra money hiring that person but you meet with them, you learn a little bit more about it. They teach you or even give you a standard operating procedure that you could use and then they also help you hire someone that’s basic or mid tier person so that when they go and do it on an ongoing level, you’re not paying that super high rate, they just helped you get to a place where you can hire the other people.

Shannon: That’s really helpful and a brilliant model. I mean – and that’s what I do with a lot of companies is for my level, for Amazon expertise and certainly more high level and I tell companies like, “If you want to be successful, just do what I tell you to do. Like, I’m going to tell you what to do.”

Connor: OK.

Shannon: I’ll tell you exactly what to do but this is the strategy. I don’t have to be the guy going in there, building to flat file templates, writing the copy, doing graphic design. I’m OK at those. But where I really add value is in the higher level strategy. And I think the same thing is true so in social media. I think the same thing is true with a lot of other aspects in business. Once you get passed at the like you said, you know again, with social media as an example, I’ve got somebody that I’m hiring to do the high level strategy and then they’re going to help me in the same way to use that find somebody who sort of that mid to lower level tier who can execute the strategy because that’s a huge investment of dollars, well spent. And a good example of what you pointed out earlier is I don’t have to hire that expert strategist full-time.

Connor: Right.

Shannon: Like that would be a huge overhead on my payroll. I can just hire them for the time that I need them and  then we can hire somebody at the mid to low level to execute it and still get the same results, still get the success we need ongoing.

This is my favorite topic and I think after you guys have reached out to me and said, “Hey, we want to provide you with like some initial credits…” you know I forgot what it was but “…some initial credits used on FreeeUp.” And it probably had been like a month and a half and I still haven’t used them. And the reason wasn’t because the platform was you know was not intuitive, it’s super intuitive. It wasn’t because it was complicated. They were all internal hurdles and obstacles that I had that I had to overcome. And I remember calling you up, we had like a half-hour conversation about it.

Connor: Yeah.

Internal hurdles to Outsourcing

Shannon: Let’s talk about the internal hurdles and obstacles to outsourcing because I think in a lot of cases, a lot of people are like me. I can find people using the platform and logistically pay to hire somebody. That’s not the challenge. Challenge is inside. Let’s spend a few minutes and talk about the internal obstacles to hiring and outsourcing.

Connor: Yeah, of course. So, I think the biggest one that I hear most from clients who are just getting started with us is a lot about trust. So, you know, I run business here. I built it to a good level. I have access to all these things. How can I trust someone potentially on the other side of the world or on the other side of the country with all of this hard work that I put into my business, how can I trust they’re going to do their work properly, they’re not going to overbill their hours, they’re not going to try to cheat me out of everything that I’ve built up for myself? I think that’s one of the biggest hurdles to get over. I definitely faced it myself when we were first hiring people and outsourcing.

And one of the things I’ve eventually come to the realization about with freelancers is that a lot of the people and especially the ones that we vet and come on to the FreeeUp marketplace, they’re all running their own running their own businesses as well. So, they have an expertise. “I’m great at social media. I don’t want to work for a company full-time, I’m going to go out and try to build my business and offer it to other clients around the world.” So, a lot of them, their purpose isn’t to get an extra $5, $10, $15 out of you. It’s really to build that relationship and be able to grow their business and your business at the same time. And I think that that was something tough to come to realization about and it took some time but I think that’s a good way to look at it when you’re looking to outsource as opposed to you know having so many trust issues internally. But, what about you? How about your thoughts on that?

Shannon: Well, yeah, I mean that was the biggest challenge is how can I trust somebody that I haven’t met face-to-face? And I’ll tell you, this is a really good example of it is Skype, Zoom, Google. There are all these really great opportunities where you have the ability to get as close to an in- person conversation and be able to chat with somebody face-to-face even if you’re not in person. And that does calm a lot of those fears or anxieties and say, “I really like this person. They seem very smart, they’re competent.”

Connor: Yeah.

Shannon: But for me, the biggest challenge was I just – it felt overwhelming and I didn’t know how to do it because I hadn’t been good at it. I hadn’t done it before.

Connor: Yeah.

Shannon: But that’s true. Every aspect of business and you know what’s challenging for me that you know over different periods, I looked at other people who were really, really successful. They were very good. They had no problems hiring people. I remember hearing this great story on the How I Built This podcast, which is…

Connor: Oh yes.

Shannon: …one of my favorite business podcast. Guy Raz was interviewing Blake Mycoskie talking about how he started TOMS shoes. And you know first week, they were in the window of a store and then they get to a magazine article or a newspaper article about him blew up. And he’s like, I just called like 15 people on Craigslist and had them all in my apartment like you know email and calling people back and letting them know when their shoes are going to be delivered, if we even have that inventory in stock. And I just thought there was no way I would do that. He had no problem immediately outsourcing, having 15 people from Craigslist in his apartment.

And the challenge is there are a lot of business owners like myself who will look at other people and go, how come they can do it and I can’t do it? And a lot of it just has to do with being willing to overcome the fear. Maybe they have the fear and they overcame it. Maybe they didn’t have the fear and you have to. That’s just going to be your bag. So, the ability to face into it is super huge and just say, “If I want to be successful, I have to do X, Y and Z.”

And Henry Cloud, one of my favorite business authors and leadership authors, he talks about this idea of facing into our challenges. So, instead of like I’ve got this huge challenge and it’s causing a variety of stress, the idea of leaning into it, facing into it, addressing it and hitting it head on so that you can deal with it. And honestly, for me, selling my very first product on Amazon, I had to do that process. I had to – I look at all the reasons why I wasn’t doing it, why I hadn’t done it yet, every single one of them had to with fear and every single one of them was rational. Once I faced into those, I was able to overcome it and be successful.

Connor: Yes.

Shannon: So, the other quote that Henry Cloud talks about which is perfectly critical in this instance is he said, “Successful people leverage their strengths.” We get that. That makes sense. He said, “Super successful people leverage the strengths of other people.” And that’s what services like FreeeUp allow you to do. You’re not just leveraging your strengths, you’re like, “I might not be good on anything. I’m not good at web design and social media.” They’re like, “Yeah, but your website is awesome and your social media is awesome.” And you’re like, “Yeah, but I leverage all of these other people’s strengths to do that.”

And another favorite business leader, he said, “When you do what only you can do which is run your business coupled with strategy, your business will reflect all of your strengths and none of your weaknesses.” And that’s you know an Andy Stanley quote. But I just love that idea, if you hire your weaknesses, if you hire the people to support you, your business will reflect all of your strengths and none of your weaknesses. And that’s what all of us what to be. And you know, what I find so far is this platform allows you to do that. So…

Connor: Yes.

Shannon: Let’s hit on the next topic because this kind of plays into dealing with some of those internal hurdles. I’ve read an article a couple of weeks ago called Doing Things You’re Not Good at is Good for You. So, just understand if you’re not good at outsourcing, it’s going to be a growth step for you. That’s OK, understand that it’s hard at first and will get easier and you’ll get better at it. You’ll develop patterns and relationships and understand how the system works and then you can you can really throw, you know, grow and thrive your business.

Best Practices for Vetting & Hiring Outsourced Contractors

So, let’s talk about the best practices for vetting and hiring outsource contractors. Now, you guys talk about it in FreeeUp, how you make it super simple. But regardless of where people are hiring somebody like I said it could be Fiverr or Upwork or whatever, talk about some of the best practices for vetting and hiring outsource contractors.

Connor: Awesome. Yeah. So, the first step, I always like to encourage people to take is to really identify who your ideal candidate is. And also to know the tasks that you’re looking to take off your plate. So, you had talk about this a little bit before you’re talking with your coach, you had this big list and he was like, “Oh cool, executive assistant, you know, that’s what you need.”

Shannon: Right.

Connor: And so, getting that list of tasks out first and maybe even identifying one of the ones that’s taking up the most of your time but it also one of the simplest, that’s probably a good place to start because it’s not going to take too much on boarding, training, and you’ll be able to tell really quickly of the person is good for it or not. So, first off, get that task list out, figure out what that simple and time-consuming task is that you want to get off your plate. And then figure out who your ideal candidate is. And you can kind of break that down in a number of categories.

So, you can look at location. Do you have a preference for US versus non-US, how important is that? You can talk about the rate you know how much budget do you have? How comfortable are you paying a certain rate for a certain people? Something that I like to look out a lot because a lot of it comes down to how you actually work with that person is what are their personal values? So, are they hard workers? Do they value money or impact more? Do they – how do they work with clients and things along those lines. Those can make a big difference and how you’re able to work with them.

Few other things is hammer down what skills you need them to know. So, if it has to do with a certain software, maybe you really need them to know how to use Gmail and Google Docs and Google Sheets extremely well, make sure you’re asking about those and you touch on those in your interview with them. And then also think about availability. You had said that it was important that they were working on the same hours as you, if that’s a big factor, make sure you have that down as well. And what this does for you is when you put together this model of your ideal candidate, it makes it a lot easier to go through with that hiring process because as you’re talking to these people, you’re going through your checklist, “Oh ok, there’s two red flags. They don’t meet up.” “Hey, that’s OK. We’ll find someone else that does meet up with all of your checklist.” And it just makes it easier for you to know exactly who you’re looking for.

So I would say that’s one of my first things is really understand that and use that as a part of your hiring. And then once you actually find someone, once you’re ready to hire them, I like to encourage people to start slow. So don’t toss them into 20, 30 hours a week and kind of hope that everything goes well. Assign test projects. If it’s a social media person, give them an hour of work to schedule things out of content that you’ve already created. See how they deal with it, see how they communicate with you, and understand how that working relationship will go.

Do that slowly, 4, 5, 6 times so you’ll understand what that work looks like between you and them. And then you can get them more into a schedule and have them working on alone. But it’s smart to start slow, give those test projects, understand your process first before you jump in to anything so you don’t look back on it 20 hours later and you’re regretting why you paid that much money for the work that person did.

Shannon: Yeah. I think that’s a really good and helpful insight. And again, I think there’s – if you’re listening to this or watching this and you’re new, you’re not used to hiring other people outsourcing, know that you’re going to make mistakes. And what I mean by that is know that you’re to hire people that don’t work out. That’s business. That’s life. And I think that again, those are the internal hurdles and obstacles was like, “Well, I tried that once and it didn’t work.”

Connor: Right.

Shannon: Like you know?

Connor: Yes.

Shannon: It’s like saying “Well, I tried dating one time and it didn’t work out so I’m not doing that again.” You’re going to have to go on lots of dates to find the right contract, find the right feeling where that fits.  And if you can minimize the risk and the amount of time that it takes, you know, where like you said, “You’re spending 15 or 20 bucks to give him a test project to see how it does. That’s way different than doing a whole foot through interview process bringing somebody on that’s part-time or even temp employee and trying it out for a couple of weeks which is going to be really expensive to find out “Hey, it’s not a good fit personality, attention really or whatever.” So, be willing to take those risks, start small, try it, understand that you might go through a few people before you find the right person. But once you do, it will be a game changer or change your life or allow you to build and grow you business. Anything else in terms of best practices for hiring?

Connor: Ah, yes, something you just kind of mentioned there and I think it builds back into the fear of hiring and having people working with you is that ability of fire fast. I think that’s really important when you’re hiring contractors. They may hit all your checklist, you may have a good first test project with them but then something happens where it just doesn’t work out. It’s OK to let people go and just move on to another person. It’s also even more OK I think with contractors and freelancers because they understand that they’re working with multiple clients at any given time, if they lose one person, OK, they’re going to go out and find another one. So, don’t have that fear of “Oh man, am I going to ruin this person’s life by firing them fast?” and you know kind of setting every – setting that person up for failure. It’s OK. You can find someone else. They’ll be OK. And it’s not the end of the world if you have to do that.

Shannon: Yeah, I mean I think the long-term maxim you know “slow to hire, quick to fire”. In the case of outsourcing and freelancers, it should actually “quick to hire, quick to fire”. And so, yeah, you find somebody, think they might be a good fit, hire them for a couple of hours and if it doesn’t work out then you’re done. Because the faster you go through people, the faster you’re going to find the right person.

Connor: Yeah.

Best Practices for Managing and Communicating with Outsourced Contractors

Shannon: Now, that being said, let’s move in to the last part that I want to talk about and this is best practices for managing and communicating with outsource contractors and this is huge because I think there’s a lot of people, myself included, who did this part wrong and felt like they didn’t work out. When in reality, I hadn’t given them – we hadn’t communicated effectively what we needed. We had to figure out, you know, OK, how does this thing work? Like, are you just supposed to know what I want? You’re the expert so I’m just going to give you this task and expect it to be exactly what I wanted and it turns out we weren’t on the same page at all.

So, I think the communication and managing that relationship is critical for the success of that regardless of how good they are. So they can be the perfect person, the perfect fit but if you don’t manage the communication aspect of it and those touch points and the expectations, it’s probably not going to work out at all. And you could think it was a failure because you know, well, it didn’t work. But let’s delve into this because I think this is going to be really helpful. Let’s talk about some best practices for managing and communicating with those freelancers.

Connor: Awesome. Yeah, I completely agree with you too. I’ve met tons of people who have gone through this point and then they for some reason or another, the communication didn’t work and they went away frorm outsourcing and hiring contractors. So, it’s a critical point of hiring and working with a freelancer. And I’ve got some cool tips that I used on a regular basis and I found to be extremely useful.

So, the first one is to choose a communication channel. You know, find one that you’re going to use and that’s how you’re going to communicate with that contractor or freelancer. For myself, I use Skype. It’s just what our business uses. I’m always on it. Most of the freelancers that use our platform are on it as well. And that’s where I just know I can get in touch with that person at any time. For video meetings and things along those lines, I use Zoom. So, those are my two main communication channels. I established that with them upfront and just make it very clear that’s how we’re going to communicate. So there aren’t any confusions there.

The second thing, I like to set daily check-ins with anyone that I work with. And that’s through Skype. So, “Hey, I like you to work on a project tomorrow. It’s going to be about two hours. Let’s plan on working from 10:00AM Eastern to 12:00PM Eastern. When you start at 10:00, just go ahead and check-in with me on Skype. Let me know what you’re going to be working on. I’ll share any feedback or any details I have for the work that you’re going to be doing. And then at the end of the shift, just check out with me. Let me know what you worked on. Let me know what you completed. If you need anything from me or if you run into any issues…” And from you right there, even as a busy business owner, if I’m not there at that time, I know that if I come back to that chat at a later time in the day, I see what they did. I see when they ended, I can give them feedback. I can see what issues they had. And we have a direct communication channel going at all times.

Shannon: So, it doesn’t necessarily have to be a video chat. Sometimes it can just be a – they’re just chatting, just text chat, just give you an update of what’s going on and what they’ve worked on.

Connor: Exactly. Exactly. And then to the video chat, so, I like to do usually about once a week or once every two weeks, I will, I’ll gave a video chat and we’ll sit down, we’ll talk through the goals that they’re working through. I’ll give them updates on the business. I’ll answer any questions they have. I’ll kind of put things on my task list of what they need from me. And what that does is it allows to build that relationship further. You’re never going to become a buddy-buddy of a someone if you never meet with them at all. So, having that Facetime with them, even if it’s just 30 minutes, once a week, once every two weeks, it allows them to buy more into your business – you’ll be able to buy more into their abilities and what they can do for you and it keeps you guys on the same page for actually working together.

Shannon: Yeah. And I think that was the biggest challenge that I faced with previous hires was not having a scheduled pre-established time of check-in. Especially because everybody was remote and so in that capacity, you’re not running into people at the water cooler. Your office isn’t next door, you’re not able to just pop in and chat. So, it’s not going to happen automatically. You have to go ahead and schedule it.

The next thing that I want to talk about is the idea of setting a clear task with a goal and a deadline. And so, I think that from that aspect of it, measurable, attainable and time bound. You know, in business, we’re following to MAT principles. You have to give them the task that’s measurable, attainable and time bound. And if you do that and clearly communicate, that’s going to drastically increase because sometimes I’d say, “Here’s the next task.” And then a week later it’s like, “Where is it?”

Connor: Yeah, right.

Shannon: “Well, you didn’t give me a deadline so you know it wasn’t top of my priority.” So, that’s really, really critical. Let’s talk about assigning a specific task and maybe some other best practices that you have in that arena.

Connor: Yeah, cool. Great call and definitely an issue people run into. For myself, when I’m starting a new task with someone, I actually setup a meeting so I come prepared to that meeting. Usually, if it’s a little bit more in-depth, I’ll have a Google doc either with the process of what they should be following or what I’ve seen success with in the past. Or, if it’s just something smaller, there’s – I have notes of you know what they’re working towards, what deadline is and how I expect to get updates as they’re working through that on a regular basis so that I’m up to speed  and I know what’s going on.

Another expectation you can set is listen, we’re always going to set deadlines together and we want to work as hard as possible to hit all of them. But if it comes a time let’s say you now deadline is two weeks out and a weekend you know you don’t think it’s realistic that we’re going to hit on anymore. Let’s talk about it. You know, communicate with me. Let me know want issues you’re running into. Let’s set a new deadline or let’s figure out how we can adjust and keep moving things forward so that we’re continuing to work towards that eventual goal.

Shannon: Yeah. One of the things that I learned that sort of the three-step process which is funny that even though I believe in the philosophy I don’t always execute it right. But my three-step process for training is: one, you have to give them some type of written or recorded resource. And video right now is so easy. So, for Zoom, I use that for almost all of my trainings and communication because I can very easily record it, save it as a Dropbox style making the reference at any time.

The other thing that this does, I was talking to a friend of mine and she’s got tons of contractors she uses. She said that in the same way that you put together your Amazon courses, with all these videos [0:42:10] stuff, you have to do the same thing with your freelancers and contractors. You got to have that you know list of for this task here’s the checklist and here’s the video to watch how to do it.

The reason that’s so helpful is two. One, you can train and onboard people really easily. And two, it makes it much easier for you if you have to bring in somebody else or you wind up replacing somebody. They no longer become available or you need to bring in somebody else. Then you’ve got this whole training system that you’ve essentially established and then you don’t have to start over from square one. It’s like watch these videos, go through the checklist and you’ll know how to do it.

So the first is that you have give them something like they can go back to and reference. And then beyond that, it’s the first time, I do it and you watch, if we’re talking about like repetitive tasks so maybe accounting for example, I use zero for accounting. I’m going to do it and you watch and I’m going to explain it to you. You’re going to go back to this resource and you’re going to go through the checklist and the video. And then the last thing is you do it and I watch. That way I can catch any mistakes or make sure that you know that there’s something you’re missing.

And that three-step process has worked really well. And it’s just a matter of making sure and having the discipline of no matter how menial the task is, if I go back to that and use it, it works. So, here’s your rhythm or record resource, you do it, I watch or I do while you’re watching and you do while I watch. It really makes it thorough and holistic and then people – they’re going to be able to get it and they’re going to be able to get it right.

Connor: Yeah. And it helps with that trust factor too. I love the last step where they do it, you watch because as a business owner you may be wondering, all right, I’m giving them these resources but can they actually do it? Are they understanding everything? Are they asking the questions they should be? When you flip the tables and you watch them do it and can give them live feedback that makes the world of a difference and then you leave that session trusting what they can do and they can go and handle that for your business.

Shannon: The other thing that I want to mention, there are just two things that come to mind. I’ll try not to forget them but…

Connor: Yeah.

Shannon: The first one is specifically for things like graphic design, copyrighting, this is really huge for Amazon listings or websites or social media. Find the examples that you like and give them to them, right?

Connor: Yes.

Shannon: Fiverr is something that I use for really simple one-off graphics, it’s really simple and a great service to use. And I’ll actually go through the different profiles or the portfolios look at different ones that I like and say hey, in fact, I ordered some Facebook ad graphics the other day.

Connor: Nice.

Shannon: And I said, “I like this one that you did. I like this style.” And then I basically gave him, “Here’s the text. Here are some raw images.” And giving them that example, it cuts down on so much communication than going in the wrong direction. So, I think that if you take the time to say, “I’m getting my new website designed, I like these three websites. I like this one because it’s simple. I like this one because of the color scheme. I like this one because of the layout.” That’s going to make it 10 times easier to do that. I know it takes work to do that but it’s much better than throwing spaghetti on the lawn and saying, “OK, go build me a website.” And let’s hope that it works out and let’s hope that I like it.

So, it’s really important to find examples that you really like and that you know are effective. If you’re looking at a best seller on Amazon, I’m not saying that they’re always perfectly optimized but usually they do a good job that’s why they got there. Take the time to do the research and provide the specific links, upload the graphics as attachments, whatever you need to do to show them what it is that you want and are looking for because that’s going to cut down on the potential miscommunication and also makes you happier with their end result.

Connor: Nice. Yeah, I 100% agree with that, I do that with all of our designers, writers, web designers, dev type of stuff. And then it’s super useful. Another think I would know is just with that type of work, with creative type of work, just expect there to be a few revisions at first. Even if you give them those, the inspiration kind of the examples, just expect the first time it comes back. It’s OK to give feedback. Let them go make a few more changes, do that two or three times until you get a perfect product. If you work with the same person over the long term, they’re going to understand your preferences and then be able to just to do it without many revisions. But at first, that’s kind of how you communicate and get one the same page with creative type of work.

Shannon: Yeah, and then there’s something else that I want to mention about FreeeUp because going through like hiring a couple of different people for graphic design and copy for Amazon and SEO, a lot of people expect it to be a longer term relationship and the platform is really designed to establish that. This is going to be somebody that you can hire for a long time. Obviously, you don’t have to if you have a shorter project or one-off project. That works but for an executive assistant, I’m like “I do not want to hire somebody for a month. I want somebody to be with me for the next two or three years.”

Connor: Yeah.

Shannon: And again, having those training processes in place makes it really easy for me to ever change somebody. So, if they like you said become unavaible, thinking about it from an executive assistant standpoint which I was an executive assistant in the entertainment world. And I won’t tell who this story is about but – but people in the Hollywood especially celebrity type, they’re notorious for not doing anything themselves. They want somebody else to be pretty much every task. And on one hand, from the assistants it’s like “Oh gosh, like can’t you do something?” but if you look at their use of their time, they are so effective because they delegate every aspect of their lives.

Connor: Sure.

Shannon: And it frees them up to be able to one, they have more recreational time because they are not handling all these odds and ends Then two, a majority of their time is spent doing what only they can do. And it does make them very, very effective. The funny story is we have a boss who was in New York, we’re in LA and he called his assistant on the phone in LA and asked her to call them to the lobby of the hotel to bring up some hot water for tea. We’re thinking like, I know she’s on speed dial but like it’s hitting zero on your phone to go to that lobby.

Connor: He was just wired to do that.

Shannon: He’s just wired, and everything goes the assistant.

Connor: Yeah.

Shannon: So even if it’s ordering tea from the lobby then you know you go through your system. But the idea with that is once you get a trained assistant and I even told my assistant this, I said, “If you ever leave, you have to train your replacement.”

Connor: For sure.

Shannon: “Like I just want you to know that I want to get to a system where all of these things that I’m delegating to you are handled and taken care of.” And that way when I go to the next person, I don’t have to start over. I want you to train them. And we saw that process. I mean the executive assistant world – that’s exactly what they do if somebody will give a two-week notice OK, we hired your replacement, now you got to go through and train them and if they have questions, they’re going to follow-up and call you the next few weeks.

So, I think just understanding that your goal is not to do a one-off but to build a lifestyle of again, supplementing your weaknesses and somebody else’s strengths to be able to empower you to effectively run your business is huge, it’s actually a game changer and it’s going to make a big difference in your business and any business that you’re working.

Connor: Yeah, absolutely. Completely agree with that. It’s all mindset at the end of the day when it comes to this type of stuff and we talked about some mental hurdles that you have to get over to get there. But once you do, I mean it’s amazing. I work with 20 plus VAs on a regular basis and it’s great. You know, like you said, they’re stronger in a lot of areas that I’m not. I stay focused on you know my breadwinners and where I’m great and then – but they do a lot of amazing work for me and I’ve been able to build some amazing personal relationships with them as well and that’s a lot – that’s very fulfilling too when you’re working with people and they’re doing great work that you also know them well and you can relate to them and you’re building something together.

Shannon: Yeah. I think that is huge and you know it is, it’s important to build a business but you’re also sort of building your life. I think the other thing that I just want to mention is, if you’re ready to wrap up, is the idea that you have a system for communication like you mentioned. When I hired my executive assistant, she said “I use Trello.” And she’s like and here’s how I set it up and here’s how we’re going to communicate. And you know that’s just one example I know that there’s Asauna.

Connor: Sure.

Shannon: …and tons of other you know ones but having a system where I can easily create a task, I drag it to the day that I wanted to do it. She adds comments and she adds those. You got all kinds of integrations where you come up with files from Dropbox and do all these kinds of integrations and calendaring and scheduling. It really is helpful to ensure that the tasks that you want are done when you want them and how you want them. And there’s way for them to ask questions in default and like you said, and I do revisions because it’s never going to be perfect the first time. But if you can start to make those shifts and challenges, overcome those challenges, it can make a huge impact in the business.

So, just want to wrap up here, any final thoughts for people who are thinking about getting started using an outsource you know freelancer, any sort of sage words of advice that you would give somebody as we close out here.

Connor: Yeah, absolutely. So, I mean we really went through the full spectrum of everything today from you know the mental hurdles to actually hiring and going through that process, to working with someone on the backend. And I think for people listening, if they’re new to it or even if they’re just getting started with it, all of it even though we’ve I think we’ve explained it pretty well, it can be a little bit overwhelming. I think at the end of the day as an entrepreneur or business owner, you really just like you said you need to jump in. Go ahead and take a shot. Take 50 bucks. Go in with $50 see what comes out of it.

You never know, you could meet someone that you end up working with for five plus years down the road. You may learn an amazing lesson and realized that you made a big mistake. And OK, it’s going to take another $50 to find that perfect person. But you’re never going to get to that lifestyle that we talked about unless you kind of put two feet forward, give it shot and see what comes of it. So, I think it’s just kind of a little bit of a mental push for everyone that’s listening.

Shannon: Yeah. And I could tell you right now, if you haven’t done it, once you do you’ll never go back. Just once you take a leap and then it becomes easier and easier like I said doing things we’re not good at is good for us. And you know, things that used to be really difficult are easy for me now. But it’s not a matter of what I can do. And I think this is actually a hurdle and a challenge that a lot of people face. I used to be a jack of all trades, still am in many ways. I’m good in a lot of different things. I’m not great but I’m competent. So, building the website or social media like I can figure things out at pretty technical savvy, I can learn new things fast. But that is not the best use of my time. And I think that that’s the important thing.

Now, you guys actually have a special that if – we’ll have the landing page and the link underneath the webinar, underneath the video here on YouTube, or on Facebook wherever you’re watching that you can click that link. And if you sign up using that link to FreeeUp, they’ll actually give you a $25 FreeeUp coupon to use which is super cool to help you get started.

It’s MarketplaceSellerCourse25, again, that’s MarketplaceSellerCourse25. I am an affiliate of FreeeUp. I became an affiliate because I believed in the software, believed in the tool and saw the difference that it made in my life and hoping that it can make the same in yours.

So, Connor, thank you so much for joining me. Everybody, thank you for joining us. And I look forward to catching up again soon.

Connor: Awesome. Thanks, Shannon.