How to Hire the Right Contractor or Employee for Your Online Business

Sean Jackson on April 27, 2017

It can be intimidating hiring contractors or employees for your online business. But it doesn’t have to be that way if you know how to do it.

At some point as your online business grows, you will need outside help. And making that transition from a “soloprenuer” to running a team can be a little scary.

But the truth is, bringing in the right help at the right time is an essential part of growing a successful business.

So the question is when and whom? Should you bring them in early in your business growth, or later? Should you hire a contractor to do continuous work or hire an employee?

We cover all of this and more with our very special guest, Jess Ostroff from Don’t Panic Management.

In this 41-minute episode, Sean Jackson, Jessica Frick, and Jess Ostroff discuss the key components of hiring, including…

  • The pros and cons of bringing in help early or later
  • The best way to start the process
  • Why contractors working a regular schedule may be the best way to start
  • When to make the leap and hire a full-time employee
  • The best methods for integrating staff into your business
  • And when and why you should let them go
  • Finally, our question for the week – How unique is too unique when creating your unique selling proposition?

The Show Notes

How to Hire the Right Contractor or Employee for Your Online Business

Voiceover: Rainmaker FM. You’re listening to The Digital Entrepreneur, the show for folks who want to discover smarter ways to create and sell profitable digital goods and services. This podcast is a production of Digital Commerce Institute, the place to be for digital entrepreneurs. For more information go to Rainmaker.FM/DigitalCommerce, that’s Rainmaker.FM/DigitalCommerce.

Sean Jackson: Welcome to The Digital Entrepreneur, everyone. I am Sean Jackson, and I am joined, as always, by the delightful Jessica Frick. Jessica, how the Frick are you today?

Jessica Frick: Delightful, Sean. How the Jackson are you?

Sean Jackson: Good. I’m going to have to start looking through my thesaurus and find more synonyms that I can start using to reference you.

Jessica Frick: I was going to say, I’ve been called worse.

Sean Jackson: I know, and mostly by me.

Jessica Frick: Not in the podcast, Sean. Not in the podcast.

Sean Jackson: No. We left everyone hanging last week with our question of the week, which is about when should you bring in outside help, or when should you bring in a contractor or an employee into your organization. Jess, you took the position of bringing them in early in the process, right?

Jessica Frick: Absolutely, otherwise you’re going to go crazy, and we want to avoid that.

Sean Jackson: Give the argument for bringing someone in from the outside early.

Jessica Frick: First off, I’ll say I understand where you’re coming from. You want to wait until you absolutely need them because you don’t want to spend money on things — that’s presuming that’s where you’re going to go with that. I think that it’s worth the money — when you know you’re going to need them eventually anyway — to have somebody come in and own the job. I used to work with a client who would say that if he was the smartest guy on his team he was doing it wrong.

Sean Jackson: Right.

Jessica Frick: He would hire these brilliant people, present company obviously included. We would come in and bring our expertise for things he would never even think of. He was able to grow his business and sell it off. I’m not sure he’s working now. I think he’s just hanging out with those piles of money. I’m not sure. I’ve got to check in with that guy.

I know that I have seen it happen before where businesses will be built and they go through so many strains and pains that your company starts losing morale, you start losing business, and you can’t attend to the business you already have. Thus, you need to get that help before you think you need it, because chances are you’re not going to know you need it until it’s too late.

Sean Jackson: Yeah, I think there’s a case to be made for that. Let me give you the argument against. I think you can’t bring anyone in until you know your business to an extent that you can direct them in the place that you want them to go. Let me explain that. I think there is an evolution to every online business or to every business in general. We all start with the one or two things that we’re doing, and then over time we have more things and more things. We start to say, “The pressure is building. I really need some help.”

But too often, if we bring them in too early, we haven’t thought through what is that help that we need. Defining what we need done and understanding the best way to get it done based on the unique culture that you have in the business. I think sometimes we jump the gun a little bit and say, “I just need to bring somebody in right now. If they’re really smart they’ll figure this whole thing out, because I don’t have any time to talk to them.” I think that’s the mistake you have when you bring them in early. But, of course, to your point, you would say bring them early benefits you how?

Jessica Frick: Because they can expand upon your capabilities and save you from losing your mind.

Sean Jackson: Yeah, that’s a foregone conclusion in some cases.

Jessica Frick: Yeah, you have to be a certain kind of crazy to do this.

Sean Jackson: Yes, I think you had to be crazy to start your own online business, are you kidding me?

Jessica Frick: I think you cannot buy amazing customer service. You just give it. And you give it early and you give it often, because once you screw that up, you can’t get that back.

Sean Jackson: Yeah, what you’re referring to is the fact that if you don’t bring in somebody early enough then you may find that you are losing people quickly because you can’t service them in the way that they were used to when you were smaller and it was just you and maybe just a few customers, a few clients, etc. Right?

Jessica Frick: Exactly.

Sean Jackson: Putting people in early allows you time to train them before things get crazy. It allows you time to sit there and really understand the task at hand and how to service that best. Before the crazy comes on you when you’ve got 20,000 things that are occupying your time and attention. That would be the argument for early. The argument for late is very simple: if you don’t know what you need people to do, then you’re going to be bashing your head against the wall because you haven’t really figured out, “What are those tasks? What are those projects?” Sometimes taking the time to understand them so you can make a strategic move, that helps with time, which means later in the process.

You know what, Jess? It really comes down to what does our audience think. What do they think? Should you bring somebody in early? Should you bring them in later? That’s what it really comes down to, what do you think about that? We have the best mechanism for you to give us that feedback by visiting our page and leaving a comment. Letting us know when you — based on your personal experience — have found it right to bring in those outside people. When we get back from the break, we have …

Jessica Frick: The lovely and talented Jess Ostroff from Don’t Panic Management.

Sean Jackson: Jess is amazing — both our Jessica as well as Jess. But Jess is amazing because she’s built a whole business both with employees and contractors and helping other business owners reach out and have the resources that they need to build their business.

So for today’s interview, we decided that … We had too many Seans on before, right, Jess? We’ve had so many Seans on the show recently that I wanted to confuse our audience even more and bring a Jess on to contrast with our lovely Jessica. Jessica, will you introduce our guest today?

Jessica Frick: I will. She’s one of my favorite people in the whole wide world. She makes me so happy whenever I see her. It’s so fitting that she is CEO and Director of Calm of her company, Don’t Panic Management, which works with small business owners, entrepreneurs, and executives to help them organize and execute their day-to-day operations, giving them the ability to focus on the things that matter most. She is a wonderful human being, a “get ‘er done” girl, and her favorite kind of cheese is aged goat gouda. I introduce you to the lovely Jess Ostroff.

Jess Ostroff: Quite the intro. Thank you, my fellow Jess. It’s so great to be here. Thank you, Sean.

Sean Jackson: Of course.

Jess Ostroff: I’m glad to meet you.

The Pros and Cons of Bringing in Help Early or Later

Sean Jackson: You know, to keep it simple, I’m going to call Jessica Frick “Jessica,” and I’m going to call you Jess. That way our audience won’t get completely confused. So Jess, let’s go through this. Because this is a very important topic, and you are in a very unique position to give the pros and cons. Let’s go through this general setup.

I have been working my online business primarily by myself for some time now. Maybe I’ve used a contractor here and there in pieces and parts, but infrequently. Given the success of my online business, things are starting to grow, I’m making some real money, and my time is really busy. When do you think, based on your experience, should a business owner start to consider putting someone more on a continual contract basis as a part of the organization or bring them in as an employee? What is the triggering event, do you think, to start to consider personnel as a big part of your online business?

Jess Ostroff: In my own experience — it is an interesting position to be in, because not only do I provide these services for other people now, but I also went through this myself as an entrepreneur. Where I got to the point where I had so many clients and so many hours of work that it was actually impeding my quality of life. For me, part of the reason why I started my own business was because I wanted to have the freedom. I wanted to have a flexible lifestyle. The second where I felt like all this money was going into the bank but I didn’t have any time to spend it, that was the time where I decided to bring on more help. I think for a lot of entrepreneurs there’s that friction point where the cost of getting help and of getting some of your time and your sanity back is worth it.

Everyone has a different setup, a different level of profit margin, so I think that cost element is the differentiating factor between whether you should hire a contractor or an employee. Overall, the time when you get overwhelmed and you get to the point where you’re not enjoying what you’re doing and you’re not able to spend any time living your life, I think is when you should start thinking about hiring someone in the first place.

Then, for most people, it’s a slow build. I think that’s why people start with a contractor or freelancer relationship. Because — especially in online businesses and service-based businesses — you can’t always guarantee that you’re going to have X amount of sales or X amount of clients to pay the bills. Starting someone small — maybe five or 10 hours a week — and having the opportunity to grow … When I start working with people, I always ask them what they are doing in the rest of their lives. A lot of them are mothers or fathers, or they’re actors or they’re chefs — they do have other hobbies. But if I wanted to bring them from, say, 10 hours to 15 hours a week, I have the flexibility of doing that.

That’s why that’s a really good option for people. On the other hand, if you’ve all the sudden gone from 10 clients to 50 clients and you really need day-to-day, full-time support, and you know that maybe it’s even administrative things like scheduling your meetings or booking your flights that you’re not getting to … We had a client recently that I’m thinking about who ended up in Vegas a week early for an event because he booked his own travel. That was the pain point for him where he was like, “I’m so busy with my clients that I can’t even book my own flights.”

It’s the pain of screwing up and doing things wrong that was the impetus for him. But there is something really nice about being able to share the burden. That’s what I use my employees for, is having someone there all the time, someone that I can call on. You have to get to a certain level to be able to justify that kind of cost.

The Best Way To Start the Process

Sean Jackson: Let’s talk about that, because I think in the natural evolution of anyone’s business there is going to be that point where you’re looking forward and saying, “I’m going to need some help.” Now, I would hope that you need help because you have so much business coming in and you have so much money that you’re really like, “I’ve got to do something now.” I think for most people it’s a gradual shift between, “I’m going to bring somebody in to start with — maybe on a contract basis, but a very regular contract basis, not ad hoc,” and then moving them to an employee. I’m going to talk about that.

I want to talk about the difference between the regular contractor — which is a service that you provide, obviously, so you have a lot of understanding of that — versus that decision when you’re going to say, “I’m going to put them in as employee.” Because there are trade-offs to both.

Let’s start with what’s in your wheelhouse. Talk about the — I want to call it “continuous contractor.” Not a permanent person, but a continuous contractor. What is the basic thing someone should be looking at when they are considering that type of service, be it a programmer, a writer, a personal assistant? It really doesn’t matter. This is someone on a regular basis. Let’s talk about the decision process on that. Specifically, what should they be looking for? How should they set that up?

Jess Ostroff: I think that when you’re going to work with someone like that on a continual contractor basis, you have to think about what type of tasks you’re going to delegate. If they are the kinds of tasks where they could be done at any hour of the day from anywhere in the world, as long as there’s a deadline and people understand what the instructions are, they’ll get them done. That’s the perfect kind of job for a freelancer or continual contractor relationship.

That’s because usually these kinds of contractors are what we call the digital nomads, or people who actually value their independence and their freedom more than they value — or at least equally as much as they value their career. They might be working from Bali one day and then they might be working from Tennessee another day. For them it’s more about a deadline. As long as they get their work done by this time, it doesn’t matter if they’re holding a nine to five schedule or not.

Sean Jackson: Let’s talk about that, because that’s important, what you just said. The deadline and task-oriented approach. Do you bring in, for instance, some sort of to-do list managing that? I think you’re right. I think you hit on something, which is bringing in that continuous contractor, it’s very much task-oriented. A clearly defined “what I need and when I need it.” Am I using some sort of tool to do that? Is it fairly ad hoc via email? What is the best way to manage that process? I think if you do that you’re going to see success, but the problem is, if you’re so busy, you may forget when they’re supposed to have things to you.

Jess Ostroff: Totally. That’s a huge problem for a lot of people. I frankly don’t think that you can be a successful entrepreneur without having some level of organization. That’s tough love for a lot of people because they think, “I’m the ideas person. I just think of things and then they happen.” No, that’s not how it works. If you are the ideas person, I think doing soul-searching …

That’s something that I work on with a lot of my clients. I have these conversations all the time where people are like, “I know I need help, I just don’t know what I need help with.” I say, “You need to figure that out first. I’m not here to tell you what you need help with. I can consult you on that. I can take you through these processes that help you figure out what to delegate.” But it’s really a soul-searching process, because you’re trying to figure out who you are and what your value is as the business owner, what you’re best at.

Really, once you figure that out, you should be delegating everything else. If you are the ideas person and you’re not detail-oriented and you’re not good at project management or anything like that, then you probably need to get someone to do that first before you even consider hiring anybody else. Like you said, someone does have to manage the tasks. It might be through a tool, it might be through email, it might be through a calendar — that part doesn’t really matter. Everybody has their own preference on that. What matters is that someone’s there managing it and making sure it gets done.

Now, sometimes a contractor can do that. Sometimes these people are super-organized and, like I said, deadline and task-focused, so they are able to manage themselves. I would say the best freelancers and contractors are those self-starters who will say, “If I have a deadline on Friday and it’s Wednesday and I haven’t gotten what I need from my client to get the thing done, I’m going to be poking you for it.”

Whereas there are other people out there who are going to wait and let the deadline pass and say, “You didn’t get me what I needed.” I don’t think that’s the kind of person you want — whether you’re organized and busy and detail-oriented or not. You want to be able to hire … I would say the main benefit of hiring a freelancer or a contractor is that they are self-starter. They are most likely a business owner themselves, so they know how to get work done. They know how to hold themselves accountable and ask for what they need when they need it.

Why Contractors Working a Regular Schedule May Be the Best Way To Start

Sean Jackson: Let’s go through the contractor scenario a little bit more. I do want to jump into the employee side, but on the contractor side, let’s talk about money. How should you look with that continuous contractor in paying them? Is it going to be project-oriented? Should it be just a steady fee? Talk to me a little bit about how you’ve seen clients as well as your own people think about the money side of it. Again, that comes into my factor too. Yeah, I want to bring somebody in — heck I may even hire a project manager as a contractor to manage my other contractors — but what is the fee schedule? Is it continuous, meaning, “I’m going to pay you the same every week,” or is it really, “Hey, you do this, then you get that”?

Jess Ostroff: I think it depends on what you’re working on, but for both sides I think it’s definitely easier to have a fixed monthly fee for a set number of outcomes. It’s not just, “Okay, put in these hours,” necessarily. It’s actually, “Complete these projects and do these tasks.” And actually that’s really important from a legal perspective. You’ve got to be careful with being able to prove that they are on their own time and they have these set of deliverables, because if you ever got audited by the Department of Labor — which I have — you have to be able to prove that they have contracts in place for that.

If you can say, “You’re getting this much done. You’re getting paid for this many,” even if it is hours and you agree on a set hourly rate or you set up a set project rate, I definitely think it’s easier for everyone to pay that way. But if you’re in a situation where your client load really does grow and shrink on a monthly or quarterly basis, you might not want to commit to that. I think that’s okay if the contractor is okay with it.

You just have to figure out what works best for you as the owner. And you have to make sure that your margins are going to cover the freelancer. That’s the thing about contractors, a lot of times they are more expensive because you’re not paying for their health insurance, you’re not paying for their supplies, and you’re not paying to have them in the office. So you have to consider that you might be paying a little more per hour for a freelancer, but overall there’s less risk.

Sean Jackson: Let’s go through the biggest things that you see. What are the two biggest mistakes? I want to talk about employees next. Two biggest mistakes you see — first from the client perspective and second from the contractor perspective. What are the two biggest mistakes that are repeatedly seen in your industry that people are making?

Jess Ostroff: From the client perspective, the biggest mistake is forgetting that a contractor is not an employee and thinking that you have them on the payroll and you can call them and email them and text them at all hours of the day. That’s not how it works. I think that’s a problem. Sometimes it’s a problem on the contractor side, where they haven’t given the client the proper expectation. “I only work for you for ten hours a week, so that means it’s about two hours a day. That’s what this might look like in my relationship with you.” We’ve seen so many clients disrespect that boundary and not remember that a lot of times, like I said, these contractors are their own boss and they are business owners themselves, and they need to be treated that way.

From the contractor side, I think that — not on my team, of course, but other contractors that I’ve seen are unrealistic with how much they can get done and how they can manage themselves and their schedule. Living a freelancer life is not for everybody. Same thing with being an entrepreneur, it’s not for everybody. You’re not really accountable to anybody but yourself. If you don’t do your work and you miss a client deadline, that client’s probably going to fire you. But you may not be motivated by that. I think the biggest contractor mistake I’ve seen — and I’ve heard horror stories from current clients — is that they are good at what they do, but they’re not good at managing themselves and they’re not good at managing their time.

When to Make the Leap and Hire a Full-Time Employee

Sean Jackson: All right, Jessica, let’s go into the employee side. I’ll let you take that over. When I said Jessica, I mean Jessica Frick. See, we’re confusing our audience. Jessica, I want you to talk about the employee side with Jess.

Jessica Frick: My first question is where do you find them?

Jess Ostroff: For me, I have started — anyone that’s become an employee at Don’t Panic started as a contractor. A lot of times they start with me because they maybe needed a little extra money or they’re unhappy at their job. We talk about the “side hustle.” I started that way. A lot of us start by being in a job that we’re not particularly satisfied in. You’re looking for something else, so we freelance a little bit on the side.

That’s how I found my people. They come, they work, and they prove themselves. Then I say, “You know … ” There’s that tipping point where I feel like I want to bring them in full-time and maybe don’t quite have the revenue to cover them yet. I don’t tell them that. But I know that by hiring them it’s an investment. And I know that when I hire them I will be able to make that money, because I’ll have that much more support on my side so I can focus more on the business development and the processes — all the things I’m supposed to do as a CEO.

That’s how I’ve historically found people. I’ve been doing this since 2011. At this point, there are a lot more places that you can look to find these kinds of people. There are more virtual assistants out there, there are more freelancers and web developers out there. I think it’s really about the cultural fit, because if these people can do whatever they want for whatever clients they want, why would they want to become an employee of yours? You have to think about it from that side too.

I found that a lot of people just don’t want to be their own boss, they don’t want to be responsible for finding clients and paying taxes and all the annoying things that you have to do as a business owner. It has not been that difficult for me to find people that want to freelance for me and then want to come on as a full-time employee because of that. They want someone to manage them. They want someone to give them work.

I think finding someone who is younger — not necessarily younger, but at that more entry-level place who’s interested in either leaving their job or growing significantly in the number of hours they’re giving you — and be a mentor to them. Be a good role model for what they want to do in their career, and you’ll be able to develop the relationship to the point where you trust each other enough to actually work together. I think the best employee/employer relationships are the ones that are built on trust and stability.

Jessica Frick: That brings up my next question. You find the right people, and whether they’re full-time or whether you’ve hired a virtual assistant, aside from the money, how do you keep them happy?

The Best Methods for Integrating Staff Into Your Business

Jess Ostroff: It’s really hard in a virtual environment. It’s something that you have to pay attention to more than if you were in an office. Because if I have my corner office on Madison Avenue and someone can pop over and see that I’m just staring out the window and not doing any work, they might not be super happy to continue working for me. But I could be doing that here in my home and they would never know.

Jessica Frick: I’m doing it right now.

Jess Ostroff: Totally. We’re all doing it, I think. But we’ve had to work really hard at that. For me, I’m a little bit more of an extroverted introvert. That was part of why I wanted to leave my job and work at home, because I didn’t really want to talk to people. But I realize that it is important. We do a couple of different things.

One of the first people I hired as a full-time person was an HR-type role. She’s our cheerleader. She keeps the team happy. She sends out Monday motivation. She does things to keep spirits high. She thinks of things like, “Oh, so and so’s mother-in-law went in to the hospital, let’s send them flowers.” She’s the one that thinks of little things like that, because I realized I wasn’t very good at that.

Like I said before, figure out the things you’re not good at and hire for that. We also have a private Facebook group. Some people do Slack channels, HipChat — there’s all kinds of ways to stay connected. We have a virtual office tool called Sococo, where it looks like a floor plan and we all have our own little cubicles, so people can see when we’re working and when we’re not, technically. Someone can pop over my office and say, “Hey, I have a question about this client,” or, “Hey, my pay check’s wrong.” Whatever it is. They know that I’m there and available.

And I’ll change my status. Like right now — we actually have a room in our Sococo office called “the sound booth,” and that’s where we go if we’re recording a podcast. I have my own podcast now, so when I’m recording episodes it’s like, “I’m still here. I’m still working. But don’t bother me because I’m in the sound booth.”

Sean Jackson: That’s great.

Jess Ostroff: Yeah, it’s awesome. It’s just another way for everyone to feel like there’s a little thread connecting us. We employ a lot of women, and women tend to be a little more touchy-feely about that stuff. They just want to know they’re not alone. It can be really lonely as a freelancer or as an entrepreneur working from home. It’s just a little way for us to stay in touch in the times when we feel that way — or even if we don’t.

We also do — once a month we do these little lunch and learn things where a different person from our team will share for an hour something that they’ve been working on. We try to highlight our team’s personal achievements. Like I said, a lot of them are parents, a lot of them are doing other things and have other hobbies in their lives.

I feel like, as an entrepreneur, I’m supporting those by hiring them. I’m supporting those other dreams that they have. But I want to support them in other ways too. Make them feel like … It’s actually good for you to go out and play at things in your garden or cook things in your kitchen, because I think that that holistic human hobby thing makes you a better employee and a better worker. I love that.

Sean Jackson: Let’s go through this. I think you brought up some amazing points, but I also want to go to the bad side. Being the only guy on the call, I’m going to think of some bad things because you’re so piffy at positives.

Jess Ostroff: Thanks, Sean.

When and Why Should You Let Your Staff Go

Sean Jackson: Let’s talk about when you have to make that gut-wrenching call to cut off the contractor. To fire the employee. Inevitably you’ve worked very hard to build processes, and you’ve worked very hard to make sure that everyone knows what they are supposed to do — building some camaraderie, as well as helping the client feel like they are getting value from the service. But at the same time, there are just some times where people don’t fit.

Most of the time it’s a cultural thing. It’s not the skills of the person, it’s sometimes the cultural aspect. The client can’t get along with them, or you’ve been working with them and they just don’t fit inside the environment. Talk about the contractor side. When do you recognize that you need to cut off that continuous contractor? And then, conversely, about the employee side? When do you need to cut that relationship? Let’s end on that side, which I know is not very positive, but does come up.

Jess Ostroff: I’m going to make it positive, Sean, if it’s the last thing I do.

Sean Jackson: Good.

Jess Ostroff: Just kidding. This is something that you think you know and then you don’t know. You don’t really get taught how to deal with this. One of the things that we’ve done at this point is we’ve implemented a three-strikes rule. I don’t really like to call it that, because it seems very cut and dry — it’s not.

When we figured out what the things were … Like you said, sometimes it’s just they’re not getting their work done, or they’re not getting it done on time, or they’re not getting it done well. Sometimes it’s the fit thing — and we work really hard in the hiring process to try to avoid that. I would say not only on the hiring process of the assistant side, but also on figuring out who we want our clients to be. We’re really picky about who we’re even going to bring on as a client, because we don’t want to go through that. We don’t want to have to say, “Hey, you’re not a good fit. Bye.”

We want to keep them forever. We’ve had some of our clients for five, six, seven, eight years, and that’s part of why we’ve been successful. I think that, as the business owner, you have your own metrics of what success looks like — or you should. If you don’t, you need to determine that before you hire somebody, because then you can say, “I really like this person but they’re not hitting these metrics. They’re not responding to my emails in a timely manner. They’re not giving me the right attitude when I give them feedback.” Whatever those metrics are, it should be really easy for you to see whether or not somebody is hitting them that you’ve hired.

For me, I think I’m really good at compartmentalizing work and personal. The lines get blurry when you’re in these relationships, because when you have a personal assistant they’re seeing your life, and it can get super personal. You have to be able to delineate between, “Okay, do I like this person and is that why I’m keeping them?” Or, “Are they just not doing a good job, or are they not a good fit for me?”

I would never let someone go without giving them feedback. I would always try to work with them and get them to the place I want them to be. This is another thing, I would say, is the second biggest mistake that clients make with hiring someone. They think their assistant or their contractor can jump into their brain and just know what they want.

That would be awesome. If I could invent that technology and be able to do that I would, but you can’t. There’s an investment on the client side. There’s an investment of time and giving someone that training. Giving someone the expectations that you need for them to be successful. And if you’re not willing to do that, then all of a sudden, “Oh, they didn’t do it the way I want it. I’m firing them.” That’s unreasonable. You need to tell them exactly what you want, when you want it, how you want it. Then, over time they can start to learn, and hopefully preempt your instructions because they start to know you so well.

That doesn’t happen overnight. You need to be able to invest that time. One, I would always give feedback. Two, I would try to separate the personal and professional. Even if you like them, if it’s not a good fit, let them go. It’s better to let them go sooner than later. That’s something that I’ve learned the hard way in the past and now I just don’t. I say, “Hey, you’re not a good fit. I’m happy to help you if you want to get another position or if you want to try something else, but we’re done here.”

The good thing for me — I’d say the good thing for a lot of business owners today — is that the freelancer pool is enormous. The amount of people who want to work in this capacity is enormous. So even if you let one person go, there’s going to be another person there and there’s probably going to be a better person out there for you.

Sean Jackson: Sure. Jess, I think you bring up a very good point. When you do bring someone in — whether they are a constant contractor, full-time employee, or even a part-time employee — when you’re bringing them in, you take a responsibility on to educate them, to train them, and to communicate with them. I think that’s probably something that we feel when we’re working on our own. “Well, they should just get it, just like I get it because I’ve been doing it all the time,” forgetting that you know it because you do it all the time.

I think when you fundamentally look to outside resources, you have to be committed to investing the time, knowing that the payoff on that is that they will get really good. If they don’t, you have to cut them loose. But it’s okay, because they’re probably going to find something that is a better fit in the long term. Would you say that’s a pretty accurate statement?

Jess Ostroff: Definitely. I would say — if you want to lessen the burden a little bit — if this is the first time you’re hiring someone and training them, as you’re going through those trainings with them, record them. Do them on a screen flow or do them on some kind of video or something, where the next time — if it doesn’t work out — you’ve invested the time, but you don’t have to invest the same time again. You have it all recorded and then you can give it to the next person.

Sean Jackson: Jess, this has been phenomenal. Jessica and I can’t thank you enough for being here today, because you really are someone who has to live with all of these issues. I loved the insight that you provided today, so thank you again for being on our show.

Jess Ostroff: Thank you so much for having me. I love you guys. I love the show. And I look forward to more.

Jessica Frick: Thank you, Jess.

Sean Jackson: We will be right back after this short break.

Hey, everyone, this is Sean Jackson, the host of The Digital Entrepreneur. I want to ask you a simple question. What is your business framework for selling digital goods online? Now, if the question perplexes you, don’t worry, you’re not alone. Most people don’t realize that the most successful digital entrepreneurs have a framework or general process for creating and selling their digital goods in the online space. One of the best free resources is Digital Commerce Academy. Digital Commerce Academy combines online learning with case studies and webinars created by people who make a living selling digital goods online. The best part is that this material is free when you register.

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Welcome back from the break, Jess, it is our time for recommendations. What do you have?

Jessica Frick: Since we have Jess on the show today, I want to recommend another great book on a similar topic by Chris Ducker, one of our —

Sean Jackson: Who?

Jessica Frick: Chris Ducker, everybody knows Chris.

Sean Jackson: I know.

Jessica Frick: If you don’t know him, you’re about to know him. Check out VirtualFreedomBook.com. Chris outlines in detail exactly what you need to do when working with virtual staff to get more time and, in turn, be more productive.

Sean Jackson: That’s a good book for the topic we covered this week. I am going to key off something that Jess mentioned in the show, which is Sococo, because that little tool — with having your own little virtual rooms for a virtual organization — makes a huge amount of sense to me, especially when she said she had a podcasting room. So I think everyone should at least check it out.

If you’re running a virtual organization with multiple people, whether they are contractors on a constant basis or employees, let’s take a look at that Sococo tool — which has the worst name, but is an awesome tool. Let’s put that as my recommendation for the week. We’ll, of course, include both of these in the show notes on the page for the episode. Which leads us to the end of the show and our question for the week. Jess, are you ready?

Jessica Frick: I am, Sean.

Sean Jackson: Okay, here is the question. We all know about the unique selling proposition and its importance in any business. However, there’s one question related to how unique should you really be. In other words, how much should you really try to stand out, versus just a little bit of standing out? What do you say? Should you be really weird and so original that you are unrelatable? Should you be unique enough that you’re remarkable and memorable, but not so much that people are like, “Who’s the crazy person?”

Jessica Frick: Asking me is like walking around the asylum looking for a crazy diagnosis. Yeah, I say go as weird as you need.

Sean Jackson: Go as weird as you need. Okay.

Jessica Frick: Get weird.

Sean Jackson: I will take the more restrained aspect, given my nature and personality, that you want to be remarkable but not completely out there, however —

Jessica Frick: Sean, that’s totally you. You’ll wear this fancy suit and then you’ve got your expensive skull ring just hiding.

Sean Jackson: You know what? Folks, what do you think? Should you really be out there and be so unique that it is different, or should you be a little bit more restrained and more memorable? What do you think? We’re going to cover this topic in our next episode of The Digital Entrepreneur. Everyone, have a great week.

Jessica Frick: Thanks for listening.