119. 10 Lessons from My Team Break-Ups

10 Lessons from My Team Break-Ups

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Are you struggling to manage the relationships with your employees and contractors as you build your business? Join me in this podcast episode as I share my top 10 tips for successfully navigating the complexities of staffing your business, drawn from my own experiences in building a multi-seven-figure enterprise. My goal is to help you create a successful team while maintaining healthy working relationships with your employees and contractors.

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Listen to episode 119, follow along so you never miss an episode, and leave a review to help introduce the show to more online business owners just like you!

Tip #1: Communication is Key

Maintain open lines of communication and be transparent about expectations, goals, and feedback. This helps ensure everyone is on the same page and working towards common objectives.

Tip #2: Set Clear Expectations

Outline specific deliverables, deadlines, and outcomes from the start to avoid confusion and disappointment. Make sure everyone knows what’s expected of them.

Tip #3: Trust Your Intuition When Hiring

While it’s essential to trust your gut, also be open to giving people a chance to prove themselves. Sometimes, the best employees and contractors are the ones who surprise you.

Tip #4: Keep a Professional Distance

Avoid friendships with your contractors or employees, as this can complicate your working relationships. Maintain a professional boundary to ensure smoother interactions.

Tip #5: Be Prompt and Professional When Ending Relationships

Treat the situation with respect and be straightforward about your decision. This will help minimize any potential animosity or misunderstanding.

Tip #6: Reflect on Your Role in Failed Relationships

Consider how you could have been a better manager or communicated more effectively. Use these experiences to learn and grow as a leader.

Tip #7: Don’t Hesitate to Let Someone Go

If an employee or contractor is not meeting expectations, parting ways can be the best decision for both parties. Trust your judgment and make the tough call when necessary.

Tip #8: Own Your Mistakes

Take responsibility for your part in failed working relationships and learn from these experiences. This will help you become a better leader in the long run.

Tip #9: Seek Support from Others

Turn to friends, family, or mentors for advice and perspective when facing tough staffing decisions. Their insights can be invaluable.

Tip #10: Treat Your Business Like a Real Company

Even if you only have one employee, implement contracts, handbooks, and company policies to establish a solid foundation for growth. This will set the tone for a professional working environment.

In addition to these tips, I highly recommend working with professionals like Paradigm HR when hiring full-time employees, as the process can be time-consuming and complex. I’ll also share resources such as a contract template for independent contractors and links to other helpful resources discussed in the podcast episode.

To stay updated on more tips, insights, and behind-the-scenes advice on building a successful business, make sure to sign up for my email list. You’ll receive weekly legal tips, marketing secrets, and more – all aimed at helping you grow your business and navigate the challenges that come with it.

Episode Transcript

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Sam Vander Wielen: Hey, and welcome back to On Your Terms. I’m your host, Sam Vander Wielen. I’m an attorney turned entrepreneur who helps online coaches, course creators, educators legally protect and grow their online businesses using my DIY legal templates and my bestselling Ultimate Bundle.

So, thank you so much for being here this week. I am so excited to chat with you today about what I’ve learned from contractor and employee breakups in my company because there are so many great lessons about hiring, firing, building teams, everything in between. And so, I’m hoping that you’re able to take some of what I’ve learned so far and apply it to your own business.

Now, because this is a May episode, if you’ve been listening to the podcast, you know that every single episode in May is kicking off with a quick tip from my dad, Norm. My Norm Tip of the episode, and they are not crazy novel tips. They are just tips. Norm was a simple guy, so you can’t expect much more than that.

But this week’s Norm Tip for you was that Norm said that you always had to have canned veggies on hand in case of a power outage. And he really thought it was important to have something with protein. So, he would always have like cans of beans and he would make this five-bean salad with kidney beans and garbanzo beans and green beans and all this stuff. But he also had canned veggies. And he loved beets, he loved pickled beets, so he’d also have pickled things. It was just really funny. But he was always preparing for some terrible hurricane or something to come or some terrible snowstorm. He hated the cold, so he was like, "You have to have canned veggies."

So, when he would come to my house, he would literally investigate the pantry and be like, "You don’t have enough canned veggies to make it through a storm." And I was like, "Well, we’re going to be all right." So, I have enough canned coconut milk to last a really, really long time. So, there’s something in that, healthy fat. Okay. Cool. So, with that, thank you for indulging my Norm Tip of the week. I hope you enjoyed it.

I’m really excited to chat with you today about what I’ve learned from contractor and employee breakups because I feel like I’ve learned a lot. And I think when it comes to hiring, managing a team, being more of a leader in your online business, we’re sort of flying blind here for many different reasons. For one, hiring in our industry is really different. We hire for different positions than a "normal company."

But I also think even on our lingo, I remember when I was starting out and I was like, "I want to hire a VA." And I would tell other people, they would be like, "What’s a VA?" People didn’t even understand what that was. Even these roles themselves, like a VA, an OBM, they’re relatively new in the scheme of hiring or in employment. So, it’s not like all this stuff is super clear cut and there’s a great simple process out there that you’re supposed to follow.

We also just don’t know what we don’t know about hiring. And I think like so many hiring, whether you’re hiring your first VA or hiring a full time employee, hiring a new contractor, there’s just a lot to be said for going through the process and learning.

The downside is that there are people involved and there’s time and there’s money when you’re the business owner. So, it’s really hard, but I do feel like a lot of people just learn by doing this stuff and getting into it. And I feel like we get really excited about people helping us – and I’m going to have a really good tip for you in a couple of minutes about this – maybe you even get excited about a specific person that you find and you’re just like, "I just want that person to work for me or I want that person to be in my business." And we don’t really have a whole lot of clarity. And we make sometimes decisions that just don’t end up panning out.

And sometimes a lot of what I see in the online business world, I remember when I started out, it became really popular for people to hire an OBM and it became a status symbol of like, "Yeah. I have an OBM. Do you have an OBM?" Like, I didn’t have anybody who worked for me for a really long time, but I remember thinking I was doing something wrong because I saw other people hiring people and I thought I had to hire somebody similar.

So, I have hired all sorts of people. I have hired contractors. I have hired contractors of all varieties, like people to work on just a project, people to work on a retainer, people who just work as we need them. Then, I’ve hired fulltime employees, like actual fulltime employees. Some people, it’s worked out great with. Some people have left without any issues, just because they were moving in a different direction or something in their life changed, their business changed. Others, not so much. It’s been a mix.

And I have learned and I take ownership for every single one of them. I don’t have a bad feeling about anybody. I just try to learn from it. And I try to own my part of it about what could have gone better or could have gone differently. And I also try to see what our team could have done differently, anybody in a leadership position, like if something went wrong or just looking back on it, like, "Oh, we could have done this a little differently." It’s always a learning lesson.

And I hope this goes without saying for anyone who knows me well enough, but this episode is definitely not about anyone in particular. It’s not even about three people in particular. It’s collectively. Like, I’ve hired people and lost contractors for years and years that probably nobody even knows about who have worked or who currently work for me. People who worked for me don’t even know I had these contractors. I’ve worked with so many people, so what I really did today was boil down the most – I don’t know -common issues that I saw amongst all of these people, and all of my decisions, and my relationships, and hiring. Not a person. So, I think that goes without saying.

So, let’s go through all of my tips. I have ten tips for you on what I’ve learned from contractor and employee breakups that you can implement in your own business. They’re all so important.

The first one is so important because the first tip is that you need to know what you’re looking for. I want you to look at the more the legal fit. So, first you have to look at Am I looking for a part-time employee or a full time employee, like an hourly employee or a fulltime employee? Am I looking for a contractor? And if I’m looking for a contractor, am I looking for somebody to just complete a project?

Like, I want to hire a copywriter to write a sales page. That’s a contractor and a project role. You hire them for a project. When they’re done that project, they’re done working for you. You can always re-hire them for a new project, but they’re not on tap. Versus, hiring a copywriter on retainer where you pay for five emails to be written a month and they’re writing them every single month for you, or ten hours a month of time, or something like that.

If you want to learn more about – let me go back because this is important to know. A lot of times people think that you can think of what kind of role you want in your business – like you want to hire a VA – and you want that person to be a contractor. That’s not how it works. So, instead, we have to get really, really clear on what you’re hiring for, and we’ll talk about that more in tip number four. But you need to know about what you’re hiring for, and then the position itself dictates whether or not this person is a contractor or an employee.

I talk about this in Episode 64 of the show in Hiring Contractors 101. I’ll link to it in the show notes. But I talk about this because a lot of people get confused about the fact of thinking that this is a choice. So, if you want somebody to work for you and you want to control their time, like you want them to work 9:00 to noon and you want them to attend all your meetings and you want them to do – I don’t know – certain things in your business, you’re not looking at that and defining all the tasks that you want them to do and then being like, "I want this person to be a contractor." That person legally is an employee for a number of different reasons, that I go into in Episode 64, and you don’t get a choice in that.

So, it’s more about designing the role and really knowing what you’re looking for. Like, Am I looking for somebody who I need them to be here all the time? Am I looking for somebody who they can just have a list of tasks and they can knock out those tasks on their own time?

Like my first VA, who still works for me, Leanne, she’s worked for me for years and years, we give her a whole set of tasks but she can do these tasks on her time. We’re not saying you have to work from 10:00 to noon Eastern or whatever. So, she has a young child, so sometimes she does this stuff at different hours, whatever works for her. If she wants to catch up on the weekend, she can catch up on the weekend. If she wants to work at night, she can work at night. It’s up to her. It’s more task oriented. I’m not controlling that kind of stuff.

At least I want you to shift your perspective that this is not something that’s a choice necessarily for you that you’re like, "This is the person I want. I’m going to make them a contractor." It might be that the role itself demands the level of employee or not. So, listen to Episode 64 if you want to dive deeper into that whole breakdown.

Okay. The second tip I have for you, what I’ve learned from contractor-employee breakups is something actually that I learned from Amy Porterfield a long time ago, and I want to be better about, which is hiring slow and firing fast. So, what Amy is referring to is that a lot of people hire really quickly because they get excited about somebody and then they take way too long, usually, to fire somebody once it’s not working out. And instead, I’ve heard Amy talk about the fact that it’s actually better to hire slowly and fire quickly.

And by the way, if you don’t know, I just had Amy on the show last month, so I’ll link to our interview below. But we talked about being leaders, and having a team, and having to manage people, and how it’s a whole new ballgame. So, we did talk about this a little bit in that episode, so I’ll link to that below in the show notes.

The third thing I think I also learned from Amy, I’m not sure, maybe, or something that somebody said in an episode of hers that I listened to. Honestly, I am not sure so I apologize in advance if I did. But it’s just one of those things I feel like I heard this one time and it really stuck with me.

So, my third tip is that you never hire for the person, you hire for the position. This is really, really important because, in online business especially, I think sometimes we can make personal relationships with people or be friends with people. And you have somebody who you just really like as a person and then you’re like, "I just want you to be around. I want you to work for me and we’ll find a place to fit you, like we’ll stick you somewhere." And that is not a good idea.

So, if you ever feel that way – like we had this recently and I said this to Lindsey, my director of operations, I was like, "Instead, what we have to do is we have to write out the job description of what we really need as a company, what tasks do we need fulfilled, what experience does that person need, all that kind of stuff, what qualifications, what demands do we have, whatever." We write all that out. And then, you go back and you look at this person that you’re smitten with and you see objectively as a business person, does that person fit in to the job description that you’ve written out?

Instead of just liking the person and being like, "I’m just going to squeeze you into something and it’s going to work out, we’re going to hope it works out." Not good. This leads to tip number four, because tip number four is that you have to be really, really clear on what exactly you want help with in your business and why.

So, I went to that retreat in Mexico in March, and I was telling the other people at the retreat how a lot of times people don’t think about hiring in terms of managers and executors or leadership people and executors. And so, it’s really helpful for me the first question I always ask myself is Am I looking for somebody to execute stuff? Or am I looking for more strategic visionary?

Because in my business at least, I don’t need somebody who’s going to come up with a whole bunch of more ideas because I’m good on that. I wake up in the middle of the night, I think of podcast ideas. I’m overflowing with subject lines, and titles, and little story quips, and blah, blah, blah. It’s constant. It’s an affliction. So, I don’t need another idea person.

What I do need or what I have liked in the past is somebody who can implement all of my ideas, an executor. So, an executor can take my idea and they can write the copy, or they can write the email, or they can lay out the strategy for a promo that I have the idea for. I need executors. I need people to set up the landing pages, test the tech, be on the calls to answer customers questions, manage my inbox, manage my marketing schedule, edit my podcast. I need executors a lot of times.

So, it’s really important to get clear on that part of are you looking for somebody to execute tasks or to manage certain something or strategize certain something. And then, within that, What tasks? And so, that’s where I like to get really clear, in tip number five, about what kind of task do I need to get somebody else to do that I don’t need to do. I’m not required. It doesn’t require me or it’s a task that I’m currently doing that’s not moving the business forward, but it needs to get done.

Like onboarding new clients, like sending in signing contracts, and setting up their portals, responding to customer service, emails, tech stuff, taxes, bookkeeping, legal, copywriting for promos. I mean, that moves the business forward but that’s something where it’s like you don’t need to do that because somebody else is probably a lot better at it who’s trained in conversion copywriting, for example. Web design and maintenance is another one. It doesn’t move your business forward, ultimately, and it’s something that somebody else has a high level skill and can get it done much faster.

So, when you make a list of all the tasks that need to get done and you’re really clear on like, "Oh, these are all tasks of things that have to be executed on" versus strategy, and then we’re very clear on the position and we’re not hiring for the person, we’re hiring for the position, the stuff can start to move a lot smoother.

So, moving into tip number six, most of the rest of the tips are kind of like once somebody is onboard and starts working for you in any capacity. These are some of the things that I think come up and I can hopefully offer some tips on.

So, tip number six is to communicate early and often with whoever works for you. I like the phrase, and I’ve decided to adopt the phrase, feedback is to be expected and it will come early and often. So, feedback is not a bad thing. It’s all about how it’s delivered and it’s a skill. It’s something that I’m working on. I’m trying to figure out how to do it, how to do it best, how to figure out how people like to receive feedback. You have to ask how do you like to receive feedback. Start having those conversations.

But I think this idea of, at least for me, waiting and waiting on something that you don’t like or that doesn’t feel right or it’s not sitting right and you wait and wait and you let it build, it never goes well. And this is not just talking about my own business. I’m talking about so many friends. And I worked with an HR company, I’ve heard their stories about stuff. It just does not go well if you don’t communicate early and often about feedback.

And, you know, I think one of the things that I learned about, too, is having to create a culture of, yes, you will be complimented and praised when things are good. Although, there’s this part of me that’s kind of, I don’t know, hard ass part of me, I guess, that my mom was just always like, "It’s to be expected." Like, when you do a good job, it’s a job, you’re getting paid a lot of money. And you’re here to do this, I can’t thank you every single time. It’s kind of to be expected.

But there’s also the part of me that’s like, "No. I want to create a nice environment." And I do want to recognize when things are really exceptional or great or I just really like something. But I don’t want to create the culture that you’re constantly getting all this positive feedback, but then you’re never able to give some more constructive feedback too. I also don’t want to create the culture that if I offer you constructive feedback, I have to pair it with something positive. So, I think it’s a real learning process and it’s not something that I’m necessarily good at or anything like that, but I can tell you it’s an issue and it’s something that comes up for a lot of people.

And I’m liking to think of it these days as reps in a gym. Like, just the more reps we can get in, just like to be expected, it’s not to be personalized. That’s the tone that I’m trying to set on the team, like this stuff is not personal, a lot of what we do is super subjective. A lot of times when people are trying to find my voice, or my style, my design style, it’s all subjective. My way of writing, my way of design is not the right way. It’s not the best way. It’s just the way I like it. And so, I’m very honest and upfront about that.

But I also can’t explain that every single time. As the CEO, I just don’t have time to do that anymore and I don’t want to do it anymore. I want to own it. I’ve built this business. This business is really, really strong and it’s successful. And a lot of why it is like that is because of me executing things this way, and so this is how I would like it to be done. If you have a reason where you want to pitch me a different strategy, and you have some stuff to back it up, and you want to try it out, and you’re going to tell me how you’re going to try it out, and how we’re going to track it and all that kind of stuff, let me know. But otherwise, this is how I want to do it. So, a lot of communication.

I’ll tell you, managing a team really makes you step into yourself, step into your power, which leads to tip number seven, which is learning how to become a leader and a manager is an entirely new skill that, unless you’ve done it before, is really uncomfortable and foreign. I don’t think it comes naturally to a lot of people.

But when you become a CEO and you want to hire people, whether it’s contractors or employees, it’s now part of your job to be a leader or a manager or both. Everybody, by the way, hits this point in their business. Like when my business first started to grow, I hired a bunch of contractors. I hired those executors. And when I did, I then felt like I was a manager. I went from being the CEO of the business and creating all the content to feeling like I was spending my whole day answering slack questions and checking over people’s work and then posting their work for them and doing little stuff.

And on Friday night when something broke in the funnel, I was on there fixing it myself and always on my phone and all that kind of stuff. And that’s when I learned I needed a manager for all the contractors. And that’s when I hired Lindsey, my director of operations. So, you know, that’s how we learn.

But everybody goes through this and it’s this process of becoming the manager of these people, that was a learning curve. And then, becoming more of the leader who hires a manager to manage all the contractors. It’s tough. It is a learning experience for sure.

Tip number eight is to take ownership of your part in every single relationship of somebody who works for you. I truly believe that everything is not all good or all bad or everybody’s not all right or all wrong for the most part. And I think that it’s really important that we work on our own stuff. And a lot of what I’ve seen in teams, not just in mine or not really even so much in mine, but as much as I’ve seen it with other people, friends, colleagues, is, people recreate their own family issues or communication issues, like the structure of their family or family dynamics, within their company. They bring their own stuff and they throw it on their team.

And a lot of people make the mistake of treating their team like a family. And I think that there’s a way to create a really nice, positive, warm, inviting culture without the toxicity of being like, "You’re my family. You’re my family." It’s still work. We have to be respectful. We want to have boundaries and be friends, but it’s just different. And so, I think that’s kind of important, though, for you not then putting all your shit onto them, to be honest.

And when anything has gone "wrong" or someone’s left or anything like that, I take full ownership for it. I’m like, "That’s on me. I see what I did wrong." I should have done this differently. I should have hired slower or fired faster. Or I should have been clearer on what I was hiring for. Or I should have not hired for the person I should have hired for the position. One of the tips that I’ve probably given you already, and I’m like, "That’s on me. And this person didn’t do anything wrong because I didn’t have the structure or the skills to deal with it and to know." Because if I had, then it wouldn’t have ever gotten here. So, I take ownership. The buck stops with me. That’s my position across the board in the company.

Tip number nine is from one of my favorite people in the whole wide world, Jen Diaz. So, I’ll link to her below. But Jen is my mindset coach and Jen’s just an incredible human. I highly recommend going and joining her JAVA method, by the way. It’s her membership. Her visualizations are incredible and she’s incredible. But Jen told me something really awesome that was actually, I think, from one of her clients in the past. And Jen, when I was struggling with some stuff related to team building over the last couple of years, she was like, "You are responsible to them, not for them."

So, I’m responsible to them. Meaning, I have to be a responsible leader. I have to be kind. And I have to be professional and put together and do all these things. And offer them a safe work environment. And all of those things. And I have to give them the tools that they need, and access to resources, and provide a lending ear, and have an open door policy, which I always have.

But I am not responsible for them. Meaning that if I give feedback and someone doesn’t love it, I’m not responsible for their reaction. I’m responsible to deliver that feedback early and often, like I said. I’m responsible to do it in a kind, compassionate, respectful way. But I am not responsible if they have a freak out or I’m not responsible if someone quits because they don’t want to hear feedback or whatever. I’m not responsible for that part.

So, learning that lesson over the last several years – and this goes back, like, years and years – I’ve played this back now, this saying of your responsible to them but not for them now in my mind to relationships, like, for the last five years being like, "Oh, yeah. I see how I was making myself responsible to them and for them five years ago." So, it’s something that I’m practicing right now.

And I actually think this is just a really good tip for life, by the way, of I could see how this could really help family members or friends, whoever you have to share feedback with or have any sort of relationship with.

Last but not least, tip number ten – you know that I couldn’t skip this one – is that it is really, really helpful to start acting like a real company from the start, whether you have one employee, one contractor, your first VA, your first fulltime employee. Have legit contracts, like use an independent contractor agreement for any contractors that you hire.

I have a really easy contract template for independent contractors you can download and fill out in 15 minutes or less, so I will link to that below. It’s in my template shop on my website, samvanderwielen.com/shop. So, you can check that out.

Also, if you hire fulltime employees, you want to explore having an employee handbook. That is not required, but an employee handbook has company policies, company culture, holidays, how to request time off, blah, blah, blah, all that kind of stuff. But as Kira says from Paradigm HR, she always says, don’t have an employee handbook if you’re not going to follow it. So, if you’re going to say all this stuff that you do or don’t do and then not do it, forget it because you’re not required to have it. But if you do start hiring employees, then I recommend kind of getting started with those things.

So, getting that stuff in place, really acting like a real company, once I was ready to hire fulltime employees, I stepped up my game. I was like, "Okay. I want to offer them a 401K. And I want to offer some wellness perks. And I want to have unlimited paid time off." And then, once I actually went on and hired my first fulltime employee, Lindsey, I learned a lot about that process. And I’m a lawyer and this was shocking to me, but there was an insane amount of paperwork and setting up on payroll and all that good stuff. And then, you have to get certain insurances once you have fulltime employees. It’s a whole thing.

So, I highly recommend, I worked with Paradigm HR. I’ll link to them below. But I highly recommend working with a professional once you get to that level of wanting to hire a fulltime employee because it was a lot and I could see it derailing your business. Especially if you have a business where you have a lot of client work to do, it would be pretty tough.

So, those are my ten tips on what I’ve learned so far from contractor and employee breakups. Like I said, I would kind of hope that it’s like romantic breakups where you don’t have super bad beef with anyone. But I have no idea how people feel about me, and I can’t control that, but I take ownership either way. If anyone ever talked to me about it, I’d be like, "Yeah. Totally. I own that." I’m not somebody who’s like, "You did everything wrong and I’m the victim." Like, I can really just sit and own my part of it, and hope that I just get better and learn.

So, I hope that some of these were helpful to you. I will link below to that Episode 64 on hiring contractors, because in that, I break down the difference between contractors and employees. And I’ll link to everything else that we’ve talked about in today’s episode.

If you like hearing about these kinds of tips, if you want to get weekly legal tips in your inbox or you want to learn my marketing secrets for building a multi-seven figure business, all the behind the scenes juicy stuff, make sure you click the easy email list sign up below. That will just automatically sign you up to receive my emails without going through any sort of marketing funnel. So, it’s a great way to start receiving my emails, hear about what’s coming up, get special offers, but really just hear my kind of most vulnerable behind the scenes advice on what it’s really like to build this kind of business. The best thing for you to do is to sign up for my easy emails below.

So, thank you so much for listening to this episode. Send me a DM on Instagram, @samvanderweilen, and let me know if you liked it, what came up for you. Let me know what was the number one thing you learned from this episode, I would love to know that.

And if this episode was helpful for you and you think it would be great for somebody else, text it to a friend. Leave a quick review or a rating wherever you listen. I just so appreciate you taking one small step today. If you could just do one thing, whether it’s to send it to somebody, leave a rating or review, send me a DM about it, if you could do one small thing to help move this podcast forward and get it into the hands of other online business owners, I would be immensely appreciative. So, thank you so much and I will chat with you next week.

Thanks so much for listening to the On Your Terms Podcast. Make sure to follow on Apple Podcasts, Spotify, or wherever you like to listen to podcasts. You can also check out all of our podcast episodes, show notes, links, and more at samvanderwielen.com/podcast. You can learn more about legally protecting your business and take my free legal workshop, Five Steps to Legally Protect and Grow Your Online Business, at samvanderwielen.com. And to stay connected and follow along, follow me on Instagram, @samvanderwielen, and send me a DM to say hi.

Just remember that although I am a attorney, I am not your attorney and I am not offering you legal advice in today’s episode. This episode and all of my episodes are informational and educational only. It is not a substitute for seeking out your own advice from your own lawyer. And please keep in mind that I can’t offer you legal advice. I don’t ever offer any legal services. But I think I offer some pretty good information.


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  • ConvertKit // what I use to build my email list, send emails to my list, and create opt-in forms & pages

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