How to Work Successfully with a Team of Contractors

business strategy Dec 09, 2020

This has been a topic that has been a long time coming. I feel that so many of the issues on teams, or with hiring, or in managing teams - all stem from one primary differentiation - whether you are working with a team of contractors or employees (or maybe a combination of the two.) So many team building issues stem from hiring contractors when what you really need is employees. Now I’m not going to get into all the legalities of hiring employees vs. contractors, I’m not an expert in that plus it varies in every state, so that’s on you to make sure you’re following the laws of your state in regards to hiring. But I do want to talk about how to work most effectively with a team of contractors, as well as what how to know which type of team member you need.

Let’s start with the understanding that online business is weird. We all run businesses, sometimes very large and high revenue generating businesses, from our homes and our PJ’s,. We work from our couches, and sometimes even from our beds. (I’ve been known on occasion to do a work from bed day). Also we often work with teams comprised of people we’ve never even met in person. Like how weird is that? My content manager has been on my team for over a year now and we talk pretty much every day and we’ve never met in person. (I mean part of the reason is 2020 so this year was kind of a wash for traveling, but still.) We can build these awesome businesses, make an income, and work with amazing people, all online.

We are very different from brick & mortars or typical corporations, so the way we build and manage our teams has to be different as well. Most hiring for online entrepreneurs is contractors. Especially at the earlier stages in business. As your business grows you might start bringing on employees, but for many of us, we are working with a team comprised entirely of contractors.

Having a team of compromised of contractors has both pros and cons. I mean of course there’s the significant pro of not having to worry about taxes, benefits, and all the other things that go along with hiring employees, which let’s be honest is probably the real reason most online business owners prefer to work with contractors. Another huge pro is that you can hire someone who is an expert in their zone of genius for a fraction of the cost of bringing on a full time (or even a part time) employee. For example, I don’t need someone who is an expert at copywriting for 40 or even 20 hours a week. My business doesn’t require that much copy to be written. I just need an expert for a few hours each week, therefore I use a contractor in this role.

A third pro in working with contractors is that you get to benefit from all the experience they are gaining from the other teams they are a part of, industries they are in, and the CEO’s they work for. I run and manage launches, but I also get to witness so many different launches and I’m always learning something new. I am on teams with different ad strategists, funnel strategists, and seeing all the other things they are trying and working on so I’m always learning from them. So you as a CEO, get to benefit from all that other experience that your contractors are getting.

But there are some big things that you need to understand and consider when you have a team comprised of contractors.

You do not have control over their time: they do. So you don’t get to dictate when or how they do their work. Now yes you can give them a due date for something, but you can’t say “I’m going to need you to work on this on Monday from 3-5pm”. So along with this, CEO’s need to be giving their contractors adequate time to get things done (meaning not dropping tasks on them last minute) and respecting their boundaries as far as their time goes. If they tell you they have a 5 day turnaround for tasks assigned, then you need to be sure you are giving them assignments 5 days before you need them. That means you have to be planning out your projects ahead of time and you can’t be changing things up all the time. Now this one might hurt for some of you reading, but if you want a team who can turn on a dime, or you are a CEO who hates making and sticking to long term plans and wants to be able to change directions whenever you feel like it, a team of contractors definitely isn’t for you.

And tying into that is the idea of how much work you want them to do. As I said above, a huge benefit to working with a team of contractors is that you can get expert help in small quantities of time. But you may not need a small quantity of time, you might need a customer support specialist for 30 hours per week. If that’s the case, great! But since that will require you having a lot more control over this person’s time and because it’s so much time every week, you might be ready for an employee instead.

Another thing to consider when building teams of contractors is that they don’t just work for you. Your contractors have many clients most likely, and so you will not always be the first priority. I tend to prioritize based on launches. So if I’m in the middle of a big launch with a client, you can bet that I’m listening to their Voxer messages first that week or jumping into their Asana workspace first and more often throughout the day. And all contractors will have a different way of prioritizing their workload. I do want to emphasize, I never leave any of my clients hanging, all of them get my attention and focus at some point every week, but I have to prioritize different teams at different times. But if you want to be the priority for your team members, always, then hiring an employee that works only for you or maybe just for you and one or two other people will be the better route.

Lastly, I want to say that you can absolutely build and lead a team of contractors that all work really well together, that feels like a team, that has trust in each other, and that has your back. I work on several teams that feel this way and some of these teams have been together for years now. It’s totally possible, but here are some tips to make that happen:

  • Know that it might take some time to find the right contractors for your team. You might not be able to tell if someone with mesh perfectly with your team until you try working with them for several months. And if they aren’t jiving with the rest of the group, it’s ok to let them go
  • Even though you are hiring a contracted position, make sure you are hiring someone who is aligned with your values and who will fit the culture of the team. This is still important even for a team member who might only be working 5 hours per month for you. Always always always go back to core values. All of your team members should know what they are and agree with them.
  • I’ve said this one before, and I can’t take credit for it because I heard it somewhere else but it was gold: if you want A level team members, be an A level leader. Lead by example. If you want your team to get their work done on time, always do you work on time. If you want your team members to go the extra mile, make sure you’re always going the extra mile. Whatever you want out of your team members, be the model for it.
  • Plan out goals and projects in advance and stick to the plan. Quickest way to overwhelm your team members is to give them tasks last minute or change directions. I already touched on this one earlier so I won’t get into it again but plans are your friend. Your team should always know the upcoming projects, goals, and objectives, and know exactly what their roles, tasks, and responsibilities are for those, and when everything is due. With plenty of notice.
  • Thank your team and thank them often. Remember if you have a team of contractors, they likely have many clients so they don’t need you as much as you need them. I know that sounds harsh but it’s true. So make sure they feel needed and wanted and appreciated.

To hear about the rest of my tips for creating a strong team of contractors, tune into this episode of Planning for Profit.


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