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3 Major Pros & Cons to Hiring a Team of Contractors

May 15, 2020

Chances are, you launched your service-based business as a sole operation—handling everything thrown your way with your own two hands:

  • From dreaming up a new product to painstakingly watching YouTube videos in slow-mo as you execute on your ideas
  • From DIY-ing your branding to integrating your website with your email marketing platform or eCommerce shop
  • From pushing yourself to attend yet-another-networking event (more clients!) to avoiding your inbox in fear of another inquiry you just don’t have enough time to support

As a stellar service provider, you’ll eventually reach a point in your business where you have a full client load, but your own business will start falling into second place.

You’ll start thinking about hiring contractors to expand your capacity… but it can be a really difficult transition to go from the solopreneur to the CEO.

Here are some pros and cons to consider while you prepare for hiring contractors to support your small business.

Pro #1: You No Longer Have To Do Everything Yourself

When you reach the point in your business where you don’t have to do everything yourself it can feel so freeing… but just be aware that there will be a big time investment upfront in order to realize this payoff.

You will have to train your team, and you may have to come to terms with how the way they complete their tasks is not exactly how you would have.

As a result, you might feel like you are spending so much time trying to find the right help, or giving more background details to the task, or walking them through every step of the process.

It might take a few months, but dedicating the time to on-boarding your new contractors will take time off of your plate in the long run. So enjoy that extra time you have to go find more clients or show up better in a different aspect of your business or life.

Pro #2: You Gain Expert Eyes on Everything

Whether you’re creating a new program or improving an old one, it can be helpful to have an outside perspective. Collaborating with your team to capture their thoughts and experiences can be a wonderful exercise in making your product bigger and better than ever.

Not only will you enjoy the personal insights of everyone on your team, but you’ll also gain perspective from their other clients.

If you’re hiring contractors who serve multiple clients, they have seen the behind-the-scenes of many businesses and often learn lessons on what works and what doesn’t. This kind of insight is invaluable (and what you’re paying for when you hire a 1099).

Pro #3: You Can Finally Tackle Those Big Projects

You probably have a project or two that keeps getting pushed off into the unknown, never to be completed. With a good plan and team support, you can make significant progress you otherwise wouldn’t be able to. Imagine that!

Oh, and another benefit to this?

Once you actually get that new product off the ground, your team is likely to share what you’re working on with their own respective networks.

Con #1: Progress May Feel Slower or Come in Bursts

This is probably one of the hardest things to adjust to as a former solopreneur.Gone are the days of having an idea at 11pm, jumping onto your phone to start working on it, and getting it up and out the door the next morning.

When you have a team supporting you, you have to actually communicate your vision and lay out a plan to execute it.

Then, you have to wait for them to digest that information, do their own research, come up with their own ideas, and start the work.

Oh, and keep in mind that they probably have other clients and won’t always be able to start on your new brain child immediately.

The bigger the team, the harder a quick pivot can become.

Con #2: Communication is Difficult

When you’re the only one in your business, you have the ideas and you execute on them all on your own… so the only person you need to talk to is yourself.

Unfortunately, that won’t work very well with a team.

You need to be able to talk to your team often and have regular check-ins to make sure they have all of the information they need to move forward and are actually doing the work. You want to make sure that they have a direct line to you to communicate any questions.

Another barrier to communication comes in when you’re running a virtual team. There are so many available systems out there (Asana, Slack, Teamwork, Voxer, etc.) that it can be overwhelming if you don’t have a proper communication strategy in place.

The most important thing is not which system you decide on, but that you lay out the expectation of which one it is and at what times to use each one. For example, I would use Asana for task-oriented items and Voxer to clarify any of those tasks and additional ideas. It keeps everything nice and efficient.

Con #3: Understanding Your Team’s Personalities and Giving the Proper Accolades

In an office environment, you walk past your coworkers every morning, stop to chat with your boss in the afternoon, or make coffee while small-talking with an employee from another department.

If you’ve been working as a virtual soloprenuer for a long time, it can be easy to forget that you now have other people in the background that are helping you launch these amazing things because you don’t see them.

As a leader who wants to continue growing her business, it falls on you to ensure you’re providing a team environment for success, recognition, and open dialogue.

One of the things I do with my clients is to create a profile for each member of the team.

We include work profiles, like their StrengthsFinder results, Love Language preferences, and their Myer’s Briggs personality type. But we also discover a few of their favorite things, so we can easily pop a pair of crazy socks or bag of sour patch kids in the mail to show our appreciation for them during busier seasons and projects.

One Final Consideration As You Begin to Hire Contractors

As the CEO, you still need to remember to do the work. You can sometimes get blindsided by this when you hire a team, thinking you can just hand everything off to them and walk away.

Remember, you are the captain of the ship. As a small solo rowboat, you can pivot however you want. Leading a cruise ship however, you need to make sure you are intentionally taking everyone on your journey.

So as the CEO, you still need to get invested in the things that you are working on. Sometimes you’ll need to jump in and write a whole series of emails that you weren’t planning on doing!

You might have days where you wonder why you’re working harder after hiring a team. The work you do now with a team, however, is probably much more laser-focused. The level of work you’re producing is of higher quality.

You’re now able to come up with bigger ideas and getting more things executed, and jumping in to help get things done, but you’re not doing everything end-to-end alone.

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