Getting Organized Before Hiring Your First Contractor

Getting Organized Before Hiring Your First Contractor

Are you thinking about hiring your first contractor? First, congratulations - that’s an amazing step in your business and something to celebrate! Before you make your first hire, there are some things you should organize before you bring them onto your team. You want to make the transition to your company as seamless and easy as possible for you and the contractor. That will start your working relationship out on the right foot. 

Deciding the Right Time to Hire

How do you know it’s the right time to hire? These are some of the thoughts and feelings I had before I hired my first contractor - that’s how I knew it was time. 

You Can’t Scale Your Business

There comes a point when you simply can’t do everything yourself. There’s too much on your plate, and you constantly feel overwhelmed and stressed when you look at the never ending to-do list. Your business can’t grow more without someone helping you. That’s a great time to look into hiring help.

You’re Working Overtime

Hey, if you’re into working overtime, then go you. But most people don’t want to be working overtime (or all the time) for the sake of their business. If you…

  • Are working too many hours for your liking

  • Feel like there aren’t enough minutes in the day to get things done

  • Are neglecting people or hobbies that are important to you because of work

  • Aren’t taking time off

…it’s time to hire. There’s no shame in admitting you need some help. In fact, it’s a sign of growth! To build a stable business, you’ll need to hire. It’s not sustainable to do everything yourself. 

You’re Doing Tasks You Don’t Want to be Doing

As business owners, it feels like we need to be doing everything. But everyone has weak areas or things they dread doing. Those should be the first things you outsource. The work you do in your business should be something you enjoy. If you’re constantly doing things you hate, it can become draining, and you’ll get burned out very quickly. Prevent that from happening by hiring someone else to do those tasks for you.

Questions to Consider as You’re Getting Ready to Hire

Before you hire someone, consider these questions.

What are you willing and able to pay a contractor?

Consider the going rate for the tasks you’re looking for help with. If you want to hire a social media manager, for example, do some research on what quality social media managers are charging. That way, you can offer a fair rate and find someone who’s great at what they do. I also recommend meeting with your bookkeeper (if you have one) and deciding an appropriate hourly rate. 

What are the Tasks You Need Help With?

You probably have a list of a mile long of things you want to take off your plate (isn’t it fun to make a plan to actually get it off your plate?!). Start by grouping tasks that go together. For instance, if you have posting to social media, keeping up with algorithms, and creating graphics on your list, you could hire a social media manager. 

I recommend hiring someone who specializes in a specific area, such as a social media manager. You wouldn’t want someone who advertises their services simply as “marketing.” That’s extremely broad, maybe too broad. They probably are able to do many things within marketing, but since they don’t specialize in anything, they may not be amazing in the task you need help with.

When you hire a contractor, you want to find the best person with those skills within your budget. Hiring people who specialize or are actively working to specialize in something is the best way to go.

What Are You Willing and Able to Pass Off?

I think this is the scariest part for business owners. You’ve built this business from the ground up, and now you’re giving part of it away to someone else. If you’ve never done it before, it’s terrifying! You want things to go perfectly. Well, it’s a good thing you’re reading this blog. 

Look back at the list of tasks you don’t want to be doing. Are you willing to pass any of those tasks off to someone else? Even more so, are you able to? There are some tasks I wouldn’t hand off to a contractor because it’s either confidential information between myself and my client, or I simply don’t feel comfortable giving something over to a contractor. Think about some things that you’re willing and able to pass off.

Should you hire someone as a 1099 or W2?

A 1099 contractor is what most entrepreneurs hire. 1099 contractors work part-time and are responsible for their own insurance, taxes, etc. They typically work on a project basis and can have quite a few clients depending on their specialty. Many people who work as 1099 contractors consider themselves or are called freelancers in job postings. 

W-2 employees can be part- or full-time, and the business owner is responsible for paying extra employee benefits. They typically work for a designated hourly rate on an ongoing basis. They may or may not sign contracts designating how much work will be provided each month. Part-time W-2 employees are technically employees, but typically don’t report to a “boss” in the same way as full-time workers do. 

As a small company, I’ve always hired contractors/freelancers and have had great experiences by going that route. Either way, it’s a good ideas to talk to a lawyer to get proper contracts in place.

It’s an exciting time when you feel ready to hire.

It means you’ve reached a point in your business where you can’t do everything yourself any longer. Hopefully, you’ve realized this before you're burned out, but it’s never too late to bring on a contractor. 

Before you do so, you need to get organized. Decide what tasks you need help with, set a budget to pay the person or persons, and analyze whether you want to hire a 1099 contractor or W-2 employee. Good luck!

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