How to Hire Your First Contractor

If your business is to the point where you can’t grow anymore without hiring help, this is for you! Before you hire, you'll need to get organized. When you have a solid organizational foundation in place, these are  exact steps to take when hiring your first contractor. They include everything you need to know when hiring a 3rd party, including where to find contractors, how to interview them and decide who is best for you, and getting a contract in place.  

Where to Find Contractors

The first step is to figure out where contractors market themselves. For most business services, I’ve had luck finding freelancers in at least one of these three ways.

Facebook Groups

There are hundreds (maybe even thousands!) of Facebook groups out there. They can be broad like “marketing,” or more niche like “female social media managers for small businesses." I suggest joining a few in multiple categories. Make sure to take a look at the group rules to make sure you’re following them before posting your job opportunity. You don’t want to be kicked out before you even start! 

You can go about getting applicants for your job opportunities in several ways. Try asking for applications in:

• Direct message pitches

• An online form

• Posted as a comment

• Sent in an email

On of my favorite ways to collect interest is through an online application form. Doing it this way means all submissions will be organized and formatted, so you can sort through them without needing to respond to everyone (if there's a high enough volume). You’ll also get all the information you need at once. Post the link to the form with a short description of what you’re looking for help with.

You’re bound to get plenty of people to choose from! As a general rule, I recommend reaching out to applicants to let them know one way or another. Getting ghosted by a potential client or employer is almost always worse than a polite email wishing them the best. 

Fiverr

Fiverr is a freelance site where you can either search for contractors offering a specific service or post your job and wait for freelancers to apply for it. You can find just about any business service you could imagine. You can also indicate if it’s a one-time job or an ongoing opportunity. If you choose to post a job, you can have freelancers answer interview questions and submit their portfolios.

You can either have them pitch you on pricing or post your budget for the job. You will also get a lot of applicants on Fiverr! Upwork works in the same way. Understand that these platforms charge the freelancer money off the top of their earnings, so make sure to pay a fair wage for the work they'll be doing. 

Referrals

A referral is my favorite way to find contractors. I ask my network if they know anyone offering the services I’m looking for. If they do, I ask for a virtual introduction and wait to see what the contractor says.

I love this method of searching for freelancers because they were referred to me by people I trust. They aren’t random people like I might find in Facebook groups. I can ask my business friend about their work and pricing privately before indicating interest in connecting. Hands down, referrals are the best way to find both clients and freelancers for your business. 

Interviewing

Now that you have a few applicants you’re interested in learning more about, you need to interview them. This is the next step to narrowing it down to ultimately finding your new employee. I suggest interviewing via video so you can see their face and body language. That can tell you a lot about a person.

Interview Questions

Make a list of questions that are important to you. Hopefully, by this point, you know they’re qualified for the job. The goal of the interview is to find out more about them and if you would work well together. Here are a few common interview questions to consider:

• How do you prefer to communicate?

• What are your typical working hours?

• Tell me about your current workload and what you feel comfortable taking on.

• Explain a time when you had a disagreement with a client and how you worked through it.

• What makes you excited about this role?

• What do you feel are some of your biggest strengths? What would you love learning more about? 

These questions focus more on who the person is rather than their qualifications. Your online application should cover their qualifications and portfolio so you could make sure right off the bat that they can provide the level of deliverables you're asking for. Of course, you can always ask follow-up questions if there was something you were confused about or felt you needed to know more about. 

Personality

You can tell a good amount about a person when you talk to them. Are they easy to talk to? Do they smile and engage with you? How do they present themselves and talk about themselves and their work? These are all things to look out for when interviewing a potential worker.

Some people are nervous interviewers, but it's usually not too difficult to tell nerves from someone who is disingenuous. You need someone who will fit well with your working style and be comfortable talking to you on a person-to-person basis. After all, we're all people first. 

Contract

Once you find a great match, send them a contract to sign. You should always have a contract in place with contractors. Contracts protect both you and the contractor in the case of disagreements. It lays out specific expectations so everyone is on the same page. Make sure to include these components in your contract:

• Payments

• Term of the contract

• Confidentiality expectations

• Deliverables from the contractor

I suggest hiring a lawyer or purchasing a template from a lawyer to ensure legality. Destination Legal is a great place to find contract templates for small businesses.

Hiring your first contractor is exciting, but it does take thought and effort to make it happen. You probably don't want to hire the first person you find. Take time to find several applicants in Facebook groups, on Fiverr or Upwork, or through referrals. Interview your favorite candidates and learn more about who they are and what they can bring to the table to support your business.

Take time to consider how you could help them grow, too. After all, every relationship is a two way street! They're helping you, but as a leader, you should also be able to figure out ways to help them develop professionally.

When you find your perfect match, send them a contract to sign that outlines the working relationship. You’ll both be covered in case of disagreements. Be patient, and your perfect match will come along soon enough!

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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