How to Hire Your First Contractor

hiring a 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!