5 Questions to Ask Before Hiring an Independent Contractor

Thinking of hiring an independent contractor or freelancer? Ask these 5 questions.

As a small business owner, you will inevitably wear many hats. In addition to making the major business decisions, you're also responsible for the marketing, branding, finance, and administrative duties.

But sometimes, doing "all the things" does more damage than good. Not only does it pull you away from focusing your time on the things that matter most (such as connecting with your customers or spending time with loved ones), but eventually, it starts to take a toll on your mental health!

Outsourcing work to an independent contractor is a solution to help you reach your small business goals without taking away from your precious time to do other things in your business or personal life. However, doing so isn't something to take lightly. Bringing an outsider in to take over the most important functions can quickly spell disaster if not done correctly.

Here are 5 questions to ask before hiring an independent contractor for your small business:

1. Do I need an independent contractor or employee?

First and foremost, it's essential to talk about and understand the difference between an independent contractor and an employee. In a nutshell:

An employee works under an employer's direction and control in exchange for compensation or a salary. The employer determines the hours, the pay, where the work is done, and how work is performed.

On the other hand, a 1099 independent contractor runs their own business and provides services under a contract for those services. They generally set their hours, their rates, work off-site (usually remotely), and the terms for how they perform the contracted work.

Hiring an independent contractor can mean significant pros and cons for you as a small business:

Pros:

  • It will typically cost you less than hiring a full-time, salaried employee after considering that you don't have to pay for their insurance, taxes, benefits, and office equipment or provide them office space.

  • There's more flexibility across duties versus hiring specific employees for specific roles.

  • You will spend less time and money on training since they are already specialists in their field.

Cons:

  • You have less control over how and when they do their work.

  • They do not work exclusively for your business (which means they can potentially work for one of your competitors).

  • There is a higher level of turnover.

  • Unless your contract specifies otherwise, you may not have full ownership of the deliverables they provide you.

  • You have to trust that they will keep your sensitive information private.

If, after assessing your needs, you find that the cons outweigh the pros, you may consider hiring an employee instead.


Being clear about the roles and expectations on both ends leads to much higher job satisfaction and less unexpected turnover.


2. What am I trying to accomplish by hiring them?

Before hiring an independent contractor, take some time to think about what your goals are and how hiring an independent contractor will help you accomplish those goals. Here are a few questions to think about:

  • What duties will they be responsible for each day?

  • How often do you expect to communicate with them about the project(s)?

  • How long will you need their services?

  • What metrics will you have in place to measure job completion?

Being clear about the roles and expectations on both ends leads to much higher job satisfaction and less unexpected turnover.

3. How well do they know me and my business?

Before starting with a contractor, you've got to do your homework!

Many independent contractors will initiate a discovery call, where they will ask a series of informational questions about you and your business to uncover whether or not they are a good fit for the solution. Additionally, some independent contractors may provide you with a clarity questionnaire instead of a call or opt to provide you with a questionnaire and a follow-up discovery call.

These calls and questionnaires should be prioritized, as they allow you to talk to them about your business, its mission and values, your needs, and your expectations. Be wary of independent contractors who do not take the time to learn more about you or your business, as it may be a sign that they will not be fully committed to your business's success or well-being!

However, the discovery call isn't just about them learning about you and your business needs! It's also an opportunity for you to learn about them and how they have helped others. This leads me to the next question you should ask before hiring an independent contractor:

4. How well do I know them?

Although a discovery call allows the independent contractor to assess whether their services can help you reach your goals, it also enables you to decide whether the two of you will work well together!

Often, a business or entrepreneur will choose a contractor because they seem to have the most knowledge in their area of expertise. However, having more expertise doesn't necessarily mean that their personalities or working style will "mesh" well with yours!

During the first conversation, you want to ask them questions to learn about their work and communication style. You also want to ask questions to uncover whether or not their beliefs or values are aligned with yours and whether different beliefs and values could potentially be a problem for the business relationship.

You should also do a background check to ensure they have not had any significant problems or conflicts with prior clients. You also want to thoroughly research their skills and previous work and ask for a portfolio and several references if available.

5. Are contracts and paperwork in order?

Last but certainly not least, bringing on an independent contractor means paperwork. Here's some of the paperwork you'll need to complete before bringing on an independent contractor:

  • Contract: A signed contract is perhaps one of the most critical pieces of paperwork to have between you and your independent contractor. The contract will create a binding agreement between both parties regarding pay, the scope of work, expectations, and intellectual property rights.

  • W-9: Before paying an independent contractor, you'll need to collect their tax information in case the IRS requests it. A W-9 form is how you would ask for and store this information.

  • Non-disclosure agreement: A non-disclosure agreement prohibits the independent contractor from sharing your business information with a third party.


 

Hiring an independent contractor is a big step, but it can reap many benefits when done correctly. With the above five questions, you'll be on your way to finding an independent contractor who won't just help your small business thrive but help it continue to grow!

Ready to start outsourcing your small business marketing or branding? Let's chat!

 
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