Hiring Freelancers For Your Business: Job Postings, Interview Questions, and the Onboarding Checklist

If you are looking to hire some outside help, I’d start with hiring part-time freelancers who work on an as-needed basis. They will bring the specialized skills you need to the team. You won’t have to set up infrastructure, like payroll, benefits packages, and their own place to work. Freelancers or contract workers usually work remotely.

The best place to start is by creating a job post that you can add to your website under your “Work with Us” page. You can also use websites like Upwork, Freelancer, or Indeed. You can even jump on Facebook and search groups for what it is you’re hiring. Many groups will allow you to post that you are looking for work. This is a great way to connect and get some resumes as well!

Over the past few decades, I have created forms to post a job, take applicants, and a checklist to ensure the onboarding process goes smoothly.

If you use these forms, you can save a ton of time tracking down this information as you go, and it creates four checkpoints when hiring someone. If you don’t use these forms, you can get bogged down with collecting information you need for taxes, security, and getting them onboarded quickly and efficiently.

Here are the four checkpoints to working with another person:

  • Job posting
  • Job application
  • New contractor information
  • New hire onboarding checklist

Job posting

In your job posting, be sure to elaborate on the culture and work processes of your company, role responsibilities and details, preferred and required qualifications, and application instructions.

Reviewing applications

When reviewing resumes and applications, find your top 3-5 candidates, and set up interviews. I separated my applications into two piles. Nos and maybes for the first round. Then, of the Maybes, I’ll find the top 3-5 for interviews. These are all based upon a curve of who applies, so pick your favorite candidate based on the application/resume, but don’t rank them in stone until after you conduct an interview to know more about them.

Interview questions

I’ll be honest with you. I don’t really have interview questions that I work from, but I do have a kickoff question and a closing statement that facilitates interviews well. Because I’m a person that thinks of himself as intuitive, I like to conduct my interviews either in person or over video. I try to stay away from email interviews or even phone interviews because I don’t get enough non-verbal cues as I like to have when I interview someone in person.

Next, I have a list of questions that you can pick and choose from to get your interviews up and running.

Make sure you take care of them from here on out. “Did you find the place okay?” If not, remember that for the next person, you can offer a few tips to make finding the place easier. “Would you like some water?” The more you serve them, from this point on, the better the chance of them taking care of your company.

Start by telling them a bit about the business. Show them anything you can that helps them get a picture of what we do, the quality of work, and even meet some of the others in leadership.

After that, I turn it to them by saying, “So tell me a bit about you.” Try and really get to know them. See what their underlying motivations are. If they talk about working with a team, and being creative, cool. If they ask questions about “how many hours can I get?” then you might have a problem. They are looking for a paycheck and it’s not about generating results. Ask them about their career goals and see if that aligns with the job posting at all.

If you are hiring someone that is going to be a social media manager for you, but when you ask them about their goals, talking about traveling around the world as a dancer might not be the consistent personality you need in this role.

According to Society for Human Resource Management, it costs an average of $4,129 per hire and over 42 days to fill a position. Now, I know that is for employees and not contractor labor, but even if it is half that, it is substantial money and effort to start to clone yourself.

You don’t have to start with anyone but 5 hours a week will go really far in reclaiming your time and effort back to what your business needs most.

Some of the first rolls I replaced for me, were ones that took a lot of my time but didn’t yield expert-needed results. Finding an admin assistant or virtual assistant is a great first hire. You can delegate tasks like travel, appointment settings, and email logistics to them, as well as posting them on your behalf to social media. They can also serve as your editor, as needed.

Interview questions examples

Check out this article from The Muse, here are 50 interview questions that you can use to learn more about your interviewee. I’d only pick 5-10 of these questions, and I recommend that you know what questions you want to ask before the interview session.

Hiring a new team member

Having cash flow to pay for this new hire is key to maintaining your investment. You should plan to have at least three months of savings allocated to pay that person if you were to run into an income dry spell.

If they have access to sensitive data or are customer-facing, and do more than just behind the scenes work for me, I will also have them fill out a contractor information form, so if I ever need to track them down, (god help me) I can. Lastly, I provide my new hire with an onboarding checklist to get them comfortable working within our ecosystem of SOPs and softwares.

Download a copy of our free team marketing worksheets here. Want to learn even more? Check out our book and video course, Unify Your Marketing.