Let's Talk

We offer a variety of personalized bookkeeping and accounting services.  Choose an option that is right for you.

Copyright 2025 Reconciled Solutions

What to know before hiring a freelancer

What to know before hiring a freelancer

Are you one of the businesses that desperately needs additional staff, but the search for full-time employees has been fruitless? It might be time to get creative with who is responsible for which tasks in your business. Just because the ideal candidate for your full-time position with a detailed skillset is not showing up in your inbox does not mean you cannot re-swizzle some job responsibilities. Keep reading to find out why you should consider hiring a freelancer and how to do it the right way.

The Great Resignation continues during these dog days of winter, with many businesses of all shapes and sizes trying to fill open jobs. The freelance workforce has certainly been gaining in popularity. By the numbers, the freelance platform Upwork reports that 20% of current employees (that’s 10 million people in the USA – holy cow!) are considering doing freelance work right now. Reasons to go freelance have certainly been heightened by the pandemic:

  • More flexibility in scheduling work shifts and hours around other life commitments  
  • The golden rule in real estate extends to businesses looking for onsite employees: location matters! The work location of choice these days is one’s home or even a vacation destination…a little bit of work, a little bit of play…

Consider who you already know

Think about all of the talented people you already know in your network. Can you transfer certain low-gain job responsibilities to a freelancer or contractor? This will allow you to keep your higher-skill jobs for your most skilled workers, thereby supporting better time utilization. 

Here are some folks to consider when getting your arms around how freelancers could potentially support your business: 

Interns

Students looking for work can be an excellent source of very cheap and talented labor in industry-specific niches.

Teens and college students

They grew up with technology at their fingertips. Perhaps there is a teen or college student in your life who could help you get your tech stack humming!

Retirees

Talk about a lifetime of knowledge!  One thing I know about retirees is they are accustomed to face-to-face communication, not the techy ways younger generations do it now. That said, what small biz owner doesn’t need a few scripts written for how to communicate in certain sticky situations? Wouldn’t it be great if you could use that wealth of communication knowledge to help you with client relationship scripts and documenting workflows and processes?

Executive Assistants

What an under-utilized position for small business owners trying to live a sustainable lifestyle at both work and home!  An Executive Assistant is like a virtual assistant on steroids, in such a good way. They help you plan your time and wag their no-no finger at you when you are committing yourself in too many different directions. Look no further than a stay-at-home parent to find a wonderful Executive Assistant who has already honed their skills of simultaneously making lunch, supervising play, and household management.

Specialists for special jobs

These are people with specific skill sets that can be hired in small quantities, like bookkeepers, web designers, grant writers, and e-commerce videos. There are some great sites available to find these specialists, such as Fiverr, Upwork, and Guru.

Technology

So many great apps, so little time. Is there an app that you could set up to do a job in your business that is more manual now, thus you would not need a person to do that job? In the past couple of years, we started fully utilizing proposal software, which has cut down on both errors in language as well as time spent writing contracts.  Another great example is automating your marketing funnels in Active Campaign or other software.  A third great example of tech that can be used to replace a manual job might be found in Project Management software like Monday, Asana or Trello.   

Make sure your freelancers are in compliance

We have some ideas flowing about what subcontractors and freelancers can handle in your biz to free up time. Now, let’s talk about making sure the freelancers are in compliance with work guidelines. The IRS has some specific requirements for utilizing subcontractors in your business. You want to be aware of these things so that they do not give the impression of being an employee in your business.

As a business owner, you are responsible for paying payroll withholding taxes on behalf of your employees, but not your contractors. Here are some things that you can do so the freelancer does not act as an employee in your business:   

Freelancers send you (their client) a bill for their work.

It is important that your freelancer treats you like a client and sends you a bill for work performed. Usually, a freelancer also has more than one client. Your business is not their only client, so hopefully, they are sending out bills to other clients, too.

Freelancers come to the job with skills already in hand.

You are certainly able to train a freelancer on the nuances of the way you complete work in your company, but they should already have the majority of skills that you need.  For example, if I hire a freelancer to build a Powerpoint presentation for me, I would expect them to know Powerpoint in advance of accepting the job.

Freelancers generally have their own insurance policies and their own equipment.

In professional services, this can be a bit of a problem when it comes to technology. I would buy a computer and set it up with my company’s security protocols if the worker were an employee in my company. If I hire a freelancer, I would expect that the freelancer would be using their own computer and the computer would be installed with its own safety and security protocols to prevent hackers and online theft. This is important as online ransom and other attacks are growing at unprecedented rates. One must fully vet any freelancer that they are considering hiring. Since you don’t get to choose the computer and the security on the freelancer’s machine, this opens you up to more risk. It also assumes that the freelancer you chose had the money and the wherewithal to purchase a device that meets or exceeds job requirements.

Freelancers typically get paid by the job; paying them is a transactional affair.

We negotiate a rate for a job and the freelancer can accept or negotiate that rate, but they don’t usually get any type of incentive pay or bonus added onto their pay.

Freelancers typically set their own schedules and work when they want to work.

You can certainly give them a deadline so you’re on the same page with on-time deliverables, but if your employees work standard business hours and the freelancer wants to work in the middle of the night, they have every right to do so.

Freelancers do not get paid overtime or any sort of workers compensation.

Freelancers are not employees. This means that freelancers, for the most part, do not participate in any employer-sponsored benefits plans like health insurance or retirement funds. When a freelancer is used, no payroll taxes are paid on their behalf by the company. 

How to best utilize freelance services

If hiring a freelancer in your biz is still sounding doable at this point, I would like to offer a few final suggestions for best practices in HOW to utilize the services of a freelancer: 

Hire freelancers for jobs and tasks that are well-defined.

Leaving things too “open-ended” leaves too much to chance and likely results in poor completions. You know what they say about pointing fingers…every time you point a finger in scorn, there are three fingers pointing right back at you. If you have an important job for a freelancer, be specific.

Establish good communication with your freelancer.

Train your freelancer on how to best communicate with your team, clients, vendors, and associates. Allow them access to those communication portals that are in use. If they will be a regular freelancer inside your organization, consider giving them a company email so that they look fully professional.

Track your freelancer’s work.

Stay on the same page using a practice management system or regular and consistent meetings with your freelancer. This allows you to check their progress. Then, if work is getting off-track, you can get back on path before anybody gets angry.

Remember that if hiring freelancers is going to become a regular process in your business, you must treat them well.

Negotiate fair work for fair rates. Be clear about when and how often you will pay your freelancers for work completed. Include them in company communication efforts to keep all team members on the same page. It is important to remember that this is a community. If you treat one freelancer poorly, word will travel fast. It could result in you not being an employer of choice for the community.   

It is said that when one door closes, another opens. Many of us find ourselves in a position where the pandemic has limited the talent pool of prospective employees. Perhaps it is time to re-think things and find another way to deal with this Great Resignation period.  Freelancers might be a great option in running a lean, mean efficient business.

Avatar photo
Angie Noll
angien@reconciledsolutions.net

Angie Noll is the founder of Reconciled Solutions, a Chicago-based bookkeeping and profit advisory firm she started in 2006. She is a Certified Profit First Advisor at the Designer level, a Certified Fix This Next Advisor, and a QuickBooks Online ProAdvisor. Angie works with service-based businesses — managed IT providers, Direct Primary Care and concierge physicians, law firms, and mental health practices — helping owners understand what their numbers actually mean and build businesses that pay them well. She holds an MBA, is a Forbes Business Council contributor, a graduate of Goldman Sachs 10,000 Small Businesses, and immediate past president of NAWBO Chicago.