Tips for Hiring and Managing Freelancers for Your Firm or Business

Gusto Editors

In today’s ever-evolving business landscape, having a pool of expert freelancers you can draw from is invaluable. So how do you go about successfully hiring and managing freelancers?

Gusto is committed to helping you achieve sustainable success, tackle challenges as they arise, and stay ahead of the curve. So we’re thrilled to share expert advice on working with freelancers with our partners at CPA Academy.

The webinar “How to Stop Turning Away Work by Hiring Freelance Accountants” featured Jeff Phillips, co-founder of Accountingfly. You can check out the full webinar here. Jeff unpacked the trend towards a freelance economy and laid out important strategies for successfully working with freelancers. In this article, we’re offering you valuable details from the second section of the webinar.

Jeff is passionate about helping businesses thrive through leveraging a freelance workforce, which makes him the perfect person to lead this discussion about hiring freelance workers for your firm. Let’s get started!

The case for freelance remote workers

What is freelancing? Do you picture a remote freelancer as a lazy millennial on a beach slacking off and avoiding responsibility? Jeff clarified these common misconceptions by explaining that the typical freelance accountant is an expert with years of specialized training in traditional settings. 

Even more compelling, the rising demand for freelance jobs will undoubtedly change the hiring landscape. The freelance labor force is growing by 8%, while the traditional workforce is growing by only 2.5%. A full 30% of the workforce identifies as freelance experts and will not take a traditional job.

Jeff asserted that companies who don’t meet this change head-on are likely to be left behind by their competitors. Since it’s not a matter of if you’ll need to work with freelancers, but when, there’s no time like today to develop your strategy. Jeff masterfully walked us through the process.

Classifying employment terms — 1099 or W-2?

The first thing you’ll need to determine when hiring a freelance accountant is how to classify their employment. You’ll need to have a good understanding of what constitutes an independent contractor, which you can review at the IRS website

In general, an independent contractor will:

  • Decide how they will complete a project (such as their strategy, materials, software, etc.)
  • Determine their own hours
  • Work using their own equipment, from wherever they choose
  • Be paid per project or on a short-term basis
  • Pay their own taxes
  • Be responsible for their own health insurance and other benefits typically given to full-time employees

In addition, laws determining who can be hired with a 1099 form vary from state to state. California is one example in which you’ll find the laws leaning towards hiring an employee with a W-2 form. Of course, hiring someone this way will cost you more money, but it’s essential that you pay your due diligence and follow all laws within your state. You may also wish to consult an attorney if anything is unclear.

Tips Hiring Managing Freelancers

What to look for in remote candidates

Jeff highlighted the importance of hiring freelancers who have worked remotely before and who are experienced in the type of project they’ll be working on. Because there is no “honeymoon period” that you’d expect to see with a new full-time hire, a contractor will need to produce good work right off the bat.

“We should see multiple listings of projects that look just like the project you need done on their resume for you to be comfortable with them, but typically what you’re getting is somebody who doesn’t have to be trained in your software. They have to be trained maybe in the context of your project, but they’ve done this kind of thing before, and they could probably teach you how to get the work done.”

Jeff Phillips

Not only should you ask the candidate to walk you through the projects they’ve done, but you should also find out how they tend to work remotely. Ask them how they’ve communicated with their project managers in the past and what type of software or platforms they’ve used, such as specific accounting software, Zoom, and Slack.

In addition to vetting candidates for experience, you’ll also want to do a solid background check. You’re probably not meeting the recruit in person, and you want to make sure they’re who they say they are. Confirm  employment history and verified projects. GoodHire provides comprehensive and cost-effective background checks. 

Building a talent pool — the long game and the short game

According to Jeff, 70% of millennials aspire to work for themselves. But that doesn’t mean 70% are already doing so. To get ahead of this trend, it’s important to think of both the short term and long term when building a freelance talent pool. 

It’s always easiest to start with who you know. Look first to alumni and retirees of your firm. While newer businesses may need to focus on building out those contacts, established firms should have a solid pool to start with. Either way, consider everyone who works for you as a potential future freelancer. Know their value and stay in touch with them. 

You’ll also want to find ways to quickly get in touch with your pool during busy periods. Whatever your ATS (Applicant Tracking System) is—whether it’s a software program, email, or even your cell phone—make sure it’s streamlined. The goal is to have a system in which you can get the word out easily and get quick responses from available freelancers as projects arise.

In the short term, turn to freelance recruitment sites such as Accountingfly and Upwork. You’ll have access to a wide variety of talent, and these agencies will handle onboarding and payments, among other things. Finally, you can simply post an ad on Indeed or Craigslist; however, keep in mind that you’ll need to properly vet these candidates to ensure their credibility.    

Treat contractors like clients — collaboration is key

One of Jeff’s most insightful ideas was his take on the employee contractor relationship:

“The overarching philosophy here I want you to think about with hiring and managing is you want them to come work for you again. So you treat them like a client, not really a hire because the good ones are worth their weight in gold.”

Jeff Phillips

Jeff’s take on working with freelancers is undoubtedly progressive. He advocates for a collaborative approach between contractors and employers that reflects changing dynamics in the workforce. Having a freelancer with expertise, whom you trust and know can perform well, is incredibly valuable.

“Let’s say you’re a tax firm, and you need a reviewer who knows ProSystem FX and knows the exact type of clients you work with, and they are at a rate you agree with. They’re going to do a great job for you, and you’re going to want them back next February.”

Jeff Phillips
Tips Hiring Managing Freelancers

Establishing trust with your freelance accountant starts with onboarding. Jeff advises making this process easy and stress-free, using Gusto’s onboarding tools. Having a new hire start on a Friday is also an excellent idea, as it relieves stress for everyone involved and allows both parties to focus on making a positive impression. 

Once you’ve hired a contractor, be sure to make them feel like one of the team. Encourage full-time staff to build relationships with them, gift them with any team swag, and incorporate them into your culture. And very importantly, pay them on time. Unfortunately, many businesses are in the habit of delaying payments to freelancers. This is a great way to drive away talented people who have many other options for freelance jobs.

Managing a remote freelance workforce

Working with freelance accountants brings a host of unique challenges. Jeff explained that managing a remote workforce requires a different management approach.

“Like hiring any remote staff, it’s important when you’re thinking about managing the hires, you’re going to be managing by objective. … Managing by objective answers three questions, who is doing what by when, and all of that is organized by project inside your company and when you go remote, … it really becomes more about the results, the output, the production and that’s management by objective, who does what by when.”

Jeff Phillips

A freelancer is there to work on a specific project, usually for a short period of time. In order to accomplish objectives smoothly and efficiently, you’ll need to err on the side of over-communicating. Be very clear about what the project requires, what the expectations are, and what resources the freelancer will need to accomplish them. Establish right away how you’ll communicate and when. Accounting software such as Karbon, Jetpack Workflow, and XPM are great for project management. Weekly check-ins are also useful.

Finally, you’ll want to keep privacy and security in mind when working with a freelancer. Use your company email in case you need to cut off access to sensitive data if there is an emergency, the freelancer leaves, or you need to fire them. You can strengthen security even more if you’re able to send them designated equipment, such as a laptop, that they only use for work purposes. Jeff acknowledged that this may not always be possible due to logistics.

Learn more about successfully working with freelancers 

If you’re not working with expert freelancers, you may be losing top talent to competitors. Freelance experts can fill critical roles in your firm and help it run more efficiently. It’s an exciting time for everyone involved!

As with all changes, you’ll need to be smart about how you adapt. Plan for the future by viewing all employees as potential future freelancers. Focus on building trust with contractors, and make them feel warm and welcome on your team. You’ll need to make changes in the way you recruit, onboard, and manage them, but it will be so worth it in the end.

If you want to learn more about setting up your business for remote work, make sure to check out the full webinar here. And if you haven’t already, check out Part One of the webinar “How to Stop Turning Away Work by Hiring Freelance Accountants” for invaluable information about the exciting shifts towards a freelance economy. 

You can read more tips about running your business on the hiring and growth and team management sections of our blog.

Gusto Editors Gusto Editors, contributing authors on Gusto, provide actionable tips and expert advice on HR and payroll for successful business management.
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