Team Management

How to Make Independent Contractors Feel Like Part of the Team

Deanna deBara Freelance writer and journalist 
How to Make Independent Contractors Feel Like Part of the Team - Gusto

There are a huge variety of business models that rely on independent contractors. For example, the creative talent that develops campaigns for ad agencies (like copywriters, graphic designers, and art directors) are often freelance. The construction workers who bring properties to life (like electricians, painters, and bricklayers) don’t typically work full-time for a single construction company; instead, they work as independent contractors on a variety of projects. And many small businesses don’t handle their books in-house—instead, they hire an accountant as an independent contractor to keep their finances in check.

If you work with independent contractors in your business, you know their time, work, and efforts can play an integral part in the success of your company. But there are a ton of business owners out there who just don’t know how to manage contractors effectively.

They never fully integrate them into their business, take the time to onboard them properly, or instruct the rest of their team on how to work with contractors. And, as a result, the contractor never feels empowered to settle into the team and do their best work—and both the contractor and the business can suffer.

If you want to inspire the best work from your independent contractors, they need to feel like a part of your team. But how, exactly, do you make them feel welcome, appreciated, and integrated into your company?

Let’s take a dive into how to manage contractors in a way that integrates them into your business and makes them feel like an indispensable part of your team.

Why integrating contractors is better for your business

Before we jump into best practices on how to manage contractors, let’s quickly cover why effective contractor management is so important.

There are a few reasons why integrating contractors—instead of treating them like an independent or separate entity—is better for your business:

  • It creates a cohesive team experience. In order to produce their best work, your team needs to work like a well-oiled machine. But creating a sense of separation between your employees and your contractors can make it hard for them to work together in a cohesive way—and your business suffers as a result.
  • It can help you retain top talent… If an independent contractor feels like they’re not being treated with respect or are looked at as an “outsider” in your company, they may quickly move on to other projects. Integrating contractors into your team will help to ensure they stay through the length of the project and are willing to work with you in the future—which can help you keep high-quality talent on your roster.
  • …and attract top talent. When it comes to attracting top talent—whether that’s full-time or contract-based—your reputation is everything. If you get a reputation as a company that embraces independent contractors as part of the team, more independent contractors will want to work with you—and you’ll get access to more talent when you need to hire a contractor for a project.
  • It helps you get to know your independent contractor better—which can inspire better work. The more you integrate your contractor into your team, the better you’ll get to know where they shine (and where they struggle). This can help you tailor your projects to play on the contractor’s strengths—and get better work as a result.

Now, keep in mind that while integrating your independent contractor into your team is important, it’s just as important to recognize what being an independent contractor actually is—and respect those boundaries accordingly. Otherwise, you could find yourself dealing with classification issues (more on that later). 

Best practices for integrating contractors

Clearly, putting in the time and effort to integrate contractors is a solid move for your business. But what are the best ways to manage the integration process—and ensure your independent contractors feel like a full-fledged part of the team?

Set them up for success from day one

When you hire a new employee, you make sure you set them up for success from the beginning by putting them through a thorough onboarding process. You introduce them to the business, walk them through any relevant procedures and policies, and invest in any training they’ll need to hit the ground running and thrive in their new role.

But for whatever reason, a lot of companies don’t invest that same kind of energy into onboarding independent contractors. They tell them about the project they’re being hired for, let them know when they expect deliverables, and send them on their way. 

You want your independent contractors to be successful during their time with your company—and in order for them to be successful, they need context, which means they need to be properly onboarded.

Now, you don’t have to invest the same kind of time, energy, and money into onboarding a contractor who is going to be working for your company for two weeks as you would a new full-time employee. But even if an independent contractor is only going to be working with you for a short time, you still need to spend time getting them acclimated to your processes and systems, answering any questions, and getting them up-to-speed with any training they’ll need to get the job done.

Pair them with a full-time employee to help them settle into their role and the team

One of the most important parts of integrating contractors is making sure they feel like a part of the team. And the best way to do that? Pairing them with someone that’s already an established part of the team.

Having a full-time employee work with an independent contractor, introduce them to the rest of the team, and make sure they’re settling into their role can go a long way in helping contractors feel a part of the day-to-day operations at your company—and it also has the added benefit of taking the responsibility of integrating the contractor off your shoulders.

The key to success with this strategy is to make sure you choose the right employee to help your independent contractor establish themselves within the team. Ideally, you’ll choose an employee that takes a mentorship role with more junior team members, is friendly and welcoming, and is working on the same team or project as the independent contractor (so they can show them the ropes, introduce them to other key team members on the project, and make themselves available to answer any questions). 

Offer benefits

One of the perks of being an independent contractor is it offers more flexibility; when you work on a contract basis, you have the opportunity to work on a variety of projects with a variety of clients.

But one of the downsides of all that flexibility is that, generally, none of those clients are going to offer the kind of health care benefits they offer to their employees—even if the contractor is working on a long-term contract.

Paying for health insurance can be a huge cost (and hassle) to independent contractors. So, if you really want to make independent contractors feel like part of the team, you might want to consider extending your employee benefits.

While independent contractors aren’t allowed to receive tax-free benefits from their clients, many health plans do allow companies to add independent contractors to their health insurance, with either the business or the contractor paying the premiums (if your business pays the premiums, the contractor may need to pay taxes on the premium costs).

But because group health insurance plans often have lower premiums than many of the independent plans freelancers have access to on the marketplace, extending your company’s health benefits to your independent contractors could help them save on insurance costs—even if they pay the premiums themselves.

If you’re thinking about extending your employee health insurance to your independent contractors, talk to your insurance provider to see what your options are—and then walk through those options with your contractor to see if receiving health benefits through your company is the right fit for them.

Treat them the same way you treat your employees…

The best way you can make independent contractors feel like a part of the team is by… treating them like they’re part of the team.

If your company offers perks to employees—like catered lunches or access to a fitness platform for at-home workouts—offer those same perks to your contractors. If you host a company-wide event, extend the invitation to your contractors. If you’re getting your employees together for a Zoom call to discuss the progress of your project, make sure the contractor is in the loop and gets to present their contributions along with the rest of the team.

It sounds obvious, but the more you treat your contractors like a part of the team, the more they’ll feel like a part of the team—and the better they’ll integrate into your organization.

…unless it would lead to classification issues

You want to treat your contractors like the rest of your employees—but it’s important to understand the legal differences between W-2 employees and 1099 contractors (and respect those differences) to avoid classification issues.

For example, independent contractors have more flexibility in when, how, and where they work—while you can require your full-time employees to work in the office at specific times. As a business owner, you’re responsible for withholding taxes from your employee’s paychecks—but independent contractors pay their own taxes.

You want to make your independent contractors feel like a part of your team—but make sure you’re respecting the legal distinctions between contractor and employee.

Create a better experience for your independent contractors—and watch your business thrive as a result

The more your independent contractors feel like a part of the team, the better their experience will be at your company—and the better work they’ll do while they work for you. So get out there, create a positive experience for your contractors, and watch your business thrive as a result!

Updated: November 25, 2020

Deanna deBara
Deanna deBara Deanna deBara is a freelance writer and journalist based in Portland, Oregon.

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