How to work with freelancers: Benefits, challenges, tips

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Running a business may have been your life’s dream. Being your own boss, making the decisions, and seeing your vision come to life is exciting and satisfying to say the least. 

However, properly growing a company can be challenging no matter how solid your product or service is. Maybe you need help with setting up the framework of fledgling departments, creating social posts for a major campaign, or meeting an unexpected client need. You may ponder what to do next because you don’t need, or can’t afford, a part-time or full-time employee. 

No need to spread your team too thin! Hiring freelancers can be the perfect solution for short-term or long-term needs. 

Our guide digs into the advantages and challenges of using freelancers and gives you best practices to ensure the business-freelancer relationship is a win-win.

The benefits of working with freelancers

Here are four worthwhile ways that freelancers can scale up, strengthen, and upskill your operations: 

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They’re more cost-effective than hiring a full-time employee

We all know that when companies bring on employees, salary is only one part of the overall cost. There’s the benefits package, training costs, equipment costs, paid time off, and more. These expenditures can overload a small business that’s trying to grow, especially if you need multiple teammates.

On the other hand, freelancers are already trained on what you’re hiring them to do, so there’s less ramp-up time and no training costs. In addition, they’re independent contractors, so you don’t have to pay for benefits like you would full-time staff. Even if a freelancer’s compensation rate seems steep, when factored into the big picture, most of the time a freelancer saves the company money. You may also be able to negotiate pay structure, like a monthly retainer instead of a more expensive hourly rate.

You can tap into very specific skill sets

Upwork's Freelance Forward Economist Report estimates that 36% of the United States workforce was freelancing in 2021. Whatever area of expertise you need, there's probably a freelancer to do it!

Hiring freelancers gives your company the ability to get a high-quality, experienced professional to perform the project you need completed. Your project management tasks may require someone with specific knowledge about a process or topic. For example, let’s say you need a graphic designer who’s skilled in email content and well-versed in HTML (or your go-to email software).

This freelancer can increase the quality of your deliverable, or maybe your turnaround time, ensuring you impress your client, build a good reputation, and keep growing your business.

You’re able to cover seasonal, project-based, or temporary workload increases

Running a business can seem like feast or famine on a regular basis. Having too much business is never a bad thing. You just have to plan how to handle it all. Freelancers can fill holes in your team’s capacity, keeping them on task and progressing efficiently.

Freelancers can be your answer to unexpected projects dropped in your lap, a chance to work with a new client, and increased business from seasonal demands. By addressing upticks in business with freelancers, you can stay on top of project milestones and take advantage of opportunities to grow your business without working yourself or your current staff into the ground.

Manage your resources efficiently to keep yourself, your staff, and your freelancers focused and on track.

You can scale your business while keeping your risk low

Every decision you make comes with business risk. Hiring staff is a potentially risky endeavor each time. What if they can’t learn the job, misrepresent themselves during the interview process, or decide to leave in a few months after all that training?

Instead of hiring and onboarding traditional employees, hiring freelancers gives your business the fuel it needs to grow and thrive while keeping your risk low. If a freelancer doesn’t work out, your company hasn’t invested the time and money into them that would be required if you added a new employee.

The challenges of working with freelancers

While you can enjoy some unique benefits, using freelancers for your projects isn’t always sunshine and roses. 

Depending on freelancers to handle your projects and deliver them in a timely manner can come with headaches you might not experience with traditional employees. Here are four of the biggest potential downsides of hiring freelancers.

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There may be less loyalty and morale 

Being part of the company’s culture and contributing to its vision is compelling to many people. These ideals keep them feeling like motivated, engaged, and invested professionals, which can positively affect the quality of their work.

These feelings don’t usually translate to freelance gigs. While your freelancer may be professional, dependable, conscientious, and knowledgeable, they likely won’t have the same sense of loyalty or connection to the company or client as your full-time teammates. 

That’s alright, but make sure you still have freelancer appreciation and retention strategies in place. Simple thank you messages and detailed, positive feedback can go a long way toward building these relationships. This is especially key if you have a go-to, talented freelancer who you want to keep working with (instead of them taking other clients’ work). 

There’s a chance of being ghosted during a project 

Businesses generally have less insight into a freelancer’s background and work ethic than their staff. Full or part-time employees most likely won’t disappear from the office or virtual work environment one day. Freelancers might. 

If you get ghosted by a freelancer, it can leave you in the lurch and cause major workflow problems, missed deadlines, and very irritated clients or customers. The good news is that you can proactively take steps to prevent this issue, which we’ll discuss below.

There may be communication hurdles 

Freelancers may be doing remote work across the world in a different time zone. This distance might make it difficult to communicate your project needs in sync or meet sudden turnarounds. 

If communication breaks down, the freelancer might not return the work you wanted, and may even miss their deadline because they don’t understand the project. If you’re going to hire and work with freelancers, plan out processes that foster asynchronous and synchronous communication and accommodate delays.

Your company isn’t their sole priority

Running a freelance business typically means making a living without the benefit of a secure full-time job. While your full-time employees are most likely only working for your company, your project is just another freelance job to an independent contractor. Chances are good they have other clients and priorities in addition to yours, potentially even in a similar industry or sector. 

This situation may make them less inclined to enthusiastically jump on last-minute changes or rush jobs, and sometimes a slower response than you would get from full-time employees. 

6 best practices for working with freelancers

As we’ve touched on, managing the business-freelancer relationship takes a different approach than the traditional employee relationship. If you decide to use freelancers for your business, get the most out of it and avoid some drawbacks by using these best practices.

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1) Properly vet out freelancers before making your decision

Before hiring a freelancer, you’ve got to explore and evaluate their body of work, education/credentials, customer reviews (if they have them), and work terms in-depth before hiring them! 

This will help you avoid issues like low-quality work or more serious problems like plagiarism. You can save time by using a freelance website to find one that meets your needs and vet their profile. Some of the most popular sites are Fiverr, Upwork, WriterAccess, and FlexJobs. These allow you to join, view freelancer profiles, and reach out for an exploratory conversation.

You can also advertise on job boards and social media channels like LinkedIn if you want to vet the freelancers through your own process.

2) Clearly define goals and objectives prior to starting contracts

Make sure you have a clear-cut goal and plan to manage your freelancers and their deliverables so your team achieves that goal. 

Being upfront and transparent about your needs and expectations is one of the best ways to receive what you need from a freelancer. Whether you’re using one for graphic design, freelance writing, web development, copywriting, social media management, or another task, use clear language and lay out your expectations in writing. Encourage them to ask questions if they need clarification or assistance.

Now is also the time to introduce and confirm the tools you’ll use to manage the relationship. Mention any messaging, conferencing, and time-tracking apps they’ll need access to.

Finally, agree to a price, payment and invoicing terms, and get everything in writing and signed by all relevant parties.

3) Always provide relevant resources to your freelancers

Don’t expect the freelancer to automatically know what you want from them. The more time and energy you invest in providing the instructions, insights, and materials they need to do the job, the more thorough, complete, and high-quality the resulting freelance work will be.

Share information on your company and brand, examples of other companies and projects you admire, and specific instructions about the project. Reiterate any milestones or deadlines you expect them to meet. Add in any other project information they’ll need during their work.

Give them the contact information for other teammates they’ll need to tap to complete their projects. That way, there isn’t downtime if the freelancer has questions. Arming them with everything they need on the front end decreases the chances of them turning in low-quality work or missing deadlines down the road.

4) Encourage open lines of communication with your freelancers

Even though freelancers aren’t employees, you shouldn’t expect them to function in a silo. Share multiple ways for them to reach their points of contacts. Email, phone, instant chat, and video conferencing tools are all acceptable ways of communicating with freelancers. 

Another benefit to this is that they’ll feel closer to the overall project and can easily reach a contact with questions or advice if they get stuck or have an idea. If they reach out, make sure they get a prompt, thoughtful response that helps them progress with their work.

5) Treat freelancers the same way as full-time employees

Just like you would with your in-house team members, be respectful of a freelancer’s time, respond promptly to their communication, and maintain a professional demeanor when dealing with them. You may be interacting with your freelancers every day or during crunch times when stresses are high. Keeping the relationship friendly makes for pleasant interactions, and is just an all-around smart business practice.

6) Always pay your freelancers on time

Money talks, folks. Freelancers are usually self-employed people trying to make a living. Don’t hold up payment or make them wait longer than agreed on. 

Once the work has been completed and approved, or however the terms were laid out in your freelance agreement or site terms, submit full payment for their services. Paying on time builds loyalty and, if they have to choose between a project from a client who’s slow to pay or your team, guess who they’ll pick to work with?

Create better workflows for freelancers with Teamwork

If you’re trying to scale your business effectively but want to keep your budget in line and your risk low, consider hiring freelancers for regular projects and workload spikes. Yes, there are challenges to managing freelancers, but you can minimize them by properly vetting candidates, setting clear expectations, and providing the resources they need to deliver a quality project (whether it’s a quick chat or brand guidelines.)

Do you need a way to simplify communication with your freelancers and keep them on track across different tasks, projects, or clients? Trust Teamwork to provide seamless communication channels and powerful project management tools for your business: See it for yourself with a free trial.

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