Want to Work Better With Your Freelancers? Here are 9 Things They Wish You Knew

Once upon a time, I worked as a freelancer. It was enlightening, thrilling at times, but also extremely tough.

And it wasn't until later on in my career that I realized just how much marketers depend on contractors. Freelance designers, web developers, copywriters, video editors, SEO specialists, PR consultants, or translators -- all of these folks play a vital role on the extended team of many marketers.

Trouble is, coordinating effective communication between teams can be tough. I know this from experience. So to help you establish a more productive working relationship with your contractors, I put together a list of things I always wished my customers knew about freelancing. Check it out below.

9 Things Your Freelancers Want You to Know

1) “You’re paying for more than just the service in question.”

Freelancers are a one-person show, and as a result, they have to do much of the same work as a small business owner. When I was a freelancer, I was amazed at how much time I had to spend on invoicing and collections.

Many freelancers, especially those in creative fields, deplore such mind-numbing tasks as calculating invoice amounts and calling up customers to check on payment status. They might even find it demeaning.

Pro Tip: Process payments as quickly as you possibly can. Stay on top of accounts payable and make sure your company expedites payments to your freelancers right after the work has been delivered.

Paying freelancers on time is very different from paying larger vendors. Your on-time payment can mean your freelancer’s ability to pay his or her rent on time. This is often one of the simplest things you can do that makes the biggest difference for freelancers.

2) “I’d love a steady stream of work from you.”

Freelancers have the luxury of choosing their own hours and their own projects, but when it comes down to it, they would usually prefer to avoid the notorious “peaks and valleys” that come along with contract work.

Often, the best clients will work out longer-term, recurring arrangements with freelancers. This approach helps smooth out bumps in income, but also enables you to secure your contractors’ availability if you’re dependent on them. This can also help raise your status as a priority client.

Pro Tip: Consider offering your freelancers a fixed monthly retainer if you like their work and plan to keep sending projects their way. Include a set amount of work in the monthly retainer, and get their rates for any work that falls outside of it, so they can bill you the extra as needed. Many will allow you to carry hours or work over to another month if you don’t use it all in a given month.

3) “Err on the side of providing me with more information.”

As a freelancer, my favorite customers were always the ones who gave me plenty of background information and context about a given project. The more I understood about their goals, the better I could think creatively to deliver what they needed. In some cases, this actually helped them to accomplish their goals and stay on budget while enabling me to earn more and obtain repeat business.

For example, as a freelance translator, I once had a client with a unique need: They had customer emails that they needed translated and delivered back within an hour. As a translator, I was normally paid by the word, but I knew that in this case, they had given me the context of why they needed this service, and made it clear that what they valued was speed. So, I proposed that instead of paying me by the word along with a rush fee for fast turn-around, which is typical, that they pay me a consistent monthly retainer, for which I would agree to be “on call” to translate emails during certain business hours, so long as they didn’t exceed a certain volume. 

Pro Tip: Don’t just rely on written text. Schedule a video or voice call to convey more details. While it might seem like it takes too much time, doing this up front can actually improve clarity, prevent misunderstandings, and save time later on. This also helps you establish a closer connection. In fact, don’t limit interactions with freelancers to just your own. Connect them to more team members to help them learn about your projects and business.

4) “I choose to work with you, too.” 

The best freelancers are in very high demand. They can pick and choose their clients. In fact, freelancers might decide to stop working with you entirely if you don’t treat them well. I certainly stopped accepting projects from clients that didn’t communicate clearly about expectations up front, or worse yet, failed to pay on time.

Remember when you’re working with a freelancer that you’re not purchasing a one-off project: you’re building an important relationship that you will likely want to grow with time.

Pro Tip: Ask your freelancers what their best clients do differently. Tell them you want to be one of their best customers. The surprise? Most won’t ask for more money, but rather, will talk about other things their clients do well. Let them clue you in on how to get the most from the relationship with them. High-quality professionals take great pride in a job well done, and that includes customer service.

5) “Don’t reduce our relationship to price alone.”

Have you ever asked a freelancer to lower their rates because you got better rates from someone else? That’s somewhat like asking a restaurant to match the price of the same meal you ate in another restaurant, with a completely different chef, in a very different part of town. If you try to ask freelancers to match the rates of others, you might be equating the work of a Cordon Bleu-trained master chef to the work of a short order cook. While you’re probably just trying to be financially responsible for your company, be sensitive to the fact that many freelancers find a price-centered focus demeaning, as it devalues and unfairly commoditizes their work. 

Pro Tip: Ask freelancers for a clear explanation of their rates. If your budget won’t stretch, explain that you’re not making a decision based on price alone, but ask them if they ever have any flexibility on price, and if so, for which circumstances. Sometimes, sending them more guaranteed work on a recurring basis, pre-paying for work, or expanding their services, may prove to be a win-win situation.

6) “Ask me for my advice more often.”

When it comes to the types of projects they do each day with other companies like yours, freelancers have likely seen it all. Yet, you might not think to ask them for their advice on how to best structure a project, or how to improve the output. Often, a quick conversation with your contractor can yield great suggestions that will help the entire project go more smoothly. Don’t forget, they are professionals who are specialized, and this expertise is what you are paying for, not just the service itself.

Pro Tip: Get on a call with your freelancer and ask:

• How can I set you up to do the best possible job on this project?
• What else do you need from me?
• What could we do differently?
• Where do projects like these typically go wrong? 

7) “I’d love to dive even deeper into your company.”

Many freelancers are very excited to get to work with a new customer, and will often look up information about your brand, and even you as their main point of contact, to educate themselves on their new client. However, that time represents hours they would otherwise be billing to other clients, and they can’t spend countless unpaid hours immersing themselves in your business. 

Pro Tip: Pay your freelancers for time to learn about your business. This might seem radical, but if quality improvement is your goal, this will go a long way. If you already have a training program, send your contractors through it. Or, at the very least, send them the materials and allow them to take any corresponding tests.

At HubSpot, we recently began paying our freelance translators a set incentive amount to take the Inbound Certification, so they could become more familiar with inbound marketing in general. This guarantees that they can allocate the time to learning your business instead of another’s.

8) “My performance depends directly on yours.”

Often, clients are quick to point the blame at a freelancer when a project goes awry. I’ve seen many marketers throw up their hands in frustration, saying, “Why is it so hard to find a good freelancer?”

In reality, the problems are often due to a lack of communication and willingness to put in enough prep time on your side. Freelancers are usually very motivated to complete a job on time, and to your satisfaction. Instead of just shifting the blame in one direction, ask yourself what you can do better next time around.

Pro Tip: Would you fire an employee if they didn’t perform well in their very first week, or would you ask yourself if you set them up for success? Give your freelancer a chance to ramp up and learn your preferences and needs. If you routinely switch freelancers after trying them out on just one project, you’re not giving them the opportunity to ramp up properly. After your first project, schedule a call to do a detailed review with your contractor. Discuss the expectations, where things might have fallen short, and where both of you can do better next time.

9) “I take vacations, too.”

Don’t expect your contractors to be at your beck and call. They have lives, just like anyone else, so quick turnaround projects should be the exception, not the rule. Plan ahead with them. When planning your projects, give freelancers at least as much advance notice as you would give when, say, making an appointment with your hairdresser. You owe them that professional courtesy. And, make sure that if you become highly dependent on a freelancer, that you work their vacation plans into your schedule, just like you would for any full-time member of your team.

Pro Tip: Ask your freelancer if they have any times of the year that they are typically unavailable. Block these dates in your calendar and set reminders for yourself two months before to book any projects around their availability and work with them to make any back-up plans if needed. Often, freelancers will even sub-contract to other people they trust. Feel free to ask them if they have that type of arrangement for when they are out or need to reduce their workload. 

Start Contractor Relationships With Growth in Mind 

Lastly, remember that your freelancers are not “just” contractors, but important parts of your extended marketing team. This is especially true if your marketing team is small, or your company is in growth mode. When recruiting contractors, set the expectation up front that if the work is of high quality, your hope is to expand the relationship and send more work over time. 

You never know where these relationships will lead. Several years and jobs ago, I worked with a talented freelance writer and SEO specialist, and found myself sending her more and more work over time. Eventually, she ended up accepting a full-time remote position on my team, and today, even though we no longer work in the same company, we still remain close friends and colleagues.

As you work with freelancers, seek to truly get to know them as individuals in order to get the highest quality of service. Implement some of these tips and share them with others on your team in order to start building what may ultimately become mission-critical business relationships for you, your team, and your company.

What are your best tips for working with freelancers? Share them in the comments section below.