7 Time Saving Tips for Working With Freelancers

Use Your (Billable) Time Wisely

There are many reasons to bring Freelancers into an organization. They can be invaluable when you need a specific type of expertise, an important project completed quickly, or simply a fresh pair of eyes on your company. However, without the right tools and processes, outsourcing can be more trouble than it’s worth. Here are some tips to streamline your onboarding and collaboration process, so neither your company – or your freelancers – are wasting valuable time.

1 | Welcome Freelancers into the Office

Establishing a good relationship with your independent talent is essential to creating content you’re both pleased with. A good way to start off on the right foot is to have them work from the office while they’re getting started. You’ll often find that the work better represents your brand if the freelancer has spent some time steeped in your company culture. It also significantly expedites projects, because any issues or questions can be addressed in person, on the spot. Even if the freelancer doesn’t spend the duration of the project in your space, they will be more comfortable coming to you quickly and casually when problems arise, rather than agonizing over formal emails or waiting for conference calls.

Freelancers value independence and the ability to work where they please, so they won’t be accepting invitations to work somewhere hostile, uncomfortable, or unengaging. Make them feel special. Welcome them with open arms, introduce them to the team, and start building the trust you’ll need to maintain a long-distance relationship.

2 | Don’t Wait Until the Last Minute

It’s hard to find quality talent on short notice. If you’re scrambling to find freelancers for a quickly approaching deadline, they likely won’t be the best suited for the job. Plan ahead. Identify the need for freelancers before you’ve started the project. That way, you not only have time to find the best people for the job, but are also able to integrate their unique skills with your permanent team in the planning phase, so everyone can play to their strengths.

Obviously, you can’t always plan when you’ll need an extra hand. You can, however, have a list of reliable freelancers to pull from so you’re ready when the time comes. Identify a reliable list of freelancers for your last minute needs, a small pool of top notch freelancers for important projects, and a JV team for smaller projects that you have time to prepare for. Keep a record of the freelancers you’ve worked with, and what they brought to the table, so you’ll know where to turn in the future. It can be helpful to use specialized services like MBO, Catalant, or Paro to find vetted talent on short notice.

3 | Expedite the Contracting Process

Nothing slows down the on boarding process like liability insurance. Insurance requirements are a tedious but necessary part of nearly every contract. They can delay a freelancer’s start date by weeks, and cause unnecessary friction between them and the company. There are a few ways to make this process quick and (relatively) painless. The first thing you can do is make sure your insurance requirements for 1099 workers are up to date. Outdated insurance requirements are often much higher than necessary, in some cases causing the cost of insurance to outweigh the profit for freelancers. This can lead to one of two things – you’ll either be caught up in weeks worth of email negotiations with the freelancer, or they’ll bail and you’ll have to start your search from square one.

The best way to make sure insurance doesn’t become too big of a barrier is to embed it right into the contracting process. Bunker has made this possible for the first time with an online platform that allows you to create and share insurance requirements with your freelancers right from their site. Freelancers simply click a link and purchase the required insurance online, with terms as short as three months. This saves the freelancers money by allowing them to tailor their insurance to the requirements and length of their contracts, rather than locking them into annual policies. The software even offers COI tracking and management, which can take over 30 minutes per Certificate of Insurance when attempted internally. Bunker’s advisors are always available to review your insurance requirements and field any questions your freelancers have, which can save hours of emails each week.

For more on Usage Based Insurance, watch this demo.

4 | Hire Freelancers Who Fit The Project

Seems like an obvious one, right? But really think about what that means for freelancers. You have the opportunity to find someone with a skillset as specific as the project you need them for. Often, companies will hire freelancers like they hire employees – they look for a broad range of skills that overlaps with what they need for the role. With freelancers, you can be much more specific. If you’re hiring for a social media campaign, hire someone who specializes in social media. You don’t need a well-rounded candidate if the task at hand requires specific expertise.

It’s equally as important to hire the right level of freelancer for the job. If you need a large quantity of low-level copy written, don’t turn to a seasoned writer. An overqualified freelancer will not necessarily get the project done more quickly or efficiently – but it will definitely be more expensive. If you need a polished, well-researched article, don’t hire an agency that specializes in listicles and product descriptions. This will lead to multiple rewrites, vigorous editing, and in some cases more time than you would have spent creating the content yourself. Which leads us to the next timesaver:

5 | Cut Down On Rewrites

The most common road to rewrites is being unclear about your expectations for a project. Make sure you’re very clear not only about the content but the quality you’re looking for as well. It can be tempting to downplay the difficulty of a project to attract freelancers at a lower rate but remember: you get what you paid for. If you need a topical blog post, clarify that you don’t expect the freelancer to waste time or resources on research. If you expect a higher level of content, tell them that up front. Of course, when you begin a new relationship with a freelancer or agency, it may take some back and forth to land on the content you’re both happy with. However, if you’re spending so much time editing a freelancer’s work that you’ve basically rewritten it by the end, then hiring them was a waste of time for both of you.

6 | Don’t Outsource by Default

This leads to the most important consideration: is outsourcing the answer? Before seeking outside help on a project, think about whether you could pull it together with the resources you have in house. A good exercise is to think about the time it would take to find, brief, and critique a freelancer, compared to the overall time they’ll spend on a project. If the project is smaller, you may be able to finish 75% of it in the time it would take to onboard a freelancer. In this case, delegate, work with your team and push the project out in house. It can help to offer a small bonus to the team members who put in extra work to get it done. Dividing the freelancer’s fee in half and splitting it among team members will show appreciation, boost morale, and still cut your overhead by 50%.

7 | Have The Right Tools in Hand

There are a million tools on the market designed to help the workplace run more smoothly – which becomes even more important when you add freelancers to the mix. While no specific tool or software will be a one-size-fits-all solution for every company, make sure you find a tool within each of these categories that work for you:

Task Management

Task management tools are essential to keep everyone on the same page, especially when you’re not all in the same physical location. They vary in layout and capabilities, so it’s a good idea to try a few out with your team – some work great for marketing but aren’t set up for tech development teams, and visa versa. If you’re looking for a good all-around task management tool, Asana, Basecamp and Trello are a great place to start!


Easy messaging between coworkers creates an efficient, collaborative, and comfortable workplace, keeping everyone (including remote employees) in the loop. When it comes to chat, there’s really nothing that beats Slack. With endless possibilities for integrations, groups, and team building apps like HeyTaco!, Slack creates a workplace community like no other.


Nothing will ever match the improvement Google Drive made to the collaboration process, but when google sheets isn’t going to cut it, there are plenty of ways to organize your collaborative projects more easily. Again, these should be tailored to the needs of your company – and even specific teams within your company. For example, CoSchedule is specifically created to help with content creation and distribution, integrating with social media, email apps, google drive, and more.


Want to learn more about Bunker’s on-demand insurance solutions? Email enterprise@buildbunker.com, or watch a demo to see how easy compliance can be!