Tapping into the freelance workforce gives companies access to a rich and varied pool of talent. The number of freelance or contract workers has been rising for years, since technology has made remote work far more feasible — in fact, according to a 2017 study, freelancers are expected to outnumber employees within a decade.
Managing freelancers can be a challenge, especially the ones who work remotely. They don’t fit as neatly into the existing corporate structure as employees do; if your company isn’t in the habit of working with contractors, you may even have to invent your own project management processes. The tools below can make the job of managing remote freelancers much easier.
Organizing your project
When your team is dispersed across the country or even the planet, keeping track of who’s working on what can be quite the challenge. Airtable is a combination spreadsheet and database that’s almost infinitely customizable. The company has numerous templates you can use to jump-start your own setup. And it integrates with hundreds of other programs, making data importing a snap.
Airtable’s basic product package is free; you can subscribe to one of the paid plans if you want the optional features, such as a longer revision history or more data storage space.
How this tool can help: The purpose of a project management system is to keep everybody aware of how each project (and each task within that project) is faring. At a minimum, you’ll want to know the deadline for each task, the person responsible for that task, and the order of steps needed to complete the task. It’s also wise to advise your freelancers to reach out to you immediately if they think they won’t be able to hit a deadline, since other team members may be depending on that task to accomplish their own tasks.
Most projects call for at least some level of documentation, but swapping Word documents back and forth via email can get awfully confusing and almost guarantees that some detail will get lost along the way. Documents created with Google Docs are in the cloud, so you and your freelancers can access each document at any time and revise it as needed. Google Docs has a “track changes” feature similar to Word’s, so you’ll be able to see what’s been changed and retrieve old versions of the document if necessary.
And unlike Word, Google Docs is free to use. You can also sign up for the company’s G Suite package, which lets you set up company email, shared calendars, and cloud storage and costs between $5, $10, or $25 per month, depending on which package you need.
How this tool can help: When you have team members in different locations collaborating on a single set of documents, it’s really important to make sure that everyone’s working with the same version of each document. If a freelancer somehow misses the latest update of a Word document, then any changes he or she makes will probably have to be discarded; in a worst-case scenario, if different team members have different versions of the same document, you may never be able to unsnarl the mess. Using cloud documents makes it nearly impossible for this kind of disaster to occur, so the more documents you have in your project, and the more team members you have working on a given document, the more helpful it is to use cloud-based documents instead of those off-line.
Using cloud documents can save you a lot of back-and-forth, but you’ll probably have other files you’ll need to exchange across the team. Email is the easy and obvious way to send files but makes it tough to keep track of what you’ve exchanged, and it won’t work for larger files. That’s why Dropbox can be a big help for remote teams. With Dropbox, you can upload a file of practically any size, and the recipient can download it from Dropbox’s servers.
A basic Dropbox account is free but provides only 2 GB of storage; the paid subscription plans give you anywhere from 1 TB to infinite storage space as well as extra features not available on the free plan.
How this tool can help: Being able to keep track of documents and other files can be critical to any project. Things can get messy when you have different versions of the same file flying between different team members. Using cloud documents will take care of the risk for word-processing files but won’t help with other types of files, such as images. By directing your freelancers to use a central repository for all project-related files, you can minimize the risk that someone will use the wrong version of a file as the basis for their tasks.
Staying in communication
Remote teams need a way to communicate in real time, and Slack is one of the best team communication options around. Slack lets you set up different channels so that you can keep your discussions organized, it has built-in screen sharing and even some light videoconferencing options; and it comes with a huge number of apps and integrations so that you can plug your Slack account into a wide range of other programs and services.
The basic Slack plan is free; you can get additional features (such as unlimited apps) with one of the two paid plans.
How this tool can help: Encourage your freelancers to interact frequently and provide task updates via chat. That will make it easy to track progress as well as monitor everyone’s state of mind. Using Slack’s many emojis helps with the latter; one of the disadvantages of chat software is that you miss out on the chance to read the other person’s facial expressions and body language. Emojis aren’t quite as good, but they at least make it easier to avoid misunderstandings about the “tone” of a message.
Sometimes chat and email just aren’t good enough for communication purposes; you’ll need to set up the occasional face-to-face meeting, even if the other person is several thousand miles away. Zoom is one of the more robust video-communication options and can handle large numbers of attendees with ease. The meeting scheduler is a snap to use, and scheduling information flows easily into Google Calendar.
Zoom’s basic package is free; you can also buy one of their monthly packages if you need to add extra features to the service.
How this tool can help: Since one of the fringe benefits enjoyed by freelancers is being able to work in their pajamas, some of your contractors may not be thrilled about getting presentable to join a video chat with you on a regular basis. But being able to at least see their faces will make getting to know your freelancers and managing them much easier. It’s a good idea to schedule a regular meeting — say, once or twice a month — just to make sure that everything’s on track and that you and your freelancers are happy with the way the project is going.
Budgeting and expense management
Whether you pay your freelancers by the hour or by the project, it’s important to know just how much time your people are putting into specific tasks. Without that information, you won’t be able to come up with a realistic budget or figure out how long your freelance projects will take. Toggl is a great tool for time tracking; you can use it to track projects or even pieces of projects via a web interface or a downloadable dashboard widget. Using Toggl is as simple as clicking a button when you want to start tracking time on a particular project and then clicking it again when you’re ready to stop tracking.
Toggl comes in both free and paid versions, depending on which features you want.
How this tool can help: If your freelancers aren’t used to tracking their time, getting them to consistently use your chosen time-tracking software can be a bit of a challenge. Usually, it’s just a matter of encouraging them to get into the habit of starting the clock before they start working on a given task. You can point out that knowing how long they’re spending on each task will help your freelancers figure out how much to bill for similar projects in the future to keep their profit margins reasonable.
If you’ve decided to use Slack for real-time chat, then Teampay is a natural option for managing freelancer expenses (though you can use Teampay whether or not you have a Slack account). The Teampay app pairs with Slack, so your freelancers can simply chat with the bot to get their expenses approved and paid by you. And because Teampay works by issuing virtual credit cards, it’s easy for you to track expenses in real time and through reports generated later. The system also eliminates the need for reimbursements, which greatly simplifies expensing and keeps your freelancers happy.
Teampay’s cost varies, depending on the number of transactions you have each month.
How this tool can help: Tracking expenses by project and by type is a crucial part of setting a realistic budget — and the more expenses you have in a project, the more important it is to correctly categorize them. Virtual credit cards make tracking a whole lot easier because your freelancers will have to spell out what it is they want to buy before Teampay will assign them a virtual card to use for the purchase.
The Finance Stack of Top Performing Startups
If you want to have a good long-term working relationship with a freelancer, you’ll need to do some performance management just as you would with an employee. Lattice can greatly simplify performance management by creating a real-time feedback environment for your team members. You can use Lattice to set goals, post both praise and constructive criticism, and track each freelancer’s performance over time.
Lattice’s pricing is variable, depending on your needs and on which plan you choose, but the minimum annual contract is $2,000. Thus, Lattice is probably a good choice only if you have a large team of freelancers or you want to use it for employee performance management as well.
How this tool can help: While most companies have formal performance-management processes for employees, including annual reviews and the like, few organizations bother to apply similar processes to freelancers. If all your freelancers are hired for single projects, then there is some validity to that approach. But if you’re bringing back freelancers repeatedly, providing a structured performance-management system will help guarantee that both you and the freelancers are happy with the relationship. You don’t have to build a complicated process for feedback; just make sure that everybody knows when and how to expect feedback and show them that you’re consistent about providing it as planned.
The technology that makes remote work — especially freelancing — viable on a large scale has also provided the tools you need to manage freelancers effectively. It’s just a matter of finding the right tools and working them into your processes.