Two metal cog gears

There are five steps you can take when working with freelancers to get your project moving in the right direction. A solid framework can help you see the results you want for your project and your team.

When you aren’t used to working with freelancers, you can feel a bit like you’re walking blindfolded to get the final deliverable. How can you trust the work of a freelancer you’ve never met?

Many teams start new partnerships with a paid test project—a small project that might be similar to the work to be done or even the first phase of your larger project. This can be a great opportunity to flex your collaboration skills and go beyond a freelancer’s proposal to see what they’re capable of.

After due diligence and careful consideration, at some point you have to have faith in your decision, remember that trust is a two-way street, and start moving forward. A plan that’s structured to help you get the results you want. This may include:

  • Ensuring a clear understanding of the project from the beginning
  • Confirming mutual expectations
  • Polishing up your communication skills
  • Being quick to spot and act on potential problems

Let’s get started!

1. Give talent access to the information they need

A common challenge when you work with remote talent isn’t understanding what information they’ll need to do the work—it’s figuring out how to get it to them. How can you share internal information and data in a way that won’t leave your company exposed to unnecessary risk?

First, consider the level of risk involved. Data can generally be organized into five categories:

  • Sensitive
  • Confidential
  • Private
  • Proprietary
  • Public

For instance, the information required for a graphic design project may already be available, which means there’s little-to-no risk if it gets out to the public. However, a sales or customer service-related project may depend on internal customer data that’s much more sensitive and high risk. Sending it by email may not be an option.

Second, confirm your collaboration strategy. What’s the best way for the freelancer to contact you with questions or clarifications? Will they need access to your company’s virtual private network? If they need access to an internal system, how can you set them up with their own unique user ID? Talk to your IT team about collaboration tools and protocols that will meet your company’s security requirements.

2. Agree on your expectations

Before your project begins, schedule a kickoff meeting to review details and set clear expectations. The goal: to confirm the requirements, timeline, and deliverables. You’ve likely already shared these details in your original job post, interview, and other correspondence. So use the opportunity to see if you’re on the same page by letting the freelancer take the lead.

Some of the finer points will still be up for discussion, but by Day One a freelancer should be able to explain the broad strokes, such as:

  • How they’ll approach the work
  • The timeline and key dates you’ve shared
  • How they’ll communicate about challenges
  • Realistic goals and expectations, given the project’s parameters

As you listen, ensure the freelancer’s perspective matches yours—and if not, address any concerns right away. And remember, they’re the expert. Don’t be afraid to lean on that expertise as you determine the next steps.

3. Use milestones to create a feedback loop

Milestones are events that mark the different stages of a project. They can also be an effective way to prevent miscommunication and confirm that everyone’s expectations are still in sync, particularly if used as part of a fixed-price project on Upwork.

Most projects naturally break into distinct phases, and your milestones should align with the deliverables for each. Depending on the length of your project, three to five milestones can be a good number to start with. For example, a WordPress install might include:

  • Preliminary design
  • Installation and customization of theme, plugins, and the addition of content
  • A round of design adjustments, if needed
  • Pre-launch testing and optimization
  • Launch

Effective milestones generally have:

  • Deadlines that align with key dates in your overall timeline
  • Specific deliverables attached
  • A reasonable amount of space between them — you want to keep things moving forward, and too many milestones can grind momentum to a halt

4. Rethink how (and when) you email

Good communication is essential to any good collaboration, and that’s particularly true when you’re working remotely with a freelancer. Milestones can help establish a natural feedback loop for the length of your project, and taking a fresh look at your day-to-day communication style can make things run more smoothly between those check-ins.

Working with a distributed team relies on something called asynchronous communication—a technical-sounding term to explain that you often won’t be online at the same time. This means adjusting not just your expectations but how you send and receive information. Email and instant messages can be great for small chunks of information or ongoing discussions. However, if you have a lot of information to share, consider a video call instead.

“When communicating asynchronously, you need to keep in mind that the recipient needs more information than they otherwise would, because there’s a chance that you won’t be around to answer important follow-up questions.”
— Benjamin Brandall, Process Street
The Complete Guide to Asynchronous Communication in Remote Teams

Since written correspondence is typically the main method of communication, here are a few tips to keep in mind:

  • Keep your message as concise as possible. It’s easier to miss details if your email gets too lengthy.
  • Be specific. To avoid confusion and a lot of back-and-forths, be very precise with any questions you ask.
  • Try to anticipate follow-up questions. Thinking through additional questions might mean a longer email up-front, but you’ll be much more likely to get the response you need.
  • Outline next steps. If you clearly state what should happen next, it’s much easier for the recipient to take the appropriate action.

Another way you can tailor your email is to get to know your audience. Cross-cultural communication can pose different challenges that can be easy to address—if you’re aware of them. Assuming everyone is alike is a common issue: you may have a lot in common, but different cultures, experiences, and backgrounds can influence how, when, and why each of us responds in any given situation. So, if you’re working with a freelancer in a different country, it can be valuable to get to know both who they are and where they’re coming from.


Misunderstandings and miscommunications are a reality of doing business. Rather than letting them derail your project, take action as soon as you realize things are going off-course. Milestones and regular communication can help you spot problems before they have much of a chance to take root. And if you can’t get things to align despite your best efforts. If you are unhappy with a freelancer’s work, your project may qualify for payment protection or Upwork’s dispute resolution services.

A clear understanding of goals and expectations, paired with solid communication practices, are at the root of any successful project. With these things in place, your project will be on the right track toward success.