How to effectively communicate with your freelancers

How to Communicate with Freelancers


By Nicole Bandes

Founder, CEO of Virtual A Team

Read more by Nicole

So, you’ve tackled the first step towards outsourcing your business and now it's time to communicate with your freelancers! 

Congratulations on making the best decision to grow your empire towards its max potential!

Hiring your first freelancer may have been a daunting experience, but now that you have an entire team, it’s time to boss up, ladies and gentlemen!

Working with freelancers is a wonderful way to delegate tasks that slow you down while focusing on your priorities in business. 

It makes life easier; you can finally afford to sit with your dog and enjoy a glass (or an entire bottle) of wine while binge-watching the latest season of Stranger Things on Netflix. 

While this level of being a Zen-boss lady is not far out of our reach, it does take a team and a plan.

You might be thinking that working with several freelancers could turn out to be more than you bargained for: A chaotic mess.

Let me stop you right there.

Any organization has the potential of turning into a huge pile of OH NO’s when they don’t follow a simple step: Communication! 

Today, we’re going to run through tips and strategies that will make you an expert at communicating with freelancers on your team. 

How to Effectively Communicate With  Freelancers

Start With a Win!

The first thing you can do to communicate with your freelancers is to take time to onboard them.

Onboarding involves helping your freelancers understand the business and you. Have an initial meeting to help them get to know things like:

  • Your big goals and vision
  • How you like to communicate
  • What are your expectations regarding work completion, turnaround times, availability, etc...?
  • The tools and systems you are currently using
  • Who else they may be working with
  • What do do when something doesn't go right. (Hey, it happens and if they know how you prefer to handle it, things will work better overall).

Set Regular Meetings 

You can set the tone with the entire team by hosting a meeting using group video call once a week or based on a schedule that makes sense for the workload. Use this time to prep and communicate with freelancers on your team and keep them aware of the newest developments. Remember to help them understand the big picture and not just their small piece.

Create a standard agenda that covers:

  • A quick assessment of the performance from last week.
  • Discussing ongoing projects and bring them up to speed with new contracts or changes in the organization.
  • Setting the priorities for the current week along with delegating tasks.
  • Brainstorming creative ideas.

Be sure to include time for your freelancers to ask questions or discuss their concerns with you. And encourage them to do so. They have to feel safe expressing things to you or they won't.

Pro Tip

This isn’t about friendship, it’s about appreciation and understanding. 

Set Clear and Realistic Deadlines 

It's important to communicate with freelancers about deadlines in advance. Set a deadline by double confirming with your team members. This is especially helpful when you are on a tight schedule. When you consistently encourage your team to share their feedback and input, they will let you know if your deadlines aren't realistic. If you don't encourage this, the lack of communication with freelancers can result in missed deadlines or poor quality work.

If they say they can do it, make sure that they keep their word, which brings us to the next tip.

Request Routine Updates

Keep in touch and communicate with freelancers via email or a project management program. Prompt for updates within the same thread as the ongoing project to avoid confusion and wasted time searching for the right communication. Make sure that all the freelancers connected to the same project are included in the thread.

Regular Feedback And Progress Reports

Feedback is probably just as important as your routine meetings. If you think there’s a scope of improvement with a certain freelancer, let them know. They will appreciate you for letting them know of a possible blind spot. When they’re doing well, don’t forget to pat them on the back and thank them for their dedication.

Utilize Tools

One of the things that can really boost your relationship with the team is modern tools that allow you to manage all the communication and even automate them for that matter.

We highly recommend integrating your business communication with project-management and other tools that can dramatically improve your results with your freelancers.


Teamwork is an amazing cloud-based project management solution. It also happens to be the one that Virtual A Team uses so we may be a little biased.

What makes it so impressive is the way it integrates all the functions from a two-party perspective, i.e. the project manager as well as the team members. The features include task lists, time tracking, file uploads and messaging. You’ll be able to assign tasks, schedule updates and keep a track of ongoing processes in real-time.


Zoom facilitates communication by bringing face-to-face conversation to teams around the world. Jump on video calls, record them and share communications with team members across the globe.


Slack is a workflow builder based on simplicity. By creating a system that promotes automation, oversight, proper planning and team collaboration, slack helps you manage all the pieces of your work starting from meeting to tracking a project.

While this tool is loved by many organizations, Virtual A Team has found it to cause more distractions than benefits. If using Slack, be sure to allow your team to have certain closed door hours to get their heads down and focus.

Loom is a handy way to do a quick recording or walkthrough of something you'd like to communicate to freelancers when you aren't on the same schedule. It's handy for sharing feedback on projects, or giving a visual walkthrough of processes.

So, now when you have everything ready at the backend, how to get started with assigning and delegating tasks to your freelancers? Let’s find out.

How to Request Tasks from Freelancers

As entrepreneurs with fresh ideas, it's tempting to want every new idea done today! When you have a new task waiting to be started with, you may not want to push too much on to a team member’s plate. Not only can this lead your business in the wrong direction, chasing too many shiny objects, but it can overload your freelancers with too much work.

Once you've determined that your idea really is valid and should take life, talk with your freelancers before getting started.

  • Ask for their availability and interest in a new task through email.
  • Send a brief for the new task once the member sends an affirmative response.
  • Keep track of their work by asking for a snippet before completing the entire task.

To help your freelancers out, you can also:

  • Be Thorough; add samples and sources for reference and guidance.
  • Make sure you clear the doubts and questions of your freelancers.
  • Follow a Procedure and course-correct while editing their snippets.
  • Provide genuine feedback on how they’re doing.

Interactive Tips for Interpersonal Communication with Freelancers

It's not enough to just communicate your specific needs with your freelancers. The best client/freelancer relationships will also include some quality interpersonal communication.

communication with freelancers

Inviting and Appreciating their Honest Opinion on a Project

Since you chose your freelancers, we know they have to have some amazing skills and work experience. When it comes to ongoing and new projects, invite new perspectives and ideas. Maybe they can help you make it better than you ever imagined!

Being Open to Feedback

You providing feedback is just one side of the coin of a team. Ask your freelancers about things that could use improvement, and take it under consideration. Individual experiences can help your business grow exponentially through a fresh set of eyes.

Saying it as it is

When you work with a team of freelancers, there’s no sugarcoating anything. Being honest about the work you’re getting done will give you better results.

Checking Up on Your Team’s Wellbeing and Personal Progress

Work aside; it is also essential that business leaders build a bond or kinship among their team members. Asking about their overall wellbeing and personal milestones (if they’re receptive to it) is a nice way to establish a better connection. Familiarity helps more than strangers working with each other!

Pro Tip

Set meetings at regular times every week so that meetings are a habit not an event

Celebrating Victories Together

As a team, it’s a different experience to celebrate the small and big milestones together. Rewarding your team and involving them in the success of your growth will boost their morale, make them feel like they belong and are appreciated.

Wrapping Up

Since freelancers are extremely talented free spirits, each of them may have a different mechanism of getting things done. But, while juggling several of these magical unicorns who turn your business into a cakewalk, you can’t afford to spend too much time.

If you’re a coach or a consultant trying to improve the life of your clientele, you understand the importance of clear and effective communication. While your clients look up to you to light the way, your team does too!

Are you facing troubles communicating effectively with your virtual team? We have just the right solutions for you at Virtual A Team. We have pre-built communication systems in place to help you get started with a few clicks!


The Ultimate Guide to Delegating

Don't stop now! You'll also love this other great content...