communicate with freelancers


The key to organizing a business run by freelance hires is to have a good system to communicate with freelancers. Hiring freelancers can become addictive, but it can also get overwhelming. They can be scattered all over the globe, or working at different times of the day and night even if they’re in your time zone. Keeping track of who’s doing what and when can take up hours of your precious time. Getting things organized so you can communicate with freelancers without disrupting your entire schedule is so important.

Below is a tried and tested 4-pronged system that you as a business owner can use to easily communicate with freelancers, regardless of how many you manage.

(1) Daily check-ins on Skype

You don’t want to be talking to freelancers all day long, but it’s important to check in with you every day that they are working on your projects. Communicate with freelancers that you expect them to let you know when they start work, what they’re working on, and when they finish. This establishes accountability, which is vitally important to your professional relationship and the work itself.

Once a freelancer checks in, make the effort to ask them how things are going. You can do this every day for the first few months after they’re hired, then you can taper off as they prove themselves responsible. Be sure to also communicate with freelancers that you are there to answer any questions that they might have as they are doing the work. They need to know that you can help them in case they get stuck or are not sure how to proceed. It eliminates a lot of mistakes, which is important for you – fewer mistakes means less time spent fixing them, and less money wasted.

You might see daily meetings as a drain on your time, but you only need to get freelancers used to the system. You won’t really have to communicate with freelancers on a deeper level every single day, but having this system helps to keep the channel open so that any problems that come up can be addressed swiftly and properly.

A good tool to use for these check-ins is an instant messaging app like Skype. If you are already using a project or content management system like Slack, you can simply communicate with freelancers through the chat feature that is already integrated.

(2) Daily Email Summaries

Apart from your start and stop notifications and the occasional question, communicate with freelancers via email as well. Ask them to email you a more detailed report of what they did for however many hours they worked. This way, you can stay updated on how projects are progressing and keep freelancers on their toes when it comes to deadlines.

If you’re hiring through FreeeUp, the freelancers you hire will already be adding comments directly in the timeclock app. You can then simply ask the freelancers to make sure they submit detailed comments, and review them as you go through your account. If you want to be able to ask freelancers about specific tasks, however, asking the same details to be sent to your email will make it much more convenient for you to hit reply and say, hey, can you give me more info on this?

Again, using a tool like Slack or Trello or Asana can help you organize these updates as well as track progress. The point is that you have a system for getting detailed daily updates on ongoing work.

(3) Weekly 1 on 1 Meetings

Make it a point to communicate with freelancers on a deeper level once a week. This is when you can really get into what’s been happening throughout the past week, and what is laid out for the following week. Go over how they are enjoying the tasks, how well they are handling them, and what you both think can be done to make things better. Feedback is a very important aspect to communicate with freelancers, and it goes both ways. You have hired area-specific specialist who can give you very valuable insights on how to streamline things on their end. You can also give them important tips on how you prefer things to be done from your end, and because you know your business best.

Make it a point to also communicate with freelancers how things are going in the area that they are working on. Anyone will become more productive when they are more connected with the work that they’re doing. Share things about growth and goals so they can feel like they are really a part of the greater whole, even if they work far away from you.

This weekly 1 on 1 is also a good opportunity to go into further detail on any issues that a freelancer may have raised during a check-in. You have both had time to think on it a bit more, and now you can share suggestions and find the best solution.

(4) Weekly All Hands Meetings

Once a week, you should also get together with the whole group. During this meeting, communicate with freelancers what you particularly liked so that they can all share in congratulating the key persons involved. This helps to create a community atmosphere that is great for morale and also generate a healthy atmosphere of competition. Encourage those who do well and those who need to improve will be encouraged to step it up as well.

Share larger updates at this meeting – what’s happening with the business in general. Allow freelancers to see how their combined efforts are working to push the business forward. It’s always good to get a glimpse of how the other wheels are turning. It encourages freelancers to reach out to one another and share information that could help solve problems in other areas.

The weekly all hands meeting keeps everyone in the loop on the bigger picture. It creates an atmosphere of collaboration and motivates these scattered freelancers to develop greater cooperation to get things done faster and in the best way possible. These meetings don’t have to run too long, although they may take longer at the beginning. Once everyone gets into a good flow, however, you will see that they do become more efficient.

Final Notes on Meetings

Always remember to communicate with freelancers very clearly. Especially if they have not been working with you for very long, they will not know you or be familiar with your style. This is even more true when you hire people from different places where the culture is different. Give them time to adjust to how you operate, taking into account what they are used to.

There are always growing pains when you start working with someone new, so keep in mind that you need to give them some leeway at first. Set your expectations upfront about how you prefer to communicate with freelancers, and make sure that each freelancer understands and is able to comply. Some freelancers may not be familiar with the tools that you use, for instance. Ask them if they are comfortable checking in on Skype or if they can use Slack fluently. Knowing these little things straight away can prevent a lot of issues later on concerning.

Make sure that you also set meetings at convenient times for everyone. They are freelancers, after all, and not bound to regular hours. You may also find that you can’t actually have a single meeting for everyone depending on where they are based. Reach out to them and make an effort to take their availability into consideration.

Fairly regular meeting times and clear agendas are best for everyone all around, even though you as a business owner and they as freelancers may not really keep strict schedules. It gives the work structure, which is key to productivity. Try to get a good 30 minutes blocked off on your calendars, preferably on the first day of the workweek. It sets a good example for everyone and helps them get into the flow after taking a day off.

Your Turn

Start organizing communications with daily check-ins and updates. From there, tweak the system and port it over to all hands meetings. Then start holding more regular, longer meetings with each freelancer. Take it a step at a time, and you’ll  soon see how much time you are actually freeing up and how many issues you are avoiding when you have this system in place.

If you feel that you are still spending too much time managing freelancers after trying these steps, consider hiring a freelance project manager to take care of the check-ins and general updates. This way, you are only communicating with one freelancer who can then take care of the group. Don’t disappear altogether, though – you should still have your 1 on 1 meetings to develop that much needed rapport, and be present at the all hands meetings, even if you let a project manager take the lead.


3 thoughts on “How to Effectively Communicate With Freelancers

    1. Hey Ashley, it does seem that way, and may be at first. But if you get through the first weeks and have everything properly set up, what you’re really doing is setting up freelancers to work independently so you can save much more time in the long run.

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