Working with Freelancers: Tips for a Successful Relationship

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You may be wondering what to expect when working with a freelancer for the first time.

Challenges often stem from a lack of understanding of how to work with freelancers – which can lead to miscommunication, missed deadlines, and low-quality work.

That’s why we created this article to help you manage expectations and communicate effectively with freelancers so that you can prevent having to look for someone new every few months.

1. Establish clear expectations from the beginning

When you first start working with a freelancer, it’s important to establish clear expectations. This means agreeing on things like the project timeline, what work is expected, and how you will communicate. By setting clear expectations up front, you can avoid any confusion or misunderstandings later on.

Here are some of the areas you want to make sure you communicate before your working relationship begins: 

Project timeline

When the freelancer will start and finish the project? How much work is expected to be done per week? Are there certain milestones that need to be reached in the project by a certain time? If it’s an ongoing relationship, you’ll want to address what each week/day will look like so you’re not left wondering what’s getting done and when.

What work is expected

If it’s not clear from the start, you’ll want to be specific about what you are expecting them to do. Having clear performance expectations for efficiency and satisfaction for both parties is important here. We suggest making sure these expectations are documented in some way – preferably in a project management tool like ClickUp, Asana, or Trello


How will you communicate? Will you use Slack, email, chat, or phone? Will you have a weekly meeting to communicate the status of your project? Having a set way of communicating will help avoid any misinterpretations. 

Most freelancers will address this when they onboard you. They should have certain days/hours they are available to communicate and work on your business. Remember they are most likely working with other clients and will have structured processes to work efficiently.

2. Communicate frequently and effectively

Good communication is key to a successful working relationship with a freelancer. This means communicating on a weekly or monthly basis for check-ins depending on the project and scope of work. By talking often, you can avoid any misunderstandings and make sure that both you and your freelancer are on the same page.

Ask the freelancer how they plan to communicate the status of their projects with you. Will they send a daily or weekly email report? Would they like to meet with you on a regular basis? Will they use a project management tool that you have access to so you can see the status of your project in real-time? Addressing these questions before you begin working with your freelancer will clear up a lot of the confusion that can happen when you begin working with someone new. 

It’s also important to be clear and specific when communicating. This will help ensure that there is no confusion about what needs to be done. And, if any problems do arise, bring them up quickly. Don’t linger in a state of “wondering” what the freelancer is up to. If you’re curious – just ask! 

3. Pay on time

Paying your freelancer on time is important not only because it’s polite, but because it helps to maintain a good working relationship. When you pay a freelancer late, it can cause frustration and resentment. This can lead to missed deadlines, poor quality work, and even termination of the working relationship.

So, if you want to maintain a good relationship with your freelancer – and get the best work out of them – be sure to pay them on time. 

4. Give feedback – both positive and negative

One of the best ways to ensure that a freelancer is providing quality work is to give feedback – both positive and negative. By giving feedback, you can help them understand what they’re doing well and where they can improve.

It’s also important to give feedback in a timely manner. This will help ensure that the freelancer has enough time to make any necessary changes.

Giving feedback can be tricky, but it’s important to do it in a way that’s helpful for the freelancer. Here are a few tips:

Be specific

When you give feedback, be specific about what you liked and didn’t like about the freelancer’s work. This will help them understand exactly what they need to improve on. Giving examples of the work you’d like to see can be extremely helpful. If you can’t pinpoint what you don’t like, it’s almost impossible to come to a resolution.

Offer constructive criticism

Freelancers are always looking to improve their skills, so offer constructive criticism that will help them do just that. Critique the work, not the freelancer.

Be polite

No one likes to receive negative feedback, so be polite when giving it. Remember that you’re giving the feedback because you want the freelancer to improve their work, not because you’re angry or upset. Also, take time to highlight some of the things you appreciate about the freelancer’s work (and be specific!). 

5. Respect their time and work schedule

Your freelancer is likely working with other clients, so it’s important to respect their time and work schedule. This means not contacting them during their off hours or expecting them to work more than they agreed to.

You will have a better working relationship when these expectations are set from the beginning. Remember, a freelancer CANNOT meet or exceed expectations that are never communicated! 

You’re set for success!

If you’re new to working with freelancers, just make sure to establish clear communication from the beginning, stay in communication frequently, give constructive feedback and develop mutual respect for each other. By following these tips, you can create a successful working relationship with your freelancer.

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