Tips on working with freelancers/contractors

Has your business reached the point where it’s time to hire some freelance help? Maybe you’re in the market for a virtual assistant, graphic designer, copywriter, or other freelance pro.

Or maybe it isn’t part of your business plan quite yet, but it’s just around the corner. Either way, it’s an exciting time! But it can also feel a little overwhelming. Today I’m here to equip you with some tips to help you hire the freelancer of your dreams.

But first…


What are the advantages to hiring a freelancer?

When you hire a freelancer, you’re able to bring on help much earlier than you’d be able to if you’d had to wait for your business to grow large enough to hire a full-time (or even part-time) employee. You won’t be responsible for employee expenses like extensive employee training, health benefits, vacation time, and more.

It’s also super-convenient to bring in freelancers on an as-needed basis instead of feeling like you need to find something to occupy an employee’s time. If a special task needs to be done and you don’t have those specific skills yourself, you can hire an amazing freelancer for that one-time job. She’ll bring her expertise to the table and you won’t have to employ someone you might not need once your project is finished.

If you find the right freelancer, you’ll find that most of them love their work (just like we do)! As a result, they’re always motivated to do a high-quality job. It’s good for her business to be completely reliable and even go beyond your expectations. You’ll need to set up clear expectations (we’ll go deeper into that below) but in general your new freelancer will probably be very used to working solo and will be completely self-motivated.

Overall, freelancers tend to be creative and innovative people. They might even come up with some new approaches you’ll love! High-quality freelancers tend to build up lots of experience as they work with lots of different businesses, often from all over the world.

If you find the right freelancer, she probably has perfected her craft – and your business will benefit!

So how exactly do you find an incredible freelancer and create a positive working relationship? Keep on reading for some tried-and-true tips!


1. Know where to look.

Personal networks/contacts. If you’re searching for, say, a graphic designer, try simply putting the word out there among your friends and family. You could get a feel for recommendations pretty much anywhere you spend time: your place of worship, your yoga class, even the local dog park! Who knows where you’ll find the one? You’ll never know until you ask around.

Freelance platforms. These include websites like Upwork, Freelancer, Guru, Toptal, and many more. These are useful resources that put tons of freelancers from all over the world right at your fingertips. You’ll be able to choose from different levels of skillsets and specialties, too.

There are some possible hiccups you’ll want to keep in mind while perusing these job boards, though. For example, if you hire a freelancer outside your region in a completely different time zone, will you two ever be able to communicate at the same time? Depending on your deadlines and your other needs, this could become important.

For instance, you might wake up to review the work your freelancer completed overnight from the other side of the world, suggest some revisions, and email her a request for changes. Would it be okay with you if your freelancer can’t make the changes until the next day, which means you won’t see the results until the following day? Sometimes this is no problem at all! Other times, it’s crucial that your freelancer be more available at the same times you are.

Also remember that on these job boards you often get what you pay for. It may cost you a bit more to hire a true professional with lots of experience, but it’s always worth it to find the right person.

As you consider each freelancer, mentally walk through the stumbling blocks that might come up with each one. Then make sure you talk about it with her as you move through the hiring process!

Referrals from professionals in your industry. As a creative maker and shaker, you’ve probably connected with fellow pros within your industry at some point. Maybe you’ve bounced ideas off each other or even collaborated. Who are their go-to freelancers? It can be much easier to work with a freelancer who knows your industry! And it always feels good to have a direct referral from someone you already know and trust.


2. Make sure you’re both in sync when it comes to style.

Everyone out there has a different style, especially creatives like us! So you’ll want to make sure to hire someone who matches up with the style of your business. Take a look at your potential freelancer’s sense of design and her brand voice. Style-wise, do you two “get” each other? Could you see yourself working with her? Does her work represent the skill and detail you’re looking for?

Be sure to check out her portfolio, too. At the very least, an experienced pro should be able to share samples and tell you about projects she’s worked on. Make sure to ask questions about the projects you like best – you might even ask her how she approached a specific project so you can get a sense for how she might approach working with you.


3. Don’t overwhelm your new freelancer.

At the beginning of your working relationship with your freelancer, you’ll want to start small. No matter how much vetting and research you’ve done, it’s always a little leap of faith to launch a collaboration. Start with projects that are smaller and non-critical as a way to test both the new freelancer’s skills and your working chemistry.

During this smaller initial project, observe how your freelancer communicates and deals with deadlines. Also keep tabs on the number of revisions it takes before you arrive at the result you love. If it all feels good, you can work up to larger and more critical projects.


4. Provide clear guidelines right from the start.

A positive working relationship with your freelancer needs plenty of communication. Make sure your freelancer isn’t guessing when it comes to what you want! Spell out your payment terms (how much, via which method, and when), the hours of work you expect, etc. Provide clear and precise instructions for how you want to get the job done.

You might also supply your freelancer with a brief that lays out your expectations for the deliverables. Keep in mind that if the scope of the work changes, it may change your original agreement. Don’t leave anything up in the air!


5. Set reasonable deadlines.

Remember: “your” freelancer actually works on many projects, not just yours! It’s part of why she has such a well-developed skillset.

It’s your responsibility to provide your freelancer with as much notice as possible. This of course has huge benefits for you, too – you don’t want to be frantically searching around for freelancers as you realize you need them! There may not be any available when you have the biggest need. And if you need to meet a deadline in a pinch, offer to pay your freelancer an extra rush fee.

Working with freelancers can be amazing for your business! You get to tap into some of the best talent out there, take your business to the next level, and best of all, you can free up time for yourself as business owner while you focus on that CEO to-do list that only you can check off!


Have you hired a freelancer before?

I’d love to hear your tips below in the comments!



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  • As a freelancer myself, I prefer if the client gives all the guidelines even before I start working from him/ her. It sets the expectations of both parties and avoid confusion mid-project.