As a business grows one of the main decisions that needs to be made is whether to hire in-house or to outsource to freelancers.

As a business grows one of the main decisions that needs to be made is whether to hire in-house or to outsource to freelancers.

To be clear:

In-house is an employee that’s paid a salary. They have a title and an official role in the company. In the States, this would be a W-2.

A freelancer. Usually paid either on retainer or project-based. This would be your 1099s (or a W8-Ben if they’re not a US citizen).

Now, personally, I find freelancers a huge asset to your growing business. They keep you nimble and they are usually pretty flexible. There is less of a human resources type of management needed.


Do your due diligence in hiring the right people.

Look for proof of their work.

If you’re on LinkedIn, look into their recommendations and reach out to their former (or current) clients to ask any questions that you may have.

And yet, the real “but” I want to talk about is this different.

The thing about outsourcing to freelancers is that they're not going to always be onboard with whatever tools and processes that you have in place.

And this can cause a problem when it comes to updates and communication.

So, what's the solution?

If you have the right processes in place and you set up automations, there is indeed a way to minimize the touch points.

Do your freelancers need to use your tools?

I've actually been deliberating this myself, because on the one hand, you want to know where all of your projects are standing. On the other hand, you also know that the freelancers aren't necessarily going to update every task in your project management tool. Even if they have great intentions, you can't always force them to use your own processes.

The thing to keep in mind is that freelancers have several other clients they serve, who have several other project management tools (or lack thereof) for them, to follow along with several other processes as well. And with many different kinds of projects of various sizes and scope.

The solution that I found is to create automations that will support your process.

What does this mean?

Well, let's take, for example, video production. If I record the original files and I want to send it to a video editor, I can put the clip in a specific folder. Dropping the file in that folder will then trigger a set of automations that will update my database of the new clip location. It will also send an email to my post production editor with the direct link and any special instructions for the file.

I can generate an automation that will create a task in my project management tool. And then I can assign that task to the video editor. And if he's on board with using my product project management tool. Great.

But if not even just triggering an email to him saying “here’s the file and it’s ready to be edited” will still trigger them to begin their process anyway! (Plus, it’s easy to update the status of the clip in my project management tool automatically.)

Regardless of my project management tools, the video editor can then start working on the task. It's up to him if he wants to manage his projects on the project management tool or not.

Does it bother me that he's not in my project or process? Absolutely.

But once again, I can't force the freelancer to use my tools.

The automation will keep the two of you closer and up-to-date.

In that same automation, what will happen is the status of the clip will be changed to “in editing” while the editor is editing the file.

When the editor completes editing the file, he places the final cut version in a different folder. Naming conventions have to be used here so we can follow up and trigger more automations.

But if the correct naming conventions are used, the fact that the editor places the clip in the final folder will then trigger another set of automations that will update the status of the file, that will update the location of the file, that will update whoever needs to review the file.

Once again, all the editor did was upload the file to a specific location and use a specific naming convention.

Is this my preferred way to go? Not exactly, but it is doable.

The sequences of automations that follow trigger creating the thumbnail for the clip for YouTube.

All of these can be put in place to make this process extremely smooth and streamlined with minimal touch points within the project management tool itself.

And yet it still gives you an overview of where the production phase is at every step of the way. This is one example of a process that can be almost fully automated. There are many others.

A question for you.

How involved do you need to be and how much do you need to know from your freelancers (or employees) to stay on top of a project?

Because if you are waiting to know if something is ready, based on someone changing the status from, “in process” to “done”, you could be waiting for a long time.

If there's a trigger that you can use that will automatically change the status, you're saving yourself a lot of heartache running after people to make sure that they change the status.

I'm not saying that that's right.

Freelancers should definitely know to go in and change the status if that's the process in your company or in your business.

But wherever you can, try to find ways to automatically trigger that status so that you're always up to date on where things stand in your own company or in your own process.

Final thoughts

Let me say again, freelancers are the backbone of many successful companies and small businesses. They provide the expertise and masterful work in a much more flexible way than an in-house person (who also has their own set of advantages over freelancers).

But with freelancers comes challenges of staying up-to-date on projects in the way you prefer.

Rather than getting upset or angry, set clear ground rules ahead of time, and also set automations that will enable freelancers to be closer to you so you don’t always have to chase them down and cause a lot of stress (for yourself!). Setting up a few things ahead of time can bring you peace of mind.