Guest Blog by Connor Gillivan, CMO and co-owner of

Outsourcing is one of the best advantages that businesses have in this day and age. It can help you scale your business faster because of one simple fact:  traditional hiring is one of the greatest burdens that businesses have faced, and outsourcing is the paradigm shift that changes the face of hiring and turns hiring drawbacks into benefits.

Here’s how you can leverage outsourcing to scale your business faster:

1.  When to Outsource

The absolute best time to start outsourcing tasks is BEFORE you get overwhelmed.

Many business owners wait until they are pulling their hair out before they break down and decide to get some help. This may be the only way it seems doable for them, particularly if they are bootstrapping. The struggle is real. However, it can also cause a lot of stress and put off growth, which negatively affects the business.

To scale your business faster, you have to maximize your business’s potential. This means outsourcing at the most strategic times. Here’s how to do that:

Realize when your plate is filling up.

The busyness of life is a top threat to business. Yes, you’ve gotta hustle to keep things going. But you can’t just keep plugging away until you collapse. Take a beat and look at your schedule, do a health check, and take notice of how much you’re piling on.

Be aware of what is too much and when that’s going to happen so you can prepare.

Get yourself into a longer-term mindset.

When you’re doing too many things, the only way to keep your head above water is to take things one at a time. But this means narrowing your view to just what’s right in front of you. You don’t have a huge budget. You need to get that product launched. Sales first. And pretty soon, you lose sight of what’s going to be most beneficial for your business.

Take a step back and realize that a little bit of help to get things prioritized and expertly done is what you need to get out of the rut.

2.  How to Choose Which Tasks to Outsource

There’s a 3-fold guideline that we use at FreeeUp – and Nathan and I use this ourselves, too! – to help clients determine what to outsource. I’m sharing this with you here:


Ask yourself, “What are those tasks that I shouldn’t be spending my time on as a business owner?”

You are the captain of the ship. Your time is valuable. Don’t try to do all those mundane and repetitive tasks to try and save a buck. You’ll lose a lot more in the long run. Instead, think about the time that you can save to focus on more VALUE-ADDING tasks that can help you scale your business faster. Then these tasks can become more value-adding as well, in the hands of an assistant.

Make a list of these necessary yet time-consuming tasks that you need to outsource so you can start spending your time where you are most needed.


Ask yourself, “What are those tasks that I am not really talented at or trained for?”

You can probably get these tasks done, no question. But there will always be a limit to HOW WELL they can get done in any area where you lack expertise and experience. Moreover, it will always TAKE LONGER to do a task that isn’t in your wheelhouse. As above, continuing to do these tasks is not value-adding to your business, and can cause you stress that just makes you less productive than you could actually be.

When you decide to outsource these types of tasks to niche freelancers, you are getting an infusion of high skill and experience. This means higher productivity in less time, which translates to being able to scale your business faster. Any additional expense is well worth what you will save.

Make a list of these tasks that require specific skills and prepare to outsource them so you can start focusing on using your skillset for your business.


Ask yourself, “What are those tasks that I really hate doing?”

Don’t underestimate the power of passion. You may be used to just powering through, and this can be great in a crisis. But this is one of the most UNPRODUCTIVE practices over the long term. If you’ve been pinch-hitting, that’s fine. But if you’re doing tasks every day that just make you cringe, you need to get those off your plate.

A happy you is a productive you, and that means success for your business, too. Pass these tasks off to someone who actually likes doing them. Then you can start doing tasks that you like too. It’s a win-win.

3.  How to Interview and Hire

So you know what you want to outsource to scale your business faster, and it’s time to start looking for the right people. Here’s what you need to do to make this stage as smooth and effective as possible:

Task Preparation

The first step in this process is preparing detailed task descriptions. The more detail you can get in there about each task and how you want it done, the better. This is what will attract the most suitable candidates so you don’t get a bunch of irrelevant applications.

The next step is to do some research online to get familiar with the different common rate ranges for the tasks you are looking to outsource. Note that you will see a lot of variance based on location and skill level. Taking a close look here will take some time, but is going to be very useful as you determine what you need to spend to get the right fit.

Candidate Search

Armed with your task descriptions and rate ranges, you can start posting online to gather applicants to screen. There are MANY freelance websites out there, so you want to do some research into these.

Look for marketplaces that:

-specialize in the tasks that you are outsourcing.

-offer you premium support without asking for the moon in return.

-don’t require inordinate amounts of time and effort to make a hire.

-offer you the most experienced freelance assistants with the best attitudes.

Choose the marketplace that best suits your needs and begin accepting applicants.

Conducting Interviews

Interviews can take a lot of time, but they are so important. At FreeeUp, we always say, “Hire slow.” You need to take your time to determine if someone is the perfect fit. And you need to find that person because settling for anything less will mean loss upon loss down the road.

Before you schedule a hundred interviews, narrow down your list of applicants by checking their resumes and portfolios, if applicable. You can also ask for a cover letter or give them questions that will get you more details about why they are a good fit for the role.

When you interview, focus on their skills, attitude, and experience – another of FreeeUp’s 3-fold guidelines. Here’s a list of a few things you don’t want to miss:

-Verify the candidate’s skills by giving them sample scenarios specific to  your business and asking them how they would proceed.

-Watch out for red flags that indicate disinterest in the task, poor past performance, a lack of initiative, poor integrity, and the like.

-Verify the candidate’s experience by asking them about previous work in detail.

4.  Best Practices for Onboarding and Managing Remotely

Once you find the best person for each task, you must onboard them before you send them off to work. This is a very important bridging process that will properly integrate them so that they can work most effectively for your unique business.

There are many things that you need to include when onboarding to make the working relationship stronger and the work itself smoother. Basically, they cover specifics about your business and personal preferences on both sides that will affect how the work is done.

Here are some things you should discuss and agree on:

-working times and hours per week

-communication channels and frequency of reporting

-other SOPs to follow

-business goals / mission / vision

-pet peeves

If you get on the same page at the very beginning, you will find managing the freelancers you hire to be a painless process. Just make sure you stay in touch and make yourself available for questions and feedback.

Final Thoughts

Don’t get carried away when you’re outsourcing for the first time. You want to take it slow as you get into a good groove so you don’t get overwhelmed by the hiring process. There’s a lot to do, and it can become a burdensome experience if you jump the gun.

Take your time, take it step by step, and you will have a great hiring experience and may soon find yourself addicted to outsourcing!

Connor Gillivan is the CMO and co-owner of, a rapidly growing freelance marketplace making hiring online simpler. He has sold over $30 million online, has hired hundreds of freelancers to build his companies, is a published author, and is the owner of He currently lives in Denver, Colorado.

You can follow Connor and learn more about FreeeUp at:   @ConnorGillivan