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Connor Gillivan

Connor Gillivan is the author of Free Up Your Business: 50 Secrets to Bootstrap Million Dollar Companies, a serial entrepreneur, and the CMO and co-founder of When he's not bringing together hundreds of freelancers and business owners, he's mentoring entrepreneurs through his site, He currently lives in Denver, Colorado.

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5 Action Steps to Start Outsourcing Tasks Within Your Business Today

December 15, 2017 / Leave a comment / by Connor Gillivan

As an entrepreneur, do you always find yourself running out of time for your other tasks?

Do you always end up with more items on your to-do list left undone than you have checked off?

If the answer is yes, then you know that something needs to change. But don’t worry, because most business owners run into the same problem. It’s easy to get caught up with everything that’s going on, including every task that you need to accomplish on a daily basis.

When you’re busy and laser-focused on what you do, time can easily pass you by and you may not even notice. The problem there is that as a business owner, your time is too valuable to be wasted.

The good news is there are things that can be done to avoid running into this problem day in and day out. You don’t have to do everything on your own because doing that often leads to disaster. Not only will you get burned out, but your business will suffer too.

It’s all about delegation, and with that said, below are 5 steps you can take to start intelligently outsourcing some of the key tasks within your business.

1. Identify the first tasks to take off your plate

Your business surely has a lot of tasks that can be farmed out to a freelancer or contractor, but how do you identify which ones?

Before you outsource, make sure to identify the core areas of your business. When we say core areas, we mean tasks that have a direct impact on the product or service your customers get from you. A good example is if your business specializes in computer programming. You definitely wouldn’t want to outsource that because it’s what your business is all about. It is your main deliverable. What you can outsource instead are repetitive tasks like data entry, or specialized tasks that require certain expertise like social media management, blogging, or copywriting.

Once you’ve identified your business’ core areas, it would be easier to narrow down which particular tasks you can entrust to another person.

2. Create an avatar of your ideal assistant

The best way to identify what kind of assistant you would like to work with is to put yourself in his or her shoes by creating an avatar for your ideal assistant.

What is an avatar anyway? Your ideal assistant avatar is a fictitious character that represents your ideal assistant. This character is a composite of all the characteristics you’re looking for in an assistant including their demographic, psychographic, motivations and aspirations in life.

The more detailed and specific you can get, the better. This is so you know exactly what you’re looking for and can more easily attract exactly the ideal candidate. Below is a good example of an avatar for your ideal assistant:

“Kevin is a 30-year old husband and father of three from the Philippines who quit his day job to pursue a career in freelancing because he wants to be able to earn a living for his family and spend as much time with them as possible. He works 10-hour days and even works on weekends. He wants to start his own business because he doesn’t quite feel comfortable in a corporate environment and wants to be able to do what he does best freely without someone limiting his creativity as a social media manager and writer. He is proactive and meticulous, treating each of the clients he works with as a business partner and every project as a priority.”

Once you have this detailed description of what you are looking for, finding that kind of assistant will be easier.

3. Request for an assistant with the help of Freelancing sites

Once you’ve identified your ideal assistant, you will be ready to hire one. Doing this today has become a lot easier with the help of freelancing sites like Upwork, Elance or FreeeUp, where you can find thousands of people with varying expertise at a rate you can afford.

The great thing about these freelance marketplaces is that you are one step closer to the hiring process. These platforms have already pooled a good slice of the global talent pool. The only thing left for you to do is to check if they fit into your preferences and requirements. Once you’ve met your match, they can start right away. No need for tedious onboarding and training periods like they do in the corporate world.

4. Setting clear expectations with your assistant

Hiring someone is one thing. Getting the right person is another.

The important thing to remember before you start working with your assistant is to set very clear expectations to avoid any misunderstandings. Here are a few examples of questions that you might want to get cleared up before work begins:

  • How many hours do you require?
  • What is the frequency with which you need repetitive tasks done? (e.g. how many social media posts per week)
  • What specific time of the day do you need him or her to be online?
  • Do you need him or her on weekends?
  • What specific requirements do you have for each assignment? (e.g. the word count for blog posts)

These are just some of the specifics you can talk about. The key is to be totally clear and detailed with your expectations. Encourage him or her to ask questions if there’s confusion on their part so that you’ll have a smooth-sailing working relationship through the course of the project.

5. Manage your assistant

One of the common mistakes business owners make is leaving everything to their assistant after expectations have been set. Unfortunately, your involvement doesn’t end there. Your assistant, just like an employee in a corporate setup, needs someone to manage him or her.

You can’t leave them to work on the project and not monitor their performance or the quality of their work. You need to able to track their progress, tell them about areas for improvement and be able to lend a helping hand when they need it.

You need to make sure that they have everything they need to perform their tasks well. For instance, do they have complete access to the tools and the websites they need to work on? Do they know where to go to get access?

Having regular talks will help as well. It is through these conversations that you will learn what they’re going through, what difficulties they’re having, and how you can motivate them to perform better.

You hired them to help you take some of the burden off your shoulders, but you still need to make sure that those tasks you let go of are being performed properly and that you are giving them the necessary support if they’re having difficulties.


A business owner’s time is valuable, and since we only have 24 hours in a day, it’s going to be impossible for you to do every single task needed to make your business run.

You can’t do it all, which is why outsourcing some of them is one of the best decisions you’ll ever make. You’re not only avoiding stress, you’re also giving your business the opportunity to grow with the help of other people.



Connor Gillivan is the author of Free Up Your Business: 50 Secrets to Bootstrap Million Dollar Companies, a serial entrepreneur, and the CMO and co-founder of When he's not bringing together hundreds of freelancers and business owners, he's mentoring entrepreneurs through his site, He currently lives in Denver, Colorado.