A Guide on How to Succeed at Outsourcing

Outsourcing and getting freelancers is something that many people have tried and failed at. It's something that is so incredibly useful and cost effective, although unfortunately more often than not, people often have only had poor experiences, because after their first (bad) attempt, they gave up. In this article you'll learn how to not suck at it, and hire top talent!

(PS I recommend using UpWork for all your freelancing needs. It's what I will be referring to later in this post. Check it out.)

Know Exactly What You Need.

First off, one of the biggest mistakes that people make is that they have some idea of what they need, but they just throw up a job and expect the freelancer to know exactly what to do. You could not be more wrong. Imagine someone came up to you and said 'Hey, you're a designer. If I pay you, can you design my website?' with barely any extra information. Do you think you'd nail it? I doubt it very seriously. You would give it a go, but it is almost impossible that you'll do it exactly the way the had imagined. Freelancers are not mind readers, so how are they meant to know what to do if you don't tell them! This ties in with my next point.

Clearly Explain Everything.

Once you know exactly what you want, describe it simply and clearly, with as much detail as possible. I STRONGLY recommend having training documents and / or videos. For the documents, this can be as simple as headings and dot points in a word doc or Google doc. It doesn't need to be complex (and don't worry at all about the design), it just needs to be clear. Let's just say you needed someone to do data research for you, collecting emails. It could be something like:

1. Search the name of the place on Facebook.
2. Click on 'About'.
3. Click on 'Page Info'
4. Copy the email address and paste into spreadsheet.
5. Repeat.

This is literally all it has to be, and the more basic the better. For videos, you can use Quicktime to do a screencast. All you need to do is open Quicktime > File > New Screen Recording. This will record your screen and your voice. This makes it so much easier to understand for the freelancer, and it only takes you a few minutes. For PCs use whatever screencast software is available. 

Post the Job Correctly.

When you post a job, make sure you have a heading that clearly explains the role, and then include:

  • A summary of the job.
  • The key activities that will be carried out.
  • The key skills required.
  • A little bit about your company.
  • Why it's a great opportunity for the right person.

Importantly, don't forget to make it compelling! Make it exciting, it will attract better freelancers. Here's the first sentence of my job as an example:

"At AroundAbout we are excited to announce a position for a ROCKSTAR data research freelancer with an eye for design and attention to detail, to help us gather information on restaurants, bars and attractions in selected areas for our innovative mobile app! "

I've included the full job description for you to use an example at the bottom of this article.

Request a Cover Letter and Key Question/s

On UpWork you have an option to 'Require a Cover Letter' before an application an be made. Definitely do this, you can see straight off the bat who is clever and genuinely interested by the way they submit it. The best freelancer I've hired had a very well written cover letter that was clearly tailored to my job, it wasn't just some generic text that he copy and pasted. He was funny, energetic and creative. It made a good first impression and it definitely translated into his work. I have been very happy with him ever since!

You can also make them answer a compulsory question. I recommend this as well, because the way that they answer the question is another indicator for how good they will be. Here's an example of the question I had for freelancers before they could express their interest: 

"Our app is VERY visual, so the quality of pictures collected is CRITICAL. With our guidance and examples, do you have the skill to recognise quality content and pictures?"

Ask a similar question, request a cover letter and you will be able to get a better idea for who is the best talent from the beginning.

Do Trials.

Once you post your job, you will get applicants straight away (like really fast). You will get a range of freelancers, some very cheap, some quite expensive and everywhere in between. Most people's first instinct is just to go straight for the cheapest one. DON'T DO THIS. Do a 1 - 2 hour trial for few people to see who does the best job. It is very unlikely they will refuse to do it, but if they do, there are many others to choose from. After all, you're looking for someone that really wants to work with you.

Send them a message, thank them for applying and say you've chosen them as one of the potential candidates. Politely ask them if they would like to do a trial, and when they agree, this is where you give them the training documents and / or videos. Clearly outline what they are required to do. Tell them that there is only one position (if there's more, tell them there are scarce availabilities), that you've selected a few freelancers to do trials, and the one with the best results will get the job. This creates healthy competition and they will do their best work, instead of being lazy or slow. 

Review the Results

Once the trial is done, thank the freelancer and then take a look at the work. Whatever it is you're looking for, see who did it the best. For me I needed accuracy of the data, high quality photos and speed. I actually had two people do quite well so I hired two instead of one.

This is where you can look at the results, look at their rate, and then make a decision on who you want to hire. Simply weigh it up. Keep in mind their price does not always directly reflect their talent. The guy I hired actually had one of the lowest rates and he is great. Whilst I don't recommend getting someone that's too expensive, in my opinion I think it's always worth paying for quality. If someone is a clear winner and their hourly rate is slightly higher, it's worth hiring them. 

Once you've chosen who you think is the best, politely thank all of the people that did the trials. If there were several that did a good job but there was only room for one, let them know that even though there was one spot available, you'll keep them in mind should another opportunity arise. It's good to have talented people on hand that you've tested if you need them later.

Hire Them!

Time to make someone's day! You've checked the results, you're happy and it's time to hire the winner. Welcome them to your business and make them feel special. Tell them that you are a team, that they are working WITH you, not just FOR you, and you are exciting to have them on board. A friendly company culture is important. They will be happier, and they will do a better job for someone they respect. After this, let them know your standards. Make them feel welcome, but then clearly state what you expect. Something along the lines of:

"Welcome (name)!!! I am excited to have on the team. I look forward to helping you through this process and working side by side. We are a very friendly company that will look after you and any questions you have. However everybody on this team delivers - if your work quality or output is not up to our standard, I will let you know first. If it repeats, our agreement will end. Although I'm sure that won't happen! I will arrange the new videos for you and prepare everything for you by tomorrow".

This way they like you, they respect you, and they know that you know your stuff. Get off on the right foot from the start.

Teach Them.

This is very important. Once they come on board, walk them through everything that needs to be done. Be available to answer any of their questions (I recommend adding them on Skype) and understand that it is a learning process. They will make a few errors, but so do you. They will get more efficient as time goes on.

Look After Them.

If your freelancer is doing an ongoing role, make sure you look after them. Treat them with respect, give them a bonus when they are doing well, if they are in a tough part of the world make sure they can look after their family. If somebody is working with me I consider them as part of my family, and family looks after each other. 



So there you have it! With these tips in mind, you can now go out and hire a great freelancer. Check out UpWork and get started today! (My job description example / template is at the bottom),


(Twitter @mitchills)

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AroundAbout Job Description Example

Help Collect & Build the Database for an Extremely Exciting & Innovative Mobile App!

At AroundAbout we are excited to announce a position for a ROCKSTAR data research freelancer with an eye for design and attention to detail, to help us gather information on restaurants, bars and attractions in selected areas for our app! 

We are a free swiping app that helps you find food, drinks and activities around your location. We are basically Tinder for eating, drinking and exploring! Aside from our product we are a very fun company. We've also got training videos and documents ready for you!


  • Collecting HIGH QUALITY photos from Websites & Facebook pages.
  • Collecting ACCURATE data such as open hours, address, 


  • Attention to detail.
  • Good eye for design.


  • Work with a friendly, innovative and motivated team.
  • Ongoing role and continued income for the RIGHT person.
  • We are incredibly respectful, polite and easy to work with. Nobody is every considered below anyone else.
  • Training videos and documents supplied!

If YOU are the right person, take this GREAT opportunity to work with the best! We can't wait to have you!