Outsource Like a Boss!

Andrew Curnow
10 min readNov 11, 2017

July 19, 2017

How to use Freelancers to your advantage.

If you’re anything like me you never fail to have a chuckle every time the Airtasker — Like a Boss ads come on TV. If you haven’t seen them yet, do so. You can thank me later.

For many entrepreneurs, startups and existing companies, taking on freelancers just makes sense. Not only do freelancers have work-ready talents with specific skills that can be used for new and isolated projects, they can also be extremely cost effective.

From social media expertise to content writing, UX design to full stack development , freelancers can help take your project to the next level.

However there can be drawbacks. While the best kinds of freelancers can deliver on projects that your or your team has little experience in with greater efficiency, the worst can cost you time, money and even your reputation.

Choosing the right freelancer.

For the uninitiated the job of choosing a freelancer for the first time can seem a daunting task. A typical job posting on a site like Upwork, Elance, or Freelancer will attract dozens of responses from prospective candidates all vying for your approval. However applying a few basic principles can help you make the right choice and will often lead to a long and mutually beneficial partnership.

First things first. Defining your project.

A poorly or loosely defined project will lead to headaches down the track for both you and your chosen freelancer. The advantage in utilising freelancers comes from being able to leverage someone else’s skills to further your vision. If that vision is not clear from the outset, you greatly increase the chance of running over time and over budget or worse still ending up with only a partially completed project.

Try to be as detailed in your project description as you can. This should include clear instructions as to:

  • What you will be providing to the freelancer in order to complete the project. For example if you are building a mobile application the app developer will need graphic assets, back end development and hosting. Are you providing these ready to go, or are you expecting the freelancer to produce these also? Sometimes you will only discover things you need after discussions with potential candidates so be ready to adapt your expectations if required.
  • What exactly do you expect to receive from the freelancer at the completion of the project. If you are requesting logo design for example, what format do you want the final product delivered in? And in what resolution? Do you need more than one version?
  • Set a completion date for the project and let candidates know that payment won’t be made for projects that do not reach completion by the due date. Be firm but also realistic. If you’re not sure how long something should take, get some estimates from several candidates and then set a firm date in your final agreement.
  • Include any files that the selected freelancer will need to complete the task in the project description itself. This way if there are any unforeseen issues (read: they need more information) they can be resolved prior to the commencement of the project. If the material is sensitive then use a duplicate set of files that contain the same types of information so there there are no surprises later on.
  • When setting up your project it pays to consider the old adage — Cheap. Fast. Good. Pick two. You should select a budget based on what you can afford. While a higher budget will almost always get you a better finished product, you might be surprised what you can get with a bit of negotiation. Using the tips in this post I was able to build a fully operational Android social media app for less than five thousand dollars, something that would have cost ten times that using a traditional developer.

Assessing the candidates

When you post your project you will start start receiving quotes almost instantly and the higher your estimate budget the more bids you will receive. Keep in mind that many of these are placeholder bids that get sent automatically before the prospective freelancer has actually read your project. I always wait at least 24 hours before I start looking at bids in earnest.

Once you’ve received your bids it’s to start sorting the good from the bad and the downright ugly. While cost is usually at the forefront of every entrepreneur’s mind there are a couple of things you should always consider before bringing the bid amount into consideration.

Completion rate

Most freelancer sites will show a percentage of completed jobs for each candidate. This is a key indicator of not only the freelancer’s skill but also offers a vital insight into what they might be like to work with. Filter out any candidates with less than 90% of jobs completed.

Star Rating

Do not consider any freelancer with a star rating of less than 4.5 or based on less than 20 reviews. While you can sometimes hit the jackpot with a new freelancer who will offer a vastly underpriced quote in order to get their foot in the door, you are far better off going with a proven performer.

Rehire Rate

This is a really valuable metric as a freelancer that is hired multiple times by the same client likely not only delivers high quality work but at a competitive price. However it can also be a little misleading as some projects (eg. mobile application development) don’t necessarily lend themselves to repeat hires. Compare the candidates repeat hire rates vs. others on your short list and look through their reviews to find multiple reviews from the same client to see if you can work out what types of projects they’re getting rehired for and if that matches your project brief.


Exclude any prospects who have more than one or two poor reviews within the last 12 months. A single poor review can often be the fault of the client rather than the freelancer if all the other reviews are glowing, but if there are several then it’s cause for concern. Also keep in mind that many freelancers are actually teams or small companies with rotating rosters so look for recent reviews which will give you a better understanding of who you’re going to be working with now.


A prospective freelancer should have an existing portfolio of work they can show you that is applicable to the project you want completed. Have a look through their portfolio in detail and ask yourself if you would be satisfied if your project was completed to the same standard.

Skills vs. Tools

Understand the difference between skills and tools. As an example Photoshop is a tool whereas logo design is a skill. A freelancer having a tool does not necessarily mean they have the skill you require. Or vice versa. Check their portfolio for projects they’ve completed that match your project brief.


Once you’ve taken these other factors into account it’s time to look at the bids themselves. Although it shouldn’t be your only decision-making consideration, cost is a real factor in hiring the right freelancer.

Interviewing your candidates

Now you have got your shortlist it’s time to start a conversation with the applicants to find out more about their skills, background and how they envisage carrying out the project. This will help you to make a final decision.

Ask them to provide you with their understanding of the project and your requirements and if they have any questions. If you have to repeat yourself often or they say they have no questions at this time, it might be wise to cut them from the pack. A good freelancer will always have at least a couple of questions to further understand the project and if you are finding communication difficult at the interview stage it is only going to compound once your project gets started.

After speaking with each of your remaining candidates get your top one or two to provide you with a written breakdown of their understanding of the project and how they intend to complete it along with deliverables and milestones. Go back and forth over any unclear points until you are both happy. This is known as a Scope Document and will form the basis for your contract of work. You can see an example of a scope document for an mobile application here.

Getting the best result

Once you’ve chosen your freelancer, to ensure that you’re getting the most out of them and that they’re producing the best work, here are some further tips to keep in mind.

Draw up a contract that indicates clear deadlines and expectations

Fingers crossed no problems arise when your freelancer is working on your project. However, in case they do, you’ll want to make sure that you protect your interests by drawing up a contract. Use the aforementioned Scope Doc as a guide.

More than just giving you a sense of security, though, a contract can be a great way to define your project expectations to your freelancer. Having deadlines and standards written out and outlined will make it easier for the two of you to refer to should any confusions come up.

Pay for the project, not the time

Instead of focusing on project time, focus on delivery. It’s a very different sort of management than the typical 9–5 work structure, but paying a freelancer based on a project deliverables will likely deliver the optimum results you want. Plus it will save you costs in the long run.

After discussing the project at length with your desired freelancer consider how long it should take your to complete each milestone and give them some leg room for a completion date. A missed hard deadline can cause unnecessary tension. These deadlines should be included in the contract of work.

Define clear deliverables

One of the biggest risks in outsourcing is the prospect of an incomplete project. The very nature of the relationship means it’s possible that a freelancer might just up and leave forcing you to start from scratch, often at a loss. You can mitigate this risk by defining clear deliverables with individual milestones. For example, for a mobile application you might require the freelancer provide you with not only the .apk file but the source files also at each stage of development. This way you can pick up right from where they left off should the worst case scenario eventuate.

Stick to the brief

Any time a change occurs that will affect a freelancer’s work, you might be asked by the freelancer to tack on an extra payment and it’s likely that the payment won’t be at the heavily discounted rate they offered to win the work in the first place. As such you should try and stick to the original project brief as much as possible. If a change can be left until after the project is completed without having a significant impact you should consider doing it later to avoid disagreements over how the change affects the rest of the project.

If you absolutely must change the brief part way through discuss it openly with the freelancer and redo the contact of work to include the change and any costs involved so you have a clear path forward. Don’t expect them to do additional work for free. This will only strain the relationship.

Treat your freelancers like they’re part of the team

Pushing for team morale extends to your freelancers too. Even workers who prefer the independence of a freelance gig like to feel included in teamwork. Just like regular employees, freelancers are more likely to stick around and feel a sense of loyalty to a company or project if they feel personally invested.

Give an incentive to see a freelancer’s best work

I usually negotiate fairly hard with potential freelancers to get a good deal, often playing them off against each other to ensure I’m getting the best price. As a trade off, I typically offer the successful candidate a bonus at the end of the project based purely on my discretion and valued somewhere around 10–15% of the total value of the project. This encourages the freelancer to not only see the project through to fruition but also to make sure that they do all the little things to polish off the project and make it the best it can be, rather than taking on a near enough is good enough attitude.

Final Tips

Here’s a couple of final tips to help you get the most out of your freelancing activities. Happy outsourcing!

Use competitions instead of small projects

If you are thinking of running a small, clearly defined project, consider running it as a competition instead. This allows you to stick to a very specific budget and look at a number of proposals before choosing one or more winners. Plus it costs you nothing if none of the entrants deliver what you’re asking for. Competitions are great for design based projects.

Stay on site

Some freelancers may ask you to pay them privately via PayPal or discuss the project using Skype or Whatsapp or similar. They’ll tell you they can do it a little cheaper as they don’t have to pay the sites fees. Don’t do it!

Professional freelancer marketplaces offer you protections against fraud and dodgy operators. Keep all your communications and transactions on site to ensure transparency and the best result.

Define your currency

Make sure you and your freelancer are speaking the same language and put it in your contract. There’s nothing worse that coming to an agreement on price in dollars (AUD) only for your freelancer to say they were quoting in dollars (USD).

Use your own tools

Most professional freelancer marketplaces offer tools or badges for assessing a potential candidate’s skills and proficiencies. While these can be useful for filtering out large numbers of applications (based on English language proficiency for example) I have always found it better to talk with each short listed applicant in detail to assess them personally, rather than relying on the site tools alone as these can often vary depending on which freelancer in the team you actually get.

Trust your gut

A good freelancer will focus first on your satisfaction and then on being paid. If a freelancer is hounding you to release a milestone before a task is completed or if it’s been completed to a poor standard, it might be time to rethink the relationship.

Small (10% or less) upfront payments are okay as they help establish trust early on, particularly if the freelancer has already put in a lot of work with you to win the job by way of detailed proposals etc. Remember, the freelancer has the same fears of being ripped off that you do.

However if you are being asked to make significant payment just to start the work, walk the other way.

Once a task or milestone has been completed and to your satisfaction you should pay your freelancer promptly and in full.

BONUS: You can use this link to get $20USD to use for your first project/contest when you sign up with Freelancer.com so jump in and have a go yourself!



Andrew Curnow

Founder of Miit. Interested in breaking down barriers to human connection.