How to hire a freelancer – 25 useful tips

Over the years I’ve had many opportunities to work with freelancers. Recently a friend had a bad experience looking for freelancers, and I tried to help her find new ones. That prompted me to write a bit about my method. While not completely foolproof, it will increase your chances of finding better freelancers.

Defining the job offer

Before we start, there are a few questions you need to ask yourself.

1) Is this for a job I know how to do myself, but just need someone else to do it, or is it for a job I don’t know how to do myself?

Sometimes, I need someone to do some programming for me. Sometimes it’s some programming that I know how to do but just need manpower, and sometimes it’s in an area that I’m really unfamiliar with, say, machine-learning image analysis. Sometimes it’s for something completely different – e.g. narration, or graphic design – where I really can’t do it myself.

2) For a job that I don’t know how to do myself, do I know how to evaluate the quality of the work?

Let’s say I’m looking for a narrator – I can certainly judge the quality of the work. My judgement might not be the best – I will probably miss some finer points, but I will still be able to see if someone did a good job and it sounds good to me. On the other hand, let’s say I’m looking for someone to port my system to Azure for me, and at best I’m familiar with AWS. They might be making major mistakes in design and I wouldn’t know, because I’m not familiar with Azure.

3) Do I know how to evaluate the quality of the freelancer?

Prior to hiring the freelancer and looking at the result of their work, how well can I predict how good of a job they will do? Of course, looking at past work is the most obvious thing, but sometimes that’s also hard. Many people can boast of impressive demo projects but still will not be able to do what I want them to. Sometimes, their past work is protected by NDAs, e.g. security advisors. In these cases I will usually need to rely on recommendations.

4) Do I have fixed requirements, or is this a project with changing requirements?

Sometimes the requirements are very clear – I need some narration done, a background drawn, some specific functionality implemented. Sometimes, I want a large feature developed, with the details not yet specified, and I need the first mockup version implemented to be able to be specific. Sometimes, I need a result “make my DB go faster” or “make my website secure” – and the particular actions to take are as yet unknown.

5) Is this a long term or a short term, one time engagement?

Sometimes you just need some small task done. Sometimes you are looking for someone to work with for the long term. If I’m looking for a short term and fixed price project, then the requirements must be well known beforehand, and I must be able to judge the quality of the result.
Long term projects can be opportunities for freelancers, so they provide you a way to get a better price or more leeway in changes requested.

6) What is my budget for this project?

That’s one of the most critical questions. You might have a total project budget – or just a monthly budget for work done. Having a tight budget might force you to be very strict about your plans and requirements. Having some experimentation budget might allow you to hire multiple freelancers and pick the best one.

Specific techniques

Once you are clear with yourself about the answers to all of these questions, many decisions will become much easier to make. Here are some techniques to handle various situations.

My requirements are around results and I don’t know what steps need to be done. Examples: “Make my code faster”, “Make my website secure”, “Propose a design to my website pretty”

7. Make sure you know how to measure or evaluate the results. Specify clear criteria for success.
8. Do you need just proposals for changes, or actual implementation? Actual implementation is better, unless you can clearly evaluate the proposed changes.
9. When looking for freelancers, ask them what steps they will take to do their work, and what they expect the proposed changes are going to be. Then compare the results of multiple experts, this will allow you to evaluate who makes sense and who does not.
10. Building on the previous step – if you had one freelancer suggest that he will do X and the other not suggest it – ask the first “Why did you propose X?” and the second “Why didn’t you propose X?”. For example, when optimizing a database, one freelancer can suggest she will “Set up a read replicate”. Ask the other one why he didn’t suggest it.

I have a lot of budget and I want to get the best freelancers

11. It depends on what you mean by “a lot of budget” – but one easy way to get good freelancers is to hire multiple freelancers to do the job of just one, and pick the best result.
12. A cheaper alternative, is to hire multiple freelancers to do a test task, and keep only the best. You won’t even need a lot of budget for that, and if the project is critical for you, there’s a very good chance it’s worth it.
13. If you’re working with developers, and you are hiring multiple freelancers, consider having them code-review each other. This will increase overall quality and give you another opportunity to evaluate their work.

I am looking for a freelancer for a long-term engagement

14. The first task must be an evaluation task, and this should be communicated to the freelancer.
15. Similar to the previous situation – you can use the evaluation task to pick the best freelancer out of a group. You can have all freelancers do the same task, or give each one a different task, as you still get to keep the results even if you don’t continue working with them.

General advice

16. Always communicate clearly what are your requirements, and what is the evaluation criteria you will be using. This applies to all communications; to the first message, and to your reply when the job is done.
17. Don’t be afraid to disagree with the freelancer. Don’t be afraid to say that you want changes. Just be clear and upfront about your expectations, and keep to the terms you agreed.
18. If you’re not an expert in the area – get a friend to give you some advice, especially if a lot of money is at stake.
19. Don’t be afraid to add requirements and questions when you are selecting a freelancer. Worst case – they will decide not to work with you.
20. When choosing which freelancer to work with, don’t forget to evaluate the freelancer on their communication ability. If someone doesn’t answer your job interview questions, or doesn’t understand them – how will they complete your requirements? How will they understand the urgent bug you’re trying to explain?
21. When hiring developers – you MUST either know how to manage a development project, or have a team manager, or at least have a friend advising you.
22. If you’re hiring for a small non-programming work, consider using fiverr.com.
23. If you’re hiring for a more complex project or engagement, consider using upwork.
24. If you’re using upwork, my preference is to filter on >90% job success, and prefer freelancers with significant experience on the platform – which means a lot of money earned or many job-hours done.
25. For an additional useful listen (in Hebrew), try https://omny.fm/shows/odpodcast/shahar-erez-15-growth which I listened to recently – a lot of useful advice there.

I hope this is useful for you, please share with me in the comments your own techniques for hiring freelancers!