10 tips for those working with freelancers for the first time

Freelancers are increasingly becoming a more important element in your talent strategy. As organisations become more familiarised with flexible and remote working, the leap towards working with freelancers will become smaller. 

Hiring freelancers is a great way to expand the total pool of talents available to an organisation. Other benefits of working with freelancers include shorter recruitment timeline, simpler onboarding process, and cost effectiveness will compound the value of freelancers to your organisation.

However, working with freelancers is very different from working with your full time colleagues. They are often not co-located with you, they have different schedules, and might even live in completely different timezones. In our years of working with thousands of freelancers, we have accumulated several tips that might be helpful in your journey to hiring your first freelance talents.


1. Have a SMART goal in mind before engaging a freelancer

Freelancers often work on a project-basis. For you to work with freelancers effectively, you need to have a clear idea of what you want to achieve. 

A simple SMART framework will make sure you get what you need from your freelancers:

SMART = Specific, Measurable, Actionable, Results-based, Time-specific goals

Having your goals clearly laid out helps freelancers align your expectations. They will come into your project with a full understanding. It includes your expectations, current processes in your company, and the timeline you are working with.

Starting with a clear goal also helps you determine the kind of freelancers you want to work with.


2. Vet vet vet

With so many open marketplaces right now, many people can easily claim expertise in areas they have no experience in. The last thing you want is to get a freelancer that cannot deliver, and end up having to do all the work internally.

You need to vet your freelancers, just like how you vet your full time employees. When you are assessing your freelancer candidates, make sure you get their full background. Have their portfolio (at the minimum), past client referral letters, and even have a chat with them before commissioning any work. If you have a big project, it is worthwhile to meet your freelancer in person too to make sure that he/she can get along with your team and are comfortable with your processes.

Another positive indicator that you have to look out for during your vetting is the rate of repeat clientele this freelancer has. The more repeat clients they have, the likelier for them to be good at what they do.


3. Set a cadence

It is important for you to set a regular check-in cadence with your freelancers. This is especially important if your freelancer is working remotely and is in a different timezone. During these check-ins, make sure they show you tangible outputs of their work. They can be scribbles, concept drawings, or just thoughts that have been written down. These might seem trivial, but these are extremely important. These shows that they are making progress towards the final deliverables.

The purpose of this is not to micro-manage them, but to ensure alignment in the direction of the work. You do not want to have your freelancers deliver close to final work at the 11th hour only to realise their work is not according to your expectations or worse, your requirements.

By setting a regular cadence, you are also helping the freelancers fall into your team’s regular schedule. It makes it easier for you and your team to plan for work and you don’t have to keep asking for updates. This improves the working experience itself, and is likely to help you build better relationship with your freelancers.


4. Choose someone who can communicate well

We all know that communication skills are very important when it comes to work. But it becomes critical for freelancers. Communication is an even bigger part of their job even though that’s not what you hire them for in the first place.

Think about it. Your freelancers will unlikely be colocated with you, which means that every interaction with them needs to be scheduled and planned for. Your freelancers will not have access to any informal conversations or discussions that usually happen in the office. This could result in their missing important context and details about the project. Your freelancers will need to deliver their work according to the specifications. This means they need to know how to manage expectations, clarify scope, and explain their ideas well.

Choose a freelancer that is comfortable speaking AND writing in the language your team communicates in. The writing bit is important too as they will likely communicate with you mostly in written forms through messages, emails, chats, etc.


5. Choose someone who is responsive

Freelancers are free agents. They come and they go when you need them. But that should not be how you communicate and work with them.

When you have someone who is generating a critical piece of work for you, they can either be a blocker or the sole cause of a total failure in a project. You do not want other people’s work to get held up just because someone takes 2 days to reply to an email. Choose a freelancer that you know can be responsive and responsible for their piece of work.

While it is important to have someone who is responsive, remember to also have reasonable expectations with your freelancers’ response speed. They are also human and they need a break as well. Do not expect your midnight email to be replied within the next 20 minutes.


6. Choose freelancers in the right timezone

Having people working in the same timezones has its benefits. So does having people in different timezones. Depending on your project requirements and the role you need to fill, choosing a talent based on their timezone can be beneficial to your project.

If you are working on a project that requires a lot of discussions and synchronous collaboration, try to choose someone who is working in a timezone with significant overlap to yours. You want to make sure that you can schedule calls and work with them easily.

On the other hand, working with freelancers in different timezones can be extremely beneficial in certain cases. For example, if you are working on a project that is waterfall in nature and needs continuous uptime within your team. This ensures there is continuity in your work, and gives your team a good momentum. There will be progress every time someone starts their workday. Despite that, make sure you still have 1-2 hours of overlaps in everyone’s time for that catch up meetings to align everyone on the project.


7. Choose a freelancer that is digitally-savvy

Not all freelancers are digitally-savvy. For your project team to work well with freelancers, you want people who can adopt new tools quickly. Your team may already have their preferred collaboration tools, and you will want to onboard your freelancers onto these platforms quickly.

Having someone who can pick up new collaboration tools quickly makes a big difference to your team’s productivity. You want someone who not only knows how to use these tools, but make full use of them. Imagine having to review an article with someone who does not know how to use the commenting tools in your text editing software. Or having to make design edits with someone who does not know to look at their notifications for annotations your team has made.


8. Choose a freelancer that has the time

Freelance talents often have multiple projects they are juggling at the same time. We know that you should not purely make your hiring decision based on how many projects someone is working on. However, it is important to make sure you choose someone who can give you the time required to generate the quality you need.

Freelancers can easily get distracted if they have too much on their plates. They are agents whose income is solely based on projects, so it’s often very difficult for them to turn away projects especially after a sales drought. While you do not want to penalise people who are in-demand (they are likely very good, which is why they are busy), you want to make sure that they are able to adhere to your timeline and requirements.

Before awarding a project to a freelancer, make sure you have a clear timeline that they can review so both parties know if the project is feasible from a time perspective. Having a freelancer who can give you their full attention may affect the quality of your project significantly.


9. They are vocal and proactive

You want to hire freelancers that are proactive with their work. Freelancers do not have anyone reviewing their work constantly, or anyone to bounce ideas off easily. Having someone who speaks their mind, even in an environment full of new team members, ensures constant ideation and builds a strong feedback loop to iterate on ideas.

Most of the time you hire freelancers with skills that you do not possess in the organisation too. It is likely that these people are the ones who know best about their trade. You surely would want them to share their knowledge and share their thoughts on how you could solve a particular problem. Having someone who is vocal and proactive will ensure you get the most of their skills and time.


10. Know that they are human too

While you only work with freelancers for a short amount of time, that does not mean you want to “get the most” out of them. Remember that freelancers are human too and their work is equally important to the work done by your team internally.

Be respectful of their opinions even if they seem divergent to the perspective your team or company has. That’s why you hired them in the first place: to get an outsider’s expertise and perspective. Be respectful of their time too. Don’t be tardy with your internal timeline and yet expect your freelancers to still deliver on time. Give them enough head’s up so that they can plan their day and life. You are not their only client, and they have a life to live outside of their work.

These tips are meant to help you generate better output from working with freelancers. By output, we do not just mean deliverables, but also working experience with these talents. Freelancers can be a very valuable repository of expertise, advice and skills, and they can help you save cost. But that is only possible if you are able to build a long-term relationship with them and help them understand how your business works and what you need from them.

Ravenry is an on-demand platform that connects you with Asia’s top 5% of writers, analysts, and consultants within 24 hours, so you can save on all that interview time. A strict vetting process is also of top priority, so you can be certain to get matched with only talents of the best quality, catered to the productivity needs of your business.

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