Freelancer Club
6 min readFeb 11, 2020


Although outsourcing projects to a freelance workforce is a logical, cost-effective growth strategy, companies often lose value during the recruitment and management process resulting in high turnover of freelance personnel, underwhelming hires, or time wasted on repetitive training.

The freelance/client relationship has interested us for many years and having facilitated over 200,000 freelance hires in that time, we’ve learned a few things during that time. In addition, the Freelancer Club is run exclusively using a freelance workforce that has come with highs, lows and a lot of lessons learned. Here are a few pointers we’ve picked up along the way.

The key to a healthy relationship is clear communication

A freelancer will often be working on multiple projects for a range of clients simultaneously, all of whom require their focus, creativity and time. Whilst a freelancer will give their all to each client whilst clocked in, they are not always accessible to change or adapt work outside of these hours.

It is vital to create a streamlined and regular means of communication with the freelancer so both parties feel engaged and committed to completing the project. Equally, knowing your boundaries, when and when not is acceptable to reach out and whether or not you’re on the clock if you do are all important to clarify early doors. Understanding the daily and weekly ‘rhythm’ of a freelancer is critical, particularly if they are working remotely. Are they out of their office for part of the week? Do they work on your project in the morning? Are you available when they are available? Discuss timings before signing a contract and find a rhythm that works for you both.

Regular communication also helps freelancers create cohesive working relationships with other colleagues in your team, as there isn’t always enough time for them to really integrate into a company. Email is fine, although it can feel unnecessarily formal after a while, whereas some companies are comfortable using Skype chat or even WhatsApp to communicate.

The Slack App is our preferred middle-ground at Freelancer Club. Not only is it easy to use and intuitive, but it also enables our freelance team to chat in groups and to individuals within the team. It’s mobile and facilitates everything from third-party integrations to image or video sharing. Their pro account facilitates screen-sharing too although Skype, Chrome Remote Desktop or Teamviewer can all do this without having to upgrade.

Milestones and motivation

Staying on top of a project is vital, whether a freelancer is working remotely or not. Carly Vidal Wallace from fashion company Not Just A Label (NJAL) says that she uses “different project management systems from Asana to Wunderlist as well as the multiple types of video conferencing apps which exist to regularly be in communication visually as well.” Advancements in the way we can connect via video, screen sharing and voice is facilitating remote working relationships like never before.

“Using a combination of live chat, video calls and screen sharing has made it possible for us to manage a large team of remote workers. Although the tech is getting better every year, it’s still hard to beat a freelancer sitting beside you in the office. Often, it depends on the nature of the project, however, our preference for most of our freelance team is remote work with a couple of days in the office per month to touch base. This saves on office overheads whilst keeping a close connection with the team.” Freelancer Club founder, Matt Dowling,

Motivating a freelancer workforce requires a very different approach to a staff of full-timers. Not only will most freelancers feel patronised when using traditional motivational techniques but they are often not with you long enough for the benefits to take hold. A key aspect to motivating freelancers is respect, trust and the cultivation of brand values. If a freelancer feels invested in the brand, the project and the people, and you treat them with respect and maturity, you’ll get the most out of your freelance workforce. Setting milestones or using a system like ‘Sprint’ is also a good way keep the project on track.

Freelancers will often be used to a range of CRM and project management tools so don’t shy away from integrating them into your system, even if it’s a short project. Hubspot have an awesome free CRM that is very user-friendly while the new kid on the block, Monday App, is getting positive reviews. Whether you use a third party app, have your own CRM system or use good old spreadsheets, a freelancer will appreciate the milestones to keep them on track. When juggling multiple clients at a time, a clear project management structure benefits both parties.

Feeling like part of the family

When it comes to getting the job done, freelancers have one huge advantage. They are much less likely to be involved in the company’s social structure and office politics, which means they are free to exclusively concentrate on the work at hand. Remember, the hierarchical structure of employer and employee doesn’t work as well when it comes to freelancers. We’ve found that treating freelancers like business partners or collaborators will provide the foundation for a healthy working relationship.

Tip: sit side by side when in a meeting, not face to face. Use the one laptop, scrap of paper or tablet. This creates a collaborative atmosphere as if solving a problem together rather than an interrogation that can feel confrontational or hierarchical.

Freelancers are the CEOs of their own businesses, meaning that they generally have a level of professionalism and independence. Throw in the mix that they most likely set up their business to avoid having a boss tell them what to do and you’ve got a good sense of a freelancer’s character.

A freelancer’s income depends on building great relationships with clients and, although they aren’t dedicated to one particular company, they are dedicated to producing their best work for your company. Trust that they will do this and you’ll reap the rewards.

Capitalising on their skillset

A freelancer’s unique set of skills often produces fresh perspectives and ideas that full-time employees wouldn’t have thought of. Matt Dowling notes how “the best part about working with freelancers is that they are masters of their craft and often bring a huge amount of value to a project above and beyond my expectations. They are typically more versed in self-management and don’t require as much of my time as an employee.”

This is reiterated by Vidal Wallace who notes “as freelancers are working on so many different types of projects for multiple clients, they never get stale and always have innovative ideas. We also find they are ready to jump in and embrace any size project.”

Even if a company is primarily seeking freelancers to ‘fill in’ for full-time employees, having an expert carry out a project exposes your business to a plethora of specialised skills. Will Godfrey from host management company Airsorted mentions how the marketing team usually reaches out to freelancers “when we require specialist skills that are not available in our team.”


Despite the challenges, hiring freelancers in the UK and internationally is not slowing down. In fact, it’s rapidly speeding up. The UK’s is now home to an “estimated 5 million self-employed people,” according to

Managing freelancers is something that should be integrated into how your business is run. Unlike working with full-time employees, it doesn’t cost enormous amounts of your resources, time and money to look after a freelance workforce when you get it right.

To summarise, implement a killer line of communication and provide the freelancer with clear briefs, work on building the business relationship as two equals and look for the skills that you don’t already have. With this, freelancers will be more than happy to crack on with a project.

Freelancer Club is transforming the way companies connect with freelancers and contractors. We use cutting edge technology to narrow your search to find exceptional content creators, designers, writers and influencers for your projects. We’ve also developed a streamlined communication tool that cuts out the formalities and helps you hire in a matter of minutes and our new Concierge Service is changing the way companies hire and manage freelance talent. Get in touch to arrange a consultation.

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