Freelancer retention: How to keep your best talent coming back

The evolution of employment in recent years – firstly with more flexible working conditions and now the massive rise in the contingent workforce – has changed the ways in which companies will build a talent pool to solve specific skills requirements. Finding the right people – and retaining them – requires an evolution in recruitment processes, as well as changing attitudes to how freelance workers are managed and supported in the workplace.

This brings with it a new metric for HR departments to grapple with; freelancer or contractor retention. Those companies that embrace freelancer retention are likely to benefit from a whole series of opportunities off the back of improved and more flexible working relationships. Not least of these is reducing the productivity loss and recruitment cost, never mind the IP leakage, that comes with constantly churning talent. Traditionally, employers have thought about retention only within the context of the permanent workforce.

This was because of two reasons: one, permanent employees made up the majority of the workforce, so that's where it made sense to focus the effort; and two, freelancers were thought of as much more transient and temporary by definition, and therefore completely counter to a retention strategy. The pervading sentiment held by many employers, even today, is that if you want to retain a freelancer’s skills, you just hire them full-time. Of course, the major flaw in that thinking is assuming a freelancer is simply waiting for one of their clients to make a full-time employment offer. Or the assumption that even if they were looking for a perm role, that they would choose your business.

A permanent employment arrangement may be the perfect solution for the employer, but the freelancer may see it as a huge step backwards in their own career and working conditions. Freelancer retention is therefore not about full-time employment, but about ensuring that you can call upon the same proven freelance skills whenever new projects or requirements arise. And that means the freelancer has to want to work with you again.

Renewing your vows

Companies need to get a sense of how good they are to work with, because, unlike the permanent workforce, freelancers will just leave. Many contingent worker contracts only run for a few months, with the option to extend should both parties agree. Each time a contract is up for renewal, the freelancer has an opportunity to reassess their priorities as well as their relationship with the employer. And if they’re no longer keen to stick around, the freelancer can simply walk away by not agreeing to renew. Of course, you may not even be given the real reason why they choose not to renew, nor why they always seem to be booked out and unavailable whenever you approach them with future work; it’s the freelancer equivalent of “It’s not you, it’s me”. This is why some companies have started to focus a lot more on developing a culture of engagement and carrying out various checks to understand how their freelancers are doing.

A pulse check on your freelance recruitment process

While HR managers need to gather feedback on the company’s performance and its freelance culture, it should be collected with a light touch. The last thing a freelancer needs is further bureaucracy, friction or conflict to contend with. For example, you don’t want to subject freelancers to rigorous and compulsory feedback processes – full of complex forms, formal review interviews and combative complaint structures – as this sort of bureaucratic approach is anathema to the flexible, collaborative and comfortable freelance culture the feedback is intended to enable. Instead, you and your managers need to be extremely sensitive to any signals of discomfort or exasperation your freelancers might reveal in the course of their work. If your inflexible 70-day policy on paying invoices regularly provokes friction, take note that this may be one of the pebbles in a freelancer’s shoe that might discourage them from walking your way again. Even seemingly trivial gripes offered in passing might offer clues: that email chasing up an unpaid invoice, the extra hoops IT made them jump through to access email, the slightly less-cheery reception your could-have-waited-until-next-week calls and emails received when interrupting their work with another client. Taken individually, these minor inconveniences may not be enough to prevent a freelancer from working with you again but, cumulatively, they might make the overall experience of working with you more uncomfortable or inconvenient than it should be. Even if there is little or no feedback to be gleaned from the freelancer, the HR department can still assess a company’s performance by reviewing how the company “behaved” throughout the project.

For example;

  • On-time payments: Was the payment process clear and easy? Were any payments late (whether the freelancer complained or not)? Scope adherence: Was the agreed scope of work respected or did it keep changing or growing?
  • Clarity of instruction: Was it always clear who was responsible for each task, how to complete it and by when? Were all workflows clear, time bounded and with realistic expectations?
  • Management: How was the freelancer handled, including communications, approvals and decision making? Did management ever hold up the work (such as waiting for stakeholder feedback)?
  • Quality of the workplace: Was the freelancer able to work in a comfortable area with convenient access to all necessary tools and people (including the option to work remotely and/or with their own tools when appropriate)?
  • Culture: Did the culture within the workplace make the freelancer feel supported, welcome and a part of the team? Did factors like legacy processes and internal politics unnecessarily impact the freelancer’s ability to work effectively?

In the near future, how a business navigates new challenges and opportunities will increasingly rely on its ability to find the right people and build a talent pool to meet specific skills requirements. However, managing the various freelancers and consultants can also present a major challenge and a major cost. By understanding how to better retain talent and set them up for success, you can make sure that any managers who hire consultants or freelancers know how to manage them properly, supported by training that is informed by feedback from the freelancers themselves.

Key Takeaways

  • Freelancer retention has become a crucial metric for HR departments eager to build a reliable talent pool.
  • This requires companies to constantly assess their own performance when managing freelancers to remove friction and improve the overall experience.
  • Gathering feedback and identifying areas for improvement should be an ongoing activity, without adding extra layers of bureaucracy or complicating recruitment processes.
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Transforming a large organisation into a freelancer-friendly environment takes time and careful planning.

Find out more by downloading our free e-book: Building a freelancer culture.

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Bridget Loudon
Bridget is an accomplished entrepreneur, strategy consultant and private equity professional with a track record for success and a passion for change. Bridget has lived, worked and/or studied in Australia, Ireland, Canada, France, Hong Kong and the United States.

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