Employer Tips: 4 Steps to Improve Your Outsourcing Process

In this post, the Rapid Business Lessons team shares 4 ways to strengthen remote working relationships. Read on to learn how to protect yourself from risk and get better results when outsourcing work to freelancers.


  • Adopt a milestone payment system. Most freelance hiring horror stories boil down to the same thing: the money was paid, but the work wasn’t done – at least not to a level the employer expected. Using a milestone payment system eliminates most of the risk in this regard.
  • Get to know your freelancer. It’s generally believed that an individual can protect themselves from a bully –  or even a serial killer – if they tell the aggressor their name. It’s obviously not a hard and fast rule, but sharing personal details has a humanizing effect, which makes it harder for the aggressor to inflict whatever violence they intended. Likewise, if you think your freelancer might be out to kill your project, sharing some personal details can really help. A freelancer who you connect with on a personal level is much less likely to abandon the project when things get tough. I outline ways to build a strong connection with your freelancers – without compromising your professional authority –  in my online course for employers.
  • Pull no punches during the interview process. Most employers don’t even bother with interviews when they outsourcing work to freelancers: an obvious mistake. But even if you do make time to Skype or speak over the phone, you could be leaving yourself vulnerable to unsuitable hires simply because you’re asking the wrong questions. When you’re outsourcing work to freelancers, you need to abandon the traditional interview style. Forget those arbitrary questions about “their biggest flaws” or their ability to “work as a team.” Outsourcing is less about the freelancer’s fit into your organizational culture, and more about whether or not they can get the job done. With that in mind, your interview time should be spent outlining the project’s exact parameters and timeline expectations. Use this opportunity to discuss their qualifications, and to describe exactly what you want from their end. If the freelancer hesitates or shirks from anything you’re saying, consider that a red flag.
  • Educate your freelancers. Freelancers come from all backgrounds, regions, and walks of life. This means that even a very skilled individual could be used to working in a way that’s unfamiliar to you; maybe they don’t make a habit of keeping their clients informed of progress, or they have a different idea of what a ”perfect project” looks like. Whatever the case may be, it’s become clear to me that the freelancer and employer must be working from the same “playbook” in order for things to run smoothly. This is one of the main reasons I created my freelance course. Synergy is tough to achieve with remote working relationships, but it’s possible when you’re both informed by the same policies, communication techniques, and business best practices. If you’re being educated out of the same “textbook,” you can make a long-distance collaboration work. I’m currently offering my freelancer course at no charge. There’s no catch – it’s totally open-access and free, and you can share it with all of your prospective freelancers.

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