How to Find, Hire and Keep the Most Competent Freelancers

25/03/ 2015   |   Joanna Paula Cailas  |   Outsourcing

Your ‘office’ is open to the whole world. Who do you hire? How do you find the best of them, and how do you keep them when you’ve got them?

It’s quite addicting, delegating tasks externally. Ideas keep popping up because your mind is free from quotidian concerns. More ideas, more to assign to your freelancers. It’s a happy cycle when you’ve learned to pick people for projects, or if you no longer even have to pick and already have a good individual or team who could work for you as needed.

Because it’s the biggest cog in the wheel, it’s also the biggest challenge of outsourcing: finding, hiring and keeping the most competent talents around.

Finding the perfect assistants

Not being hampered by location is a perk AND a disadvantage, but only if you see yourself being buried under applications. It doesn’t have to be that way.

Rather than just opening the door and letting applicants rush in, why not walk out the door and pull the likely ones instead? In my years as a freelancer, the majority of my jobs came from job invitations rather than applications. Clients invited me. Many of these jobs were even “invite-only” postings.

Proactive rather than passive

We at USource wouldn’t recommend closing yourself off–you might miss great freelancers also proactively seeking jobs. But use filters, and take the time to write about the position carefully. You weed out the weak applicants by being detailed and comprehensive (without being redundant and wordy) in your job posting/interview questions.

You get better responses. Good applicants would be detailed and comprehensive (without being redundant and wordy) in return.


Is there room for charm in a job posting? Yes. Just a single sentence–a joke, a pun, a self-deprecating quip–can change your whole posting from dull to desirable. Like attracts like. What you are is what you’d draw to yourself. It’s like finding a boyfriend or a girlfriend!

Do you want charming freelancers you’d love to work with? Be charming. It’s that easy.

Especially for VAs and writers, they notice when a certain client sounds like a ‘keeper’ just from the job posting.

Who do you hire?

This is the easy part. Depending on the tasks and in addition to their qualifications, suss out three things as you look for and interview your freelancer/s:

  • problem-solving skills
  • passion
  • charisma

They need to be able to do their jobs well, without you having to do all the thinking while they just obey orders. They have initiative. They have drive to learn and do great. You can’t supervise them but you can rely on them.

They should fit in–not terribly important, but it can go a long way if you and your freelancer/s AND your team by themselves, get along. To use tech company jargon, you and your freelancer/s can have your own ‘culture’ in relation to the work and to each other.

At USource, we have inside jokes. Dan gets picked on. We have fun (the fun not necessarily the result of the former, but it often is). That’s our culture.

How do you keep them?

They’re the most competent, so of course, they’re also the most sought-after. Speaking from experience, my teammantes and I don’t like to spread ourselves too thin, so we take our pick of jobs and tasks.

How do you make sure you always get picked? And even better, how do you make it so you don’t have to be picked because your freelancer/s simply never stopped working for you? Oh, sure, you ended contracts, or you’re on an as-needed basis, but your freelancer likes you and you’re a VIP in his/her book.

It’s beyond being charming this time (though it’s a plus).

The RSA’s (the Royal Society for the Encouragement of Arts) What Drives US video reveals a stunning but always-been-there fact: we’re not motivated by money. What keeps us moving and engaged in all the things we love to do are: a sense of autonomy, the challenge of mastery, and purpose.

Autonomy is already taken care of–freelancers are self-directed, and that’s why many of us love freelancing. And doing the things we do and getting prompts, challenges and leads from our clients make us better. That’s mastery.

As for the contribution/purpose part, that’s on you.

Sure, your freelancers are individuals who should and would certainly cultivate something themselves. But even as you plan and outline and map out every move and every eventuality in your startup, create an SOP that’s not so much ‘standard’ as dynamic, practices that fuel creativity in your freelancers. Let them contribute. Let them build alongside you.

There’s always the risk of detachment when you outsource. This is what the naysayers argue about. But it’s easy to make a freelancer care about your business! Simply let him/her have a hand in it as well, even in the smallest ways. We always love what we create.