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4 Steps to Hiring IT Contractors / Freelancers Who Make Your Life Easier

4 Steps to Hiring IT Contractors / Freelancers Who Make Your Life Easier

Wednesday, August 10, 2016/Categories: independent-contractors

Late-night TV infomercials show countless ways you can improve your personal life (Snuggies! George Foreman Grills! Thighmasters!). We don't have the host with a million-megawatt smile or sparkly celebrity endorsements, but wait until you see what we have in store for your professional life: four helpful tips on how your tech business can hire the right contractors and freelancers.

1. Take a Test Drive before You Commit

When you work with a contractor for the first time, it’s often a good idea to ask them to complete a short assignment or test project before bringing them on for something more long-term. This can be especially useful if you want to confirm they have the technical skills to get the job done.

“It is definitely better to hire someone who can bring along a track record of success,” says Alexander Grosu (@AlexanderGrosu), project manager at the pre-employment testing company (@TestUPOnline). “However, when this is not possible, testing the contractors should give you an accurate idea of whether or not they are suitable for the tasks you want to assign to them.”

Build in enough time to find the right contractor for the job. Otherwise, if the first few aren’t a fit, you might scramble to hire somebody, anybody, and end up with mediocre results.

“If you wait until the last second and hire the first guy that walks through the door, it can come back to bite you,” says RJ Martino (@rjmartino), president of (@iprovonline), a digital marketing firm and IT managed service provider. “We acquired a company that hired a contractor immediately. They had worked together for years and didn’t anticipate any problems, but two years later, the relationship broke down. Unfortunately, there was no contract, no insurance by the contractor, and nobody left to blame but me.”

The takeaway: Build in enough time for new contractors to complete a test project before you commit to giving them more work. And check to see if they have contractor insurance.

2. Remember: a Freelancer Isn’t the Same as an Employee

You know a freelancer isn’t your employee, but once they start working for you, it can be easy to lose sight of that.

A freelancer may juggle multiple clients and projects or work non-traditional hours. This means they might not respond to your emails or texts immediately or even during business hours. That’s when it’s important to remember that it’s reasonable to expect work to be completed on time and in a professional manner, but you can’t hold freelancers to the same standards as you would an employee.

“Working with freelancers or contractors is different than working with employees,” says Grosu. “It is essential that you allow them to work at their own pace, within reasonable guidelines and deadlines, of course.”

So if something is time sensitive, by all means, check in with your freelancer. Just don’t constantly look over their shoulder, or they may move on to a client with less of a Big-Brother vibe.

The takeaway: Freelancers need to be free to control how they work. Make sure the work is getting done, but don’t micromanage.

3. Work on Your Relationship

Once you're past the “getting-to-know-you” stage, communicate frequently with your contractor. That way, you're confident they understand the project’s parameters, and they feel free to come to you with any questions.

“Always be very detailed about what you expect out of a freelancer and what they can expect from you,” says freelance writer and blogger Heidi Hecht (@Squidoogeek). “For example, a smart freelancer will insist on being paid for any work he has to redo because you were unclear about your expectations or any work that you request that wasn’t included in the original contract. Expect the working relationship to go south fast if you don’t do this.”

To stay on track, establish regular check-ins. During this time, you can review work completed to date, discuss upcoming deadlines, and answer any questions. Without regular communication, you run the risk of the project not meeting your expectations or not being completed.

The takeaway: Regular communication can help improve the success of your project and minimize the chance of your contractor “ghosting” you.

4. Have a Backup Plan in Case You “Break Up”

One of the biggest challenges when working with freelancers is handling the transition if they abruptly stop working for your company. For example, consider what would happen to your project if…

  • Your freelancer moved out of state.
  • Another client offered them a more lucrative gig.
  • They quit coding to follow their life-long dream of beekeeping.

To avoid chaos after a freelancer leaves, make sure you or someone at your business keeps close enough tabs on the project to step in and finish it if need be.

“As a policy, we would always buddy up the freelancer with someone from our in-house team,” says Troy Hazard (@troyhazard), a serial entrepreneur, speaker, author, and television host. “In the event the contractor could not or would not complete the job, then at least our team member could pick up where they left off.”

The takeaway: Use the buddy system so you or someone from your team can finish any uncompleted work.

But wait – there's more. Read our articles “Hiring Freelancers / Contractors? Do These 5 Things First” and “5 Contract Essentials for a Happy, Productive Relationship with Your Tech Contractors” for additional tips on managing contractors.

About the Contributors

Alexander Grosu

Alexander Grosu is a project manager at TestUP, a company providing pre-employment tests to business owners and HR professionals who want to make sure they make the best decision when it comes to hiring candidates. With a keen passion for helping his clients and team, Alexander will always be the first one to share tips and knowhow in his fields of expertise.


Troy Hazard

Troy Hazard has founded and nurtured 12 businesses in the recording, real estate, advertising, marketing, pool service, restaurant franchise, and technology industries. He is the author of the book Future-Proofing Your Business, former cable TV talk show host of Gettin’ Down 2 Business, regular co-host of The Big Biz Show on CBS Talk Radio and Business Talk Radio Network, and a former Global President of the Entrepreneurs’ Organization.


Heidi Hecht

Heidi Hecht is a freelance writer and blogger from the Orlando, Florida, area. She lives with a tuxedo cat who will give you a high five for a treat.




RJ Martino

RJ Martino founded his company iProv in 2001. The company started out creating websites for a few local businesses and grew into a multi-functional business as an IT managed service provider and digital marketing agency. RJ says running a business with two sides has made him a jack-of-all-trades in IT management and services, as well as digital and inbound marketing.

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