How to Hire a Qualified Independent Contractor

By Lindsey Novak

March 14, 2019 5 min read

Q: I worked for large companies most of my career. When I decided to go off on my own, I hired a website designer I felt I could trust. I was impressed by his sites and hired him. I didn't know enough to ask the detailed questions, but I assumed the sites were functional. He answered openly, so I felt comfortable hiring him.

Independent web designers seem to ask for a large portion of their fees upfront, so I didn't object. The site was attractive, but the design elements on each page were not consistent throughout the site. To correct these issues, he wanted more money. I thought that was inappropriate, so I decided not to spend more than his original quote. Later, IT professionals told me the site was not set up for interaction with visitors. When I called the guy to ask about it, he had no knowledge of those features.

Because I know many people leaving companies to start their own businesses, I want to warn others to do extensive research on all the aspects of a website that can make or break a new company. I have since talked to other artists and entrepreneurs who have experienced similar problems. It's an expensive lesson when people don't ask pertinent questions. Please warn people that entrepreneurship isn't all it's cracked up to be.

A: People may not need a warning about working on their own, but they definitely need to learn to plan what's necessary to work productively on their own. The trouble you experienced involves not knowing all that was needed before leaving your job. There is no guaranty of an independent contractor's performance without a written contract, and without an attorney review of the contract, instructions can get lost in the communication process.

A common problem in hiring a contractor to do anything of which you have little or no knowledge is that you can't ask questions about things you don't know, so you have no assurance the person will be able to deliver the product you desire. The greater the job's complexity, the more difficult it is to know what to ask for and to hire the right person for the job.

This is also true for regular workplaces. A human resources director received a complaint from a department head about the quality of employees applying to the job opening in his department. The HR department had advertised for qualifications that were discovered to be inadequate for what the department head wanted. HR changed the ad to attract a different level of employee. Unclear or incomplete communication can easily cause such mistakes — and not just for individuals desiring to hire an independent contractor.

You were right to not pursue your contractor for further work on your site. It might have resulted in one miscommunication after another, with neither of you understanding the problem. When searching for a freelancer or independent contractor, ask for and personally check the client referrals rather than accepting the person's word. For services in which no physical product is produced, ask previous clients if the results were completely satisfactory. Word-of-mouth advertising can be valuable, as long as you are not getting references from the person's family members.

Recent experience in IT is important if a worker is to achieve your website goals. Seek someone who, for example, worked at a large organization and has resigned to go out on their own. They will know the inner workings of what it takes to create a high-functioning website. If they can't do it all, they will likely have contacts who will be able to help.

A university IT manager said his school hires hundreds of IT employees — perhaps 300 Java developers in addition to others — to manage and update the university's site. Such an employee may be able to provide guidance or refer you to the type of worker you need. It's not just a matter of trust. It's a matter of matching a worker's experience to your goals. It may not be easy, but it is your responsibility to hire correctly.

Email your workplace issues and experiences to [email protected] For more information about career and life coach Lindsey Novak, visit, and for past columns, see

Photo credit: at Pixabay

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