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Checklist: How to Choose an IT Contractor Who Will Keep Your Data Safe

Many small-business owners hire outside help to build or install their business technology, office networks, point-of-sale systems, and custom software. However, if you're like most of these business owners, you might find yourself in a difficult position. You're not an IT expert and you may not know exactly what you need – or who can help you get what you want.

This checklist explains what to look for in a quality IT contractor, so you're not left guessing:

  • Get referrals. Start the process by reaching out to friends or professional contacts who might know an IT contractor who can help you. Finding an IT contractor someone you trust can vouch for can save you a lot of time, so be sure to publicize the fact that you're in the market for IT help.
  • Advertise your need. Websites like WorkMarket.com specifically advertise to technology freelancers. Many let you post positions free of charge.
  • Check the website. A professional IT contractor will have a website where you can at least find contact information and at best find examples of past work.
  • Ask for examples of past work. If you aren't able to find work samples on your own, ask for examples of projects similar to the one you're asking the contractor to complete. If you don't like what you see, feel free to move on to another candidate.
  • Ask about their data security practices, including how they handle data breaches. This is essential. Any IT contractor you trust with your customer data and sensitive information about your business should have a solid plan in place to keep that data safe. That includes a plan for how to respond for data breaches, which have become all but inevitable in recent years.
  • Call references for top candidates. When you find a candidate you like, request contact information for references you can call. Ask these people about the candidate: how he performed, whether he stayed on budget and on deadline, whether he communicated well, whether he was easy to work with. This is a crucial step, as some otherwise contractors who look good on paper might not be a good hire if their former clients wouldn't recommend them. Of particular note: ask references about their satisfaction with the contractor's security practices.
  • Request proof of insurance. Your IT contractor and any subcontractors she plans on bringing onto your project should have General Liability and Errors and Omissions Insurance. Ask to see a Certificate of Liability Insurance for all professionals who plan to work on the project.
  • Request price quotes. When you've found candidates you like, ask for quotes for their work. Compare these and choose the one that fits your budget.
  • Request completion timelines. Get these in writing, too. This can be crucial if things get off target down the line.