The Small-Business Owner's Checklist for Hiring an IT Contractor

If you own a small business and need to hire an IT contractor, it can be tricky to find the right one for a couple reasons:

  • You’re probably pretty busy, and you may not have time to spare searching for a new vendor.
  • If the expertise you need is in an area where you don’t have a lot of direct knowledge, like IT, the search can be even more confusing.

If you’re not sure how to get started, or even what questions to ask, don’t worry – we’re here to walk you through it.

Check, Check, Check it Out: Your IT Business Contractor Hiring Checklist

  • Identify your needs. Before you start your search, make sure you know exactly what services you need an IT contractor to provide. You don’t want to waste time interviewing a graphic designer when you actually need a software programmer.
  • Ask around. Talk to other business owners in your area. If possible, try to find an IT contractor who has worked for a business similar to yours in the past. “If they have experience with your particular industry, that could be helpful,” says Dave Ketterer (@d_ketterer), president of . “Every business is different but some things are the same, so they may have insight if they have another customer in the same industry as you.”
  • Search online. If your crowdsourcing hits a dead end, try an online search. Use keywords relevant to the skills you need, such as system networking, PC repairs, etc. Lisa Hendrickson (@callthatgirl), Microsoft Outlook expert and founder of , , says she gets the majority of her business through these types of targeted searches. “Everything is based on Internet searching now,” Hendrickson says. “If you go to Google and type in ‘Outlook expert,’ I am number one in the world.” Try a search on the Better Business Bureau, Angie’s List, or Yelp for more recommendations.
  • Come armed with questions. Prepare a list of questions to ask any potential candidates. That way you’ll know if they have the skills and experience needed for your specific project.
  • Get quotes. Once you’ve identified a few potential candidates, ask them to provide you with a quote that includes the scope of the work, so you’ll know exactly what you’re getting for that price.
  • Call their references. Ask your top candidates to provide current or past customers you can call to verify that your new potential IT contractor is as amazing as he claims to be. You can also ask for examples of past work if relevant.
  • Make sure they’re insured. Since you’ve done your due diligence, you’ve no doubt hired an IT business consultant rock star. However, it’s always a good idea to make sure that they have some kind of IT contractor insurance. Typically, a technology Errors & Omissions Insurance policy is the one to look for. If they have E&O coverage, it means their insurance carrier should be able to step in and cover a claim if they make a mistake on the project that ends up costing your business money. You should also verify that they have Workers’ Compensation Insurance. Depending on state laws, there’s a possibility that if they get injured while working on your project, you could be found liable for covering the costs of their medical care. Our blog post “4 Insurance Policies to Carry if You Offer Small Business IT Consulting” covers this topic in more detail.
  • Get it in writing. Once you’ve made your decision, get a signed agreement that clearly spells out which services the IT contractor will provide for your business. This can help avoid a potential miscommunication, and if they don’t deliver as promised, you are in a better position to take any legal action necessary.
  • Check in regularly. Consistent communication is essential in any business relationship. You don’t need to follow your IT contractor around, checking everything they do, but there’s nothing wrong with scheduling a quick meeting or phone call to ensure everything is proceeding to your satisfaction.

One Surprising Thing You Needn’t Worry about When Hiring an IT Contractor

There is one thing it may surprise you to hear that you don’t need to worry about when looking for an IT contractor: certifications.

“If I was to get a certification in Microsoft Outlook, it really doesn’t matter, because the work I do is hands on, on the streets,” Hendrickson says. “I wouldn’t say certification would make or break it for me if I was hiring somebody.”

Ketterer agrees that certifications shouldn’t factor into any hiring decisions. “Unfortunately, a lot of certifications out there, people just crammed and passed a test but don’t learn anything,” Ketterer says.