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How to Hire an IT Professional

What questions to ask to make sure your full-time IT hire knows his or her stuff.
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Ilustration© Jason Lee

Q: How do I make sure my full-time IT hire knows his or her stuff?

A: From your question, I assume that the days of enlisting everyone to jump in and help each other figure out hardware and software issues, from setting up a network to hooking up the printer, has become a waste of time. Or maybe your system crashed and you discovered that your IT contractor, the one who set up your business and knows it inside and out, is on vacation.

Whatever the case, there comes a day when a full-time IT staffer is no longer a luxury but a necessity. That day arrives for the average tech company upon reaching 20 employees, according to Spiceworks, a small-business IT management platform with clients worldwide. Nontech businesses can usually wait until they cross the 70-employee threshold.

So how do you know whether the IT candidate who answered your want ad is up to the task? We asked Nathan Brown, senior director of IT and production operations for Waltham, Mass.-based, which connects consumers with care providers, to detail his own selection process.

What kind of tests should IT candidates take?
I conclude IT interviews by having potential hires set up what will ultimately become their own computers. I'll ask them to install and configure software from scratch, and to do it as if they were setting up a standard configuration for the company. This exercise allows me to assess an applicant's ability to think long-term and big-picture, because I want my IT staff to think beyond the technology and focus on supportability, licensing and future needs of the company. If they come back to me with suggestions for improvements, updates, etc., I know they're worth a second look.

What specifics should I look for in my first IT hire?
I don't focus too much on certification; hands-on experience is more important. In particular, look for someone who understands and has worked on servers, switches, routers, firewalls and virtualization technology (where the same PC supports two completely separate users/files/programs, among other aspects). Ask your applicant what computer they have at home. If they say "Dell" and don't go into the processor, memory and operating system, they're not the geek you want.

Finally, look for someone with experience who started with desktop support and worked his or her way into networking and system administration. Understanding the support side of IT makes for a better infrastructure person. I also like to see diversity in knowledge of operating systems and hardware (i.e., Windows, Mac, Linux), as this demonstrates a broader knowledge, openness and--this is important--a general love for technology.

What about the nontechnical side of the equation?
So much of IT is customer service and relationship building. Your first IT hire needs to be someone who can be a real geek one moment and then go talk to the CEO the next and explain complex technical issues in a way that allows the CEO to make the right decisions.

If there's anything about the person that makes you question his or her ability to get along with all types of personalities, don't hire them.