Imagine this: You have two employees. Both are clueless about tech. Both are scrambling to meet a critical client deadline. Then, out of nowhere, the office Wi-Fi tanks and all progress stops. Employee One tinkers in vain with the router. Employee Two sits on hold with your Internet service provider’s customer frustration line.

Fruitless hours pass and you miss your deadline. Your client bails and you kiss their trust -- and their business -- goodbye.

Sound familiar? If so, then it could be time to hire a full-time on-site information technology (IT) support person, says Greg Bennett, veteran IT director of Shammas Group, the parent company of Downtown L.A. Auto Group and other Los Angeles-area businesses.  

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When you do, Bennett says your first step is to pool potential candidates for the job through your local tech trade school, a technical recruiter or an online career website (LinkedIn, Indeed, Glassdoor, etc.). Then, when you interview them, be sure to ask these 10 essential questions to identify the right hire:

1. How well do you work with others?
You need to be sure the person you hire can easily, clearly and patiently communicate with your employees when tempers flare over tech that won’t cooperate or simple user error.   

To get a feel for the candidate’s communication style, ask her to walk you through a tech mess she untangled for someone else. Or role play with her through a common help desk request --  the forgotten password or, worse, the dreaded Blue Screen of Death (frozen computer). Be on the lookout for candidates who speak in terms your employees can quickly grasp. Not jargon-packed technobabble.

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2. What’s your process for handling tech support requests?
Running a company’s tech help desk has to be orderly, efficient and relatively fast. The candidate should demonstrate that she has an effective help desk structure and workflow in mind. How specifically would she field, log and respond to employee requests for help? By phone? By email? By instant message?

Ideally, she would record, organize and track all requests using a reliable online help ticket solution, like DeskPRO ($30 per help desk agent per month), Kayako ($24 per agent per month) or HappyFox ($19 per agent per month for the Small Business Plan and $9 per month for the Startup Friendly Economy Plan).

3. What will you work on when you’re not putting out help desk fires?
It’s important to vet out candidates who don’t seem willing to step up and take on non-help desk-related bigger picture projects.

“They should be busy all the time, not sitting and playing World of Warcraft all day long between help desk tickets,” Bennett says.

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Other tasks the candidate should be up for spearheading include: ongoing computer and other device setup and maintenance (configuring, customizing, updating, cleaning, etc.), keeping up with the latest technologies and making employees aware of them, and crafting a long-term (three- to five-year) plan for fulfilling your company’s evolving IT needs.

Also, if you think additional IT staff will be needed down the road, the candidate should be open to recruiting, training and managing new hires.

4. Will you assess my existing information systems?
The candidate should express that she’s prepared and qualified to analyze and report on the functionality and feasibility of your company’s existing equipment and systems. This should encompass your computers, landline, VOIP and cell phones, email solutions, printers and “basically anything that plugs into a wall,” Bennett says.

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She should be able to tell you what new software applications for your current computers are needed. What can be updated, improved or removed?

If upgrades are justified, is she capable of sourcing, building a budget for and installing new hardware and software? If not, she’s off the list.  

5. What will you do to cyber-secure my technology?
With smaller companies increasingly coming under attack by cybercriminals, it’s paramount that the candidate you hire can design and deploy a plan to continually secure all of your digital information systems, especially those that house your mission-critical data. A solid strategy should involve rolling out firewalls, spam filters and anti-virus and anti-spyware solutions. Performing routine security audits is also a must.

If all else fails, what would the candidate do if your site got hacked? It’s important to know.

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Trust is critical here because, as Bennett cautions, your IT person will have full administrative login credentials, likely to the lion’s share of your business’s most sensitive information. To that end, he says you should absolutely run a criminal background check on potential hires. “You also want to avoid people who say they’re really good with computers but yet they’ve only watched YouTube how-to’s and hacked their phone.”

And, if your business deals with financial transactions, a credit check is definitely in order. “If a candidate can’t take care of their own finances, that could throw up some red flags that they’re looking for a way to take you to the cleaners,” he says.

6. What’s your experience with data backup and disaster recovery?
How and where your company’s data is stored and backed up is equally as important as securing it, Bennett says.

“Unfortunately, though, most small businesses blow off the backup and disaster recovery plans,” Bennett says. “They wait until it’s too late and then they decide they need them.”

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If you have the resources for a proper server room, make sure the IT person you’re considering has the skills to design and implement one. For example, does she know how to keep a server room from being compromised? Or how to protect it against natural disasters, including storms, floods, fires and earthquakes?

Or, if you outsource your data storage to a third-party cloud provider (like Dropbox or Amazon Web Services), as many small businesses do, they are responsible for backing up and physically securing your data on their end.

7. Are you available after-hours and on weekends?
There’s never a convenient time for a server or a computer to crash. Systems can and do fail outside of regular work hours, so it’s important that your dedicated IT person is available on-call, 24/7, on nights and weekends or whenever trouble calls. Be crystal clear about this expectation from the get-go, so you don’t hire someone who isn’t OK with this level of commitment.  

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8. What industry certifications do you have?
Although Bennett feels that drive and eagerness to learn are often more valuable than having a four-year college degree and “a ton of certifications,” the biggie he says he looks for is the Computing Technology Industry Association (CompTIA) A+.

People who earn this particular certification should “have a good understanding of what needs to be done” when troubleshooting PCs, “with a little bit of hardware in case they need to change a hard drive.” Having it also suggests that they understand basic networking for small businesses, he says.

9. Can you describe what IT infrastructure you have set up or supported in the past?
Asking this allows the candidate to highlight any relevant experiences she’s previously had (or not) with former employers or clients. Better yet, it can help you weed out potential hires “who are just blowing smoke and don’t know what they’re talking about,” Bennett says.

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If you want extra assurance that the person has the technical experience she says she has, but you’re not sure because, well, tech is all Greek to you, Bennett suggest you bring a seasoned IT consultant in to sit in on the interview and download with you after. “That way you’re not getting bamboozled by someone who’s all talk.”  

10. What’s your salary range?
How much money a candidate could put you back depends on a few factors -- the job requirements, and her experience, skills, certifications and geographic location. With so many variables at play, it’s best to come right out and ask what her ballpark is and negotiate from there, especially if you’re on a tight budget.

“Look for a technically skilled, entry-level go-getter and you’ll generally save on costs,” Bennett says, “not for a specialist networking guru with CISCO certifications all the way up and down the table because they’ll cost you an arm and a leg and they’d be overkill for a small business.”

Glassdoor lists salary ranges for IT help desk personnel here.  

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