Finding the right IT pro for the job was tough enough when everyone was human.
As GenAI tools contribute to a massive increase in job-seekers—LinkedIn applications increased by 45% last year, according to the New York Times—asking the right question can help IT hiring managers zero in on a practitioner’s special skills and expertise.
We spoke with hiring managers about what they like to ask prospective employees once they establish that the candidate is, in fact, real, and get them in the room.
Draw me a network. Let’s hope you have a pen if you want to work with Gabriel Beltran, technology director (and IT Club creator) at the middle school at Abby Kelley Foster (AKF) Charter Public School in Worcester, Massachusetts.
Beltran likes to add a skill test to an interview. For a junior role, perhaps he asks the candidate to replace a keyboard or troubleshoot a laptop that cannot print.
To get a prospective systems administrator in the later phases of interview to demonstrate their expertise, however, Beltran asks a purposely open-ended question: Design a network on paper for the school.
A “starting point” sketch might resemble a home network with a router and computer, he said. A more advanced candidate might draw a rectangle labeled “building,” and within that rectangle, a firewall, core switches, wireless access points, phones, laptops, tablets, fiber-optic cables, VPNs, and a cloud-service backup.
The question can lead to a 10- or 15-minute conversation that reveals an interviewee’s knowledge, according to Beltran. Questions like, “How would you add a second ISP? How would you decide to add more access points?” could keep the interview going and get a sense of an individual’s expertise.
“The question still can give you the feedback to know if that person has a skill to make everything work on the back end,” Beltran said.
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You’ve got a call from a difficult user… Bill Holmberg, director of IT at trucking company Wayne Transports, supports a company of about 170 office workers and more than 700 drivers.
While candidates, he said, are often quick to share their expertise in software, hardware, or networking, he wants them to understand the job requires a level of service. A go-to question, he said, might be presenting a what-would-you-do scenario for an interviewee where a frustrated user wants a tool or feature—say, an outdated CRM system—that goes against standard operating procedure.
“Your job is to get with the user and look at them as your customer, the customer of our shop,” he said.
Holmberg wants to see if they’re a “positive challenger.” Does the candidate know how to deescalate a tense situation?
“I’m looking for the soft skills to deal with people and make them feel like their problem was legitimate and that we value them as a coworker,” Holmberg said.
How have you changed things up? IT decision-makers might be the ones in need of some positive spin when it comes to the hiring process. A 2025 outlook report from talent-development company Revature found that 88% of a surveyed 230 US tech practitioners are concerned about fulfilling their IT talent needs this year.
As companies aim to innovate, hiring managers need staff that can embrace emerging technologies.
One of the favorite hiring questions from Jeff Collins, CEO at IT observability platform WanAware, is, “How have you affected change in a previous role?” Innovating and pushing boundaries is important to Collins.
“Whether it’s software developers, infrastructure teams, or DevOps teams, we need those people that have done that in the past and are willing to do that in the future,” he said.