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IT Brew

Hiring

Billy Hurley

itbrew.com

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 

, 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.

Let’s hope you have a pen if you want to work with Gabriel Beltran, technology director (

) 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.

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be presenting a what-would-you-do scenario for an interviewee where a frustrated user wants a tool or feature—say, an outdated CRM system—that goes against standard operating procedure.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.

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.

An illustration of nine hands, each holding a résumé, popping out of a laptop screen.

IT hiring managers share their favorite interview questions

Three pros share how to get a candidate to demonstrate their expertise.

Brianna Monsanto

Handing over the keys to the new driver in the family? Daunting. Handing over the keys to cloud instances at your company to a new hire? Perhaps just as daunting.

A new employee’s first day is a big deal for everyone, and especially for the IT department, which is responsible for setting up the appropriate permissions and access controls for all of the organization’s cloud-based applications. It’s a massive responsibility, given the 

 if those same permissions are not properly supervised. A 

 found that 23% of cloud identities, both human and non-human, have “critical” or “high severity” excessive permissions.

Jay Martin, CISO at IT solutions and services provider Blue Mantis, told IT Brew that the industry is in a “fairly immature state” when it comes to handling cloud permissions and that having a standardized process around it is critical.

“The last thing you want to do is onboard an administrative assistant on the HR side into your financial system,” Martin said. “So, there’s practices that need to be set up in advance.”

 Neeraj Methi, VP of cybersecurity solutions at Myriad360, told IT Brew that organizations should avoid just letting anybody have the ability to create and renege on cloud-related permissions and implement a formalized process instead.

“Define a process, open tickets, and have a trail behind everything which is being requested and denied, so that you have an idea where all these access are,” Methi said.

Kurt Seifried, chief innovation officer at the Cloud Security Alliance, added that organizations should remember that vendors are constantly adding capabilities that could shake up how things are done.

“Your cloud vendor, especially somebody like Amazon, Microsoft, Google, or Zoom even, [is] constantly adding features and security,” Seifried said. “You gotta keep up with that.”

Once an employee is successfully provisioned, the fun doesn’t stop there. Seifried told IT Brew that there are many mistakes that can be made around access permissions once set. For example, for employees who are no longer with the company, Seifried’s “lockout procedure” for Google accounts used to mean suspending the account, changing the password, and un-suspending it to hand over access to managers. That changed after he realized former employees could potentially still access the account through credentials saved on Google’s account recovery feature.

“Lessons were learned,” Seifried said.

Martin added that organizations should be mindful of appropriately adjusting cloud instance access when employees switch roles in their company, an area he said customers tend to do poorly in.

 Some companies have begun to automate the process around cloud provisioning. Methi told IT Brew that it could help bolster productivity as users are able to access cloud credentials faster and eliminate room for human error.

“If you’re doing it manually, how effective could [you] be [at] keeping track of it?” Methi said, adding that the task could become a “nightmare” for some organizations.

Karthik Ranganathan, co-founder and co-CEO of Yugabyte, an open-source distributed SQL database company, told IT Brew that the cloud provisioning process at his company is mostly automated. Ranganathan said that Yugabyte is able to constantly update its processes around onboarding and has made it a significantly shorter experience for new hires.

“Now we’re talking hours,” Ranganathan said. “So, employee starts on Monday. By Monday afternoon, we’re sending them email. They have Slack. They have everything.”

Regardless if a company chooses to partly or fully automate the cloud provisioning process, Martin said it is always important to have a formal process in place.

“You can automate as much of this as you want with technology, but the first step really is to make sure that that process is vetted, that process is documented, that you have the proper workflow,” Martin said.

What to consider when handing new employees the keys to the cloud

“The last thing you want to do is onboard an administrative assistant on the HR side into your financial system,” one CISO tells IT Brew.

Tom McKay

Quite a lot, actually. Large language models (LLMs) might have an impressive (and/or alarming) ability to mimic human art and writing, but if they’re fed garbage, they’ll dump garbage..

One of the first new jobs to emerge from the LLM frenzy is prompt engineer—professionals who refine prompts entered into artificial intelligence/machine learning (AI/ML) tools to improve the quality of responses. Some coverage touted prompt engineering as a hot job that can 

—the staggering number of variables in their data sets means it can be difficult even for their designers to debug the models when they act unpredictably.

Hence, the demand for methods to make LLMs do what their users think they’re telling them to do (and cut down on 

). Victor Sanh, lead machine learning scientist at Hugging Face, told IT Brew that research to make deep learning models 

 remains “very, very experimental” and “not super actionable right now.”

Enter: the prompt engineer, a title that can also be vague, as the roles can have 

, from general prompt debugging, to domain-specific analysis, to actually integrating AI technology into software.

 jobs in prompt engineering: Indeed.com has around 200 job listings for the search term “prompt engineer” within 100 miles of San Francisco as of Oct. 24, 2023, while ZipRecruiter has around 30. What’s more, many of those results mention prompt engineering as complementary to other desired skills, such as designing distributed systems or developing AI/ML algorithms.

Ben Stokes is the founder of PromptBase, a “prompt marketplace” for LLMs like OpenAI’s ChatGPT or Midjourney. PromptBase markets itself as helping users “save on time and API costs.”

“For most people, it’s an act of discovery, where it’s a lot of trial and error, where you’re just continually prodding the LLM, tweaking little parts of the sentence to see how that changes the output,” Stokes told IT Brew.

“I think at the extreme level, you’re tracking every single word change and how that changes the output from the prompt,” he added.

One of the key challenges facing would-be prompt engineers is that their data often loses relevance when AI/ML developers update their models. Stokes said PromptBase has mechanisms to flag or hide prompts that no longer work, but outdated prompts are as much of a general issue for LLMs as outdated training data.

“Understanding the query requires knowledge that is super recent,” Sanh said. For example, if an LLM with an older data set makes up responses about current events, “There’s no way to tell them all the ways it’s wrong.”

Sanh said many prompt engineering jobs currently have low technical barriers to entry. That’s because most LLM tooling, including integrations and UI, are still being built in-house and sold by the companies that make the models in the first place.

 prompt engineering may cease to exist in its current form, he also told IT Brew that UI for LLMs could look very different as little as a year from now.

“What’s clear to me is that in the long run, a lot of the companies who are going to rely solely on APIs—doing almost close to no technical work and building internal knowledge and technical expertise—are just going to be dependent on whatever cloud providers and the system providers do,” Sanh said.

Stokes said he doesn’t like the term “prompt engineer,” which he thinks can be offensive to those who view it as appropriating the titles of prestigious careers like software or mechanical engineering. “Then you have prompt engineering, and it’s like you’re just writing English into a chatbot,” Stokes said.

However, Stokes thinks prompts are likely to become more, not less, complex as the use cases for LLMs become even more complicated.

Sanh predicted LLMs will largely become multimodal by default and “natively integrated in a lot of products in our life.” He predicted prompt engineering will eventually become a prerequisite skill in many fields, rather than a discrete profession.

However, that decline may be offset by other types of jobs debugging LLMs, like security, Sanh said. 

“We see that with red teaming efforts, [it] also adversarially attack[s] the model to see the limits of safety in the systems,” Sanh added.

Is prompt engineering here to stay or a fleeting fad?

Prompt engineers are in part necessary because the inner workings of large language models remain mysterious.

As if it’s not bad enough to get the pink slip, some of the 

 of workers laid off by tech firms suddenly seeking to tighten their belts are finding themselves courted by those very same employers on less favorable terms.

 reported that many recently terminated employees are being pitched on the possibility of returning to their old roles—by third-party recruitment firms that often ask if they’ll come back as contractors with no benefits, and for less money. The paper specifically spoke with former workers at Amazon and Microsoft, both of which have shed or are in the process of shedding huge portions of their workforce.

The reaction these offers generate is often less than welcoming, the Times reported. One former Microsoft worker told the paper that an offer to go back was “the last thing I need,” while another Amazon alum sent back a message saying that if the company wants the position filled, “they can just not fire me.” Recruiters told the paper the trend may be due to random chance, as placement firms circulate résumés, or because some companies treat contractors as a separate labor pool.

Research has shown that returning employees typically make more than they did previously, making the current situation in tech unusual, according to Andrea Derler, principal at people analytics firm Visier’s research and value division.

 showing that between January 2019 and April 2022, 28% of “new hires” across a wide range of industries were actually employees who had resigned from the same firm within the last 36 months. (In tech, that percentage is much lower, at 14%, according to HBR.) Returning employees tended to make 

Tech firms may have realized too late that they overcorrected for a pattern of overhiring, leaving them to scramble to retain institutional knowledge, Derler told IT Brew: “Maybe they should have tried much, much harder to retain them in the first place…I don’t think that the positive story around boomerang employees can be maintained in a situation where you’re being laid off.”

It’s also possible workers are being called back not to fill their old roles per se, but those of ex-colleagues who subsequently left on their own terms. Derler pointed to other 

 on turnover contagion, or the risk of departures starting a domino effect. Her team found that one resignation can increase the risk of other departures by 7%–25%, and that a similar (but weaker) trend follows layoffs.

“That is really fascinating, because we don’t know how many organizations are actually almost counting on that when they do their calculations about layoffs,” she told IT Brew.

The sudden shift to job-slashing throughout Silicon Valley has left tech professionals in a more 

Brian Swider, a professor of management and expert on boomerang employment at the University of Florida’s Warrington School of Business, told IT Brew academics have yet to extensively study the dynamics of rehiring laid-off workers. His advice to employees receiving such an offer: tread carefully and ask a lot of questions.

“Why are you being brought back? Why were you fired? Or why were you terminated? What sort of guarantees can you get either in writing or implicit guarantees about what the terms of the return look like?” Swider told IT Brew. “If you’re an independent contractor, you should really start to get a sense of how long this relationship is expected to last.”

Laid-off Big Tech workers are getting invited to return—on unfavorable terms

The trend is unusual not just for growth-obsessed Silicon Valley, but the economy more generally, experts tell IT Brew.

Eoin Higgins

The center of gravity in the IT job market is shifting east. Washington, DC, and New York City now have more available tech jobs than Silicon Valley.

 from the Wall Street Journal, the San Francisco metro area showed 2,369 software-engineering job postings and the Silicon Valley area had 2,084 at the end of 2022. By contrast, DC had 3,815 and the New York metro area had 3,325.

“The balance has been shifting to the East Coast for some time,” David Lewis, CEO of Norwalk, Connecticut-based OperationsInc, told IT Brew in a recent interview, adding, “If you’re paying attention to the signs on the outside of the buildings, and the brands that are there, you’ve known that there’s been a big move towards tech.”

Those East Coast gigs aren’t all with large IT firms, but span a number of industries—reflecting how tech has become an integral part of nearly every business’s operations. It’s not just DC and New York City, either—Fred Voccola, CEO of software company Kaseya, is based in Miami, and isn’t going anywhere anytime soon. Kaseya moved from Silicon Valley to Miami in 2015 after Voccola took over as CEO.

“You couldn’t pay me to go back to the Valley,” he told IT Brew.

Big firm layoffs are presenting companies based on the East Coast with new opportunities. Ximena Gates, co-founder and president of DC-based BuildWithin, told IT Brew that the glut of East Coast jobs is attracting a pool of prospective employees who don’t have a ton of options in California.

“We have all taken advantage of layoffs in Silicon Valley and other places to hire more people,” Gates said.

Gates is unsurprised that DC is becoming a player in the white-collar tech world. She described a number of aspects of the region—good schools, a highly educated and diverse workforce, a younger generation of professionals, to name a few—that are appealing to employers and employees alike.

“Government affairs is going to continue to fuel energy from the tech industry in the area because the lobbying industry has grown instead of shrinking, and we only have one Congress, and it’s right here,” Gates said.

The layoffs are coming at a contradictory time for the US economy. While large tech firms are cutting positions by the thousands, the job market as a whole is tight. Unemployment is at 

 in some states, and people are still quitting their jobs to look for better work elsewhere. The job market and economic fears are “as much an oil and water moment as you possibly can find,” Lewis said.

To Lewis, tech is better described as a skill set than a sector. IT no longer means being tied to code development at one of 200 or so large tech companies. Rather, “companies across the board in all major categories of our economy, are leveraging people to be able to sort of do the things that they need to in order to be successful.”

“Tech is not just about a sector in our economy,” Lewis said. “Tech is a skill set that is as common as marketing in companies across the US—and for that matter across the globe.”—

East Coast cities overtaking Silicon Valley for tech job hotspots

‘You couldn’t pay me to go back to the Valley,’ one East Coast CEO tells IT Brew.

When it comes to employers, a spin on an old adage comes to mind: Help them help you (and help themselves).

People looking to enter the tech workforce are often faced with a large number of questions from prospective employers—and whether you’re entering the high-demand market now or changing jobs, it can be hard to know exactly what you’re going to be asked about.

IT Brew asked CIOs about what they want from employees and what they look for in the interview process. Answers varied, but all the CIOs we spoke to said they wanted something a little more than purely technical ability—though, as Angela Baskerville, AT&T’s VP for corporate systems and talent enablement, said, that’s often one of the most important things.

“These days, technical proficiency is still very much king in our company as well as in society at large,” Baskerville said. “The demand for technical skills has increased in a relatively short amount of time, even when it’s not necessarily a technical space.”

Those skills, said Cisco CIO Fletcher Previn, include “security developers, networking, and data science, DevOps, people who know how to manage cloud environments, machine learning, and more broadly, AI.” Previn added that he also wants to see signs of curiosity—usually a good indication that the person at the other end of the table is willing and able to learn new things.

“I’ll almost always hire someone for passion and curiosity over experience or a particular skill,” Previn said.

“Ideally, if it’s someone who’s further along in their career, you look for hands-on experience—that they’ve actually been in a role doing some of that work, and not just overseeing some of that kind of work,” Previn said.

IT is the “nervous system” of companies, said Sheryl Haislet, CIO at data center operator and equipment supplier Vertiv, and thus it’s necessary for prospective employees to be about business as much as they are about tech. But she’s also always on the hunt for less tangible skill sets—so-called “

” that get at the applicant’s ability to work well in the office’s environment.

“Technical skills are important for certain technologies…good soft skills are important, too,” Haislet said. “Can you work well with a team? Are you adaptable? Can you collaborate well with others?”

Flexibility is also important, Haislet said, showing that the applicant can roll with the punches in a changing environment.

Baskerville agreed, telling IT Brew that leadership traits are essential for tech workers to succeed.

“When I say leadership, I don’t mean that they necessarily have had to manage humans,” she said. “But they have collaboration skills, for example, that are also demonstrable.”

That includes accountability, and that’s what Rich Fusinski, CIO for insurer the H.W. Kaufman Group, looks for from applicants to his team. Fusinski said he uses résumé details to quickly assess if they’re blowing smoke or not.

“I’ll pick something out on somebody’s résumé, usually one of the most seemingly complex items on it, and I’m going to ask that person to tell me everything about it,” he said.

Fusinski asks them to explain the problem and solution in detail, not to catch them lying but to see how they approached the issue and worked their way around it. An incoherent response does give some insight into their character, however.

“If they can’t answer those types of questions, my assumption is that they didn’t actually do the work, or that they weren’t really associated with the work and are taking credit for it or puffing up their expertise,” Fusinski said.

Do you work in IT or have information about your IT department you want to share? Email eoin@morningbrew.com.

Employees enter and exit through revolving door

Your burning jobs questions, answered by CIOs

Passion, curiosity, accountability—these ‘soft skills’ are in demand as much as technical know-how. 

Looking for a new job? The market’s still hot for those 

Not all employers are created equal, though, and prospects should remain on high alert for signs that a new job isn’t going to turn out well. Here’s some of the red flags to look out for, according to IT leaders who spoke with IT Brew.

 Grant Fritchey, product advocate at Redgate Software, warns applicants to watch out for signs an employer subscribes to hustle culture—phrases like “work hard, play hard,” and “intense culture,” for example.

“Anytime they start talking about how passionate everyone is about the organization, it just means that there’s lots and lots of death marches,” Fritchey told IT Brew.

Management can be “honest in a dishonest way” about culture because their incentive is to hire someone for the position, Fritchey added. He advised asking potential colleagues how long they spend on-call or rolling out deployments, or how easy it is to take vacations without incurring additional obligations.

“Some organizations will throw money to fill a role, especially roles with a lot of churn,” Jason Rebholz, CISO at Corvus Insurance, wrote to IT Brew. “You should ask about role attrition to understand the average tenure and reasons for others leaving.”

Tatiana Becker, owner of tech recruiting firm NIAH Recruiting, observed warning signs can include an emphasis on artificial parts of company culture like “kegs and foosball tables,” or founders who act like their company is the “greatest thing since sliced bread,” which often correlates to unrealistic demands around pay or working hours down the line.

They see IT as just a help desk (or don’t know what it does).

 Charlie Verrey, who leads IT operations at DIY enterprise app platform Retool, advised that job-hunters should parse job ads closely and investigate any ambiguities. Subjective wording around workload, like responding to tickets in an “effective and timely” manner or within “established timeframes,” should raise questions about expectations laid out in service-level agreements, who is on call for emergencies, and the ratio of employees to IT staff.

“As a general rule of thumb, 1:100 is great, 1:200 is acceptable, and anything over 1:300 is probably going to lead to burnout after one to two years,” Verrey wrote.

Listings with stacks of excessive or even impossible qualifications often indicate the hiring manager doesn’t know what they want for the role or if their requirements are reasonable, Fritchey told IT Brew.

“PostgreSQL [15] just launched,” Fritchey added. “They’re gonna say, ‘Hey, 10 years of experience in PostgreSQL 15.’ And it’s like, wait a minute, I can’t have 10 years in 15; it’s only been out for two months.”

They won’t support your professional growth. 

Verrey cautioned applicants to stay away from organizations that don’t view IT as a collaborative partner.

“When you get the sense that there’s no opportunities to partner with the org…when there’s limited or no ability to solve problems with code…[or] there’s no options for further training or education,” Verrey said, he views that as “something to avoid at all costs.”

Rebholz urged interviewees to ask if IT is “just a business requirement, or is it a business enabler? Is it viewed as computer support, or does it help drive efficiencies within the company?”

“These dichotomies can help you understand the level of support you will receive in your role,” he wrote.

Do you work in IT or have information about your IT department you want to share? Email tomm@morningbrew.com. Want to go encrypted? Ask Tom for his Signal.

An illustration of a computer rejecting a resume.