8 unusual IT interview questions and approaches: CIOs share

Check out these IT interview questions – and what CIOs seek to learn from them
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Talent remains a top pain point for CIOs in 2018, especially as the competition for new and emerging specialists, such as DevOps engineers and IoT architects, heats up. Finding the right candidate is more important than ever. 

Get it right, and you could add value to your organization in ways that extend far beyond the candidate's resume. Get it wrong, and that new hire could be jumping ship in six months, sending you back to square one. 

It’s often not the technical prowess that sets top candidates apart: It’s their ability to fit into an organization's culture, or their soft skills. These factors, however, can be hard to determine in the traditional interview. 

[ Get our free eBooks: DevOps Hiring: The Ultimate Guide and IT job searching in 2019: A practical guide. ]

We asked IT and business leaders to share their tips for bringing out these and other key  qualities during interviews. Read on for their unique and interesting interview questions and strategies – and what the responses help them discern about candidates. And if you’re a job seeker: Learn and get ready for these strategies.

Jonathan Feldman, CIO, City of Asheville, N.C. 

"I am a hater of the weird question. I regret using weird questions in the past, because I want people to be comfortable.” 

“I like to ask ‘What do you do for fun?’ That accomplishes two things: First, I like to see that there are multiple dimensions to the candidate. It also shows the candidate I am genuinely interested in the whole person. (You could ask this for the wrong reasons – to pry – but I just want the candidate to know 'I care about you as a whole person.') Number two, there are a lot of people who come to Asheville for this high quality of life we offer. So if they say ‘I’m a trail runner’ or ‘I’m a paddler,’ it leads to a collegial conversation. On the other hand, if someone says ‘I like to upgrade routers,’ I think ‘Hmm, not a fit.’ That person is wound too tight."

Sam Elsharif, VP Development, Echoworx

“In general, I look for two primary traits in a candidate: knowledge and passion. Interestingly, they go together like hand in glove.” 

“One question I always ask is: ‘What technical skill have you learned outside of your work?’ The answer to this question enables me to better understand what kind of a developer the candidate truly is and whether he/she is passionate enough to never stop upping the ante on their skill sets - and if they are willing to ask for help.”

[ Read also: 5 laws every aspiring DevOps engineer should know. ]

Cristian Rennella, CEO, oMelhorTrato.com

"Do they prefer to be with programmers or designers better than themselves, equal to themselves, or worse?"

“Question: You have to finish a job that will take you one month but you only have 72 hours. You must convince three people to work with you. Who would you choose?” 

“I love this question because who this person prefers to work with says a lot about them. Do they prefer to be with programmers or designers better than themselves, equal to themselves, or worse? In my experience, A-quality players always look for A+ quality partners, while those of B-quality look for lower quality peers. 

I also ask about the attributes of the partners they would choose. Are they kind, respectful, attentive, responsible, good team players, etc.? What are their weak points and their virtues? In this way, I can also evaluate if this candidate is appropriate for our culture, because the candidate themselves will have a mix of the qualities they look for in those they choose to work beside.” 

Doug Saunders, VP and CIO, Advanced Disposal 

“Beyond technical aptitude, I seek employees that can communicate, have an ability and desire to learn, and are passionate. If you can’t collaborate and have passion for helping our business reach strategic objectives, you will not be successful in our culture.”

“After initial screenings, I meet with key candidates one on one. These candidates are usually smarter than me in their field so I never ask a technical question nor about their previous experience unless something is extremely unique in the candidate’s background. I tend to ask about a hobby, sport, or activity that the candidate is passionate about and dig in deeper. If I know the subject well, I ask detailed questions to push the conversation along. If I do not know the subject well, I have the candidate ‘teach’ me for 45 minutes about their interest. I have discussed music lyrics, quantum mechanics, college football, and Russian History with candidates. What I am able to find out from this:

  • Can they communicate? Articulate the subject matter to me so I understand the topic or concept.
  • Are they passionate? If the subject is of interest to them, do they display enthusiasm and zeal during their discussion?
  • How do they handle debate/conflict? I will purposely argue a point to see if they back down or defend a position.
  • Can they sell? I try and see if they can convince me to change or alter my stance/opinion.
  • How comfortable are they at being uncomfortable? When talking to business partners or execs, it can be intimidating. Do they seem to embrace the moment or shy away from it?

Zac Ruiz, Founder, Salt IO

“On some line of questioning in their subject matter expertise, I keep drilling down until I can get them to say the words, ‘I don't know.’ Not being able to admit they don't know something is a deal breaker.” 

“Second, I ask them something relatively simple but slightly obscure that is in their area of expertise. When they give the right answer, I disagree and tell them they are incorrect in a very polite way. If they try to correct me I hold my ground and tell them I think they are mistaken. I am looking for their reaction. Some candidates will challenge/argue intellectually, some will challenge/argue emotionally, many will change their answer and tell me I am right, and some say, ‘I would like to look more into that and resume conversation later.’ It is very important that everyone on my team is able to communicate honestly and openly and not always agree or say what someone wants to hear.”

Brett Derricott, CEO, Objective:

“If an interview is going well and I see potential in the candidate, I give them a scenario in which they imagine that I'm unhappy with some aspect of their performance (assuming we hired them). I then ask them to walk me through how I should handle that situation. 

This question accomplishes two things. First, it lets the candidate know that we care about performance and that we want to address issues when they come up. Second, it gives the candidate a chance to put herself/himself into the manager role and then explain how they would like to be treated by a manager. I believe having the chance to do this makes the candidate feel that their opinion matters at our company. It also lets them explain how they best receive constructive criticism, which is very helpful to know in the event we do hire them. This question often reveals concerns or past issues that a candidate has experienced at previous jobs, and helps uncover any potential red flags regarding performance and communication about performance.”

Steven John, CIO, AmeriPride Services:

"‘What has become more clear to you since the last time we met?"

“If it is a second (or third or fourth..) interview I ask a question that Emerson used to ask people he hadn’t seen for awhile – I ask: ‘What has become more clear to you since the last time we met?’ It has led to some very interesting conversations. But if they say ‘nothing,’ then it means they haven’t thought enough about our previous conversations, and for me that shows a lack of passion and reflection.  And that means they don’t get hired.

“Also, I always ask: ‘What have you done – outside of IT – that has required creativity and deep thinking?’ What I am looking for are three things. First is this someone who swims at the shallow end of the pool or the deep end? Second, is this someone whose IQ is on the right or left hand side of the bell curve? Third is this someone who can innovate – because innovation requires both creativity and deep thinking. My favorite answer was from a young man who said: ‘I designed, built, and installed a free standing spiral staircase based on a renaissance painting and the end product appeared on the cover of Architectural Digest.’ He had me at ‘spiral staircase.’ I made him an offer on the spot.”

Kristin Darby, CIO, Cancer Treatment Centers of America:

“When evaluating IT candidates for leadership roles, one area of focus is how they will approach relationship building with their customers. Relationship building is a soft skill, developed over time by executives who understand the importance of developing a strategic business partnership with customers. This expertise will prevent the IT function from slipping into the legacy viewpoint of a support or administrative service. Questions such as the following help understand a candidate’s perspective and approach around this topic:

  • When you identify your top three primary business customers, how do you approach relationship building with them?
  • How do you approach gaining the depth of knowledge around your organization’s core business to identify opportunities for innovative technology to enable your primary customer’s objectives?
  • Do you have any examples of past customer relationships that were not highly collaborative or valuable? What were the limitations you identified and how did you address that gap? Would you take a different approach if that scenario was to present itself again?"

[ Which certifications will advance your IT career, pointing you toward a CIO role? Read also: 13 top-paying IT certifications for 2019 and 7 valuable certifications for IT leaders. ]

Carla Rudder is a community manager and program manager for The Enterprisers Project. She enjoys bringing new authors into the community and helping them craft articles that showcase their voice and deliver novel, actionable insights for readers.