Main image of article Questions a CIO or CTO Might Ask in Your Next Job Interview

If you’re climbing the career ladder, you may find yourself interviewing with a senior technology leader, such as the CIO or CTO, to land your next position. Acing an interview of this magnitude requires the ability to anticipate the right questions and prepare your answers ahead of time.

In that spirit, we asked some leading tech execs what interview questions they like to ask and why. Here’s a look at the examples they shared, including the responses they’re looking for.

“In the next three years, how will A.I. reshape your role, your industry, and this company?”

When Mike Shanko asks this question, he’s looking to see if a candidate grasps the magnitude of A.I.

The SVP and chief information officer of Blue Yonder wants to know whether the candidate can think broadly. Do they recognize how A.I. is different from any technologies they may have managed previously? Do they understand the risk and compliance challenges related to new A.I. tools? Do they know how to harness A.I.’s capabilities while guiding their organization through the change?

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Shanko says the best candidates not only demonstrate an understanding of AI technology, but the governance aspects that accompany a change of this magnitude.

These successful candidates have a reasoned approach to A.I., and can articulate the business case to leaders, subject matter experts and stakeholders. They’re also adept at handling change, and are receptive to transformational efforts that could ultimately disrupt their team and even their own role.

“Can you share a time when you successfully utilized sales techniques to drive technology initiatives or secure partnerships? What was the outcome?”

While this question may seem a bit unorthodox, Manny Ramos believes that technology professionals must be able to navigate a basic sales process to thrive in today’s environment.

It’s not just about execution anymore, explained Ramos, who’s the chief solutions officer for OZ Digital Consulting and a member of the Forbes Technology Council. To drive tech initiatives today, tech pros must be able to sell their vision, gain buy-in and build effective partnerships—which is sales, anyway you slice it.

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Ramos looks for candidates who aren’t stumped by his question. The best candidates explain how they identify user pain points, along with the process they use to identify the real decision-maker: someone who has the ability to greenlight a project and approve the budget.

Of course, Ramos also wants to hear outcomes or specific statements about what you accomplished using your sales skills. At some point in your tech career, you’re going to have to sell something—whether it’s your idea, your team, or yourself.

“Can you tell me about a time when you turned around a project that was in trouble?”

If you think this question only applies to project managers, think again.

Every project has problems, and every person on the team is responsible for completing projects on time and within the budget, Ramos explained. It’s perfectly acceptable to speak about your role and your individual tasks when describing the steps you took to get yourself, your team, and the project back on track.

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Ramos looks for candidates who understand the importance of the “human element” in rescuing troubled projects. For instance, they describe how they proactively build relationships with internal and external clients to establish trust and rapport. With that foundation built, all parties are hopefully willing to “forgive each other’s sins” when a project experiences problems.

“What excites you about this opportunity?”

Everyone has different motivators, explained Matt Schwartz, CTO of Sage Hospitality Group. "I want to understand why the candidate is excited about a particular opportunity," he said. Is it the role, the title, the salary, the company, the hiring manager, the team, the location, the technology stack, or perhaps the opportunity for advancement?

Beyond that, asking this question often allows him to evaluate five qualities that he believes lead to high job performance: friendliness, patience, tenacity, commitment to continuous learning, and alignment with the company’s culture and values.

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Schwartz doesn’t care about a candidate’s motivation; he just wants to make sure that they are actually motivated to change jobs, regardless of the reason: "Ultimately, what I'm looking for is sincerity and honesty."

Don’t fall into the trap of saying what you think the interviewer wants to hear. Your best bet is to stick to the truth, especially when you’re interviewing with a CTO.

“Looking back over your last few roles, what’s something you can laugh about now?”

It’s no secret that having a healthy sense of humor helps tech pros deal with stressful situations, maintain productivity, and actually build stronger bonds with teammates.

Asking this question not only helps Schwartz gauge a candidate’s ability to learn from previous experiences, but also their ability to fit in with the team.

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Because working in tech is so stressful, you need to be able to laugh at yourself and the difficult situations that can arise during projects, especially after the fact.

When Schwartz reflects on an interview with a candidate, he always asks himself: “Did they make me laugh at least once?” If they didn’t share a chuckle or two, then he assumes that the candidate won’t fit in with his team.

While you don’t need to be a standup comedian to ace an interview with a tech exec, it’s always good to have a few humorous stories in your pocket so you can share them at the right time.