A CIO’s Guide to Hiring: 20 Questions to Ask to Hire the Best IT Talent in 2023 

A CIO's Guide to Hiring: 20 Questions to Ask to Hire the Best IT Talent in 2023 

Are you prepared to catch the best candidate in the market?

Interviewing your applicants isn’t only about them showcasing their skillsets. It’s also about discovering how well the candidate fits in with you and the rest of the team. It’s also an opportunity to find out what to offer the candidate in the event he’s the perfect fit.

Settle Down: The Start of the Interview 

Prepare yourself for the job interview that you will be conducting by identifying what the ideal candidate should be like. Create a structure that will help you get the most valuable information out of the candidates.¹ This includes the flow of your questions and a list of qualifications for your checklist. This is so you can see if they’re suitable for the position and a cultural fit for the group. Having a ready structure will also make your hiring process run smoothly.

Next is to decide how you want to do the interview. Should you do a phone interview or in person? If you think the initial interview will only last a maximum of 30 minutes, you may choose to do an interview over the phone or online. This saves the candidate the travel time to your office and assures you that you will e-meet them on time.

Once you have decided on a setup and a structure, it’s time to get on with your succeeding interviews.


Find Values: Introductory Questions 

Start by cordially introducing yourselves to each other to set the mood. The greeting you first share will define how comfortable the rest of your conversation will be.

Start with common interview questions. They aren’t bad, as long as you know it can engage your interviewee, or if it can add to the data you are trying to collect from them. You can start by asking them about light but personal ideas, something that will encourage them to start talking.

  1. “What is something you’d be happy doing every single day for the rest of your occupation in tech?”
  1. “What’s the biggest decision you had to make in the past year or two? What do you think makes it big?”
  1. “How do you define hard work?”
  1. “What motivates you to work better?”
  1. “What part of our job search posting made you want to apply for this position?”

These simple questions can give you an idea of what they prioritize and what will inspire them. Through these, interviewers may also identify what benefits or rewards they can provide the employee based on their interests, if they get hired.


Behavioral Interview Questions: Get to Know Their Personality 

Focus on how candidates handled certain situations in their previous experiences, by utilizing their skills and values. Hiring managers should make questions concrete in this segment of the interview, by asking how they did things and not how they would.

Technology needs talent that can help influence and drive decisions in an innovative field. Look for applicants who are curious and have an ownership mindset.² This isn’t only about their skillsets, but also their soft skills. You will notice through their responses how they interact with people in a situation and how they push forward.

Listen carefully to know if they got upset when someone got blamed for a mistake at work. Ask how they helped the other person. Did they get excited when they got praised, after their compassionate effort was recognized? These little signs of emotional reactions and acts of kindness can be taken as signs of their possible compatibility to your team members.

  1. “Tell me about the latest project you worked on. What were your responsibilities and how did you manage them?”
  1. “What project are you most proud of, and what did you contribute to it?”
  1. “What did you do to ensure quality in your deliverables at work?”
  1. “When was the last time you downloaded a tool or software to make your work more productive, and what was it? How did you maximize it?”³
  1. “Do you have any background in developing customer service-related tools?”


Interview Questions for the Long Run: Career Goals and Company Culture 

Knowing what they see themselves doing in the future, what kind of professional development they think they need, and what they’re looking for in a work environment gives you an idea of how long they can possibly stay with you and your team.

For this set of job interview questions, you may also include questions about their former or current employer, to compare how they will do things differently in your business. Asking these interview questions gives you an insight into what your workforce will be like the moment a certain candidate joins.

  1. “What are you looking for in terms of growth and promotion?”
  1. “What are the greatest strengths you can contribute if you get hired?”
  1. “What is something you’ve done that you would never want to repeat?”
  1. “How do you approach the perspective of a colleague whose background differs from yours?”
  1. “Are you a team player? Can you give me an example of how you worked in a group-assigned task?”


Closing the Interview: Tips to Make Them Remember 

Conclude your time with interview questions that will make them keep coming back. This means that your shared time should make them feel the need to follow up on their application status or make them interested in applying for future openings in the business.

Show that you’re interested in what they’ve discussed with you so far. Here’s also where you can do a recap of what you’ve talked about.

  1. “When can you start?”
  1. “Do you have any questions for me?”
  1. “Do you need us to provide anything to make your work more comfortable, if we hire you?”
  1. “Do you have any expectations regarding salary, benefits, or otherwise?”
  1. “Would you be interested in our other job openings in case you don’t get an offer for this one?”

If you think that an excellent applicant may also be suitable for other roles, don’t give up on them easily, even if they don’t get hired now. Contact them in the future to open more opportunities for partnerships.


Ask the Best Interview Questions to Find the Best Candidates

Preparing the most meaningful interview process draws out the best candidates for a role. They will meet you halfway by showing you their most authentic selves with their most suitable skillsets. Start structuring your own unique process today.



On-Demand Group (ODG) is a technology consulting firm that has been servicing the industry since 1996. We are greatly invested in helping our clients remove barriers while growing integrity-rich partnerships with lasting impact.

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1 “How to Start an Interview as the Interviewer: 5 Tips”. https://www.masterclass.com/articles/how-to-start-an-interview-as-the-interviewer . Updated last August 31, 2022. Accessed last March 28, 2023.

2 Carla Rudder. “IT hiring strategies – and 5 illuminating interview questions to ask candidates in 2023”. https://enterprisersproject.com/article/2022/12/it-hiring-strategies-interview-questions-ask-candidates-2023 . Published last December 20, 2022. Accessed last March 28, 2023.

3 Alison Doyle. “Technical Interview Questions (With Tips for Answering)”. https://www.thebalancemoney.com/top-technical-interview-questions-2061227 . Updated last December 26, 2022. Accessed last March 28, 2023.

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