32 Cybersecurity and IT Management Professionals Share Their Favorite CISO Interview Questions
Tom Demers
The role of the CISO (Chief Information Security Officer) is one of the most important in any organization, and finding the right professional for the job is vital. The CISO leads the company’s information security strategy and bears the ultimate responsibility for the company’s security posture and how effectively it protects its information systems.
The most successful CISOs have a finger on the pulse of the industry, with a deep understanding of the current threat landscape and best practices for protecting the company’s most valuable assets. They’re familiar with the latest tools, technologies, and emerging markets such as attack surface management (ASM). They can explain how the attack surface is expanding, the risks digital attack surface vulnerabilities pose to the company, and what security controls help to reduce the attack surface.
Effective CISOs can also communicate with key stakeholders in easy-to-understand language to communicate complex information, such as why digital supply chain visibility is vital, how ASM solutions address this need, and the difference between attack surface management and vulnerability management to gain buy-in for cybersecurity technology investments.
However, finding the right CISO requires asking the right interview questions to gain insight into how well the candidate will lead your company’s security, communicate with stakeholders, and fit in with your existing team. To help you more effectively evaluate potential CISO candidates during the interview process, we reached out to a panel of cybersecurity and IT management professionals and asked them to answer this question:
“What’s your favorite CISO interview question (and why)?”
Meet Our Panel of Cybersecurity, IT, and Data Management Professionals:
Read on to learn what our panel had to say about their favorite CISO interview questions and why they’re effective.
John Nakata
John is the Chief Technical Specialist at IBR.
“The best questions to ask in a CISO interview will vary depending on the individual’s qualifications and experience…”
However, some good questions to ask include:
- What are some of the biggest cyber security threats that your organization faces, and how are you currently addressing them?
- What are some of your biggest successes and failures in your role as CISO, and what lessons did you learn from them?
- What is your vision for the role of CISO in the future, and how do you see your department evolving?
- What are some of your favorite cybersecurity tools and techniques, and why?
- What do you think are the most important skills for a successful CISO, and how can candidates demonstrate that they possess them?
Why are these questions important to ask in a CISO interview?
The questions above are important to ask in a CISO interview because they can help you gauge the individual’s experience and expertise in the field. They can also give you a better idea of the candidate’s vision for the role of CISO and their thoughts on the future of cyber security. Additionally, the questions can help you assess the candidate’s knowledge of key tools and techniques in the industry, as well as their skills and qualifications.
James Chang
James is a senior manager at Velocity IT, a leading provider in the Enterprise Telecommunications and IT Services market.
“My favorite CISO interview question is…”
Please tell me a little about your management style.
This question will enable me to gauge how well a candidate would fit in with our workplace culture. How they manage their subordinates will reveal their personality and character.
I’m not saying that technical knowledge is not important when evaluating candidates. They are equally vital! But this aspect has already been addressed via his tests and examinations. We also sincerely believe that technical knowledge can be easily learned compared to changing a candidate’s style and methodology. Going deeper into his character and thought process is a better way of identifying whether they’ll flourish in our system.
Jon Hill
Jon Hill brings 25 years of hands-on operational experience in the upstream oil and gas industry in his role as Chairman & CEO of The Energists executive search and recruiting team. Prior to The Energists, Jonathan was VP Marketing & Technology at Schlumberger.
“My favorite CISO interview question is…”
What is the first thing you would do to improve our system security if hired into this role?
What I like about this question is that it gives you an insight into how the candidate plans to approach the position and whether they have pictured themselves in the role, which is to me a strong indicator of their success. Someone who’s fully prepared should have at least done enough research on your company to have some ideas of potential weaknesses or issues that they want to address if hired. If nothing else, they should be able to draw on their experience to outline their process for identifying security vulnerabilities and explain what that would look like in practice in your company.
Ranee Zhang
Ranee is a VP at Airgram and loves to research and execute. With a computer engineering background, he is focused on focusing on the machine learning side of the business.
“My favorite CISO interview question is…”
What are your thoughts on the current state of cybersecurity?
This question allows me to gauge the candidate’s understanding of the current landscape and their ability to think critically about the challenges we face. It also allows me to see how the candidate views their role in relation to the larger picture of cybersecurity.
Eric Florence
Eric is a Cybersecurity Analyst at Security Tech. With a strong commitment to online security and digital freedom, Eric is working hard to deliver the content and analysis his audience is looking for when he is not coaching or consulting.
“The most important thing to know about a CISO candidate is…”
How they handle a breach.
When I have consulted clients and helped them find a new CISO, I always ask: What is the most important piece of information to share with other executives after a breach? If a candidate stumbles on this, has mixed up priorities, or obviously hasn’t handled the fallout from a breach before, they don’t get the position. The correct answer is the cost of the breach. All other executives need to know what the breach will cost the company financially.
Luciano Colos
Luciano Colos is a serial entrepreneur, advisor, and investor. He launched his first startup right after completing a Fulbright fellowship that granted him a Master of Engineering at UC Berkeley in 2014. His new company, PitchGrade, develops cutting-edge AI applications for entrepreneurs, such as a pitch deck review tool that helps startup founders create compelling pitch decks so that fundraising is the least of their concerns.
“A great question to ask a prospective CISO candidate is…”
What is your experience with digital transformation?
This question can help you determine whether the candidate has the experience and expertise necessary to lead the cybersecurity team in a rapidly changing environment. Those who have successfully led a digital transformation can highlight their experience and expertise and how they’ve helped their organizations adapt to the changing landscape.
Michael Miller
Michael Miller is the CEO of VPNOnline.com, one of the fastest-growing media companies in the cybersecurity space.
“My favorite CISO interview question is…”
If you were going to encrypt and compress data for a transmission, which would you do first?
This question is important because it gets at the heart of how much someone understands the technical side of information security. It also helps me understand how they think about problems.
Encrypting data before compressing it will result in much larger files because the compression algorithms have less information to work with. Compressing data before encrypting it will make the encryption more efficient but will result in smaller files overall.
Arno Markus
Arno is the Founder & CEO, Career Strategist, and Executive Resume Writer at iCareerSolutions.
“As an IT recruiter for Fortune 500 companies, I’ve had the chance to observe many interviews…”
You may be asked something along the lines of: What are some of your best cybersecurity accomplishments? Those questions are not meant to trick you but rather to give your interviewer a good sense of what you are thinking.
There is no definitive best CISO interview question, as different questions can elicit different responses from various candidates. However, some of my favorite CISO interview questions include:
- What are some of the biggest cybersecurity challenges that you have faced in your career? This question allows me to assess a candidate’s experience and knowledge of cyber threats, as well as their ability to think critically about these challenges.
- What security solutions are you most familiar with, and why do you prefer them? This question helps me understand a candidate’s level of expertise when it comes to different cybersecurity solutions, as well as their preferences and priorities when it comes to security.
- How do you think the role of CISO is evolving, and what do you see as some of the biggest opportunities or challenges facing today’s CISOs? This question allows me to get a sense of a candidate’s vision for the future of cybersecurity, as well as their perspectives on current trends and challenges in the field.
Overall, there is no one best CISO interview question, as the most important thing is that the candidate is prepared to think critically and respond thoughtfully to whatever questions they are asked. Whether it’s discussing cyber threats and solutions, understanding cybersecurity trends and challenges, or envisioning the future of cybersecurity, the key is to be prepared, confident, and thoughtful in your responses.
Michael Chepurnyak
Michael Chepurnyak is the founder and CEO at Ein-des-ein.
“Besides standard questions about responsibilities, experience in information security, or approaches to risk management, I need to know…”
How the candidate ensured compliance with security standards in the company he worked in — I want my company to be safe from legal and financial penalties too. This is an obligatory question for this position and it is designed to assess a CISO’s compliance program (i.e., how the previous organization adhered to all relevant laws and regulations, including those governing data privacy and cybersecurity).
Hammad Afzal
Hammad is a Growth Marketing Manager at Softception.
“My favorite CISO interview question is…”
If you were a superhero, what would your superpower be, and how would you use it to protect our company’s data?
I love this question because it allows me to flex my creative muscles and come up with a truly unique and exciting answer. Plus, it’s a great way to see how potential candidates think on their feet and approach complex problems.
Another great CISO interview question is:
If you were stranded on a deserted island and could only bring three data security tools with you, what would they be and why?
Samrudha Salvi
Samrudha Salvi is the founder of BuildFBA, a company that assists online sellers in growing 6 to 7-figure Amazon businesses.
“My favorite CISO interview question is…”
Describe a security incident you have dealt with and how you responded to it.
This question enables the interviewer to gain a better understanding of the candidate’s experience and knowledge in dealing with security incidents. It also allows the candidate to demonstrate their ability to think on their feet, assess the situation, and respond appropriately. This is an excellent question to ask because it provides the interviewer with a clear picture of the candidate’s experience and capabilities, allowing them to make a more informed decision.
Chandler Rogers
Chandler Rogers is the Founder and CEO of Relay, an app that helps people overcome addiction with a team of peers.
“The CISO is probably the most important role in our organization…”
As a software company that provides a peer support application for those dealing with addictions, security is critical. We only have one chance to protect our data and maintain the trust of our clients.
The most important question I ask is: What are the attributes you consider to be essential for a CISO?
I am looking to see how well the individual understands the role. This position will not only be answering to me but also to our board and investors. They need to understand the importance of communication first and foremost. Being able to share information — including risks and potential costs — in language that is understandable to non-technical people is essential.
Other attributes I look for are innovation and decision-making. I want a CISO who is up-to-date with changes in the technology and able to ensure we have the best protection possible and who is able to make executive decisions to protect our company if necessary.
Perry Zheng
Perry Zheng is the founder and CEO of Cash Flow Marketplace, a YC-backed marketplace for all direct real estate investments. He was an engineering manager at Lyft for 5.5 years and worked as a software engineer at Twitter and Amazon.
“My favorite question to ask a CISO candidate is…”
What challenges do you foresee in this position?
The question may seem open-ended, but it will show how prepared the candidate is for the interview. It will help you evaluate if they have researched the company or not. If they can foresee the issues that might arise on the job, they can be forwarded to the next stage.
Melissa Terry
Melissa Terry is the CIS at VEM Tooling, one of the fastest-growing mold manufacturers in the world. They currently operate in over 5 countries with an aim to grow across borders.
“My favorite CISO interview question is…”
Has there ever been a time when you had to change a security policy, and if so, why?
You are in charge of reviewing security policy as CISO. This implies that there will be instances in which you must modify a security policy due to a security-related issue. This query reveals whether the applicant is up to the task of carrying out such responsibility-laden duties or not.
Dinesh Pandian
Dinesh is a finance expert and Co-founder at Lenders.fi, a project dedicated to helping people quickly find the best loan offers with just one application.
“I’ve always found that the best CISO interview question is…”
How crucial is security awareness training for your management style?
This is because it’s a question that gives you a chance to talk about your experience as a leader and how you plan to implement security awareness training in your organization.
Security awareness training is vital because it can help bridge the gap between different levels of management. When employees are trained on security issues, they’re more likely to be aware of potential threats and vulnerabilities — and they’ll be able to communicate those threats and vulnerabilities up the chain of command. This helps ensure that management has all the information it needs to make informed decisions about how best to protect the company.
Adil Advani
Adil is a CTO at Securiti.ai, a company that specializes in AI and machine learning-based security solutions. He has an extensive background in business development, marketing, and technology consulting.
“My favorite CISO interview question is…”
What are your thoughts on DevOps?
I love the question because it is a difficult question to answer without giving away too much. It forces the CISO to think about their role in the company and how they can help make it a better place.
Travis Lindemoen
Travis Lindemoen is the Managing Director of Nexus IT Group.
“As a Managing Director of our Cybersecurity Practice Area, my favorite CISO interview question is…”
How do you envision the role of a CISO in our organization?
This question provides a great opening to discuss the strengths and assets that the candidate has to offer to a company as a Chief Information Security Officer. It also allows them to introduce their thoughts and ideas on security strategy, risk management, compliance requirements, and cybersecurity tools and technologies. All of these topics are extremely important when building an effective security program, and candidates should be excited when given the opportunity to share their vision. It is a great way for them to explain exactly how they plan to support the organization with their knowledge and experience in cybersecurity.
I like to follow up their response with this question: How do you stay updated on the latest trends and technology in cybersecurity?
I like this question because it reveals how committed a candidate is to their ongoing education and understanding of best practices. The answer to this question should involve active methods for gathering insights about emerging threats and staying informed about industry news. It also communicates to me that the candidate has an appreciation for learning new things and sharpening their skills over time — key traits of a successful CISO.
Mia Garcia
Mia Garcia is the founder and CEO of iToolab with over a decade of experience in computer software.
“My favorite CISO interview question is…”
What decisions and processes have you made in your role to better secure your organization’s data?
There are many things that a CISO can do to make their organization more secure. One of these is the time it takes for an incident response team to respond.
This is the question I ask when I’m interviewing a candidate for a position in the cybersecurity field. It’s important that people know their stuff, but it’s also important to have an understanding of what their style will be and what they will bring to this role.
Questions like this one demonstrate that you’re interested in not just filling a job but rather looking for someone who has more than just technical skills — someone who is good at assessing threats, analyzing risks, and weighing opportunities.
Matt Domo
Matt Domo is the CEO and Founder of FifthVantage.
“My favorite CISO interview question is…”
Can you give me an example of a new technology you want to implement for information security? Why?
I am looking for several different components to the answer. One part is whether they can explain the technology in a way that demonstrates mastery of the subject matter. They need to understand the problem to be solved and how the technology solves it, so this is not just a checkbox exercise.
Another component is to explain why it is both relevant and essential to our technology stack in a way that ensures they can successfully do that at our company.
The final component is whether they can explain the ROI benefits of the proposed technology to our customers and company in a way that demonstrates impact and builds trust and confidence.
Jason Moss
Jason is the co-founder and President of Moss Technologies REI Marketing Solutions. He works exclusively with real estate investors to help them build credibility, gain visibility, and buy more properties.
“One of my favorite interview questions to ask a CISO is to ask…”
How would you handle a security risk assessment?
The answer determines their technical skills, methodology, and management style altogether. It helps the candidate highlight their techniques for handling security breaches, identify potential security risks, and showcase how they would take responsibility.
Nate Morris
Nate Morris is Chief Information Security Officer at Router IP Net.
“My favorite CISO interview question is…”
How do you handle the pressure?
As a Chief Information Security Officer, it is imperative to be able to handle pressure in a variety of situations. In this role, I would have to deal with a lot of sensitive data, and I would also have to manage a team of people, which can be overwhelming at times. With this question, I can get a better idea of how the candidate handles stress and whether they have experience dealing with challenging situations.
I can relate to this question personally because I have had to handle pressure in a variety of situations. For example, when I first started my role as a Chief Information Security Officer, I had to take on a lot of responsibility, and I had to learn quickly how to manage a team. It was a stressful time for me, and I had to stay focused and organized to succeed. I was able to handle the pressure and eventually, I was able to lead my team effectively.
When I am interviewing a potential candidate for the role of CISO, I like to ask them this question because I want to see how they react under pressure and how they handle challenging situations. I also want to see if they have previous experience dealing with difficult situations. I believe it is important for a CISO to have the ability to think clearly and stay organized to succeed in this role. Asking this question can help me get an idea of how candidates will handle pressure if they are hired.
Jeremy Howell
Jeremy Howell is the Director of Marketing & Business Development at Clarity Ventures, Inc.
“One of our favorite CISO interview questions is…”
What questions should I have asked you?
Because it opens the door for candidates to explore areas that they are passionate about relating to security and their direct experience, which highlights the areas they are most likely to focus on in the immediate term of their employment. Additionally, the security landscape is rapidly changing, so the question helps us understand a candidate’s ability to think on their feet and adapt to an unknown scenario quickly.
Roy Yishai
Roy has been a project manager in the field of cybersecurity for the last 5 years and is the founder of SaaS startup Wish Maker AI.
“The question I would ask would be…”
Can you describe a situation where you had to balance the needs of the business with the need to maintain strong security controls and how you approached that challenge? How did you measure the success of your solution in meeting both objectives?
This question allows the candidate to demonstrate their understanding of the often conflicting priorities in a CISO role and their ability to think creatively and strategically about finding solutions that address both security and business needs. Additionally, it also highlights their ability to measure the effectiveness of their decisions, which is crucial for a CISO role.
Dan Richings
Dan Richings is administering the position of Senior Vice President, Product Management at Adaptiva, an endpoint management for the digital workspace. His role encompasses managing Adaptiva’s support team and technical solutions group.
“My favorite CISO interview questions are…”
- Could you give me an example of a difficult security incident you dealt with in the past and how you managed to solve it? By asking this, the interviewer can get a sense of the candidate’s cybersecurity problem-solving skills and familiarity with actual security events.
- How can you keep up with the ever-changing landscape of security risks? Inquiring about the latest security threats demonstrates to the interviewer that you are proactive in staying informed about the security threats, security measures, and everything in the cybersecurity industry.
- How do you approach developing and managing a security plan for an organization? With this question, the interviewer wants to learn more about the candidate’s approach to developing and enforcing a thorough security strategy.
- How do you address a case where an employee is determined to have breached security policies? The interviewer can learn more about the candidate’s approach to handling security breaches and disciplinary action by asking this question.
- Can you describe a case in which you had to make a tough security-related decision and explain how you came to that decision? The candidate’s critical thinking and ability to make decisions will be put to the test by this question.
- Can you elaborate on cybersecurity & data protection and how to run a red team? The candidate’s capacity to provide insightful tactics and insights into the red team’s efforts will be evaluated through this question.
All these questions are crucial because they allow candidates to demonstrate their cybersecurity knowledge and the red team’s role in the process. It also gives interviewers a glimpse into the candidate’s thought process as they consider becoming a cybersecurity specialist.
Prakaash Ojha
Prakash Ojha is the Director of Information Security & Compliance, GRC at LambdaTest.
“One of the effective CISO interview questions for me is…”
Can you explain a complex security issue you had to deal with and how you approached resolving it?
This question allows the candidate to showcase their technical knowledge and problem-solving abilities, as well as their ability to communicate complex security issues in a clear and concise manner. It also provides insight into the candidate’s experience and ability to handle challenging security situations.
Sean Stevens
Sean Stevens is the Director of ImmerseEducation.
“My favorite CISO interview question is…”
Why should our company hire you for the position of CISO?
This question is frequently posed by hiring managers to gain insight into candidates’ real-world talents and accomplishments. You are not required to list all of your accomplishments, experiences, and other qualifications. The hiring manager is only interested in how your qualifications make you a good fit for the position.
Example: I am confident that I am the perfect candidate for the position. Not only do my expertise and background match the job description, but my risk management skills, adaptability, ability to work with top leaders, and team spirit distinguish me from other candidates.
Joe Troyer
Joe Troyer is the CEO & Head of Growth of DigitalTriggers.
“My favorite CISO interview question is…”
Have you constructed information security policies in the past?
It’s a specialized question designed to elicit information about your expertise in drafting information security policies. In order to adequately respond to this question, you must describe the processes you take to develop and implement information security policies. In addition, you can increase your score by describing any policies you’ve created and implemented in the past.
Sample Answer: In my former CISO position, I was responsible for developing and implementing a new security strategy for the organization. These policies tightened password restrictions, data encryption, and other essential components of digital networks. I examined historical and existing tactics and systems in depth in order to establish effective information security.
Brad Anderson
Brad Anderson is the Executive Director of FRUITION – 20 years of winning at Digital.
“My favorite CISO interview question is…”
Why should we consider hiring you?
This question is my favorite because it requires serious consideration and is your opportunity to distinguish yourself from the other candidates. You should emphasize your skills, especially those not yet stated. Simply saying, ‘Because I’m so talented,’ or, ‘I’m desperate for work,’ will not be enough.
You shouldn’t guess what other applicants’ skills or strengths are; instead, you should focus on your own. Explain to the interviewer why you are qualified for the position, what makes you a good employee, and what you can offer the organization. Maintain brevity while highlighting accomplishments.
Harmandeep Singh
Harmandeep Singh is the Director at Cyphere, a cybersecurity services company helping customers protect their most prized assets across the UK and the US.
“My favorite CISO interview question is…”
What do you see as the biggest security challenge facing companies today? This question helps to gauge the candidate’s understanding of the current security landscape while also revealing their problem-solving skills and their ability to prioritize in a complex environment.
This question also allows the interviewer to learn how well the candidate is prepared and how they think on their feet. The answer to this question can also provide some insight into how the candidate might handle future security challenges.
Jessica Glazer
Jessica Glazer is the founder of MindHR INC, an executive search, resume writing and career coaching company.
“My favorite CISO interview question is…”
Can you describe your approach to developing a comprehensive information security strategy?
This question helps to assess the candidate’s experience in information security and their ability to articulate a well-defined, holistic approach to addressing security risks.
A strong candidate will likely discuss their experience with security frameworks and standards (such as NIST, ISO, or CIS), their approach to risk management and threat intelligence, their experience with implementing security controls and technologies, and their ability to communicate security risks and strategies to executive leadership and stakeholders.
With this question, you can gauge the candidate’s technical expertise, strategic thinking, and communication skills, which are all important qualities for a CISO to have.
Finn Wheatley
Finn Wheatley is the Executive Consultant of Data & Technology at Xtrium.
“One of my favorite CISO interview questions is…”
What’s your experience with security incident management?
This question allows you to get an understanding of the candidate’s experience in dealing with security issues, as well as their ability to respond quickly and effectively to any potential threats or incidents.
When asking this question, it’s important to further delve into the details of the candidate’s experience. You can ask follow-up questions such as: What steps did you take to handle a security incident? or How did you ensure that the incident was handled correctly and that it was addressed in a timely manner?
The answers to these questions will provide insight into how the candidate would handle similar security incidents in the future. By understanding their experience with security incident management, you can ensure that the right candidate is chosen for the job.
John Willis
John Willis is the founder of Convertfree.
“My favorite CISO interview question is…”
How do you stay current with the latest security threats and trends?
This is one of my favorite questions in an interview because staying current with the latest security threats and trends is a critical aspect of the role. As a CISO, you are responsible for protecting an organization’s information and assets from potential security threats, so it’s important that you have a deep understanding of the current landscape and are able to anticipate future risks.
Your company’s CISO is one of the most important positions you’ll hire for. These interview questions help to evaluate prospective candidates and assess their skills, qualifications, and how well they keep up with the latest technologies to protect your company’s valuable digital assets.
