Introduction

So you made it to what some may call the pinnacle of your Information Security career – Chief Information Security Officer (CISO! Or at least, the job interview.

Any job interview can be tough, but for the summit of your career, it will be the culmination of your acquired information security knowledge viewed through the lens of a C-level executive. Regardless, this fact should not dissuade you from knocking the interview out of the proverbial park. This article will help you to that end – the Top 30 Chief Information Security Officer (CISO) Interview Questions and Answers for 2019.

After the predictable icebreaker level of interview questions, there are three main levels that this article will focus on: Ground Level, Mid-Level and Executive Level. If you are about to interview for this prestigious position, let this article be your guide and you should not have any problem landing the job of your dreams.

Level 1 – Ground Level

This first level of questions will be beyond the quintessential “Tell me about yourself” kind of interview questions. The type that is considered Ground Level will focus a little more on your specific experience that will carry over to this position. With that said, don’t sweat these questions as they should be fairly foundational for you at this point.

1. What Is SSL?

Think of questions like these as a sort of softball technical question. Of course you know what it is: SSL is standard security technology for creating an encrypted link between clients and servers. Knock this one out of the park!

2. What Port Do You Ping Over?

Second question in, and you already have a trick question. The trick here should be apparent to you at this point in your career, though. Ping is a Layer 3 protocol whereas ports are elements of Layer 4.

3. Is Cloud Computing a Security Risk?

Even in 2018 and 2019, cloud computing is still a risk. While there are many potential dangers involved with cloud computing, it is really up to the cloud computing customer to ensure information security. These considerations really depend upon the nature of the business as well the data being stored, so a good CISO would have to make these decisions on a case-by-case basis.

4. What Challenges Do You Foresee in This Position?

This question may seem very open-ended, but this is really just a filtering type of question. Employers want to filter out those who are not qualified, and a good way to see if someone is qualified is if they can properly foresee issues that may arise on the job. Bring up any common issues that may have occurred in your last CISO position and then apply them to the specific organization that you are interviewing with.

5. What Mistakes Have You Learned From While Working as Chief Information Security Officer?

Do not think that this question is trying to find out if you have a high propensity for mistakes. We all make mistake; the important thing is how you learn from them. The best kind of mistakes to bring up are ones that specifically involve your position as a CISO. Think of a question like this as a good opportunity to show that you can turn mistakes into strengths.

6. Board Meetings Are Important For Our Organization. Are You Able to Address the Board About Technical Matters in a Way They Can Understand?

Without a doubt you need to convey that this is within your capabilities. Oftentimes, even in 2019, boards of directors are made up of people who are not exactly tech-savvy. As a CISO, you will need to address the board in a way that they can understand while also presenting information in a way that is business-focused.

7. Have You Ever Been Faced With a Situation Where You Had To Modify a Security Policy and Why?

As CISO, you are responsible for reviewing security policy. This infers that there will be times when you have to change a security policy for a security related reason. A good example to use would be when there was a recent wide scale threat, such as the WannaCry ransomware emergency that hit the scene a few years back. Many organizations responded by requiring data encryption from that point forward.

8. Have You Ever Been Involved in an Audit and How Did It Go?

Many organizations, especially those in highly-regulated industries such as healthcare, are required to undergo regular audits. While this may sound scary to those without much experience, audits are really par for the course for organizations that are on top of their game. Unless otherwise, make sure to mention how easy it was and that you essentially just showed the auditors what they asked to see, and everything went well. If it did not go well, bring up why and how you rectified the situation and what you learned.

9. How Would You Describe Your Management Style?

There are many different management styles and some work better than others. Part of this comes down to personal management style and the environment that they will manage. Use this question as an opportunity to sell your personal management style and how it will fit in with the overall organization environment.

10. Can You Describe an Example of a Security Issue at a Previous Position and How You Managed It?

This question can be thought of as an extension of the last one, but it definitely deserves to be its own question. What this one is trying to get at is how you applied your management style to a situation and what was the result. A good example would be when there was a data breach at a previous organization: explain the steps that you took to rectify the situation and to prevent it in the future.

Level 2 – Mid-Level

You made it to the second level of CISO interview questions, or what this article refers to as Mid-Level. This does not mean mid-level as in middle management, but intermediate in terms of difficulty. This level will focus more on your specific functional CISO knowledge and experience.

Interviews can definitely be tough, but do not lose any sleep over these questions. They are just a little more difficult.

11. Tell Me About a Time When You Had to Collaborate With Stakeholders to Establish an Information Security Risk Management Program

Being a CISO means you will have to collaborate with key stakeholders in establishing information security risk management programs for the organization. What this question is looking for is that you have experience in collaborating with these stakeholders and that you have the ability to work with them in making a business-focused information security risk management program that addresses their needs. In some ways, being the CISO is like being the chief negotiator for the security team.

12. How Important Is Security Awareness Training for Your Management Style?

The interviewer is trying to get an impression of how important security awareness training will be to you if you get the position. Of course, security awareness training should be paramount to your CISO management style. Recent studies have found that the propensity for a user to be security-aware has to do with how much exposure they have to security awareness issues. A great way to expose them is with training so make sure to convey just how important security awareness training is to you.

13. Does Just-In-Time Training Have a Place at an Organization You Work For?

While this question does not technically have a “right” answer, I would err on the side of saying that it should have a place at your organization. Just-In-Time training is a great way for you to address information security issues at or near zero-day. This style of training is particularly well-suited for teachable moments that can occur at any time.

14. Give Me an Example of a New Technology You Want to Implement for Information Security

This is a time when you can show just how on top of the recent information security technology game you are. A good example to use would be artificial intelligence or machine learning to help detect security threats. You can also mention any one of the many security products that combine artificial intelligence and machine learning, such as SolarWinds Log and Event Manager.

15. How Would You Describe a Strong Organization Information Security Program?

When you are faced with a question like this, do not get bogged down by too many details, you probably have designed a few yourself that were wildly successful and have some personal touches of your own. Instead, choose an answer that focuses on the conceptual three points of a strong organization information security program – namely Confidentiality, Integrity and Availability. This will let the interviewer know that you intend to implement a competent and professional information security program.

16. In What Capacity Have You Provided Information Security Guidance to Organization Personnel?

This question is a logical follow-up to the last, as it is trying to flush out what you have actually implemented in the past regarding organizational information security. Granted, the last question focused specifically on organization information security programs, but you can definitely use your experience implementing one in the past for this question. Make sure to be detailed enough for your interviewer to see that you provided guidance clearly enough for a relatively tech-unsavvy individual to understand.

17. What KPIs or Metrics Do You Use to Measure the Effectiveness of an Information Security Program?

When you are presented with a question like this, it’s really trying to get to the heart of the skills that you are bringing to the job. The best way to go with this question is to use a two-factor approach – productivity and recovery. A good information security program will improve productivity as security improves. On the same note, a well-rounded information security program will allow for quick recovery without hindering productivity or shareholder interests.

18. What Does This Position Mean to You?

While a question like this would normally be included in a more general line of interview questioning, the fact that this position is a C-level executive position opens the door for a higher-level answer. CIOs are essentially the four-star generals of the organization and responsible for protecting the organization. You will want to mention that management is a key component to a CIO’s job, because they will be the ones directing what other non-C-level employees in the IT/information security do, at least to a certain extent.

19. Our Organization Is Small. Do You Think Outsourcing Security Would Be a Wise Decision?

Trick questions are never that fun, especially ones that intend to determine your tolerance to impose massive change at the possible expense of “rocking the boat.” Despite this, small to medium size organizations can benefit from outsourcing. There are many options for outsourcing, including hiring a Managed Service Provider, or MSP. In order to avoid seeming like you will impose great change ham-fistedly, make sure to say that there are many organization-specific considerations, so a decision like this will require a good amount of effort and thought before a decision is made.

20. If You Were Going to Encrypt and Compress Data for a Transmission, Which Would You Do First?

Questions regarding the technical aspect of information security are definitely fair game. This is especially the case, as the CISO is the brain of the information security operation of an organization. You would, of course, want to compress data before encryption because encrypting data first would reduce the effectiveness of the encryption.

Level 3 – Executive Level

When you finally make it to this level of CISO interview questions, you will see just how close to C-level the organization considers its CISO to be. While some organizations truly consider the CISO position to be C-level, others (from personal experience) hold the position to be, in a certain way, subordinate to the CIO position. The way that the organization treats the position will be on full display with the questions asked. This level of CISO interview questions will contain questions from both approaches mixed in.

21. How Comfortable Are You With Executive Decision-Making?

This question could be considered as in between the two approaches mentioned above. This question literally gives you no indication of the organization’s view of your role, giving you an opportunity to highlight your personal approach to being a CISO. I suggest mentioning that you will not make this decision until you are up to speed on the organization’s environment and common/pressing issues.

22. What Has Been the Most Profound Executive Decision You Have Ever Made in a Related Role?

Building on the previous question, the aim of this one is to flush out exactly how much experience you have had making C-level executive decisions. The meat of your answer needs to match your executive experience and even if you have not held a CISO position before, you can still ace this question. Simply reflect on your experience, grab hold of a high-level managerial decision that you have made and hit this question out of the park.

23. Can You Explain Hyper-Convergence so That a Non-Technical Executive Can Understand?

Communication is an essential part of being a good CISO. A big part of this is the ability to explain complicated technical concepts to non-technical employees in a way that they can understand – even CEOs may need concepts broken down for them. Phrase your answer to this question as saying that it is a type of IT framework that combines computing, storage and networking in a way that makes organization scalability easier. Remember, the CEO does not want all the details: just give digestible headlines and you will be golden.

24. What Is the First Question You Ask When a Beach Occurs?

If a breach occurs, the first question you ask is “When did the breach happen?” This is based on the fact that good CISOs assume they have been breached and then adjust accordingly (whether the breach occurred or not). This flows into the fact that good CISOs focus more on a model of resiliency than a model of strength. Let’s face it – many organizations get breached. This makes resiliency the most sensible way of approaching an information security breach response plan.

25. What Will Be the Effect of Compliance on Your Decision-Making?

In today’s world, compliance can be a substantial, challenging standard of practice to uphold. Regardless, compliance must be satisfied for certain controlled industries, such as Healthcare.

First, your answer needs to reflect the nature of the business of the organization you are interviewing with. Second, once you have established your familiarity with the organization’s situation, you need to convey just how much compliance will be a part of your decision-making and that you are prepared to handle it. For example, if the organization’s business deals with Healthcare, HIPAA will be the standard to follow.

26. What Do You Consider to Be Key Attributes of a CISO?

Another great way for an organization to flush out how a candidate would be as their CISO is to ask what the key attributes of the position itself are. While you can take this answer in different directions, you will want to include:

  • Communication: Above all else, communication is vital for the role of CISO. You will have to effectively communicate important, sometimes complicated, information to C-level executives and others in a way that they can easily absorb and understand.
  • Flexibility: If you can say anything about being a CISO, it’s that every day is different. Many in IT and IS think that their days are always different, but days “at the office” for CISOs are the concentrated version. They may be sitting in on board meetings regarding information security practices one day and then serving as the nerve center for the fight against a major security breach the next. It goes without saying that “work hours” include nights and weekends.
  • Partnership: CISOs are most effective when they bring a sense of business partnership to the organization by their dedication and vision for the organization’s information security environment.

27. How Important is Cost-Effectiveness in Your Vision for the Organization’s Information Security Landscape?

For every high-cost solution to a problem, there are probably a handful of more cost-effective ones available. On the other hand, the price of a solution is often a reflection of the value it can bring to the organization (including the availability of product support). With this said, a good CISO will understand the importance of balancing cost with the value the solution will add to the organization. This consideration needs to be tempered by the fact that some organizations work with a shoestring budget, and this would obviously be reflected in the information security budget, if there is even one at all!

28. To What Extent Do You Plan on Incorporating IoT Into Your Information Security Environment?

How you will want to answer this question depends on the nature of the organization itself. If the organization relies on devices and other pieces of technology that are incorporated into IoT, you will want to convey how important security is for these devices. Most times, all that needs to be changed are some basic settings to allow for increased security. Some will require an information security solution. If the organization is a more traditionally-based organization without much use for IoT-connected devices, then it will not figure into your vision for the organization as much.

29. How Important Are Emerging Risks to Your Information Security Vision?

Of all the questions yet, this one will give the interviewer the most glimpse into the dynamism of your vision for the CISO position and information security environment as a whole. To be the best CISO that you can be, you will need to keep yourself very much abreast of the current emerging risks landscape as well as what has been forecasted by experts to be the next emerging risks. The interviewing organization wants a CISO that is knowledgeable of emerging threats to the point that the other C-level executives can sleep well at night, knowing that someone is keeping an eye on emerging threats.

30. Let’s Say a Major Breach Has Occurred and Is Now Resolved. What Will Be the Most Important Thing to Tell Other Executives About How the Breach Will Impact Business?

As we all know, breaches happen, and they happen often. What is important is not so much that the breach happened, but rather how the organization bounces back.

With this said, since the organization is indeed a business, the cost of the breach will be of utmost importance. As CISO, you will have to communicate the cost – the good, the bad and the ugly of the financial numbers from the breach. In the unlikely case that your carefully-planned information security strategy is what failed, have the numbers for potential solution replacements available in case you have to argue in your own defense about this. But it’s all in a day’s work for a CISO!

 

Sources

  1. 8 Tough Questions Every CISO Should Be Ready to Answer, Bank Info Security
  2. Top 5 cybersecurity questions for the CISO in 2018, CSO Online
  3. Chief Information Security Officer interview questions – 40 tough questions for CISOs and CSOs, CIO
  4. Interview With an Expert: How Does a CISO Learn to Be a CISO?, InfoSec Institute