The role of the Chief Security Officer (CSO) is highly sought-after in the world of cybersecurity. When you become a CSO, you take on a wide-scope role, covering everything that touches your security risk as an organization.

If you reach the heady heights where you think “OK, now I’m ready to apply for a role as a CSO,” then you’ll want to make sure you are prepared. Because the role of Chief Security Officer covers many aspects of the security of a business and because the role is C-level, the variety of interview questions can be vast and challenging. The organization will be investing in you and they want to make sure that investment pays off.

Below, we have listed some of the questions we think have a good chance of coming up in the interview for the role of a Chief Security Officer. We will cover them under three different levels, “Advanced General Technical,” “CSO Basic” and “CSO Advanced.” Let’s jump straight in.

Level One: Advanced General Technical

These are general technical questions with a security slant that you would be expected to have an advanced level of knowledge about.

  1. Can you tell me what resources you use to keep up-to-date with cybersecurity threats?

It is useful to have a list prepared of what journals and authorities you use to keep your security knowledge up to date. At this level, you should already be aware of some of the key industry bodies. This includes OWASP, who compile a Top Ten list of security vulnerabilities in various areas including Cloud security. Other useful bodies that publish rich research into cybersecurity, include Information Systems Security Association (ISSA) and NIST’s Computer Security Resource Center (NIST CSRC). There is also a vast range of excellent blogs and online publications that look at various aspects of cybersecurity and offer content across the spectrum, from tutorials to expert opinions. InfoSec Institute has a number of experts who contribute to their “Resources” series to help build up a wide knowledge base around cybersecurity.

  1. Outline the basics of vulnerability management best practice.

Vulnerability management is a key task for a security department. A CSO should be fully aware of how vulnerability management fits into the complex nature of modern IT infrastructures. Vulnerability management is a multi-stage process that should be an intrinsic aspect of your general security strategy. You may want to refer to any threat and vulnerability management service you have used in previous roles. Mention the use of common vulnerability scoring systems (CVSS) to show your knowledge of industry standards.

  1. Explain the principles around the use of encryption in data life cycle protection.

Data breaches are a major issue in the enterprise. Data often has a complicated life cycle, moving across various applications and residing in cloud repositories. Protecting these data is a multi-part exercise and the methodologies used are dependent on where the data is across that life cycle.

Be prepared to talk about protecting data at rest and in motion. Mention where protocols like SSL/TLS are used and their limitation, and how and when methodologies like hard disk encryption and database encryption are applicable.

  1. Describe how social engineering works.

Social engineering is behind many of the most common attacks that an organization faces. Understanding the methods used by cybercriminals to manipulate the workforce of an organization is a way to help mitigate the risks within an enterprise. Be prepared to talk about techniques such as phishing and spearphishing and how to use security awareness training to help train staff in recognizing malicious emails.

  1. Do you hold any security certifications?

If you hold any of the industry-recognized certifications, this is the time to brag about them. Three of the most well-respected include, EC-Council Certified Ethical Hacker (CEH), the (ISC)² System Security Certified Professional (SSCP) and the Certified Information Systems Auditor (CISA). If you don’t, mention your vast experience and how you would intend to develop your certification profile going forward.

  1. What are the biggest security concerns in using connected devices and the IoT?

The Internet of Things has had a significant impact on the cybersecurity threat matrix. Endpoints are now fuzzy and highly-distributed. This leads to a number of issues for a CSO in terms of mapping resources, security patch management, and access control. There are also a number of privacy issues for consumers of IoT devices — if the organization you are interviewing for is an IoT manufacturer or has an IoT device in their portfolio, you will need to be aware of these issues. You will need to convey an understanding of the complexity that the IoT has brought to cybersecurity and how to weave IoT security into an overall cybersecurity strategy.

  1. What is your view on the use of bug bounty testing?

Bug bounty testing is used by pretty much every large organization to help security test products and services. They can be a very useful way to find out about flaws. However, they also have to be carefully managed and have a financial cost (often large) in terms of rewards. You should be prepared to answer bug bounty questions by examining the resource costs of running these programs. Bug bounty programs need to be very carefully designed and managed to be of use.

  1. How should an organization manage authentication?

Authentication is a bugbear of modern cybersecurity, being behind many of the world’s largest data breaches.

Authentication has many aspects that can be covered in this question. You can include issues such as:

  1. The importance of using multi-factor authentication for administrators
  2. How to use a mix of privileged access with multi-factor to create more secure controls
  3. The latest view on password policies from the likes of NIST
  4. The challenges of robust authentication for customers
  5. Cost and security implications when using SMS text codes
  6. Credential theft via phishing and spear phishing and how security awareness training can help prevent this
  1. Can you give me three cloud-based security issues?

Use OWASP’s Top Ten Cloud security project to keep up-to-date with the latest security issues for Cloud applications. The current top three are:

  1. Injection
  2. Weak authentication and session management
  3. XSS
  1. What benefits can security awareness training offer an organization?

Human factors are increasingly used by cybercriminals to find ways to circumvent an organization’s defenses. Insider threats, both malicious and accidental, also play a part in creating an insecure environment. In 2017, the APWG found that 76 percent of businesses were victims of a phishing attack.

Security awareness training is a company-wide initiative that educates and trains staff on the mechanics of security threats in all their forms. It is part of building a culture of security that makes it second nature to maintain security in everyday tasks.

Level Two: CSO Basic

This series will ask questions about basic exercises that a Chief Security Office would need to know when carrying out their duties.

  1. Have you ever experienced a data breach? What steps do you use to contain it?

So the worst has happened: your organization has identified a data breach. Fortunately, you have established a concrete plan of action that will minimize the impact, and staff have been fully trained on the procedures required to contain a data breach. This plan was part of your wider cybersecurity strategy and disaster recovery plans. The plan likely included a number of key steps:

  1. Stop what you’re doing. To stop the breach in its tracks, breached systems were isolated. This usually means they were disconnected from the Internet and credentials for controlling access changed.
  2. Gather your evidence. You needed to create a paper trail on what happened, when and ultimately, how.
  3. Investigate. Finding out the pathway to the breach was vital to make sure it didn’t happen again. This was done using an internal team and/or external security and auditing consultants.
  4. Fix and restore. This fixed the affected systems and got them quickly back into production.
  5. Manage the message. This is where you can demonstrate your communications with any legal and brand employees. How did you help to convey the breach to any affected parties, including the general public?
  1. What level of importance do you place on having a company-wide culture of security?

There is a general trend where human behavior is being used by cybercriminals to scam organizations. Much of this behavior is natural, but the scammer using it to encourage opening of a malicious attachment or clicking on a link in a spoof email. Cybersecurity is as much about educating and training staff in recognizing poor security behaviors as it is about applying technical solutions. Having a culture of security is part of an overall security strategy. It is also one that is being increasingly required by regulations such as ISO27001.

  1. Which regulations are you aware of that may impact your work as a CSO?

Security is now a cross-industry, cross-jurisdiction concern for all. This is being reflected in a variety of regulations and frameworks across the globe.

Some regulations may well be highly industry-specific. For example, in the U.S. the healthcare industry has the Health Insurance Portability and Accountability Act (HIPAA) to abide by which has a number of security and privacy provisions. The financial sector has the Gramm-Leach-Bliley Act (GLBA) to contend with. The General Data Protection Regulation (GDPR) has also been recently enacted and impacts across all industries that process the data of persons in an EU state. As a potential CSO, you should be aware of any industry-specific regulations as well as cross-industry ones.

  1. What are the different levels needed to classify data?

Data classification is an essential step in meeting many of the security regulation requirements. It is also vital knowledge to protect your organization in a manageable and effective way, allowing you to apply the right level of protection. How you classify your data depends on the industry you are in. You should have a data classification policy which sets out the categories of data your organization handles.

  1. How would you determine privileged access management?

Ensuring that access is on a need-to-know basis is an important part of an overall security strategy. This, coupled with robust authentication measures, can help to prevent data breaches. You should have a plan to determine who needs what access and when. You can also talk about using risk-based authentication to harden the privileged access of users.

  1. What do you think about security auditing?

Having audit logs that are focused on security events will give you vital information in fixing any breach that does occur. Security logging can also alert you to potential and ongoing security violations.

However, false alerts are becoming an issue in the industry. Be prepared to talk about measures you can use to help reduce false positives, including implementing visualization tools and machine learning into your security logging system.

  1. How can you manage the lack of experienced security personnel available in the work pool?

An (ISC)2 report has predicted a shortfall of cybersecurity staff of around 2.9 million. Finding and retaining good cybersecurity staff in an organization needs a plan of action. Talk about how you can use a mix of recruitment strategies to solve this issue. This plan should include encouraging minorities to apply, along with outsourcing to managed security services and using security awareness training with existing staff.

  1. How do you feel about remote workers and their impact on security?

The remote workforce is increasing, and it brings with it unique security challenges. Your security policy and plans need to look at remote working as a specific use case. This will touch areas such as Wi-Fi policy, authentication options and privileged access.

  1. How do you feel about using open-source software?

While open-source can offer an enterprise some good options for functionality management, it can also open up a can of worms in terms of security. Open-source software should be chosen with security as a design remit. Software development needs to be carried out using secure coding techniques and any open-source software used by the organization should have a code review performed.

  1. What ways are there to protect secret keys?

This depends on where in the organization secret keys are used. But in general, there are a few ways to protect encryption keys that are separated from data for reasons of flexibility and security. These methods include:

  • Using a hardware security module (HSM)
  • A virtual appliance for storing keys
  • Key-Management-as-as-Service
  • Cloud-based server key management

Level Three: CSO Advanced

This section will ask questions that build on the previous basic set of questions. They are a more advanced look at the knowledge and skills that fit with the role of Chief Security Officer.

  1. How do you make decisions about budget spending on security?

The many cybersecurity incidents that have taken place and made the news in recent years can help to add weight to spending money on cybersecurity. However, where you spend the money is more complicated. The decisions are often made for you because of pressing issues in a given industry. For example, if you work in manufacturing, security concerns across your vendor network may have a high weighting. You should have a plan about how to prioritize budget based on certain criteria, namely:

  1. Ensuring that the workforce is properly trained in security issues to avoid both accidental and malicious security incidents
  2. Implementation of specific security technologies to prevent known threats to your specific industry/organization
  3. Ensuring compliance with certain regulations that impact security/privacy
  4. How would you report a security risk to the CEO/Board, and what would you present?

A board is often business-heavy with one or two technical folks. Make sure you supply both a quantitative and qualitative risk assessment to the board. Present them with facts and figures that directly impact the organization and include financial costs in your analysis.

  1. What role do assets play in security?

Assets are where the cybersecurity buck stops. If you know your assets, you have the knowledge to take stock and put in the right preventative measures. Asset management is a fundamental part of an overall cybersecurity plan. This is becoming ever truer as cloud applications and IoT devices are being added to corporate assets. Show your knowledge of managing and classifying assets from a security perspective.

  1. Do you have a view on staff using social media at work?

Many organizations allow their staff to use social media in the workplace. However, there needs to be a security aspect to the policy on social media use at work. The plan should contain elements to control the uploading of any documents from work applications. You should also have some level of filtering applied to social media use in the office.

Extending this to include remote workers is more of a challenge. This is where having a security awareness training program can help to make staff aware of the dangers.

  1. How do you create a chain of custody?

Having a program for digital forensics is part of the CSO’s remit to ensure that security incidents are properly responded to and that legal counsel has evidence. A chain of custody is a process of collecting, analyzing and reporting on a cybersecurity incident. It is an important tool for a CSO to have knowledge of. Creating a chain of custody is usually done in collaboration with a cyber-forensic specialist. If you have already gone through a chain of custody process, be ready to talk about what that entailed.

  1. Why would you use key rotation?

Key rotation is used to mitigate data exposure through key compromise. It can take time for security keys to be discovered, so rotating them will reduce the risk of exposure. Having key rotation in place will help to prevent the loss of data if a key is compromised

  1. What should be the lifetime of access tokens?

Access tokens package information that can be used to circumvent security and gain access to data and other resources (such as an API). They are used widely across cloud networks and in IAM systems (for example). Because they contain very sensitive data such as session credentials, they should never have a prolonged lifetime. Always strive to set access token lifetimes to very short — minutes, if at all possible.

  1. How would you protect the use of REST APIs?

As more organizations engage in the API economy, the security of APIs is becoming more of an issue. There is no absolute answer to the protection of a RESTful API. However, there is a group of general best practice measures which include:

  1. Use secure endpoints (HTTPS)
  2. Use robust access control at the endpoints
  3. Protect token integrity
  4. Use API keys

Further options and detail can be found using OWASP’s REST Security Cheat Sheet.

  1. What methods can you use to make sure that staff are aware of company security policies?

Your company security policy will inform and determine how your organization handles security and responds to incidents. It should be developed and owned by the organization as a whole, as it should reflect your business operations. Having staff taking some ownership of your security policy can be a way to ease employees into being aware of what your policies expect of them. Any security awareness program that you engage should also reflect on and inform the development of your security policies.

  1. Should security policies be revised, and if so, when?

Yes, but there is no fixed timing. A security policy is an ongoing and dynamic document that reflects real-world issues. It should be evaluated on a regular basis and updated as needed. Any updates need to be disseminated across the workforce.

Conclusion

Going for an interview for what may be the most important job of your career is daunting. Hopefully, these questions will allow you to do some prep work before the big day. If you would like some more practice questions, take a look at Skillset, who offer practice questions for security certifications such as CISSP, Network+ and Security+ exams.

All that’s left to do is to polish those shoes and put your best CSO foot forward. Best of luck!

Sources

  1. OWASP
  2. ISSA
  3. NIST CSRC
  4. (ISC)2
  5. Digital Identity Guidelines, NIST
  6. Cloud Top 10 Security Risks, OWASP
  7. Phishing Activity Trends Report, 1st Half 2017, APWG
  8. REST Security Cheat Sheet, OWASP