Five Challenging Cybersecurity Questions Every CISO Should Ask

There are many responsibilities delegated to a chief information security officer (CISO), namely the security of a business’s information and data. You can imagine that they have a lot on their plate and have to juggle a lot of sensitive information so, what exactly do they have to know and what challenging questions should they be asking? Here are a few cybersecurity questions that a CISO should be able to broach in order to do their job effectively.

1. How Secure Is Our Organization?

cybersecurity questions

Of course, reliable cybersecurity doesn’t happen overnight, especially in a bustling business but, after having a CISO on board for a reasonable length of time, they should be able to access and address a company’s technology risk management. A CISO should ask the CIO whether, based on assessments, the preventative measures that have been taken are actually reducing the company’s risk of cybersecurity uncertainty. 

2. Are the Other Employees Able to Discuss the Bare Security Essentials?

A CISO should absolutely be able to discuss cybersecurity matters in layman’s terms with their colleagues. They should be able to ask whether everyone is up to speed on at least the bare building blocks of what makes a business secure. This sort of conversation should address specific types of cyber-attacks so all employees know exactly with what they’re dealing.

3. Is My Contribution to This Company Worth the Investment?

A competent CISO should be able to explain the whole picture to the CEO of a company. They should be able to lay out the facts when it comes to cybersecurity threats and how much it will cost if a breach occurs, along with the irreparable damage that may occur. They should also be able to ask whether they’re considered a valuable asset to their workplace.

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4. Is The CIO Confident in the Security Team’s Abilities?

There should be a comprehensible, pre-planned procedure set in place in the event of a security breach. The key to cybersecurity awareness is understanding how a cyberattack occurs. A CISO should be able to confidently ask the CEO, CIO and other IT employees if they feel safe with the security team on board in the case of an incident.

5. Do We Agree on How A Data Mapping Project Should Be Implemented?

This basically means that a company (and its CISO) should have a solid understanding of all data on record, where it’s kept and if (and how) it’s protected. This can be difficult because organizations are constantly rearranging how they keep track of data collection, etc. A CISO should always know where protected information is kept because, sometimes, this can become increasingly difficult. A CISO should be able to ask the CIO their opinion on how a “data mapping project” should be properly implemented.


These 5 cybersecurity questions will better assist a CISO in understanding the inner workings of their business, and bring an important level of awareness of cybersecurity for the company. If you’re a CISO, find the time to ask these cybersecurity questions to make sure you’re prepared for anything.

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