Executive Management Guide to Cybersecurity: A Conversation with Your IT Team

Posted on: August 29, 2017
In: Digital Insights

By: Sean Hoar, Data Privacy & Cybersecurity Practice Chair
Frank Gillman, Chief Information Officer

Given the tremendous economic and reputational costs of recent cyber attacks, executives are increasingly attempting to better understand the risk to their information systems. They’ve heard about the impact of data breaches on their peer corporations, and they’ve read about the huge fines levied by federal regulatory agencies. They’ve developed an increased sense of urgency to become better educated and are attempting to glean information from industry associations, industry journals, webinars, and conferences. What they often overlook, however, are the resources inherent in their in-house experts: their information technology personnel — their IT team. The challenge is, of course, that executives speak executive, and the IT team speaks technology. If only there was a conversational bridge…

This article will provide executive management with that conversational bridge. To begin, there are three things executives can do today which may provide some peace of mind: 

  1. Engage their IT team in a structured conversation about the state of information security in their organization;
  2. Develop and test an information security incident response plan; and
  3. Identify and transfer any risk through cyber insurance that cannot be mitigated by technology.

If these suggestions are followed, executives can begin to create order amidst the digital chaos – and they’ll have a much better chance of keeping their corporate logo out of the headlines and off the regulatory radar. This article will focus primarily on engaging the IT team in a conversation about information security. It will not discuss incident response planning or cyber insurance. Those topics will continue to be addressed in other Digital Insights posts.

As background, there are internationally recognized standards and controls that recently made it out of the information security silo and onto the front pages of industry association journals. These standards and controls include those from the National Institute of Standards and Technology (NIST) and the Center for Internet Security (CIS). The controls from the CIS are known as the 20 Critical Security Controls. The Critical Security Controls comprised a prioritized list of network actions involving architectures, processes, products, and services that have proven to be effective against the latest digital threats.

The suggested conversation with the IT team is based upon questions about the Critical Security Controls. Executives need no further background than the questions themselves, but must be prepared to listen to the responses, follow up with questions about concepts, terminology, or technology that they don’t understand, and otherwise engage the IT team in a conversation.

One note of caution: if executives are going to ask questions about what the IT team is doing to protect the corporate infrastructure, they must be prepared to answer questions about their support for the IT program. Ultimately, this conversation will provide a great opportunity for executives to get to know the IT team and obtain critical information security education.

And now for the Critical Security Controls…The following is a list of the Critical Security Controls combined with questions that can guide a conversation with the IT team about the status of an organization’s cybersecurity:

  1. Inventory of authorized and unauthorized devices: Actively manage (inventory, track, and correct) all hardware devices on the network so that only authorized devices are given access, and unauthorized and unmanaged devices are identified and prevented from gaining access.
    1. Question: What are we doing, on a daily basis, to actively manage all the devices connected to our network?
    2. Question: Do we know where all the devices on our network are located?
    3. Question: What systems do we have in place to ensure that only authorized devices have access to our network?
  2. Inventory of authorized and unauthorized software: Actively manage (inventory, track, and correct) all software on the network so that only authorized software is installed and can execute and that unauthorized and unmanaged software is found and prevented from installation or execution.
    1. Question: What are we doing, on a daily basis, to actively manage all software on the network?
    2. Question: What are we doing to ensure that only authorized software is being used?
  3. Secure configurations for hardware and software on mobile devices, laptops, workstations, and servers: Establish, implement, and actively manage (track, report on, and correct) the security configuration of laptops, servers, and workstations using a rigorous configuration management and change control process in order to prevent attackers from exploiting vulnerable services and settings.
    1. Question: What are we doing, generally, to ensure that all our hardware and software is securely configured?
    2. Question: Is everything automated or are there things we are doing manually as well?
    3. Question: Is there anything we need do to make our system more secure?
  4. Continuous vulnerability assessment and remediation: Continuously acquire, assess, and take action on new information in order to identify vulnerabilities and to remediate and minimize the window of opportunity for attackers.
    1. Question: What are we doing to identify our system vulnerabilities?
    2. Question: Once we identify a vulnerability, what steps are we taking to remediate? 
    3. Question: Do we regularly conduct self-assessments?
    4. Question: What are the biggest threats to our system?
    5. Question: What are we learning about our system’s ability to handle the threats?
  5. Controlled use of administrative privileges: Track, control, prevent, and correct the use, assignment, and configuration of administrative privileges on computers, networks, and applications.
    1. Question: Who has administrative privileges to our system?
    2. Question: What type of accountability is in place for the use of those privileges?
  6. Maintenance, monitoring, and analysis of audit logs: Collect, manage, and analyze audit logs of events that could help detect, understand, or recover from an attack.
    1. Question: What types of logs are kept in our system?
    2. Question: What type of review of those logs is conducted?
    3. Question: If our system was knocked offline, would those logs still be available?
  7. Email and web browser protection: Minimize the attack surface and the opportunities for attackers to manipulate human behavior through their interaction with web browsers and email systems.
    1. Question: What types of type of information is kept in browsers?
    2. Question: Can the content of browsers be accessed by malicious actors?
  8. Malware defenses: Control the installation, spread, and execution of malicious code at multiple points in the enterprise, while optimizing the use of automation to enable rapid updating of defense, data gathering, and corrective action.
    1. Question: What steps are we taking to keep malicious code out of our system?
    2. Question: How often do we scan our system for new strains of malicious code?
  9. Limitation and control of network ports, protocols, and services: Manage (track, control, and correct) the ongoing operational use of ports, protocols, and services on networked devices in order to minimize windows of vulnerability available to attackers.
    1. Question: Is it possible to only provide access to ports, protocols and services that are necessary for people to do their jobs? 
    2. Question: Do we disable unnecessary ports, protocols, and services?
  10. Data recovery capability: Identify and implement processes and tools to properly back up critical information with a proven methodology for timely recovery of it.
    1. Question: How often is our system data backed up? 
    2. Question: Do you conduct full or incremental backups of our data?
    3. Question: If our servers were knocked offline, would we have access to our backed up data? 
    4. Question: How would it be recovered?
  11. Secure configurations for network devices such as firewalls, routers, and switches: Establish, implement, and actively manage (track, report on, and correct) the security configuration of network infrastructure devices using a rigorous configuration management and change the control process in order to prevent attackers from exploiting vulnerable services and settings.
    1. Question: What type of configuration management process do we have in place for all our network devices?
    2. Question: Who is responsible for our configuration management?
    3. Question: What type of change management process do we have in place for our network devices?    
  12. Boundary defense: Detect, prevent, and correct the flow of information transferring networks of different trust levels with a focus on security-damaging data.
    1. Question: Do we use an intrusion detection system?
    2. Question: How does it work?
  13. Data protection: Prevent data exfiltration, mitigate the effects of exfiltrated data, and ensure the privacy and integrity of sensitive information.
    1. Question: What are we doing to monitor the outflow of data from our system?
    2. Question: Can our system detect unauthorized exfiltration of data?
    3. Question: How does it detect the unauthorized exfiltration of data?
    4. Question: Are we encrypting our sensitive information?
  14. Controlled access based on the need to know: Track, control, prevent, correct, and secure access to critical assets (e.g, information, resources, systems) according to the formal determination of which persons, computers, and applications have a need and right to access these critical assets based on an approved classification.
    1. Question: What process is used in our system to ensure that users only have access to the data they need to do their jobs?  
  15. Wireless access control: Track, control, prevent, and correct the secure use of wireless local area networks, access points, and wireless client systems.
    1. Question: What are we doing to ensure that remote access applications are not a source of security problems?
    2. Question: I would like to make sure we know who is remotely accessing our system at all times. Do we enable all remote access logging?
  16. Account monitoring and control: Actively manage the life-cycle of system and application accounts — their creation, use, dormancy, deletion — in order to minimize opportunities for attackers to leverage them.
    1. Question: What process do we have to ensure that our system only allows access to active and authorized users?
  17. Security skills assessment and appropriate training to fill gaps: Identify the specific knowledge, skills, and abilities needed to support defense of the enterprise. Develop and execute an integrated plan to assess, identify, and remediate gaps through policy, organizational planning, training, and awareness programs for all functional roles in the organization.
    1. Question: Are we doing gap assessments?
    2. Question: How often do we conduct gap assessments?
    3. Question: What were the results of our last gap assessment?
  18. Application software security: Manage the security lifecycle of all in-house developed and acquired software in order to prevent, detect, and correct security weaknesses.
    1. Question: Is the security patching of our software automated?
    2. Question: How often are security patches installed on our software?
  19. Incident response and management: Protect the organization’s information as well as its reputation by developing and implementing an incident response infrastructure (e.g., plans, defined roles, training, communications, management oversight).
    1. Assuming there is an incident response plan…
      1. Question: How often do we review and update our incident response plan? 
      2. Question: Who are the members of our incident response team? 
      3. Question: Have each of them been trained for their role on the team?
      4. Question: Has the plan been tested?
      5. Question: Is someone responsible for keeping our network map up to date so that we know all the devices used and systems operating on our network? 
      6. Question: Are we keeping all the necessary logs to use in identifying how a cybersecurity incident occurred and who caused it (firewall logs, intrusions detection system logs, security information and event management logs, remote access and proxy logs, etc.)? 
      7. Question: If our servers are knocked offline, how will we communicate? 
      8. Question: Do we have someone to serve as a liaison with law enforcement?  
    2. ​If there isn't yet an incident response plans…
      1. Question: What are we doing today to develop an incident response plan?
      2. Question: Who is involved in the planning (it should involve personnel from at least legal, information technology, physical/operational security, human resources, media relations, etc.)?
      3. Question: Since it is critical that our executive management supports the plan, what is the strategy to involve them in the planning/approval process?
      4. Question: What is the time frame for completion of the plan?
  20. Penetration tests and red team exercises: Test the  overall strength of an organization’s defenses (technology, processes, and people) by simulating the objectives and actions of an attacker.
    1. Question: I’ve heard that about “penetration” tests. Could you explain what penetration tests are and how they are done? 
    2. Question: What risk is posed to our system during penetration testing?
    3. Question: Do we use penetration testing? 
    4. Question: How often?
    5. Question: What have we learned about our system during recent penetration testing?  
    6. Question: I’ve also heard about “red team” exercises. Could you explain what they are and how they are done? 
    7. Question: Do we use them? 
    8. Question: How often?
    9. Question: What was involved in our last “red team” exercise?
    10. Question: What was learned about our system during the last “red team” exercise? 
    11. Question: Can I watch or participate in the next one? 

Don’t be afraid to ask questions! Executives can obtain some peace of mind about the state of their corporate information security through a conversation with their IT team. If the conversation produces anxiety rather than peace of mind, it obviously needed to occur. Either way, an important first step in information security is to identify what it is and then begin managing the process of helping the IT team achieve their target goals: the best practices in the industry. 

Although no one can control the threats against information systems, they can control the risks: the vulnerabilities to the threats. By increasing an organization’s security posture and reducing its vulnerabilities, the likelihood of the corporate logo being in the headlines will be reduced, as will the likely costs of an incident. And don’t forget – make sure incident response planning and the acquisition of cyber insurance are on the priority checklist! 


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