Boardroom vs breach: 20 questions every IT leader should be asking about cyber security

Cyber threats are evolving faster than most organisations can keep up.

Between new attack techniques, expanding digital estates, and the cyber skills shortage, even well-equipped IT teams are struggling to stay ahead.

It’s no longer enough to tick compliance boxes or to simply deploy the latest tools. Real security starts with asking the right questions and acting on the answers.

That’s why we’ve created Boardroom vs Breach, a 20-question self-assessment designed to help IT leaders and those responsible for cyber-security take a clear-eyed look at your current security posture, highlight blind spots, and spark critical conversations at board level.

Why this matters

The cost of a cyber breach isn’t just downtime – it’s trust, reputation, compliance fines, and lost revenue. Yet many companies don’t know if their defences are actually up to the task – do you?

These 20 questions aren’t about theory; they reflect real-world weak points that we see every day. If you can’t answer them confidently, we can help.

The 20 questions you need to answer

Visibility & monitoring

1. Do you have complete visibility of your IT assets?
2. What visibility do you have into incidents and events across your infrastructure?
3. How do you manage your security tooling?
4. How many different tools are you running — and are they working together?
5. Are your systems and endpoints patched regularly?

Our advice: Gaining complete visibility starts with consolidating event data, automating alerts, and ensuring continuous oversight across your entire estate.

Take a look at:

• Security Information and Event Management
• Vulnerability Management
• Managed Detection and Response

Threat detection & response

6. What happens if an incident occurs after hours? How do you find out? Who responds?
7. When was your last penetration test? How regularly do you conduct them?
8. What protections are in place for endpoints, email, and networks?
9. What level of visibility do you have into potential breaches?
10. Do you work with a partner that offers 24/7/365 response and real-world support?

Our advice: Improve threat visibility and reduce response times by combining real-time monitoring with expert-led incident analysis and containment.

Take a look at:

• 24/7/365 Managed Detection and Response
• Incident Response Retainers
• Penetration Testing and Red Teaming

Cloud & modern IT risk

11. Do you use public cloud services?
12. Are you confident in how they’re secured?
13. How do you manage and secure user devices remotely?
14. What vendors are you currently relying on — and are they right for your risk profile?
15. How do you secure your network beyond the firewall?

Our advice: Extend visibility beyond the traditional perimeter by applying cloud-native monitoring, endpoint telemetry, and policy-based access control.

Take a look at:

• Cloud Security Assessments
• Secure Access Service Edge (SASE)
• Endpoint Detection and Response (EDR)

People, process & planning

16. How are your users trained to detect attacks such as phishing?
17. Do you have access to expert help in a crisis? What cyber expertise exists in-house — is there a dedicated security leader?
18. How do you create a positive security culture, not just rules?
19. What threats are most relevant to your industry?
20. Are you meeting required regulations and compliance standards?

Our advice: Build better situational awareness by aligning people and processes with continuous monitoring and clearly defined escalation paths.

Take a look at:

• Security Awareness Training
• Virtual CISO Services
• Compliance and Risk Consulting

And a bonus question, with potentially the most worrying answer of all…

What would a breach cost your business — financially and operationally?

Putting it all together

While individual solutions can address specific security challenges, working with a trusted managed services and security partner ensures cohesive, round-the-clock support across every aspect of your cyber security posture — delivering greater efficiency, resilience, and long-term value.

We work with IT and security leaders across all sectors to assess risk, build resilient cyber strategies, and deliver comprehensive protection that scales with your business.

From real-world penetration testing to 24/7/365 threat detection, cloud security, and expert consultancy, we’re your trusted partner in securing the ‘now’ — and preparing for what’s next.