10 Questions Every Executive Should Ask
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Cybersecurity for business is no longer just an IT concern—it’s a business imperative. Data breaches, ransomware attacks, and regulatory penalties can upend a business overnight. And while your IT team or MSP (Managed Service Provider) handles the technical heavy lifting, leadership still holds the wheel when it comes to risk, accountability, and strategy.
Last year, ransomware attacks surged by nearly 20%, with mid-sized companies—those earning between $25 million and $100 million—experiencing a staggering 46% increase in incidents. These attacks not only became more frequent but also more severe, with the financial losses escalating by 47% compared to the previous year. -Cyber Insurance News
Cybercrime is no longer a distant threat—it’s an everyday business reality and a major driver behind the rising focus on cybersecurity for business.
Not sure where to start? You don’t need to be a tech guru. You just need to ask the right questions.
Here are 10 essential cybersecurity questions every business executive should be asking in the boardroom—no jargon, just clarity.
✅ 1. Are we actively monitoring for cyber threats 24/7?
Cybercriminals don’t operate on a 9-to-5 schedule—and neither should your defense. Ask whether your systems are being monitored around the clock and if your team has a documented response plan for alerts or breaches. It’s a basic but essential pillar of cybersecurity for business.
✅ 2. What’s our plan if we’re hit with ransomware tomorrow?
It’s not “if,” but “when.” A clear, tested ransomware response and recovery plan can mean the difference between a quick rebound and prolonged, costly downtime. Ensure backup systems are in place and regularly tested. Having a response strategy is a foundational part of cybersecurity for business, especially for mid-market organizations.
✅ 3. How often do we back up critical data—and where is it stored?
If your backups are stored on the same network that gets compromised, they’re useless. Confirm that backups are performed frequently, stored offsite or in the cloud, and encrypted—non-negotiable in modern cybersecurity frameworks.
✅ 4. Do all employees receive cybersecurity awareness training?
Employees are your first line of defense—and sometimes your weakest link. Regular training on phishing, password hygiene, and safe data handling dramatically reduces the risk of human error.
✅ 5. Are we compliant with all relevant data privacy regulations?
Whether it’s HIPAA, CMMC, or GDPR, regulatory compliance isn’t optional. Ask what frameworks apply to your industry and if your current IT security posture aligns with those standards.
✅ 6. What security measures protect our remote and hybrid workforce?
With remote work now the norm, endpoint protection, secure access (VPN or Zero Trust), and device management should be standard. If you’re unsure what tools you’re using—ask.
✅ 7. Who has access to what—and how is that access controlled?
Too much access can be as dangerous as not enough. Make sure user permissions follow the “least privilege” model and that access to sensitive systems is audited regularly.
✅ 8. Have we had a recent third-party security risk assessment?
It’s easy to miss gaps when you’re too close to the systems. An objective security assessment from an outside provider can uncover hidden vulnerabilities and provide an actionable roadmap. This is a powerful step toward maturing your cybersecurity for business posture.
✅ 9. What’s our process for updating and patching software and systems?
Outdated software is a golden ticket for hackers. Ensure there’s a process in place to track and install critical updates—especially for operating systems, firewalls, and antivirus tools.
✅ 10. Who is ultimately accountable for cybersecurity at our company?
Spoiler alert: it’s not just IT. Cybersecurity is a leadership issue, and accountability needs to start at the top. Whether you work with an MSP like SkyTide Group or manage IT internally, assign clear roles and responsibilities across leadership.
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Final Thoughts: The Executive Role in Cybersecurity
You don’t have to be fluent in cybersecurity to lead a secure organization—you just need to stay engaged, ask smart questions, and ensure your team has the right tools and support.
At SkyTide Group, we help business leaders take a proactive stance on cybersecurity for business with managed services tailored to protect your systems, your data, and your reputation. Through the strategic use of Microsoft 365’s built-in security features—including advanced threat protection, identity and access management, secure file sharing, and compliance tools—we’ve dialed in a system that helps businesses stay secure, productive, and compliant without the chaos.
Whether you’re the CEO, COO, or part of the leadership team—if you’re not sure how your company stacks up, it’s time for a conversation. Let’s Talk.
