Cybersecurity is more important than ever. With cyber threats constantly evolving, it’s essential for businesses to stay proactive in protecting their sensitive data and assets. 

One of the best ways to strengthen your cybersecurity posture is by asking your IT team the right questions.

Here are some critical questions that will help identify potential vulnerabilities and ensure your business is adequately prepared for potential cyber threats.

Risk Assessment

A thorough risk assessment evaluates your organization's cybersecurity strengths and weaknesses. Third-party assessments offer an unbiased perspective, helping to identify gaps and prioritize threats effectively.

Regular assessments help keep security measures effective and aligned with evolving cyber threats.

IT Questions to Ask:

• When was the last time a third party performed a thorough risk assessment to identify potential security vulnerabilities?
• What is our current cybersecurity risk profile? 
• Have we conducted a thorough risk assessment to identify vulnerabilities? 
• What steps have we taken to mitigate the most significant risks identified in past assessments?

Data Protection

Ensuring the secure storage and encryption of sensitive data reduces the risk of unauthorized access and data loss. Reliable backup solutions are vital for business continuity in the event of cyberattacks, hardware failures, or natural disasters.

Clear data retention policies and legal compliance are essential for protecting sensitive information.

IT Questions to Ask:

• How is sensitive customer data stored and protected? 
• What is our data backup strategy and how often are backups tested? 
• Do we have data loss prevention measures in place? 

Network Security

Firewalls, intrusion detection/prevention systems (IDS/IPS), and continuous monitoring serve as the first line of defense against cyber threats.

Keeping network security solutions updated and monitoring them 24/7 helps prevent breaches. Additionally, segmentation of network access can further mitigate risks.

IT Questions to Ask:

• What systems are in place to safeguard our network?
• Are we using intrusion detection/prevention systems (IDS/IPS)? 
• How do we monitor for suspicious network activity? 

User Access Control

Role-based access control (RBAC) minimizes the risk of unauthorized access by restricting employee access to necessary systems and data only. 

Implementing strict access policies ensures that only authorized personnel can view or modify sensitive data. Regular audits of access logs help identify potential security risks.

IT Questions to Ask:

• Does our firm have employee access permissions? 
• How are permissions determined, and how often are they reviewed?
• How do we manage employee access to sensitive data based on their roles? 

Password Management

Strong password management policies are critical to reducing the risk of unauthorized access and data breaches.

Implementing MFA and enforcing strong password requirements, such as length and complexity, adds an extra layer of security to protect sensitive accounts and systems.

IT Questions to Ask:

• What password policies do we enforce?
• Do we utilize multi-factor authentication (MFA) across all accounts? 

Employee Testing and Training

Human error remains a top cause of cybersecurity breaches. Regular training ensures employees can identify phishing scams, social engineering attacks, and other security threats.

In our survey, 72% of firms plan to increase cybersecurity training in 2025. Don’t let your business fall behind.

IT Questions to Ask:

• What cybersecurity training is provided to employees, and how often is it updated? 
• Are employees educated on phishing scams and how to identify them? 
• Are employees trained on secure remote work practices?
• How do we measure the effectiveness of our cybersecurity training programs?

Incident Response

A well-documented and tested response plan enables swift action in the event of a cyberattack, minimizing potential damage.

Clearly defining roles and responsibilities ensures a faster, more efficient response, reducing risk and downtime. Regular incident response drills can also help improve preparedness.

IT Questions to Ask:

• What is your cyber breach response plan?
• Do we have a documented incident response plan for cyberattacks? 
• How do we detect and respond to potential security breaches? 
• Who is responsible for coordinating the incident response process? 

System Updates and Patching

Regular software and hardware updates address vulnerabilities and ensure compliance with security standards. 

Implementing patch management solutions can help streamline the process and reduce human error. Additionally, testing updates in a controlled environment before deployment can help to prevent system disruptions.

IT Questions to Ask:

• What is our patch management and maintenance plan?
• How frequently are operating systems and software applications patched with security updates? 
• Do we have a process for testing updates before deploying them across the network? 

Compliance

Non-compliance with cybersecurity regulations can result in legal penalties and reputational harm. Regular audits help maintain compliance and ensure that cybersecurity policies align with industry standards including SOC2, HIPAA, and GDPR.

Businesses should also document policies and provide ongoing compliance training to ensure employees stay up to date.

IT Questions to Ask:

• Are we adhering to industry-specific cybersecurity regulations or compliance standards? 
• Do we have documentation for all security controls in place?
• How do we ensure ongoing adherence to our policies?

Third-Party Security

Vendors with access to your systems and data can pose a security risk. Ensuring their compliance helps mitigate potential threats.

In our survey, 80% of firms outsourced part of their IT management. Conducting due diligence before selecting vendors and regularly assessing their security posture is essential.

IT Questions to Ask:

• How do we assess the cybersecurity practices of our third-party vendors? 
• Do we have contracts in place with vendors outlining security requirements? 
• What actions do we take if a vendor experiences a security breach?

Cybersecurity and Cyber Insurance

Recognizing common threats—such as ransomware, phishing, and insider attacks—helps businesses implement targeted security measures.

Cyber insurance is essential and can help mitigate financial risks associated with breaches. 80% of the firms we surveyed already have a cyber insurance policy.

IT Questions to Ask:

• What are the most likely cyber threats facing our business?
• Does our organization have cyber insurance?
• Does our policy provide comprehensive protection against all types of cyber threats?
• When was the last time we updated our policy??

Get Your Questions Answered

Asking these questions will help you understand the strengths and weaknesses of your current cybersecurity practices. Regular engagement with your IT team helps your business stay ahead of evolving threats and maintain strong cybersecurity.

If you want guidance on cybersecurity or if you have more questions, don't hesitate to reach out. We’re here to help guide you through the process, offering expert advice tailored to your business needs.

Contact us for a no-pressure conversation and take the first step toward a more secure future.