Cyber Readiness Check for Small, Mid-Sized Businesses

08.10.2026
Small Business

The following article was provided by Whittlesey. It is reposted here with permission. 


Cybersecurity is no longer just an IT issue. It affects operations, finances, client trust, insurance requirements, compliance obligations, and business continuity.

Many organizations have cybersecurity controls in place, but are unsure whether those controls adequately address today’s risks.

This quick self-assessment can help determine whether your organization has a strong cybersecurity foundation and identify areas that may benefit from additional attention.

Cyber Readiness Self-Assessment

Answer yes or no to the following questions:

  • Do we understand our organization’s biggest cybersecurity risks?
  • Is multi-factor authentication enabled for email and critical systems?
  • Are employees trained to recognize phishing and social engineering attacks?
  • Are backups tested regularly and recoverable?
  • Do we have a documented incident response plan?
  • Do we regularly review who has access to sensitive information?
  • Are former employees and vendors removed promptly from systems?
  • Do we evaluate cybersecurity risks associated with vendors and third parties?
  • Are we confident we can satisfy cyber insurance security requirements?
  • Do we have a practical cybersecurity roadmap for improvement?
  • Are we performing a cybersecurity risk assessment on our organization annually?
  • Do we know what data we hold and where it is located on our systems?
  • Do we have to comply with any regulatory or state requirements?

Your Results

10–13 Yes Answers: Strong cybersecurity foundation. Continue reviewing risks and strengthening resilience as your business evolves.

5–9 Yes Answers: Important controls may be in place, but additional review may help identify gaps affecting operations, insurance readiness, or overall risk.

0–4 Yes Answers: Significant cybersecurity exposures may exist and should be prioritized.

Cyber Readiness Is an Ongoing Process

This assessment is not meant to be a pass-or-fail test. It is a starting point for understanding where your organization is well prepared and where additional attention may be needed.

Cyber risks, technology, and business operations continue to change.

Review your answers with the appropriate members of your leadership and IT teams, prioritize the most significant gaps, and establish realistic steps for improvement.

Even small, consistent actions can strengthen your organization’s ability to prevent, respond to, and recover from a cyber incident.


About the author: Chris Wisneski is an IT security and assurance services manager in Whittlesey’s Hartford office. He brings more than 20 years of information technology experience, specializing in cybersecurity.

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