Lessons from the Cyber Front

How to Lead Confidently Without Speaking Geek

Every October, Cybersecurity Awareness Month rolls around with reminders to “think before you click” and “use strong passwords.” Those messages matter—but they’re no longer enough.

Some industries are so exposed to cyber threats that insurers are increasingly hesitant to cover them—or are raising premiums, tightening exclusions, or walking away altogether.

When it comes to cybersecurity, tools and technology get all the attention. But when the breach hits—or the auditor calls—it’s not your firewall that takes center stage. It’s your documentation.

So, you’ve completed a cybersecurity self-assessment. Maybe it was part of an insurance application, a compliance review, or a tool you found online. You answered questions about MFA, backups, training, and policies—then got a score or a risk category.

Your IT provider keeps your systems running—but are they really protecting your business from cyber threats and legal exposure?

Every time a major breach hits the headlines, executives everywhere ask the same question:

If your company is breached or audited, one of the first documents regulators will ask for is your cybersecurity risk assessment.

It’s a phrase we hear all the time from business leaders: