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#CYBERinsanity – Habit 7: NOT Assessing Cyber Risk Early & Often

by | Nov 24, 2025

Still think you’ll “deal with cyber risk later?” Hackers are counting on it.

Most organizations don’t get breached because they’re irresponsible. They get breached because they delay.

Constantly delaying and pushing:

  • “After the next quarter…”
  • “When the new IT hire is on board…”
  • “Once we finish this other project…”
  • “When leadership finally approves the budget…”

But here’s the harsh #cybertruth:

Cyber risk doesn’t wait for your convenience. It compounds. Silently. Relentlessly. PREDICTABLY!

By the time most companies finally run a real risk assessment, the attackers have already mapped their systems, harvested credentials, or slipped in through a forgotten vendor account

This habit – postponing or downplaying risk assessments – is one of the most quietly catastrophic failures in modern leadership.

Pure #CYBERinsanity!

Leadership Protection Exemption = #CYBERinsanity image

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Why This Habit Is So Deadly

  1. You Can’t Protect What You Haven’t Measured (or identified)
    If you haven’t assessed your risks, you’re not secure – you’re just uninformed.
    Blind spots aren’t harmless; they’re attack surfaces. And today’s threat actors love organizations that don’t know what they don’t know.
  2. Unknown Vulnerabilities Become Known… to Hackers
    The moment a vulnerability is discovered publicly, attackers automate its exploitation within hours. If you haven’t assessed your environment recently, you aren’t “safe” – you’re just behind.
  3. Security Risks Drift & Expand Without Reassessment
    New apps. New staff. New tools. New vendors. Every change introduces new gaps. If your risk posture is based on data from last year -or last quarter- you’re already vulnerable.
  4. You Can’t Prioritize What You Can’t See
    Leadership often struggles with cybersecurity budgeting not because they’re unwilling, but because they’re uninformed. A comprehensive risk assessment gives leaders:
    – clarity
    – justification
    – prioritization
    – accountability

Assessing Risk, transforms [cyber] from a mystery cost conversation, to a critical business strategy.


How This Habit Became Normalized

For years, risk assessments have been seen as:

  • complex
  • slow
  • expensive
  • disruptive
  • optional

And many IT teams reinforced the habit by avoiding assessments themselves — fearing what leadership might discover or misunderstand.

Meanwhile, attackers built industrial-scale automation to scan the entire internet every minute of every day.

You don’t need to be individually targeted anymore. You just need to be discoverable.

And unassessed environments are the easiest targets in the world.


Breaking the Habit: What Cyber-Safe Organizations Do Differently

  1. They Assess Routinely — Not Reactively (because cyber posture is constantly changing – security is a cycle, not a moment):
    – Quarterly
    – Bi-annually
    – After major changes
    – After new hires
    – After new vendors
  2. They Use Third-Party Risk Validation
    Internal teams see what they expect to see. External assessments see what’s actually there
  3. They Treat Risk Like Finance
    You wouldn’t run your books once a year and call it responsible. Cyber shouldn’t be any different.
  4. They Tie Risk to Business Outcomes
    Risk assessments shouldn’t just list findings. They should clarify financial and operational impact with [quantitative] risk intelligence – risk becomes real when quantified:
    – This will cost us $1.2M if exploited
    – This exposes 4,000 customer records
    – This will shut down operations for 9–12 days
  5. They Hold Leadership Accountable
    Cyber risk is owned by leadership. IT only manages it.

When leaders assess early and often, their entire organization rises to match that posture.


%

Orgs Lacking Personnel for IT Security

46% of all cyber breaches impact businesses with fewer than 1,000 employees.

Implication: Nearly half of all breaches are hitting relatively small organizations – so size doesn’t make you immune. If you’re a business under 1,000 employees and treating cybersecurity as a “big-company problem,” you’re choosing to ignore half the attack surface. This means you must act like you’re in the cross-hairs now, not later.

Source: StrongDM

%

Small Firms WITHOUT full-time Cyber Expertise

Only 28% of small firms have a full-time cybersecurity expert or team.

Implication: Over 70% of small firms lack dedicated cybersecurity personnel — meaning many rely on ad-hoc IT staff, external contractors, or hope employees don’t make mistakes. That gap is precisely what attackers exploit (insider mistakes, misconfigurations, delayed patching). Without consistent oversight, your risk increases every day you ignore it.

Source: SQ Magazine

%

SMBs Aware of Increased Risk But NOT Changing Behavior

93 % of SMBs say they’re aware of cyber-threats — but only 36 % are investing in new tools.

Implication: If 93% of SMBs know cyber threats are a real and present danger, but most still haven’t changed their behavior, then awareness isn’t the problem – action is.

Awareness (absent action) means you’re blindly staring at the train coming straight for you.

Source: Businesswire


Your Next Step: If You Can’t Answer “Yes” to All of These… Your Risk Posture Is Already Compromised

  • Do you know your current cyber risk score?
  • Do you know your top 5 exploitable vulnerabilities today?
  • Do you know which vendors have access to your systems?
  • Do you know your backup integrity confidence level?
  • Do you know your MFA penetration rate across all users?
  • Do you know which privileged accounts exist — and why?
  • Do you know the financial impact of your top three cyber risks?

If your answer isn’t a confident, documented “yes” to each one – then your organization isn’t operating safely – it’s operating on luck!

And luck runs out!


Bringing It All Together: The 7 Habits Driving Today’s #CYBERinsanity

These seven behaviors aren’t rare. They’re everywhere – embedded in daily routines, leadership decisions, and outdated beliefs that attackers exploit over and over.

The real #CYBERinsanity isn’t the technology. It’s the habits we’ve normalized:

  1. Reusing & Using Simple Passwords
  2. Not Using Multi-Factor Authentication (MFA)
  3. Working with Local Admin Rights
  4. Trusting Antivirus as a Single Security Solution
  5. Using Public Wi-Fi Without a VPN
  6. Excluding Senior Leadership from Cyber Defenses
  7. Not Assessing Cyber Risk Early & Often

If you recognize even one of these habits inside your business, your risk is not theoretical — it’s active, measurable, and increasing every day.

Cybersecurity isn’t a luxury.

It’s not an IT decision.

It’s a leadership obligation and an operational discipline.

And the most dangerous habit of all is assuming you have more time before something happens.


Ready to STOP the #CYBERInsanity?

The habits are real. The risks are rising. And doing nothing? That’s not a strategy. Take the #CYBERsane next step now – while you still have a choice.


About the Author:

Matt Tankersley, CISSP is a US Navy combat veteran and the Founder & CEO of TechOnPurpose. Matt is recognized as an innovator with over 35 years of experience in Information Technology specifically in the areas of collaboration, cloud, security, and managed services. Recognizing the complexity, risk and blindsides that business owners face led Matt to create the TOPCYBER21™ Framework, which simplifies how organizations operationalize cybersecurity. Matt’s dedication to customer experience and unwavering belief that “Technology is at the Heart of Business today,” cast the foundation for our culture and simple operating philosophy: “We love what we do, who we do it with, and who we do it for.”

About TechOnPurpose:

Based in Austin, Texas, TechOnPurpose (“TOP”) delivers comprehensive managed IT and cybersecurity solutions to select clients globally. TOP’s approach to managed IT and cybersecurity continues to deliver simplified conversations and comprehensive, affordable solutions for our global customer family of Small & Medium Businesses and Non-Profits.

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