Cyber Readiness Institute
Welcome to the Cyber Readiness Institute weekly newsletter. By delivering short, no-jargon cybersecurity advice you can put to work immediately, we hope to help you build a resilient culture of cyber readiness—one tip at a time.
Last week, we focused on locking our digital front door with strong passphrases and MFA. But a locked door won’t protect your house if you leave the windows wide open. This week, we tackle the second core habit of the Core Four: Software Updates.
Here is the reality: cybercriminals don’t just search for weak passwords; they actively scan the internet for known software vulnerabilities. When a software company (like Microsoft, Apple, or Adobe) releases an update, they aren’t just adding new features—they are publishing a list of security gaps they’ve patched. Every day an update is delayed is another day a known vulnerability remains exposed. Automated tools, increasingly powered by AI, allow hackers to quickly identify systems running outdated software.
To close these windows, you can’t rely on policies alone. You must guide your team to turn on auto-update and build a proactive patching reflex. Even with auto-update turned on, it is easy for busy people to put off installing the update. Here is your leadership plan for this week:
The Problem: Employees view software updates as an annoying disruption to their workday. They do not realize that clicking “Remind Me Later” actively extends an invitation to hackers.
Your Action (Monday or Tuesday): Send this informal message in your team chat (Slack/Teams) or email:
“Hey team! We locked our front door last week with new passphrases. This week, we are making sure we don’t leave the windows open. When your computer or apps prompt you to update, it’s not just an annoying pop-up—it’s a patch for a security loophole that hackers already know about. Let’s make sure we aren’t running on outdated, vulnerable systems this week.”
The Problem: Knowing an update is important doesn’t stop people from snoozing the notification when they are busy. You need a team agreement to prioritize maintenance.
Your Action (Wednesday): At the end of a scheduled meeting, ask for a collective agreement:
“To make sure our business and client data stays safe, let’s agree to a new standard. Can we make a pact that by Friday at 4:00 PM, we will all check for and run pending updates on our laptops, phones, and primary work browsers? Let’s take 10 minutes to do it together before we head into the weekend.”
Why it works: Creating a designated, shared time to update reduces the friction of interrupting individual work.
The Problem: The default reaction to an update pop-up is to click “snooze” because of Present Bias (protecting current productivity over future security).
Your Action (Friday): Give your team a simple, painless habit reflex to bypass the procrastination loop:
“IF I see a software update prompt, THEN I will save my active work and click restart on my very next coffee or lunch break.”
Following our September 28th scorecard, keep your metrics simple, conversational, and user-driven:
On Friday afternoon, send a quick message to the group: “Who successfully ran their updates and gave their devices a fresh restart for the weekend?”
Your metric is the simple percentage of “Yes” responses over time, shifting the active responsibility to your team.
New vulnerabilities will always emerge, but timely patching can significantly reduce risk. By actively guiding your team through Awareness, Commitment, and Action this week, you turn software updates from a neglected IT chore into an immediate team-wide reflex.
Now that our doors are locked and our windows are closed, we need to learn how to identify the tricks used to bypass them entirely. In Week 3 of Cyber Awareness Month, we tackle Phishing and how to turn your team into a highly responsive defense team.
Download the Playbook, and get your copy of the Playbook Guide to start planning today.
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The Cyber Readiness Institute (CRI) is an initiative that convenes business leaders from across sectors and geographic regions to share resources and knowledge that inform the development of free cybersecurity tools for small and medium-sized businesses. Advancing the cyber readiness of small and medium-sized businesses improves the security of global value chains.
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