October Insights—Going Back to Basics, Standing By Our Values, and Asking AI to Disagree

Happy October, friends.

Ransomware is still hitting Canadian organizations, and AI keeps changing the picture for attackers and defenders alike. This month’s reads look at what the latest claims mean for small businesses and where AI fits into the basics.

We also have two leadership pieces, one on values that hold up under pressure and one on the value of AI that pushes back instead of just agreeing.

Hope you enjoy this month’s selection!

Michael

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Cybersecurity / Technology Articles

Several Canadian organizations appeared on ransomware leak sites, according to a report released October 1, included a hospital that had to close its outpatient lab and imaging services. Ransomware groups don’t pick targets by industry; instead their tools scan networks for weak spots like unpatched software, recycled passwords, missing MFA, etc. Often, small businesses read a story like this and think it can’t happen to them, but that’s what they thought too. When these stories are released, the best thing you can do is confirm your incident response plans, test your backups and make sure MFA is enabled. Check out the article for the full details of what happened.

Ransomware Claims Hit Canadian Peers: What Your Small Business Should Do Now

This Harvard Business Review article argues that AI is changing both sides of small business cybersecurity. Attackers can now write more convincing phishing messages, find weaknesses faster, and automate ransomware, but the same tools can help defenders. Start with the basics: turn on multi-factor authentication, keep backups offline, and make sure patching runs automatically. Then turn on the security features already included in tools like Microsoft 365 or Google Workspace, and bring in outside help for what your team can’t cover alone.

How AI Is Changing Cyber Threats—and Cybersecurity—for SMBs


Leadership & Personal Growth

Most company values sound good on a wall. The ones that matter are the ones you’d keep even when they cost you. This piece makes that case, and it’s a useful lens for our commitment to stay local. Staying local is a choice we make even when it’s not the easiest path, and I’d like our team to be able to say so with confidence. The article opens with a Johnson & Johnson story that’s hard to forget, then offers three practical ideas for building values that hold up under pressure.

Will Your Organization Stand By Its Values—Even When It’s Hard?

I’ve always believed there’s value in having people around you who are willing to challenge your ideas. It’s easy to surround ourselves with opinions that reinforce what we already believe, but some of the best decisions come from conversations that make us reconsider our approach. I think the same principle applies to AI. We’re getting pretty comfortable asking it to help us write, research, and solve problems, but how often are we asking it to disagree with us? I came across this interesting article about using AI to challenge our thinking rather than simply confirm it, and remember that these tools can be just as valuable for the questions they raise as the answers they provide.

Asking AI to Disagree With You May Improve Your Work


Partner Spotlight – FortWhyte Alive

This month, I wanted to take a moment to recognize an organization doing some incredible work right here in Winnipeg. FortWhyte Alive has long been a place where people of all ages can connect with nature, learn about the environment, and gain a greater appreciation for the world around us. From educational programs for students to conservation initiatives and community events, they continue to create opportunities for learning and connection in our own backyard. I think we’re incredibly fortunate to have organizations like FortWhyte Alive in our community, and I encourage you to take a look at everything they have to offer. Whether it’s your first visit or your fiftieth, there’s always something new to discover. FortWhyte Alive


Events

October 14 – Practice Connection

October 15 – SABEX Awards