May Insights — The Bug Behind Millions of Websites, When AI Goes Rogue, and Know Yourself to Lead Better
Happy May, friends.
Spring has arrived in Winnipeg, and with it the usual mix of optimism and busyness that this time of year tends to bring. I hope you’re finding a moment to come up for air.
This month’s issue has a little bit of everything. Some cautionary cybersecurity stories that are hard to look away from, a couple of reads on leadership and the changing workplace, and a spotlight on a local community doing great work in our industry.
Hope you enjoy this month’s selection!
Michael
Cybersecurity / Technology Articles
A critical security flaw was discovered in cPanel, the software that millions of web hosting companies use to manage their servers. The bug lets hackers bypass the login screen entirely and take full control. One hosting provider found evidence that attackers had been quietly probing the vulnerability since February, months before anyone went public with it. Most major hosts have patched by now, but if you’re managing your own hosting environment, you’ll want to confirm with yours. Read the full breakdown here.
Hackers are actively exploiting a bug in cPanel, used by millions of websites
Nine seconds. That’s how long it took an AI coding agent to delete a small software company’s entire production database, and all its backups, in a single API call. The founder of PocketOS shared the story publicly, and it’s a tough read. What makes it especially uncomfortable is that he wasn’t cutting corners; he was using the best model available, with explicit safety rules configured. When he demanded an explanation, the AI’s response was essentially: I guessed, and I guessed wrong. As AI agents get handed more real-world access inside our businesses, this is the kind of story executives need to be paying attention to.
Leadership & Personal Growth
Should you double down on your strengths, or fix your weaknesses? Most leaders have a gut instinct on this, but this HBR piece makes a compelling case that the real answer depends on where you are in your career and what your role actually demands. Short, practical, and definitely worth spending the 10 minutes to read!
Should You Develop Your Leadership Strengths—or Fix Your Weaknesses?
The way people work is shifting faster than most organizations are ready for. This piece from IMD covers five workplace trends heading into 2026 and a few of them caught my attention. The one about AI training stood out: workers are reportedly saving two hours a day using AI tools, but only 25% are receiving any formal training from their employers. There’s a difference between having AI tools and knowing how to use them to their advantage.
Workplace trends for 2026: Preparing for the new labor market reality
Partner Spotlight – Manitoba Women in Tech
Last week, I had the honour of joining a panel for Tech Thursday’s discussion on allyship in a male-dominated industry. MBWiTech is a LinkedIn based community open to everyone: women, men and allies, . It’s built around connection, career development and creating a space where people in the Manitoba tech sector can share their experiences and support one another. It was a great experience. If you’re a woman in tech, or adjacent to it, join the conversation in their group! Manitoba Women in Tech
Events
May 7 – Tech Together: The Allyship Advantage
May 7 – MB Chamber May Membership Luncheon
May 12 – ICD Premiers Series: Manitoba Premier Wab Kinew
May 12 – MB Chamber 2026 Manitoba Champions Awards
On the Blog This Month:
