Business

Why Are We Paying Nearly the Same Money for Less Protection?

July 2, 2026

Microsoft just raised prices across most of its business SKUs. Business Basic, Standard, E3, E5, F1, F3. All up. One plan stayed flat: Business Premium. For years, the conversation we’d have with a leader on Business Standard went something like this. “Premium costs more. Standard covers what my team uses: email, Teams, Office apps. The…

MFA is on. The floor for attacking it just dropped.

June 22, 2026

MFA was on. It had been on for years. The training had been done, the boxes had been checked. And someone still got into the business manager’s email. Leaders deserve a clearer answer than “well, no security is perfect.” MFA didn’t get weaker. The floor for attacking it dropped. Five years ago, the attacks that…

Too Many People Have Too Many Keys

June 3, 2026

When we onboard a new client, one of the first things we look at is who has the keys. Not metaphorically. Literally. Who in this Microsoft 365 tenant can do anything they want, and what else are those accounts doing all day? The answer, more often than it should be, is the owner. Or the…

Stop delegating tasks. Delegate the function.

May 19, 2026

Some leaders think they’re delegating when they’re really just dispatching. The difference shows up in how the work moves. When you delegate a task, you stay in the loop. You’re approving, nudging, checking in, holding the outcome in your head. When you delegate a function, someone else owns the outcome and moves it forward whether…

A Practical Guide to AI Data Residency in Canada

May 14, 2026

Businesses are adopting AI securely by using the security features available in paid accounts. This allows businesses to configure how their data is handled according to their security regulations and preferences. However, one critical factor often overlooked is where that data is actually stored.  This question becomes especially important for organizations responsible for managing client data, whether due to insurance requirements, legal obligations, or commitments made…

Your Cyber Insurer is Becoming Your Auditor

May 12, 2026

For most of the last decade, cyber insurance worked like this: you filled out an application, attested to a handful of controls, paid the premium, and filed the policy in a drawer. Renewal looked a lot like the year before. The questions were broad. “Do you have MFA?” Yes. “Do you have endpoint protection?” Yes.…

Buying tools is easy. Running them is the actual job.

May 1, 2026

Any IT company or team can swipe a credit card and sign up for intrusion monitoring, backup software, endpoint protection, and spam filtering before lunch. The vendors have made it that easy. Trial accounts, slick dashboards, a few green checkmarks, and you can tell leadership you’re “covered.” The trouble is, buying the tool isn’t the…

A Question That Can Reframe How You Think About IT

April 28, 2026

“I honestly have no idea if we’re spending our IT budget well. I don’t even know what question to ask.” That’s the kind of thing some leaders say when they’re thinking about their IT setup. No crisis. No systems on fire. Just a quiet, hard uncertainty that a lot of leaders share but rarely say…

A Business Guide to AI Policy

April 9, 2026

The Reality of Unstructured AI Use  AI use is already happening in most organizations, whether it’s formally approved or not. Without clear expectations, employees make individual judgment calls about what data to use, how outputs are applied, and whether results are reviewed.  This creates real challenges:  The result is increased risk, wasted time, and uneven return on AI…

Not Done

February 18, 2026

People have started asking me the question. Not directly, usually. It shows up sideways, in conversations at industry events or over coffee. “So, 25 years… what’s next?” The question carries a set of assumptions. Guy in his 50s, been at it a while, business is doing well. The script says this is where you start…