Posts written by:
Dave Monahan
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 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…
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…
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.…
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…
“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…
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…
We just had our annual Dolphin Summit. It was awesome – it always is. Every year we seem to find a better way to Summit. And this year, reflecting afterward, I realized we needed to stop doing something we’d been doing for years. We have a tradition of giving core value awards – recognizing three…
I’m wondering if this Insight will sound overly self-serving. I’ve debated with myself whether to include this in the series, but after 25 years of watching the same pattern play out, I think it’s worth saying. The way many businesses buy IT sets them up to fail. And the industry enables it. I know how…