Perspectives from people who've held the role.
Research, frameworks, and field notes from our network of former CIOs, CTOs and CISOs — written to be useful long before you ever pick up the phone.
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Field notes & briefingsUnsupported software now has a price — and it's written into your cyber insurance policy
Carriers are writing end-of-life exclusions into 2026 policies. The practical deadline for a platform decision may now be your renewal date, not your vendor's calendar.
The AI value-creation thesis has a plumbing problem
PE's 2026 surveys agree AI creates value — for the funds whose portfolio companies can execute. The constraint isn't the model. It's the platform layer underneath it.
From the archive
Field notes & briefings · January–July 2026Windows Server 2016: the deadline is January. The start-by date is now
Six months sounds like plenty of runway. Subtract the holiday change freeze, the application testing, and the server nobody remembers, and it isn't.
SQL Server 2016 has weeks of support left. Here's the unemotional version
July 14 is on the calendar. Triage by exposure, pick one of three paths, and put the next date on the calendar before it does this to you too.
Your vendor's breach is your breach
Lean IT means concentrated vendor risk. A one-page triage any executive can run — no security team required.
Agentic AI: judgment over hype, again
Everyone plans to deploy agents; few have. That gap is rational — and it's your window to get governance in place before the pilots multiply.
The VMware renewal letter, and what to do before you sign
The quote is designed to be signed quickly. The companies doing best are the ones that slowed down — with a documented alternative in hand.
Your cyber insurance renewal is now an audit
Underwriters stopped taking your word for it. What they verify now, what "proof" means, and the calendar that makes renewal boring — in the good way.
Buy-and-build without the integration hangover
Bolt-ons are carrying the mid-market playbook this year. The deal model assumes the systems come together; here's how to make that assumption true.
72 minutes: the new speed of an attack, and what it changes
The fastest attacks now move from break-in to data theft in about the time it takes to run a status meeting. Here's what that means if you don't have an enterprise security budget.
Windows 10 is gone. What the ESU invoice is really telling you
The bill isn't the problem. It's a message about how the decision got deferred — and a preview of the next one.
The IT budget conversation your CFO actually wants to have
Three categories, five questions, and one test that tells you whether your IT planning process worked — before Q3 tells you the hard way.
