Insights

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 & briefings
Field note · July 2026

Windows 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.

3-minute read

From the archive

Field notes & briefings · January–June 2026
From the archive · Field note · June 2026

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.

3-minute read
From the archive · Executive guide · June 2026

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.

3-minute read
From the archive · Briefing · May 2026

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.

4-minute read
From the archive · Field note · May 2026

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.

3-minute read
From the archive · Briefing · April 2026

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.

4-minute read
From the archive · Executive guide · March 2026

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.

4-minute read
From the archive · Briefing · February 2026

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.

3-minute read
From the archive · Field note · January 2026

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.

3-minute read
From the archive · Executive guide · January 2026

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.

4-minute read

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