But here is the thing nobody tells you - you cannot teach AI how you work until you understand how it defaults. And understanding the defaults means slowing down enough to notice them.
What if the biggest risk to your endpoint strategy is not a security breach - but the device itself?
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Over the past months - for years really - I have been talking about Windows in the cloud with customers, partners, and public sector organizations. This post is primarily about Windows devices - and Windows 11 specifically - because that is where the vast majority of enterprise endpoints sit. macOS has its place in the mix, and I will touch on that. But the strategic pressures I am seeing - pricing, supply chain, architecture shifts, provisioning debt - are most acute in the Windows ecosystem.
What if the skills you built are not as good as you think they are?
I built four custom skills in Microsoft Copilot Cowork before it occurred to me to ask whether any of them were actually good. They worked, mostly, so I assumed they were fine. Then I asked Cowork to score them, and the numbers told a more honest story than my own reading ever could. In my Exploring Microsoft Copilot Cowork skills post, I covered how to build skills - the format, the structure, the journey from GitHub Copilot instruction files to portable Agent Skills. This post picks up where that one left off. You have created your skills. Now what?
When was the last time you looked at your speaker profile and thought, “This actually represents who I am”?
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For years, I have been speaking at conferences, user groups, and community events. I submitted session proposals, stepped on stage, refined my talks, and moved on to the next one. But somewhere along the way, I neglected the one place where my speaking identity lives publicly - my Sessionize profile. If you have read my earlier posts about exploring public speaking and submitting session proposals, this post is the natural next step: what happens after you build the habit of speaking and submitting - and how do you keep your speaker profile alive and honest.
