WOO ON TECH

A client of mine was using a Claude agent to help manage some administrative work. Her sons are AI programmers in their late twenties, and they gave her a hard time about it. She was prompting the thing with “please” and “would you kindly” and “thank you so much,” and they told her she was

Your network does not take nights off. Neither does the thing trying to get into it. This is the part of the IT infrastructure that most professional services firms do not consider until something stops working. The network is invisible when it runs well, which means it tends to get attention only during the wrong

On July 19, 2024, CrowdStrike pushed a routine security update to millions of Windows machines. By mid-morning, 8.5 million systems had crashed. Airlines grounded flights. Hospitals reverted to paper. Banks went offline. It was not a cyberattack. It was a software update. That story makes the rounds whenever I tell clients they need to stay

Go look up Microsoft 365 Business Basic on Microsoft’s website right now. It is $6 per user per month. Some IT companies charge $60 for it. They do not tell you that. I have had clients come to me after years with another provider, and when I pull up what they were paying for Microsoft

Most firms set their technology priorities in January with the best of intentions. By June, those intentions have been buried under client deadlines, staff turnover, and whatever fire needed putting out that particular Tuesday. I’ve been doing this long enough to know that the gap between what a firm’s IT environment is supposed to look

Every vendor in the technology industry will tell you to move to the cloud. What they won’t tell you is whether moving to the cloud is the right decision for your firm. I’ve been doing this for 35 years. I’ve watched the industry cycle through mainframes, desktops, servers, and the cloud, and in every era,