The phrase “pulling the wool over someone’s eyes” may have rather literal beginnings. In 17th-century London, judges wore large white wigs made of wool, and if a barrister managed to confuse or mislead them, it was said the wool had been pulled down over the judge’s eyes. It’s a wonderfully visual idea — a moment of distraction beneath all that formality — and a reminder that disguise has always been part of the human toolkit.
Fast-forward a few centuries, and the wigs have gone, but the principle remains. This week, ITV News reported on an administrator who spent almost £188,000 of company money buying printer cartridges and selling them on eBay. The company only needed a few each month, yet hundreds were ordered — some even delivered to her home. The deception went unnoticed for years, exposed only when someone finally questioned why the stationery spend was spiralling so far beyond what the business could possibly use.
It’s an old-fashioned fraud, but it lands squarely in the modern world of digital risk. Today, the same behaviour could be hidden far more convincingly. AI can edit a purchase order, recreate a supplier logo, or fabricate a delivery note that looks entirely genuine. What once relied on a wig and quick thinking can now be done with a few clicks and a template generator. The wool is still there — it’s just digital now.
That’s why digital confidence isn’t just about knowing how technology works — it’s about knowing where to look. It’s about recognising that emerging tools don’t only help us work faster; they also help those who’d rather stay unnoticed. Spotting those risks means understanding how data flows, how systems interact, and which digital rocks are worth turning over once in a while.
Over the next few weeks, we’ll be hitting the road to deliver workshops on AI and cyber security at local SBM network conferences — with webinars to follow in the new year. These sessions will explore exactly this kind of issue: how traditional risks evolve as technology changes, and how school and trust leaders can stay one step ahead.
If you’re organising an event and would like us to contribute a session, we’d be delighted to join you. Because whether it’s a judge’s wig in 1680 or a doctored purchase order in 2025, the principle is timeless — stay curious, stay alert, and make sure no one, human or artificial, can pull the wool over your eyes.
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