IT Training Session Derailed When Senior Partner Asks How to Double-Click

4 February 2026

SYDNEY — A scheduled training session on the firm’s upgraded document management system was brought to a slow and painful halt this week after a senior partner, widely regarded as one of the sharpest legal minds in the building, raised a series of questions that no amount of IT preparation could comfortably accommodate.

The session, delivered by an external consultant from ProCore Legal Systems, was intended to walk staff at Hollis, Grant & Shore through the latest version of the firm’s document platform, a routine upgrade involving minor interface changes, updated filing workflows, and several new icons nobody requested.

It stalled almost immediately.

“Before we go any further,” said senior partner Malcolm Shore, 74, raising his hand with the calm authority of someone who has dismantled expert witnesses for decades, “can you just clarify this double-click thing.”

The consultant paused.

“Is it two left clicks,” Shore continued, “or is it one left and one right.”

The consultant confirmed it was two left clicks.

Shore nodded thoughtfully. “So what is a double right click, and when would you use it. Is that for something more serious.”

The consultant explained that right-clicking once brought up a menu, and that double right-clicking was not generally required.

Shore considered this. “And is there such a thing as a triple click,” he asked, “if you really need it to open.”

The room fell into the kind of silence usually reserved for adverse costs orders.

Around the room, junior staff stared fixedly at their laptops, experiencing the specific agony of watching billable time evaporate in real time while the presentation remained on slide one.

With mouse usage temporarily clarified, the consultant attempted to proceed to the upgrade itself, explaining that the system would improve document search, version control, and matter filing.

“I understand the concept,” Shore said, returning to his natural state of careful reasoning. “I’m simply trying to work out where the document actually is.”

Shore explained that for most of his career, filing had involved dictating a letter, receiving it printed, placing it in a labelled yellow folder, and knowing that the folder would remain in the cabinet until the end of time.

“With respect,” he said, “when it is all inside the computer, it feels less contained.”

The consultant assured him the system was secure, auditable, and used by leading firms globally. Shore nodded, then asked whether the system could “scan things in for him,” gesturing towards a lever-arch folder he had brought along as though it might be fed directly into the screen.

“I’m not asking it to do anything clever,” Shore clarified. “I just want it to take this and make it in there.”

The presentation drifted further when Shore asked whether the upgrade was “one of those artificial intelligence things,” mentioning he had recently heard of something called ChatGPT.

“This isn’t going to start writing emails for us, is it,” he asked. “Because I don’t want a computer improvising correspondence under my name.”

The consultant, who had prepared 38 slides on metadata and workflow optimisation, confirmed several times that the system was not sentient and could not draft advice, and that it remained, in every meaningful respect, deeply boring software designed solely to store documents.

By the end of the session, the consultant had abandoned the upgrade demonstration entirely and was instead explaining the difference between a workspace, a folder, and a shortcut, while associates in the back row quietly developed thousand-yard stares.

The firm confirmed the upgrade would proceed as planned, though next week’s training has been adjusted to include a supplementary module titled “Filing: A Conceptual Overview for People Who Miss Cabinets,” followed by an optional seminar on recognising when you are accidentally dragging something instead of clicking it.

Given that some people need warnings not to iron their clothes while wearing them, this is your reminder that this article is a parody.