People do funny things when they're learning something new.
They apologise before asking questions, as if curiosity were a parking violation. They announce that they're "not very technical" the way you might confess you've never seen Star Wars. They quietly assume everyone else in the room knows exactly what's going on, only to casually suggest the cleverest use case anyone has heard all day ten minutes later.
I spend a lot of my time helping people learn Microsoft 365 Copilot, which means I get a front-row seat as people meet unfamiliar technology in real time. There's curiosity, scepticism and delight, plus the occasional look of deep personal betrayal when a button has moved since last week. (It does that. I'm sorry. It isn't me.)
The technology is interesting, sure, but the people are far more interesting.
"This might be a silly question…"
Of all the things I hear in a session, this might be the most common, and it almost never is a silly question.
Usually, it's the one half the room wanted to ask but were too busy looking calm to say out loud. Sometimes it shows me I've skipped over something important. Other times, it sends us down a rabbit hole that turns out to be far more useful than the carefully planned next step in my session. My plans have learned to live with this.
It's strange how readily we assume everyone else understands the thing we're confused about. We forget that other people may simply be nodding with more confidence.
Learning seems to come with a brief stretch where everyone pretends to know slightly more than they do, a kind of polite group bluff. Then one brave person calls it, and the whole room breathes out.
The "not technical" people
Often, the person who asks that brave question has already introduced themselves as "not technical", although I've learned not to believe a word of it.
These are often the people who understand the work most deeply. They know where a process gets stuck, which information actually matters and what a useful answer looks like. They may not know the name of every feature, but they know the weekly report takes three hours, four systems and a mildly alarming amount of copying and pasting. They know which spreadsheet is the real one. They know not to touch column F.
That knowledge is gold. Technology skills can be learned, but understanding how work really happens, with all its exceptions, relationships and odd little workarounds held together with sticky tape, is much harder to pick up.
It's no surprise, then, that the person who feels least confident with the tool often asks the most important question of all: "Would this actually make the work better?"
In a world full of shiny, beeping things, it's a surprisingly rare question.
The quiet person with the brilliant idea
Every training group has its own personality. Some people think aloud. Some click everything immediately, including several things I hadn't planned on explaining. Others are happy to watch until they understand the shape of it all.
And somewhere in the room, there's usually a quiet person taking it all in, like a very polite owl. Eventually, they speak up and describe a problem nobody else knew existed, or connect the tool to a process in a way that suddenly makes perfect sense. The conversation shifts, and everyone starts piling on ideas.
I love these moments because the learning stops flowing in one direction. I'm no longer the person at the front with the clicker. The room starts teaching itself, and I get to sit back and look as though I planned it all along.
People compare processes, swap shortcuts and discover that someone two seats away solved the exact problem they've been wrestling with for six months. There's usually a small gasp, and sometimes I think a training session is really just a cover story for a conversation people needed to have.
Making annoying tasks less annoying
Here's my favourite secret: some of the loudest reactions in a Copilot session have nothing to do with Copilot at all. They happen when someone stumbles across a feature that has been sitting there, patiently, for years.
Shift + Enter adds a new line in a Teams message instead of sending it. This one always gets a groan, as a whole career of messages sent one half-sentence at a time flashes before their eyes.
You can edit a Teams message after sending it. No more posting "*Tuesday" underneath like a little apology note.
Version history exists. Deleting the wrong paragraph is no longer a workplace tragedy. It's barely even a workplace inconvenience.
You can freeze panes in Excel. First comes relief, then a moment of quiet grief for all the years spent scrolling down and losing the headings.
Double-clicking the edge of an Excel column resizes it automatically. People rarely do this just once. They usually do it four or five times in a row, purely for joy.
Ctrl/Cmd + Shift + V pastes as plain text in supported apps. Farewell to the mystery fonts and odd colours that come along with anything copied from another document.
There's a particular joy in watching someone realise an annoying task might become slightly less annoying. Not transformed or revolutionised, just less annoying.
We describe workplace technology with words like transformation, innovation and productivity. Meanwhile, someone is quietly thrilled that they'll never again have to stare at a blank page for forty minutes, or wrestle an Excel column into shape by hand.
Both matter, but only one of them gets a little fist pump.
When curiosity takes over
Those small wins often change how people approach the rest of the session.
At the start, people tend to want rules. What's the perfect prompt? Which magic words should I use? What's the correct way to do this? They're fair questions. New tools can feel unpredictable, and rules give us something solid to hold onto.
But there's usually a moment when people stop trying to get it right and start poking at it instead. They add more context, argue with an answer or ask the same question three different ways. Sometimes they try something slightly unhinged just to see what happens, like asking for a project update written in the voice of a pirate.
The atmosphere changes as the tool stops being a mysterious machine they're being tested on and becomes something they can question, boss around and occasionally roll their eyes at.
That shift from caution to curiosity is one of my favourite things to watch. Nobody suddenly becomes an expert, but they've given themselves permission to muck around and learn by doing.
Nobody learns alone
We tend to treat learning as a solo sport. Complete the course, watch the video, practise the skill and tick the satisfying little box.
But so much learning happens between people. It happens when someone asks the question that makes everyone pause, or when a colleague shares an example from their role. It happens when two people realise they've been using completely different definitions of the same process for years, and nobody noticed. It happens in the laughter, the confusion and the conversations in the coffee queue during the break.
The tool might be the reason everyone came into the room, but it isn't always the best thing they leave with. Sometimes it's a handy prompt or a clearer picture of their own work. Other times, it's the name of the person two seats away who they really should be having lunch with.
So if you're ever in one of my sessions and feel a silly question coming on, ask it. Half the room is probably hoping you will, and the other half is pretending they already knew.