Join me as I explore Microsoft Copilot through each letter of the alphabet. We’re only at the second letter, but it’s a big one. At the risk of sounding like I’m lecturing, this week B is for Be Careful.

We see the standard warning message everywhere: “AI generated content may be incorrect.” While that is the most obvious “gotcha” to watch out for, I’ve seen other subtle traps that can trip you up if you aren’t paying attention.

Gotcha 1: The Accuracy Trap (and what’s the information source?)

When you’re in a rush, AI seems like a lifesaver. You’re keen to trust it, get your tasks done, and move on. But Copilot actually gets things wrong quite often, even on things that seem simple enough. 

I recently asked Copilot what week of the year we were in. You’d think it would be smart enough to know the current date, but it confidently gave me the wrong answer:

I actually had to correct it.

Why did this happen?

When I looked closer, I realized I was using the Work toggle rather than the Web toggle. 

When you are in “Work” mode, Microsoft’s documentation notes that Copilot relies primarily on its Large Language Models (LLMs) to understand prompts. This means it was using its own internal “brain” without drawing on the live internet for a simple calendar check. 

When I flipped the toggle to Web, it pulled the correct week number instantly.

This works the other way around too (obviously); if I have the toggle set to Work rather than web, for any questions that I ask Copilot, I’ll get responses based on any M365 documents, emails or chats that Copilot has access to, which might again skew any answers in a particular direction. 

TLDR: Copilot’s information sources will affect the responses you get to questions that you ask it – always check the sources.  

Gotcha 2: The “Bot” Tone (Losing Your Voice)

Using Copilot in Outlook, it will give you suggestions for drafting email responses, which are helpful on the face of it, but… 

People will notice if you don’t sound like you. If you suddenly start firing off emails that are wildly different from your usual tone—perhaps moving from “chatty and informal” to “corporate policy memo”—people are going to know something is up.

I’m all for using tools to improve communication, but I still believe the person on the other end deserves some level of human effort. If I’m communicating with you, I’d like to think you took the time to actually craft the message, or at least “sprinkled” in something bespoke. AI-generated responses might save you three minutes, but they can be a net negative for building genuine relationships if they feel robotic.

TLDR: Use Copilot to draft, but always edit to inject your own personality and personal touches relevant to your recipient. 

Gotcha 3: The “Always On” Microphone (Transcription Woes)

This is perhaps the most dangerous “gotcha” of all. One of Copilot’s best features is its ability to handle meeting transcripts. Copilot has gotten so good at transcribing and recapping, I’ve almost stopped taking my own notes entirely.

However, people often forget that the transcription continues even if they think the meeting is over. I’ve heard stories of people dropping from a call, but because others stayed on to chat, the “private” discussion that followed was captured in black and white for everyone to see later.

A general rule for life is: don’t talk s**t about people. But especially don’t do it if you’re being transcribed. Nothing ruins a career faster than a high-level recap that summarizes your “unfiltered” thoughts about a colleague.

TLDR: If the little “transcription started” icon is on, behave as if the whole company (or your mum!) is watching.

I’m sure there are plenty more things to be wary of, but these are my top three “gotchas” for now. Copilot is powerful, but it isn’t a replacement for your own common sense. Don’t get lazy, and don’t get too trusting—it will trip you up eventually.

What are your biggest Copilot “fails” or warnings? Share yours in the comments (if they aren’t career-limiting!).

Next week is a bit more fun, I promise. Can you guess what C will be for?