My new gig has me working in Microsoft 365. I know this doesn’t make me unique: a quick Google suggests that over 1.3 million US companies use the product, so I know that my discomforts are due to being used to something else, as opposed to serious deficiencies in the product. Still, I’m finding it a tough transition since I’ve been a MacOS and Google Workspace user for decades. And the toughest transition of all has been moving to Outlook.

I’ve heard many, many business users say that they hate Gmail and miss the features of Outlook. But my experience is the opposite: running my calendar and email in Outlook makes me feel like I’m wearing mittens: everything is just harder to do.

So, Outlook experts, can you please share your expertise?

Calendar in a Separate Window

This one sounds silly, but it’s not. As a Google user, I’m used to having my mail open in one tab and my calendar in another. Outlook insists on putting them in the same application, which my fingers just can’t remember. Every time I want to switch from email to calendar, my mouse hunts all over the system for five seconds before I remember that the calendar is accessed via a little icon on the left side on my email window.

Is there some way to open my calendar and email in two different windows?

Send and Archive

This one is huge.

A central part of my Inbox management workflow is Gmail’s “send and archive” feature. When you turn it on, a single click will send the email draft you’re writing and archive the thread so it’s out of your Inbox. This is wonderful: once I hit that email over to your side of the net, I don’t want to see it again until you reply.

I’d like to do this on Outlook… can I, please?

Shortcut to Paste Plain Text

On there Mac, a system-wide keyboard shortcut allows me to paste plain text into any application. The same keyboard shortcut exists on Windows and works in many apps but not, it seems, in Outlook. Why? How can I make CTRL-Shift-V work in Outlook?

Disable Emoji

I hate the Emojis that come with Windows. I think they look juvenile and much prefer the text equivalents, like ;). But whenever I type them, Outlook insists or replacing them with goofy icons. I can CTRL-Z to undo the replacement, but that’s annoying. Can I disable the substitution anywhere?

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Those are the most annoying issues I have so far. Can you please help?