[Bartweiss]

I notice this pattern all the time in guides to "polite" workplace communication. Their examples are hypothetical, so they look at how positive something sounds without considering the underlying content, or go even further and change content to improve tone. The advice looks good on paper, but using it when there's an actual task at hand might just sound sarcastic or disingenuous. The worst example I've ever seen was something like:

> Instead of "I need that report by the end of the day", try saying "I really appreciate you working to get that report out soon, it's a big priority right now!"

That's absolutely insane, because those are two completely different statements. The second one sounds less demanding because it's not the same request. So the tip isn't positive communication advice, it's either a schedule rework or failing to convey a deadline.

As for this specific example:

> By adding an emoji below, it's clear that the sender is embarrassed to make this last-second request, and isn't trying to come across as sarcastic, rude, or overbearing

That wasn't clear to me at all. If you type in "embarrassed", Slack will only suggest :flushed:, although I'd also have understood :sweat_smile:. I guess the monkey was meant as "I'm hiding my face with shame", but Slack calls that emoji ":see_no_evil:", and at first glance it seemed like "I'm trying to not to look over your shoulder, but is this done yet?". If the problem is "making a last second request", there's no particular reason that emoji are the best way to address it - one example simply has more content than the other. So I like your direct phrasing, and I might add:

> Hi <name>, will you be able to have the report on X ready by <time>? I'm sorry it's such short notice, thank you!

[blackearl]

I'd really just prefer to keep emojis out of any professional requests. If after work you want to go out for :beers: :D then sure, but if you're asking me to work late on a project, no amount of emojis will improve my mood.

[iamatworknow]

I'm with you there, and it gets even worse when a company has their own emojis with a completely obscure meaning that is somehow expected to be understood. Like for some reason people in my company reply to messages sent out of the context of the channel with an emoji of the pokemon Charmander breathing fire (:charangry:). My own subtle form of protest is to use random emojis that really don't have any meaning. A personal favorite is :shallow_pan_of_food:.

[leetcrew]

imo, this is part of a more general problem with emojis. the "name" of the emoji does not always correspond to the image very well, so you have to confirm that the image actually conveys the tone you are going for. then as the recipient, you might sometimes wonder whether the image or the name of the image carries the intended meaning.