Email etiquette checker?

Sometimes, in the heat of getting a lot of things done, I don't read emails I send as closely as I should. Is there an automated way to pop up warnings before a potentially-unpolite email is sent? I'm thinking about something that would say "wait, why don't you have a 'please' or 'would you' in that message?"

I'm using Thunderbird 2 on Ubuntu 9.04. I may be willing to switch email clients if another program offers this. (Using a Mac is also an option, which I'd prefer. Not sure if Mail.app has more options, though.)

Thanks for your help!

Solution 1:

Possibly slightly off topic but I've developed a habit of entering some random nonsense into the BCC field of any emails that I compose to external customers or to management.

This way I can't accidentally (or sleepily) click on the Send button and only realise afterwards that I haven't read it properly; until I manually remove the "erkgjherjghrejh" from the BCC field then the email won't get sent.

Solution 2:

This isn't a direct answer to your question, but Gmail Labs has an Undo Send option that delays a message for a moment, so that if you hit send then realize you shouldn't have said that, you can stop the message before it goes out. For more information, Google for "Gmail Undo Send".

A similar feature for Thunderbird might help if one exists.

What you really want is to run a filter on outgoing messages. For example, you could move messages with certain words to a Suspicious Outgoing Messages folder.
For Thunderbird 2.0 there is an extension for filtering outgoing messages.

The extension documentation says 3.0 will have that built in, but a quick Web search offered no evidence of that.

Solution 3:

The Check and Send extension lets you specify a list of words. It will then warn you before sending if any are present.

When installed, go to the extension's preferences and look under the "Words" tab. Punch in a list of your preferred swear-words here.

A nice feature is that it can skip over quoted text when searching, so if your boss was swearing at you in a previous message, it doesn't warn you for the rest of the conversation (unless you swear back).

It's also possible for it to warn if text is not present; you could use this with "please".