I’ve never been a heavy Outlook user (I only recently stopped using Pine), but I was really surprised by how lost Outlook users become when you take them out of their element.  Instead of adapting and finding new (and better) workflows, they insist on trying to force Google Apps to work like Outlook.  Here is what you can expect die hard Outlook users to complain about when you ask them to switch to the web-based Google Mail.  More users are switching all the time, so expect this list to grow…

Folders, sub folders, and sub sub sub sub folders

Outlook users don’t get the concept of labels, nor do they like to use the Search feature.  They want 9 levels of nested folders even if those folders may only contain a single message.  Stop the riot with Folders 4 G-Mail – of course, then you have to wean them off Internet Explorer, which is a whole different battle.

Capture the flag

Star?  Star?  We don’t need no stinkin’ star?  A Star simply won’t do!  Where are my flags?  I must have red, blue, yellow, green, orange, and purple!

This is of High Importance:  I’ve requested a read receipt.

Outlook users assume that everyone in the world uses Outlook, and that recipients actually drop everything and leap into action when they receive a message marked with “high importance”.  “If I don’t request a read receipt, how will I know my message has been read?”.   In the real world, read receipts aren’t supported in many mail systems, and most high importance messages are flagged as spam or actively ignored by the recipient.  Google probably doesn’t support these features because they, like the rest of us, have recognized they’re useless!

If a message is important and requires a response,  use compelling subject lines and message content to get action from the recipient.  Instead of using “Re: Something Boring” as a subject line, use “Re: Something – Response Required by Friday”.

Send email messages as attachments in other emails that have e-mails as attachments.

This reminds me of pointing two mirrors at one another, or wrapping a present that’s a box within a box within a box.  Isn’t this what the Forward feature is for?  Ever heard of cut-and-paste?

Create events and tasks from mail messages

This one really surprised me.  I didn’t know Outlook could do this, but apparently if you drag an e-mail message onto the Calendar it creates an event with the content of the e-mail pasted in the details box.  Pretty cool, but GMail can do it even better.  When viewing a message in GMail, click More actions -> Create Event.  Google will parse the message and use dates and times within the body to create a calendar event.

It’s also possible to associate Google Tasks with e-mail messages.  When viewing the message, click More Actions -> Add to Tasks.  The task will then contain a link back to the e-mail message.

HTML Signatures

Wow.  Who knew that business would grind to a halt without the ability to attach a picture or crappy fonts to an e-mail signature.  Granted, the ability to include a link to your website is a nice feature. Thankfully there’s the Blank Canvas plug-in, because without it, the world as we know it would end.

Send To / Send as E-Mail

Because GMail is web based, it can’t act as the default mail client to attach documents to e-mails automatically.  Without Outlook installed, how ever are you going to e-mail that document?  Well, if creating a new message and clicking “Attach a file” is too much for you, you can always install Affixa.  Then, using the send-as-email feature will trigger Affixa to create a new draft message in GMail with the document attached.  Fill in the To,  Subject, and Message, and then Send.