Admi­nis­tra­tors should encou­rage people to use Gmail web inter­face (Gmail/web for short). Why? Less work. Do you want to handle Outlook/Thunderbird/Mail.app… pro­blems on top of Gmail? Trust me, you don’t. I have my share of Mail.app issue (bad enco­ding, winmail.dat issues; both were per­fectly hand­led by Gmail/web). Let alone Outlook.

Plus, a mail inter­face means mini­mal hassle for rea­ding their mail on an mobile device (still some, because Google has dif­ferent layout depen­ding on the device). If users only use com­pu­ters, no hassle at all (apart for the occa­sio­nal reso­lu­tion chan­ging stuff).

First step: brie­fing with Boss

1. Ask if it is OK for photo to appear on mail from employees. Say it make the com­pany more humane or stuff like this. There is no bad ans­wers, just be sure to know.
2. Check if there is any Fire­fox– or IE– exclu­sive fea­ture (that would prevent using Chrome, but don’t talk about Chrome, except if Boss is tech-savvy—Chrome is more res­pon­sive than Fire­fox 4 beta and sup­port desk­top and chat noti­fi­ca­tions; with other brow­ser, one has to down­load exter­nal noti­fiers)
3. Ask or pre­pare policy for signature
4. Ask or pre­pare policy for default fonts and colour
5. Ask if Boss is okay for you having a back­door to users’ mail account (sen­si­tive topic, explain this is for main­te­nance rea­sons). A posi­tive ans­wer is bet­ter as it will make you job easier but don’t be sur­pri­sed if you get a “no”.

Second step: configuring

In order to opti­mise the expe­rience, you’ll have to tweak Gmail first. Don’t count too much on auto­ma­ted deploiment—I heard Google Apps Pre­mier is not much bet­ter here. The fol­lo­wing ope­ra­tions will have to be made by hand on each account. Sorry, no ans­wer file thus far…

Eve­ry­thing is in Settings.

1. [Gene­ral] Select the pro­per language
2. [Gene­ral] Acti­vate shortcuts
3. [Gene­ral] [Depen­ding on brie­fing] Acti­vate Chat noti­fi­ca­tions and Desk­top notifications
4. [Gene­ral] [Depen­ding on brie­fing] Add a pic­ture (or not)
5. [Gene­ral] Force sen­ding in UTF-8 (die, pre-UTF8 enco­dings, die!)
6. [Account] [Depen­ding on brie­fing] Grant access to your­self (buggy with Google Apps–not Google regular–as of March 2011)
7. [For­war­ding] Deac­ti­vate POP, acti­vate IMAP (POP sucks)
8. [Labs] Acti­vate Apps Search, if they use Google Docs (do your­self a favour, make them use it)
   send feed­back to Google about it
9. [Labs] Acti­vate Can­ned Res­ponses. Requires pro­per trai­ning. Pre­pare trai­ning before enabling, because it is visible.
   send feed­back to Google about it
10. [Labs] Acti­vate Default ‘reply to all’. Fewer people will bug you if this lab is on rather than off.
    send feed­back to Google about it
11. [Labs] Acti­vate Default text sty­ling. You hate HTML mail, but they don’t… Make it easier for them to adapt to Gmail by tel­ling them they can change the default font. Be sure to first check with Boss about any exis­ting policy.
    send feed­back to Google about it
12. [Labs] Acti­vate Don’t for­get Bob. So far, I did not have any feed­back from my users. I should com­mu­ni­cate on this fea­ture. Use­ful for infor­mal group mai­ling (contact group is still bet­ter but it requires some work on their address book)
    send feed­back to Google about it
13. [Labs] Acti­vate Fli­ckr pre­views in mail, Google Docs pre­views in mail, Picasa pre­views in mail, Google Maps pre­views in mail. At worst, they won’t see them. At best, they will like them.
    send feed­back to Google about Fli­ckr pre­view, Google Docs pre­view, Picasa pre­view, Google Maps preview
14. [Labs] Acti­vate Got the wrong Bob?. Ano­ther use­ful fea­ture to com­mu­ni­cate on.
    send feed­back to Google about it
15. [Labs] Acti­vate Inser­ting images. Talk about it during the drag-and-drop part (where you will talk about drag-and drop attach­ment).
    send feed­back to Google about it
16. [Labs] Acti­vate Nes­ted Labels. Again, some­thing natu­ral (at least for one of my users). For some times now, it had been pos­sible to create nes­ted fol­der with a GUI. Be sure to show them the GUI way!
    send feed­back to Google about it
17. [Labs] Acti­vate Pic­tures in chat. Use­less but appre­cia­ted
    send feed­back to Google about it
18. [Labs] Acti­vate Undo Send. Defi­ni­tely some­thing to com­mu­ni­cate upon. I tend to confi­gure it to 30 seconds (you’ll have to go back to gene­ral for this), but that’s just me.
    send feed­back to Google about it
19. [Labs] Acti­vate Video chat enhan­ce­ments. It’s a double-sided sword. Use­ful for video chat­ting, but you’d bet­ter have a good com­pu­ter and a good connec­tion..
    send feed­back to Google about it

Finally, place a short­cut on their desk­top and on the qui­ck­launch (Win­dows XP-Vista), task­bar (Win­dows 7) or Dock (Mac OS X).

Notice I am well aware of seve­ral other labs (I use a lot of them myself). But they impact to much the inter­face for an ave­rage user who should not even know there are labs on.

Also: I know that labs may disappear.

Third step : training

This is where the fun begins. Show some the­ma­tics. Go cres­cendo, with some­thing expec­ted at the begin­ning and sur­prises at the end. Use two com­pu­ters (one for sen­ding, one for receiving).

Pre­pare two com­pu­ters (Com­pu­ter A and Com­pu­ter B), with win­dow not taking full screen on Com­pu­ter B. Pre­pare an image and a doc file on the desk­top, close to the win­dow. Also be sure to use a used gmail account (so that it will have memory of who you mail the most, it will come in handy when demons­tra­ting the two Bob fea­tures) and that com­pu­ter has Gmail as HTML com­po­sing (or else, the attach image won’t work).

Also: know which Mail client is used in the com­pany (usually Out­look) and pre­pare a list of all the dif­fe­rences in philosophy.

Finally, pre­pare a prin­ted sum­mary for every atten­dant, sum­ming up the main point. And when invi­ting people to the trai­ning, ask them to bring some­thing to take notes (even though you’ll give them a prin­ted summary).

Round one: Reply to a mail

1. [Com­pu­ter B] Login
2. [Com­pu­ter B] Show the inter­face. Tells that it auto-refreshes and that there is even better.
3. [Com­pu­ter A] Send a mes­sage with ano­ther of your address in Cc and an attach­ment (the audience does not need to see; click on a link to over­ride undo send).
4. [Com­pu­ter B] Let Desk­top noti­fi­ca­tion do its job (if they don’t want Chrome, get a Fire­fox extension).
5. [Com­pu­ter B] Open the mail
6. [Com­pu­ter B] Show attach­ment visua­li­sa­tion for those in Google Docs (be sure to have trai­ned on Google Docs before or at least to have plan­ned to move to Google Docs)
7. [Com­pu­ter B] Get the attach­ment out with drag-and-drop of attach­ments off the mail doesn’t work by cli­cking the icon or the Down­load link
8. Reply with reply to all (which is default). Delete the reply with the delete but­ton and reply again now with a (tell the f will do the same for for­war­ding). Make sure to “for­get” to write Thank you.. Show the audience that the mail is not saved. Dont save it, show this screen­shot about qui­ckre­ply then go back to the com­pu­ter and show how the mes­sage had been saved meanwhile.
9. Attach an image via drag-and-drop and an attach­ment the same way
10. Send it with the send but­ton, tells the audience your for­got to say Thank you and undo the sen­ding with the link. Add Thank you then send. Explain it is setup to wait 10/20/30 seconds (depen­ding on what you chose) except if you per­form an action on the win­dows (clo­sing it or cli­cking a link).
11. Once back in inbox, show the archive but­ton and say how impor­tant it is. Finish by ope­ning a read mail, and delete it with the Delete but­ton. Can­cel the action and delete it again with #/

Round two: New mail

1. Com­pose a new mail with New message. Select the address by cli­cking on To and show contact groups (tell that contact groups won’t be cove­red this time; it will be for ano­ther ses­sion, with fil­te­ring). Show links for Cc and Bcc. Delete it with the but­ton (# doesn’t work for drafts). Com­pose again, but now with c and send it with tab + enter.
2. Create a new mail (again with c, so that they see it bet­ter). This time, enter the address by hand. Enter some per­son you usually mail toge­ther and, after three such per­son, volun­ta­rily chose someone who does not belong to that group, in order to invoke Got the wrong Bob?
3. Delete the addresses, start again with some people you usually mail toge­ther. Add them until Don’t for­get Bob starts up. As for the pre­vious tip, it may take some time to have it work.
4. Type a mes­sage like I atta­ched the result. Do not actually attach any­thing. Send (with Tab + enter, for good measure).
5. Show the audience the for­got­ten attach­ment detec­tor working!

Round three: Organisation

1. Start by saying that one the main idea in Gmail is to have an empty inbox. It eases the mind and help get­ting more orga­ni­sed (note: the Sent­box, can’t be emp­tied that way; this will be a sur­prise for Out­look users).
2. Show how to create a label. Go to a mes­sage, click on label, type Urgent, create. Show that now the label lives on the left column.
3. Show mul­tiple labels. Go back to the mes­sage, select label again and start typing Part­ners, a label you will already have crea­ted; then check it, click apply). Show the audience that the mes­sage now belong to two label at the same time.
4. Create nes­ter label. Don’t show direct nes­ted label crea­tion (typing foo/bar), because it is nerdy enough and even power users will be content with a two-step creation).
5. Show drag-and-drop assi­gn­ment. Select the mes­sage and drag it to a third label on the left. Show the high­ligh­ting, the fact that it is now out of the inbox and the Can­cel link. Can­cel and do it again.
6. This time, go to the said label, select the mes­sage and show how it belongs to the label. Hover over the label and click it to show the fil­ter by label view. Go back with the mouse (so that they see the action of going back), in order to show that you can navi­gate back and forth.
7. Show how to remove the label with the small cross (show also that if remo­ved, it won’t go back to inbox but will go to All mes­sages: the only way is to search for it then open it and click Put in inbox; this is com­pli­ca­ted, so don’t men­tion it)
8. Show dele­ga­tion with grant access for assis­tant (extra page with video). If you also gran­ted access to your­self, tell it!
9. Hint at fil­ters, but don’t actually show how to create one. Just sum up what can be done (only get unread mes­sages, auto-sorting without mar­king them as read, auto-prioritising, sub-addresses…). Say there tools for bet­ter cat­ching impor­tant mails, but that would require ano­ther ses­sion and you pre­fer them to be com­for­table with Gmail before going further.

Round four: Customisation

1. Go to Set­tings, Gene­ral and show that Default new sty­ling is pos­sible, as well as chan­ging signa­ture (but first check with Boss) and vaca­tion responder.
2. Show can­ned responses.
3. Show how to fetch mail from other account. Don’t actually do it, just show the pota­bi­lity. If they have a need for it, either they’ll do it by them­selves or they’ll call you. People willing to retrieve seve­ral mails on the same account are already a bit geeky and so will pro­ba­bly be able to do it by them­selves. So, you’ll do your­self and your audience a favour by not del­ving much into it.

Conclu­sion

Say some­thing like there is much more to say, so I sug­gest set­ting up a new ses­sion in, say, one month, for dea­ling with sor­ting, fast scan­ning, can­ned res­ponses, secu­rity and address book. There you will talk about what had been left out as well as remote logout (for­got to logout at the public library? Now it’s your chance).

Note to self: fast scan­ning is next/previous conver­sa­tion (mes­sage if conver­sa­tion view is disa­bled), with k and j, as well as enabling the quick pre­view lab feature.