How to transition your work?

[Sanjay Srikonda <SSrikonda -at- invlink -dot- com>]

Hi all,

I'm leaving my current place of employment and have been tasked to train my
(newly promoted) "manager."  Now, as hopeful as I am that this person is
content-literate, she has no clue how to put together either a meaningful
sentence nor even less of a clue how to use software.  We produce 401k
software, and she can quote your regulation and verse on what is and is NOT
allowed.  However, whenever she tries to tackle anything more than pointing
and clicking something on the screen, she not only looks dumbly at the
screen, but most often hits CTL+ALT+DEL before asking for help on how to do
something.  Needless to say that when I first looked on her machine which
she had claimed had slowed to a crawl, I found approximately 400Mb of TMP
files created from all the reboots.  

My question is and this may be pedantic, but how and what should I decide to
train her on in the 2 hours she's scheduled on my last day here?  The
project documents our current software which is over 700 screens, contains
appendices, How-tos, context-sensitive help, and is mirrored in a WebHelp
system.

I've done my best to document how to create context-sensitive help for our
system.  I'm sure, once I leave, and no longer available, that the help will
go by the wayside as it had languished before I showed up (no, I'm not
kidding, when I started here, the help consisted of a 37Mb Word document
that could not be opened and had been authored by about 7 different
"authors" before me, none of which had been TWs), consisting of (in one
case) approximately 34 different styles in the template for Bold (in some
variation or another) and applied in whatever instance a particular author
felt it was necessary.

So, in the interests of professionalism, I'm trying to decide what I should
include in the 2 hour training I'm meant to do for transitioning my work to
a non-technical person.

Sugggestions?

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