sounds like a case for quality training
Sadly (and I mean that), it all stems from a dependency on leader's ability to both setup a deployment, and develop AutoLISP tools... not Visual LISP, not VBA, and certainly not dot NET... AutoLISP.
There's a handful of users that do know how to do what they want, but most, simply keep their head down to avoid provocation (i.e., His way or the highway). Thank God I'm on another team.
Same answer...why in the name of flying fish would one simply not use what is already IN the software.
And then try to figure out how to plug the holes or workaround it's failings? There's a name for this type of activity, and it isn't Proactive. 
He used to have his own company, then came here when that was lost and setup our 2006 LDT deployment, all sorts of customizations (i.e., Menus, Macros, etc.). He had direct input on Survey standards, design standards, until ultimately a CAD Committee was formed to add some degree of 'checks and balances'. That wasn't working, so a CAD Manager was hired (and it wasn't him being promoted).
^^ Begin the Holy war against 2009 ^^
He suffers from being extremely goood at what it is that he knows (like this AUGI article:
Too Good for Your Own Good)... so good, in fact that he was successful at convincing his manager to allow that team to be relegated to using only 2006 until recently being forced into 2009. 6+ months before that forced move, it was announced that we're mandated to transition to Civil 3d 2011, and that we're losing 2009 in 18 months.
I feel sorry for those poor schmucks.
