How can I enhance/develop my IT/communication/leadership skilss in a non IT freindly and arcane environment?

 Hi David

I think before you do anything, you need to establish your personal objective in this.  Ultimately what do you want to get out of it?  Is it about furthering your career/securing your position? Is it about adding value to the business? Or are you motivated by pure integrity - doing what you feel is right?

Once you've established your personal objectives (and it might be all of the above) you can then better evaluate what success will look like.  Set some markers - how will you know your strategy is working.......

And clearly your chosen strategy will be determined by your underlying objective, but here are some suggestions re strategy:

• Identify the key players in each area.  Get to know them and understand their communication preferences.  What makes them listen!
• Appreciate the obstacles and objections within the organisation as a whole (culture might be a major one).  You can then evaluate and decide how/if these are surmountable 
• Use case studies from your previous roles to illustrate benefits.  Softly, softly to start with using 'story telling' techniques to get across the messages in a non-threatening way. 
• Offer to do a more formal cost-benefit analysis, using your case studies more formally.  Make sure you personalise the analysis to this business, so stake-holders can clearly see 'WHAT'S IN IT FOR ME'.