Some of the big issues are:
1.) The system is very disorganized, there are documents from the late 90's that aren't relevant, but have to be sifted through to find more current stuff.
2.) Often documents are not where they should be and are difficult to find.
3.) No one except Bob really knows how the system works.
4.) No one really wants to use the system because of the monster it's become.
My concern is if Bob decided to leave the organization no one would be able to maintain the existing system and we would be scrambling to put something new in place. I feel, for what we want to do, Google Docs would be an excellent platform for collaborating and sharing documents. The other board members, except Bob, have agreed with me, but are worried that bringing the issues with the existing system may cause offense and ultimately cause Bob to leave. Other than being overly vested in a system he developed, Bob is an important part of our board and a very valuable member.
We're already having a difficult time finding members to serve on the board so it's very important that we don't lose any existing board members. I'm hoping that I can convince the Bob to start supporting some Google docs objects on the site and try to wean him off his existing system to something a bit more manageable and collaborative that can be passed on to new members and maintained easily.
I don't want this to turn into old dogs and new tricks. I'm not that far behind Bob in years and can appreciate the difficulty of being told it's time to give in to something more modern. I'm wondering how the situation could be approached tactfully so maybe Bob will see how much easier a new system could be for everyone, including him."