All good ideas. I think a lot of people are actually open to change as long as they feel their skill and experience is being valued. Suggest that it would be good to simplify and modernise the process and find out what ideas Bob has and the challenges he sees in implementing any changes.
Also be clear on what you want to achieve, without dictating the route to go. Suggestions are fine, but don't make is sound like you've already decided - people generally take pride in what they do and want to have input into how changes proceed. And buy-in breeds better morale.
Two problems I've encountered are top down dictators who ignore people's skills and experience; and unclear goals which make it extremely hard to move forward (e.g. "make is snazzy" is not clear enough. "Allow collaboration and make it easier to locate relevant information" is better.)
MSDOS is not dead, it just smells that way. -- Henry Spencer