Once you can answer the WIIFM question, then you are ready to talk to Bob. Bob will be asked to do work - to change the way he works, to learn a new system. In the short term, this will cause hassle, frustration, delay and extra work. Those are all negative things. Change _itself_ can be perceived as a negative thing.
To be worth it, it needs to either save Bob time, or remove one of his pain points. The board doesn't matter, no one else matters. Only Bob's pain points matter.
So, look at the existing system from Bob's point of view. What does he spend most of his time doing? How can you make that faster and less error prone? If you can do that, then you have the hook to pull in changes that benefit everyone else.