Comment What about Bob? (Score 1) 379
First off, I have to ask this:
If it's to benefit everyone else, then quityer griping and come up with a design to supplant it, and get Bob's buy in. It's that simple. If you have no design suggestions, then quit yer complaining. And if you have a design proposal that will benefit no one but yourself, well then, figure out a way to have your design and his coexist without causing rifts... The problem here is: you're making an overarching statement. It's like my nephew saying "Everyone hates that game"... A game that gets 30% rating on rottentomatoes.com, a game I loved. There's nothing wrong with wanting to do things your way, but Bob's buy in doesnt' have to be the political eggshell walk you think it is, and here's why:
You may be right! BOB may even hate what his design's manifested into, because maybe he didnt foresee the design issues. It's like God saying "Everything is acceptable," then all hell breaks loose and God finds himself being tortured in hell by Office workers beating up Printers with Baseball bats while he watches Little House on the Prairie and Gilligan's Island re runs... Then comes Terminator wars because robots are driven mad by a scientist who can't figure out how to get off a tiny island that seems to have all the supplies necessary to create an entire civilization.
There comes a point in any design, where some 'order' is needed to progress a design past 'stagnation', whether it's in a grand design of life or in the office... And as a former Enterprise Architect (Star Trek), I can assure you that when you come at Bob guns loaded (like the starship), he's going to be expecting a fight which totally changes the mood and the outcome of the conversation.
But if you approach him asking him about the design, and don't tell him it's crap... because obvious, the design was in part responsible for the success of the company, maybe he just didnt foresee the growth, and even if he had, why would he want to support the design forever? My point is, try to figure out the design for yourself. Take a hard look at Bob. Who he is as a person, why he does what he does. How does his mind think. What's his background, his experience, what does he find valuable in life... And compare it to yours.
And keep this in mind: Preliminary designs are created out of necessity. Going to the 'God' example again. Maybe God had a World War he was trying to avert, an invasion of Daleks (Doctor Who), The Borg, Terminators, and Mr Smith from the Matrix all up in his rear about simply making a decision to move forward with. AS we can see, the worst has happened in alternate realities, but in our reality, the design worked
The same thing holds true for your man, Bob. He had an idea for a system. Worked decently. Now, there's more people using it, and it's making things.. hectic.. for at the least you.. and quite possibly others. Bob should understand the dilemna that inflexibility in design presents. The idea of what his system does is still very much alive and being respected. But like anything in life, in order for life to move on, the system has to be let go by the owner so the owner can move on and enjoy the fruits of his labor, and watch as the idea of what he built takes of and others - may cause a system outage or a crash at first. But really, in the end, if he doesn't believe enough in his work to think others can take it over and honor him with new ideas of their own...
It's like the movie Tron. Life happened unexpectedly. Iso's - a miracle of life by a creation..
Now how can you honor someone more than asking him to let go of his work, just a little bit, asking for his help and guidance in building a new system, rather than force him to sit back and watch without participating...
Do you see the problem this presents?
One final note:
When you say "No one except Bob really knows how the system works.": So let me assume you've gone through and done a full analysis of all employees, old and new, and asked each how they feel about it, and gotten 100% statistical support to defend your argument...
My nephew who is 19 makes the same mistake. Assumes everyone thinks the same way.. Be careful about this... You may have to work with two systems and become a designer yourself to appease multiple interests here.
This sounds like a wonderful opportunity for you to grow as a person though!
Good luck!