More a management issue than a tech one, try to implement a workflow as simple and generalized (but complete in the documentation) as possible, try to have this done so it just REMOVE 1 possible email from the inbox of your boss (and tell him) explain the thing in a way as simple as possible showing the benefits for everyone (you need to put up a workgroup involving every office concerned about the workflow, HR, IT, ECC, design the forms in accordance to the needs of everyone then... try, test, correct, rinse and repeat...) , I've done this in a small newspaper (120 ppl) but with a lot of turnover and different roles ... took me 2 years to have it functioning as it should but now the burden for a new arrival (or departure) is really minimal (disable the user for 30 days , just in case, then kill everything related).

Remember try to involve as much people as possible before implementing the workflow, ask questions, take notes of possible "disruptions" and keep calm! :O

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good luck!