Making Requests UP the Chain

When making a request up the chain, make it easier for your boss to say 'yes'. Here's how:

1. Pick just one issue at a time - This is not time for a 'kitchen sink' strategy...unless you're planning a major initiative with multiple parts, in which case the major initiative is your issue, not its components
2. Succinctly provide relevant background information - Keyword: "Succinctly". Provide only as much as is needed to justify that the issue warrants attention. Have additional backup/documentation available, but don't assume it will be automatically relevant to the decision to move forward. That said, be sure to articulate the business justification for your request. If all you've got is a BIWI (Because I Want It) then don't bother even starting the conversation.
3. Make a specific request - State clearly and crisply what you're looking for: authorization to do something, permission to not do something, additional funding, additional non-monetary resources? Whatever it is, don't just lay out the issue and make the boss figure out what you want.
4. Be open to a counter-offer - Sometimes you can't get exactly what you propose, but if you're open to the give-and-take of a meaningful discussion on the topic, you might very well get several of the key components of it. And that may really be all you need.

Repeat with other issues as you see fit.