[TylerE]

Don't ask for $1k in a situation like that.

Ask for $10k, maybe even 15 or 20.

It's harder to get them to say yes, period, since that requires actual action on somebodies part.

So you might as well make the bigger ask, and then if negotiation ensues you can "settle" and still get more than you would have gotten by asking for a smaller amount initially.

This can make it feel like a win for both sides.