Are you a person who makes things happen, or who lets things happen?

I've found that there is a difference between staying authentically engaged with potential clients (or potential donors) and pushing too hard. If I stay authentically engaged, it might take longer, but clients and I can have fruitful relationships with great results. If I push too hard to work with a potential client, I might not get the gig, or I might get it but it won't work out the way that I'd like. 

How do you know when you're crossing the line between cultivating and pushing?