1) Get rid of "dead weight" on your Board. Then build up your Board in clumps. Two members at a time. Super cultivate them (in small group meetings with you first! and then to a full Board meeting). Call them each once a month! Clarify your "give/get policy" and ensure compliance. Anyone who is not fully participating (in some way!) will drag down the energy and support of the rest of the team. Everyone on the Board has to do something tangible.
2) Plan for 5 years! We've all heard it before and usually we are toooo busy to do it! This is NYC after all! But do it. Plan all your programs for 5 years, even if they are abstract plans. Think big. "In 2009 we will hunker down and do two staged readings of Yehuda's plays. In 2011 I want to do a full season of works by 5 EMERGING PLAYWRIGHTS around immigrant issues. We will do 2 symposiums around this and 3 master classes. In 2012 we will pilot an education program working with ________" Assess your projects for "fundability" and "marketability" and then plan your fundraising strategy around that. You can have one program that is less "accessible" but highly fundable, and another that is not so fundable but very accessible. Diversify your offerings so that the overall year is healthy and dynamic.
Funders want to plan ahead! If you go in and just try and sell them one small project (e.g. your experimental dance season) they may easily balk. But if you listen to what they are interested in and if you talk to them about your full "menu" of projects, they will have more opportunity to engage with you on multiple channels. Like any relationship: LISTEN to their desires and their mission. It is a two-way street here, not a monologue.
3) Start each Board Meeting with the ART not with the $$$. Attach each Board member to a project. Engage them in one thing. Don't just speak to them en masse with the white noise of "Go out and fundraise!" blah blah blah....Again, it is a dynamic relationship between the two of you - get them actively engaged.