Not long ago I bumped into a headhunter at a cocktail party, a woman I hadn’t seen in nearly a decade. Her second sentence (second!), after, “How are you?” was, “So, are you looking for a job?”
The easy questions in fundraising are around tactics, as in, “when is the right time to make an ask?” There’s nothing wrong with “three-meeting before making an ask” and other rules of thumb, but questions like this one essentially miss the point.
(By the way, my take on this particular rule of thumb is that it is better to ask sooner than you’d like and better to and ask for more than you feel comfortable asking for. This is primarily about getting through our own fears about asking – we usually take too long – and about recognizing that we are giving the person across the table an opportunity to do something important, and we should help them do something big, not small.)
No matter what approach you take, you’re never going to get out of the starting blocks until you’ve done the internal, personal work of getting out of that space where you see the person across from you as a transaction, as simple dollar signs. No matter how you dress up your language, if you see your “prospect” as a means to and end then she’ll feel that way. Whereas if you treat her as a person with whom you are building a real and substantive relationship, you can (counter-intuitively) talk comfortably, early on and directly about money.
It starts with you and how you see the world. Are you building something, or just taking?