Asking clients for work: “Why are lawyers so shy?”

Over the years this keeps happening:

I take a General Counsel or non-lawyer executive or CFO of a targeted client to lunch or dinner to ask for work. At some point I briefly say what my firm does and how we can help the client on particular legal issues it has. I ask a few questions. I do a short (very informal) pitch which ends with: “We like [the company] and we’d love to work with you. How can I win/earn your business?”

The client rep laughs and says something like, “That’s refreshing–because I can’t tell you how many times I have dined, gone to sporting events or played golf with lawyers and they never ask me for my business. Sometimes this goes on for years. I know that’s why they are there–but they won’t ever get to the point.”