I'm lucky in the sense that I have a world class business person to turn to anytime I have a question. I just pick up the phone and call my mom. Last week we had dinner and she was discussing her new venture, retail consulting, and she expressed how hard it is for her to "ask for the order." She built a very successful retail store called Elegant Clutter over 20+ years and one of their trademarks was no pressure sales associates. No one worked on commission and the shopping atmosphere was very relaxed. That policy was a direct reflection of her and her partner's personalities so it's no wonder she has a hard time asking for the order.
So I sent her this article today and thought I might as well post it on the blog too. First read Fred Wilson's article referenced in the first paragraph, then come back to this one. My takeaways were 1) You have to get over asking for the order and just do it, 2) You can do it creatively and it might work even better.
By the way, I probably interviewed 20 people in the last 2 months, not one asked for the job. Would have made a huge difference.