David Tower What an awesome thread you started here! My first two jobs out of college involved cold-calling 50 - 75 people a day, so take it from someone who has been there - it only gets easier as time goes on. At first you'll be super nervous with sweaty palms and a palpitating heart. After about 25 calls or so you'll be comfortable. After about 50 you'll be checking ESPN while fielding these calls. Practice makes perfect, I guess.
Glad to read that your script went out the window when talking with these people. One thing I've learned is that it's immediately apparent to the person on the other end of the phone if you're using a script - everything sounds so forced and the conversations suffers because of it. And I can't tell you how many times I've heard co-workers keep going with their pitch and completely ignore what the prospect said because they are too busy sticking to their script. Listening is key is any sales environment! However, with that said, I think a checklist to make sure you've asked all your questions/got all the information needed is important, especially when beginning. There is nothing worse than calling a prospect back because you forgot to ask a basic question.
I'm waiting on my printer to be delivered tomorrow and then I'll be sending out my first batch of yellow letters and probate mailings. You've given me some inspiration to post about my results as well. Keep on updating us and let everyone know how things are progressing. Best of luck!