When I was going through the transition from editor of a business publication to the role of publisher, I dreaded sales calls with clients.
It meant I had to ask clients for money, which was a new and uncomfortable experience. The hilarious irony of this is that, as a reporter and editor, it was my job to ask people much tougher, more-intrusive questions, and I did it with no problem -- grieving parents about the death of their child, a political candidate about his sexual escapades, a business executive about her salary.
How tough could it be for a former reporter to ask an advertiser for money? (I borrow this example from Robert Niles's book.) Not that tough, as it turns out.