During this past week, a party who is now representing themselves in one of my cases, emailed the court appointed accountant asking for an update. The accountant’s response came quickly, “As soon as my outstanding bill is paid, I will be happy to give you an update.”

When the litigant responded by, effectively, accusing the accountant of improper billing the accountant did not respond. His silence was a clear signal by him; pay me what you owe me and you will get the information. Watching this correspondence, I was extremely impressed by the accountant’s actions. He knew his self-worth and was not afraid to ask for the money due to him. 

I, often have to discuss outstanding bills with my clients. It is, generally, for me, a difficult conversation to have. I am often tentative with approaching the subject of outstanding bills. After the email correspondence with the accountant this week, I questioned a lot of lawyers about their approaches towards collecting their bills.

In my informal poll, it appeared to me that men and women approach payment discussions differently. Women appear to be a bit more tentative-like me-in asking for money than men. However, it seemed to me that the younger women I spoke to are not as tentative as the older female entrepreneurs.

Are you comfortable asking to be paid?