Here’s a classic rookie mistake with email: Using it for important communications with people you don’t know intimately.

I made that mistake on Tuesday and it cost Ripple dearly.

It was also a lesson in practicing what you preach. I tell my coworkers regularly "If what you want to say could be misconstrued – if you are entering a new relationship – call the person, don’t email them."

On Tuesday, we were at an important turning point in negotiations with a prospective client. Our prospect had a lengthy list of concessions, and in trying to boil those down I sent an email paraphrasing what I believed to be the important points; what I thought would be possible from our end. Like any important email with emotion attached, with ambiguity involved, with a virtual stranger – it was ill-advised. As is Murphy’s Law with email, it was taken the wrong way. On Tuesday I pissed off a prospective client, and damaged a relationship irrevocably. On Tuesday I didn’t take my own advice.

I told myself it was because I wanted to get all of my points made without being interrupted or distracted. But underneath I think it was probably because I didn’t want to have an uncomfortable conversation.

Stupid.