The times when you wish Clippy was useful for something

I'm currently managing several teams around the world. One of these teams is in Hyderabad, in India. One of the guys on this team lost many family members recently, in a tragedy of unimaginable proportions (well, at least I find it unimaginable, but I digress).

He and I had been exchanging some brief emails about his plans, and his need for time off (no surprise there, and I told him to take all the time he needed, not to worry about work, etc. etc.). I was writing what I hoped was a sincere message of condolence, when I glanced down to the standard signature block that my mail client is set up to auto-insert. And what did I notice? A smiley face.

That's right, a smiley face, that had I not noticed, would have gone out at the bottom of a message offering condolences for multiple deaths in this guy's family. Where the fuck was Clippy when I needed him?! You know ... why didn't he pop up and say something like:

"Hi! It looks like you're writing a letter of condolence, but you've added a smiley face at the bottom. Are you:
a) Some kind of fucking sadistic freak, who enjoys the grief of others?
b) Totally asocial, clueless, and suffering Tourette syndrome?
c) Just an insincere twat?"

While I'm relieved I spotted it, I'm also somewhat grateful I went through the near-miss experience. It reminds me there are things in life that should not be automated.