What has been your most embarrassing moment as a teacher?

In my arena, it is important to review the bio of the student before teaching them, so that the training can be tailored to their experience and heavily scheduled time can be freed.  I'm pretty religious about it.  However, one day I got a call at my desk saying an instructor hadn't showed up for a class, and asking if I could cover it since I was also certified in the material.  The student had been waiting about 10 minutes, so I ran downstairs without looking him up.

The student was a Japanese astronaut.  I'd met him before, but didn't really know him well.  About halfway through the class I could feel that instinctual itch that a teacher can feel when something isn't going well in a lesson, but I didn't know what it was.  I inferred that the student wasn't quite absorbing the material, so I repeated a bit of it and went into a bit more detail than usual.

Cultural differences can make people a little harder to read.  The student was incredibly polite and didn't interrupt me.  Suddenly that mental itch found the right network of neurons and I knew what was happening...

...I had just spent about twenty minutes describing a piece of hardware at a beginner's level to the astronaut that installed it on the ISS on a previous flight.  There were probably only a dozen people in the world that knew more about that hardware than this astronaut.  Major faux pas.

I apologized profusely and when I got back to my desk I made a spreadsheet that listed every piece of hardware mentioned in any of the lessons I taught and the astronauts/cosmonauts that installed/activated/repaired them.

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