At the beginning of my junior year of high school my English teacher, Dorothy Palme, gave me a D minus on a paper I wrote. It was the first grade below a B I had received in my entire academic career. I was flabbergasted and livid. I stayed after class to ask her why she gave me the grade and she walked through all the reasons. What it boiled down to was that I was a poor writer. I left the classroom even angrier after getting the feedback. Like the little brat I was, I brought the paper home to my parents and exclaimed that I had been cheated. They read the paper and I'll never forget their reaction. They unanimously supported Mrs. Palme's assessment that I couldn't write worth a damn. They said so themselves and I knew they were a combination of disappointed and embarrassed.
Mrs. Palme was the best teacher I ever had. Over the course of the year, she worked with me to transform the way I approached writing. She taught me about introductory prepositional phrases, how and when to appropriately use adverbs, how to coherently structure my thoughts, and so much more. She did it all on her own time outside of class, too. Her lessons will stay with me forever and it's not hyperbolic to say that she changed my life for the better.
Most teachers would have played it safe. Perhaps they would have graded the paper a B minus or a C. But Mrs. Palme wanted to teach me a lesson - that I could and must do better. It was a lesson that required her to be brutally honest, and to roll up her sleeves and take the time to help me if I wanted to fix it. And while I hated the lesson in the moment, it fondly sticks with me to this day.
The Mrs. Palme's of the world are far and few between. Over the course of my professional career, I haven't encountered a lot of people who had the courage to tell me how it is. There are two investors and board members I've worked with that particularly stand out: