I have a friend named Pete Wehner who is an amazing listener. I’ll describe some problem to him, and he’ll ask me some questions. There comes a moment in the conversation, after he’s asked four or five questions, when I expect him to start offering his opinions and recommendations. But then he surprises me and asks six or eight more questions, before eventually offering counsel or advice. Real listening, whether to others or yourself, involves that unexpected extra round of questions, stretching the asking beyond what feels natural.
