In retrospect, when I sought the counsel of these more experienced men, I had been seeking simple answers to complex questions - do this, not that - because I was unsure of myself and stressed by the demands of my new job. But simple answers like the “start high” pricing advice - so seductive in its rationality - had distracted me and kept me from asking more fundamental questions.

I also didn’t appreciate that if you ask ten questions and make ten suggestions, people may take them less seriously, even if they’re all equally good. If you have only two issues or questions, people will take your two more seriously than they may take any of your ten. During my first hundred days in the Harvard presidency, I could have had things I identified as success and could have signaled that it was a new day without dissipating as much goodwill capital, if I had been smarter.” - Lawrence Summers.

The questions she asks are intended to steer people toward the positive: Isn’t it time you forgave yourself for that? When you and your parents are close again, what will you want them to understand about this time in your life? Early in her career, she tried to understand people by asking how others treated or mistreated them. As she matured, she found it

more useful to ask, How do you treat others? How do you make them feel?

Good conversationalists ask for stories about specific events or experiences, and then they go even further. They don’t only want to talk about what happened, they want to know how you experienced what happened.

We too often think that deep conversations have to be painful or vulnerable conversations. I try to compensate for that by asking questions about the positive sides of life:

• “Tell me about a time you adapted to change.”

• “What’s working really well in your life?”

• “What are you most self-confident about?”

• “Which of your five senses is strongest?”

• “Have you ever been solitary without feeling lonely?” or

• “What has become clearer to you as you have aged?