What books have shaped you the most?
What do you feel are the defining historical events of your generation, and what do you remember about them?
How do you think those events impacted the way you see the world?
How do you think the world has changed during your lifetime?
Were there any fads during your youth that you remember vividly?
What would you consider the most important inventions during your lifetime?
How is the world different from when you were a child?
If you could witness any event of the past, present, or future, what would it be?
What is your best childhood memory?
Do you have brothers and sisters? Can you tell me a story or memory of them?
Did you have a nickname when you were growing up? If so, what was it, and why were you called that?
Do you have any nicknames now?
What did your family do for fun when you were a child?
What were your favorite toys or childhood games growing up?
Was there a chore you hated doing as a child?
What kinds of books did you like to read?
Do you remember having a favorite nursery rhyme or bedtime story? What was it?
Were you raised with abundance or modesty? What did your parents do for work?
How are you different as a parent than your parents were with you?
How did you decide upon a career? What other jobs have you had?
What do you love most about what you do?
If I was just starting out in that business, what is the most important piece of advice you’d give me?
What are the greatest career mistakes you’ve made? What have been your best decisions?
What would you consider to be the top three qualities that made you successful?
What are your greatest strengths? What comes easily for you that is more difficult for other people?
What are the characteristics of the best leader you’ve ever worked for?
What types of people do you have trouble getting along with?
What is your ideal work environment?
What is your greatest career accomplishment to date?
What was your first job?
If you had to do it all over again, would you change the way you raised your family?
What did/do you find most difficult about raising children?
What did/do you find most rewarding about being a parent?
Were/are you strict or lenient as a parent?
Did you find you had to treat each of your children differently? If so, how?
Are there any relationships you wish you would have invested more into?
Who is your best friend, and what is great about them?
What do you value most in a friendship?
How has your idea of “friendship” evolved in your life?
Complete this sentence: “I wish I had someone with whom I could share…”
How do you hope your friends describe you?
What are you most afraid of these days?
and then