Making it personal

Conversation starters:

Lifestyle

• What do you see yourself doing in 5, 10, and 20 year's time?
• What worries you?
• Do you tend to be optimistic or pessimistic?
• What events in your life have influenced your perspective about money?
• How is your health?
• How is your family's health?
• What is the most important lifestyle goal that you would like to achieve (travel, second home, etc.)?
• What are you passionate about that is related to your financial picture?

What / When / Who / How

• What things are most important to you in selecting a financial advisor?
• When do you (or will you) feel the most confident financially? 
• Who are the people most important to you?
• How do you want those people to benefit from your financial success?
• How confident do you feel about your current financial situation?

Finances

• Do you feel like you're currently accomplishing (or on track to accomplish) your financial goals?
• What was your best and worse financial or investment decision?
• What was the outcome?
• What is your current source of income and how is that likely to change in the next three years?
• What new assets do you expect to receive (stock options, inheritance, etc.)?
• Are you (or will you be) paying for education expenses for anyone in your family?
• Do you have updated estate documents (wills, power of attorney, Do Not Resuscitate document, trust agreements, etc.)? 
• Who is your executor, trustee, and/or guardian in these documents?
• Do you have a 401(k) or other retirement plan through your employer?
• How much are you contributing?
• Does the company provide a match?
• How are the funds invested?
• Do you have investment accounts outside of your employer plans?
• How is it managed?
• What is the risk level of the specific assets?
• How are you paying for it?
• What has the performance been? 
• What life insurance do you have?
• Is it enough?

Legacy

• How do you want to be remembered by your family?
• How do you want to distribute your wealth after you're gone?
• Are charitable contributions important to you? Which charities?
• What plans do you have in place to minimize taxes to your estate when you're gone?