At the outset of a brand new mentoring relationship both you and the mentee may be asking yourselves "what are we going to talk about?". You may also be asking yourselves "how much do I want to share?" As a mentor you'll need to create a space that is safe for the person to ask and answer all sorts of questions. The first step is to commit to complete confidentiality. A "nothing leaves this room" pledge is most certainly in order. The next step is to (if you wish) establish the scope of your discussions. Will it always remain in the professional realm or are discussions open to non-work related goals and issues?
At its core mentoring is a series of conversations. It's a series of 2 way conversations that are revealing, creative, expansive and thought-provoking. You'll quickly want to build rapport and build trust. One important way to do that is to exhibit empathy. "Empathy" is definitely a skill and some people come by it more easily than others. To be empathetic one needs to:
"Be sincere. This means to really care about what happens to the other person. This doesn’t mean that you have to approve of everything they do or even have to force yourself to like them, you just have to sincerely accept them as fellow humans who are struggling just like you. If you show this genuineness, people could sense it and respond accordingly. People will assume that you truly care and will accept your efforts."(from "Is Empathy A Learned Skill? How to Develop Empathy")
Show interest in the person by asking "empathetic questions". Begin a "gentle interview" - one that starts to reveal a mentee's purpose for wanting a mentoring relationship in the first place. (Be prepared to be asked and answer why you want to mentor!) Put yourself in their shoes and keep asking questions, peel back the onion and just let the conversations take you both where you naturally need to go.
On ted.com there is an excellent talk entitled "The Art of the Interview" which covers Empathetic Questions. The speaker, Marc Pachter, describes how to use empathetic questions to be the "agent of another person's self-revelation". That is exactly what you as a mentor want to achieve! Through a series of conversations and questions you want to become the agent of a mentee's self-revelation. Marc Pachter created a Smithsonian program called the National Portrait Gallery in order to document great lives. In this talk he describes his type of interviewing and his use of Empathetic Questions to break down barriers and get legends to reveal some of their lifetime secrets for the audience. He records these conversations for posterity. Listen to the talk and figure out how you can engage in this type of conversation with your mentee as you both will reap rewards beyond your imagination.
Click here for Marc Pachter's talk.