There’s a hoary saying that the reason God gave us two ears and only one mouth is so we would listen more and talk less. Whatever your religious beliefs, there is great truth in this saying when it comes to mentoring.
In many ways mentoring is similar to the Socratic method. From Wikipedia:
Socratic method, also known as maieutics, method of elenchus, elenctic method, or Socratic debate, is named after the classical Greek philosopher Socrates. Elenchus is a form of cooperative argumentative dialogue between individuals, based on asking and answering questions to stimulate critical thinking and to draw out ideas and underlying presumptions.
However, unlike the Socratic method, mentoring is NOT argumentative in any way. In fact, MIT VMS emphasizes mutual respect between mentors and entrepreneurs, for good reason.
Asking questions of the entrepreneur is one technique. Another is to ask the entrepreneur to come up with his or her own questions. For example, if they are about to meet with a potential strategic partner, rather than tell them what questions to ask, ask them what questions they think they should ask. Thus can begin the dialog and discussion that is so important in mentoring. Arguments and monologs have no place in the mentor room.
The are some exceptions, such as playing devil’s advocate:
a person who expresses a contentious opinion in order to provoke debate or test the strength of the opposing arguments: the interviewer will need to play devil’s advocate to put the other side’s case forward.
This can be a powerful technique to stimulate the entrepreneur’s thinking. But use it sparingly, as it can be abrasive.
The second exception, and one worth a post of its own, is story telling. Most mentors are seasoned entrepreneurs and have great stories to tell. Sometimes telling a relevant story can really help an entrepreneur understand their own issues.
But keep in mind that 2:1 rule, listen at minimum twice as much as you speak.
Mentorphile 
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