5 Questions To Ask New Mentees

As a mentoring expert other mentors very often ask me: “What types of questions are typically asked during the first set of conversations with a new mentee?”.

Here are some questions that I and other mentors I know typically use in the “getting to know you” phase of a new mentoring relationship. I’ve included the reasoning behind each:

  1. Why are you looking for mentoring/what do you expect to get out of mentoring? And what do you expect to give? — As with anything in life it’s key to set expectations at the beginning. We want to make sure that mentor and mentee have similar goals in mind. If there isn’t agreement early on then you know this particular pairing is unlikely to succeed. Both individuals should move on. The reason to ask the second question about what the mentee expects to give is to establish at the start that mentoring is a two way street. Typically people think of mentoring as a situation where an older, wiser person “teaches” a younger novice. Mentoring is much more than that. It’s an activity that ultimately benefits both parties when both are in it to give something to the other.
  2. Where do you see yourself in five years? — The number of years in this question (1 year? 3 years? 5 years?) isn’t as important as finding out whether or not your new mentee has a vision or a plan for themselves. Some do have a plan and seek out your help to get them there. Others don’t see their path which is why they are looking for mentoring. I like to know whether this person will need my help designing an exciting future for themselves or figuring out if the vision they currently hold is one that they really, really, really want.
  3. Have you had a mentor before and if so what worked/didn’t work? — I ask, as any good Doctor would, if the person I’m speaking with has had any bad experiences with mentoring in the past. Mentoring is an activity that demands both parties be vulnerable at some point in order to achieve the maximum benefit. Too often allowing oneself to be vulnerable does not offer the results we’d like. As I’m big on learning from mistakes and want to ensure we avoid those moving forward I get these experiences out into the open early. If the person is new to mentoring all together I take extra time setting the ground rules and expectations around such things as confidentiality and time commitments.
  4. What propels you?/What is holding you back? — It’s important to find out if your new mentee is self-aware or not. When I have someone who can’t easily answer this question I take the time to get them to be a bit more introspective. If someone provides me with clear, insightful answers then we are ahead of the game.
  5. Are you happy? — This is the grand daddy of them all…the ‘ultimate’ question! It’s the mother of all questions. Most individuals initially seek out mentors because they are unhappy with something about themselves or their career. This question is critical. The answers I get at the beginning are ones that I keep checking back into over the course of a relationship. Sometimes I simply help the mentee achieve what they’ve decided will make them happy. Other times I guide the mentee in changing (read: re-framing) their definition of what makes them happy. The latter is almost always a more powerful, awe-inspiring experience because many of us don’t recognize the core of what makes us happy. We rarely realize the number of paths we can choose that would make us truly content. Watching someone come to some of these new realizations is one of the things I enjoy most about mentoring.

Of course there are thousands of things to ask and discuss over the course of a mentoring relationship but the above 5 should be good to get you started on a productive, mutually beneficial journey. Feel free to let me know of some of your favorite questions to ask a new mentee.