5 Questions To Ask New Mentees

A very popular question I get asked by mentors is: "What questions do you typically ask a new mentee in that first conversation? How do you get started?"

Getting started with any new relationship can feel daunting. Mentoring is especially intimidating as it's a relationship where the degree of benefit is a direct function of the participants' willingness to be open and vulnerable. Mentors, who are typically more senior leaders in an organization, may understandably hesitate sharing too much at the beginning until a sense of trust forms. Mentors also want to feel like they can connect with and contribute something to the mentee in their time together.

Listed below you'll find questions that I and other experienced mentors I know ask in that first "getting to know you" phase of a new mentoring relationship. I've included the reasoning behind each. Use these as a guide to help shape how you build your connection with a mentee:

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 many things in life, a key to success in mentoring is to set expectations at the beginning. We want to make sure that mentor and mentee have similar goals in mind. For example, if the mentee wants advice on public speaking and that's not the mentor's strong suit - that could be an issue - unless both want to learn about that topic together. If each person's expectations are widely different then you know this particular pairing isn't likely to flourish. Time for everyone to move on to another pairing. The reason to ask the second question about what the mentee expects to give is to establish from the very start that mentoring is a two way street. It's an activity that ultimately benefits both parties when both are in it to share, give of themselves and build each other up.
2. Where do you see yourself in "five" years? - Whatever number of years you choose to use, the point of this question is to find out whether or not your new mentee has some kind of plan or vision for themselves. Some do have a plan and seek out a mentor to help them achieve those goals. Others don't have anything mapped out which is precisely the reason why they are looking for mentoring. I like to know early on whether my new mentee will need my help pushing through the fog to design an exciting future for themselves or simply figuring out if what they desire from their career will lead to happiness. 
3. Have you had a mentor before and if so what worked/didn't work? - It's important to figure out from the get-go if the mentee has had any bad experiences with mentoring in the past. Mentoring is an activity that requires both parties to be vulnerable so we want to tread thoughtfully and avoid wrong turns. Often in life allowing oneself to be vulnerable does not result in pleasant outcomes. As I'm big on learning from mistakes let's get those learnings out in the open early. If the mentee is brand new to mentoring, I take extra time setting the ground rules and expectations around confidentiality and time expectations.
4. What propels you?/What is holding you back? - It's important to find out how self-aware your new mentee is or is not. When I have someone who can't easily answer this question I take the time to guide them to be a bit more introspective. If someone provides me with clear, thoughtful answers then we've got a great start.
5. Are you happy? - Ah...the 'ultimate' question. The mother of them all. Many individuals initially seek out mentors because they are unhappy with something about themselves or their career. The answers I get at the beginning are ones that I use as guideposts for the next several months and sometimes for the entire relationship. Oftentimes mentees benefit from a re-framing of what they think makes them happy. For example, someone may believe that a promotion will make them happy when really what they need is a different project or broader responsibilities which can be achieved without a promotion necessarily. Successfully re-framing someone's criteria for happiness is a powerful experience. A person realizes that something that feels far off might actually be readily in their grasp. Watching someone come to new realizations is one of the things I enjoy most about mentoring.

Of course there are thousands of things to ask and talk about over the course of a mentoring relationship. These 5 questions have been proven to put participants on a good path to a productive, mutually beneficial journey. Feel free to post some of your favorite questions to ask a new mentee in the comments below.

The delicate balance of mentoring someone is not creating them in your own image, but giving them the opportunity to create themselves.    - Steven Spielberg