How to Deepen The Conversation With Your Mentor

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Stephanie Buckingham

Organizational Development Coordinator

This is part 2. Read the first one on how to find the right mentor.

Having mentors can be instrumental in your career growth.

As covered in the previous article, finding the right mentor is a critical first step. Personally, I like to have mentors inside and outside of the organization and at all different life stages to give me different perspectives. My mentors within the organization advocate for me and provide context for different situations.

My mentors outside of the organization push me to consider how the industry or other organizations are doing things differently. Selecting a mentor is exciting – you have big dreams of all the wisdom they will share and the developmental strides you will make.

However, after finding the right mentor, finding the right things to talk about is hard.

You may have a couple topics that come to mind, but the time spent with your mentor is valuable, don’t waste it talking about the weather or what you did during the weekend. Those are important in the get-to-know-you aspect of relationship building, but staying in the surface-level conversation too long won’t help you get the most of out a mentor partnership.

Never underestimate the value in planning what you’d like to discuss or ask. Scrambling 15 minutes before the meeting to come up with topics doesn’t serve you or your mentor.

Here are some topics/questions to help eliminate the awkward silence and get into deepening relationships.

  • What projects are you working on?
  • How did you get to where you’re at?
  • When you were in my place, what are some goals you set for yourself?
  • Here’s what I’m doing, what am I missing?
  • What are the steps to help me get to where I’m going?
  • Who has helped you in your career/been a champion for you?
  • What are some useful skills to have or have seen in people you work with?
  • What are some book studies/industry insights that you’ve read recently?

Other tips to get the conversation going:

  • See what you have in common by taking a strength finders/personality test.
  • Be bold and confident.
  • Avoid talking about specific people and managers. This can be frustrating to and awkward for mentors when mentees complain about people the whole time. Instead, talk about situations as often as possible. If you do have a tough situation with a specific person, approach it with a genuine problem-solving mentality and humility (see question, “What am I missing?”).
  • Set an agenda and send it out before the meeting – that way your mentor can be prepared.

Final note: the mentor-mentee relationship is just like all relationships. Sometimes you have a lot of time together and the conversations are deep and meaningful. Other times, meetings may be few and far between and may occasionally feel flat. Don’t give up too quickly if a few meetings slide or if you feel like the conversation wasn’t perfect. Stick with it, put effort into planning and be open to new ideas! 

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Stephanie Buckingham, C.P.T.D., P.H.R., is the Organizational Development Coordinator in Fort Worth.