Embarking on your mentorship journey

Mentorship matching is happening over here at Mentor Matching Central (Aka Kelly’s kitchen), fast and furiously.

For many of you who have already been matched, you might be struggling to get the conversation started with your mentor or mentee.

We thought we would give you some ideas as to what kinds of questions to ask each other, because we know that questions are a sure fire way to get deep conversations happening.

Sidebar: If you have not yet signed up to be or get a mentor, you can do so here.

Here are some suggestions for questions you can ask as you set your initial calls to get to know each other better.

Ask her about her career journey

Find out more about your mentee and their work experience by asking her about it. You can use specific questions rather than a general “tell me about your career so far” type of question.

Don’t feel you need to stick to a script. Remember, when you ask questions based on the information your mentee has already offered, it demonstrates your interest in her.

Here are some questions you may want to ask.

  • What was your educational experience like?
  • Did you plan to have this career path, or did it happen organically?
  • What was your first job?
  • What led you to your current career path?

Get to know her as a person

You don’t need to be too personal. However, asking questions can help you get to know her on a deeper, more intimate level. The right questions can lead you to find out more about your mentee to help better understand who she are and what is important to her.

Consider some of these suggestions or develop questions of your own.

  • Who are your role models you look up to or people you admire?
  • What do you love to do outside of work?
  • What inspires you?


It is our hope that as you embark on this important work that you develop meaningful, long lasting relationships. Some mentor/mentees report lifelong friendships!

As a community we are here to support you, so don’t hesitate to reach out to Deborah or I, or make a post in our LinkedIn Group if you need anything more.