To be fully engaged in your mentee’s journey it’s a good idea to journal the conversations you have. As time passes between sessions, memories will fade. You may forget important details without keeping a good record of the conversation. It’s important to me that my mentee knows that I listened the last time we talked. 

Before your next meeting, take time to review the journal. What homework is due? Check for any follow-ups you invited your mentee to complete. I make sure to prepare good questions for the next mentoring session.


I like to use a one-word check-in at the beginning of our time together. I ask my mentee for just one word that best describes their current state. Then I ask what has changed since we last met and have them elaborate on that. Ask about homework you requested of them – accountability is required for growth. Then ask a couple of probing questions to find out where your mentee is and could grow next. 

Examples of probing questions:

  1. What are the top 3 most challenging things you are facing today, this month, this year?
    • How do you feel about them?
    • On a scale of 1-10 (10 being the most prepared) assign a value to each one.
  2. What were your highest highs and lowest lows last month?
  3. What do you wish you had done differently?


The most successful mentor/mentee experiences are mutual relationships based on trust. As the mentor, you set the pace for authenticity. Be the first to be vulnerable in sharing experiences.

I don’t always have the same experiences to draw from in order to provide guidance for my mentee.  This is where the Gestalt method of experience share is very helpful. I’m grateful for my mentors who taught me this incredible life skill. 

Ge•stalt psy•chol•o•gy

/ɡəˈSHtält sīˈkäləjē/

A movement in psychology founded in Germany in 1912, seeking to explain perceptions in terms of gestalts rather than by analyzing their constituents.

The goal of Gestalt therapy is to teach people to become aware of significant sensations within themselves and their environment so that they respond fully and reasonably to situations. The gestalt experience share approach is very powerful in mentoring. Instead of the mentor telling the mentor what to do, they identify the emotion in the mentee’s need/situation and share an experience related to that emotion. 

For example:

My mentee is scared to make a bad decision because the future is unclear and they are not sure what to do. Let’s say they are in a completely different industry and I have never been in that position before. My first instinct is to try to solve the problem, but that may not be the best solution. I’ve never walked in their shoes or seen from their point of view. But if I can take a couple of steps back and ask a few questions, I can identify their core emotion. In this example it’s fear. Fortunately, I have many experiences in my life where I was fighting a fear of failure. 

An authentic next step might sound like, “You know I’ve never been in that situation before, but I’ll tell you about a time I felt like you.” Every time I’ve taken this approach, the mentee was able to identify a growth pattern or road map from my story even though it had nothing to do with their situation. 


Leave the lines of communication open between sessions. Your mentee may not feel comfortable reaching out to you unless you remind them often. 


Just because we are the mentor, does not mean that we have all the answers. I learned from my mentors, that we are only human, and sharing vulnerably what you’ve been through shows your authenticity. Mentees and mentors are all on a learning journey together. Whether it’s professionally based, or with prayer partners, they are all learning in unison. We are all growing, always.