How to Have Better Conversations
March 1, 2022

In her book, We Need to Talk, How to Have Conversations, author and public speaker, Celeste Headlee, promotes a list of basic rules for having a good conversation.  These simple rules are ideal reminders for mentors who may be hoping for more connection with their mentee.

Be present and in the moment!

When meeting with your mentee, begin by clearing your mind and take a deep breath so that you will feel grounded.  Avoid multi-tasking; put your phone down, release all of the things you are thinking about.  Focus on your present company.

Everyone you will ever meet knows something that you do not.

Step outside of yourself and remember you are in the presence of a unique individual who has experienced things you have not.  Assume that you have something to learn from your mentee.  Set an intention before your visit, “I will learn one new thing about my mentee today.”

Start with open-ended questions.

Ask questions that begin with who, what, where, and when.   Additionally, phrases like “tell me more about that” and “wow, what else” are great ways to encourage your mentee to describe their feelings and expound on their stories by opening a space for them.  Don’t let yourself get bogged down in the details.  Getting them to talk is the goal, regardless of what they share.

If you don’t know, say you don’t know.

It is okay to not have all the answers.  However, just because you do not have the answer doesn’t mean someone else does not.  Encourage your mentee to seek out the answers they need by brainstorming who would know; a teacher, counselor, or caregiver, maybe a trip to the library or Google will help.


Let them talk. Let them go off on tangents, taking the conversation in new directions.  Let them be silly or serious. Let them be themselves.

What if you arrive for your mentoring visit and your mentee seems uninvested or unhappy to see you?

Don’t take it personally.  They could be having a bad day or forgot that you were coming and made other plans.  Use your mentoring skills to help your mentee express their feelings and ask for what they need.  Making observations and asking questions like, “I am getting the feeling you were not expecting me today, are you still available to meet?”  “You seem distracted, is there something going on?”  “Are you still okay to visit today?  Should we reschedule?”  Giving your mentee the opportunity to ask for what they need shows that you are a caring person and you value them.  Sometimes, your mentee just might be having a down day and even though they are not talking to you, your presence is comforting.

Like everything worthwhile in life, building a relationship with your mentee takes time, patience and preparation.  You will have good conversations if you practice these rules and remember it is worth it!

To see the rules of conversation in action, watch this thoughtful and heartwarming exchange between a boy and a gentleman as they ask each other questions that lead to connection.

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