There is no change without commitment.

And the best mentoring relationships are a shared commitment to create consistent space for conversations that move mentees from intentions to impact.  Whether the purpose of your mentoring relationship is information or inspiration, here’s a list of questions to ask a mentor to get the conversation started.  

What Not to Do

The quality of a mentor / mentee relationship, like any relationship, is about how you show up.  And, as a long-time mentor, I’ve met the following six characters – and one standout superstar – among my mentees.  Do you recognize – or are you at risk of becoming –  anyone on this list?   

  • Generic George:  He just wants a mentor.  Any mentor.  He has no objectives or outcomes in mind.  Generic George’s fatal flaw?  He fails to offer any specifics that would move the conversation forward.  He just has his hand out hoping that I will figure out what he needs and then tell him.
  • Social Sally:  In a world full of mentors, Sally sees future friends.  She has done an immense amount of research about me personally before our meeting.  She artfully works our shared hobbies into our conversation.  And quotes from my recent blogs.  Social Sally’s fatal flaw?  Believing that being liked is the purpose of our relationship.  
  • Wandering Wally:  He’s never met an idea he doesn’t like.  He’s never had a thought he hasn’t spoken.  Every notion that hits his noggin connects to another random, unrelated idea and thought – which he can’t wait to share.  In fact, he can’t help himself.  Wandering Wally is all over the map.  He wants to be an astronaut.  He wants to save the world.  He is currently patenting an invention.  Despite his background as a CPA, he might be ready to cross over into a career in sales.  And he shares this all in our first conversation.  Wandering Wally’s fatal flaw?  He lacks a clear, concise direction and ask.
  • Egomaniac Ethan:  He’s the best there’s ever been at everything he’s ever done.  And, thankfully, he’s not too shy to share it!  He is a top performer.  He is already being recruited for numerous positions.  He was Prom King.  He is into extreme sports.  And, he knows that everyone idolizes him.  As evidenced by his 86 name dropping references.  Egomaniac Ethan’s fatal flaw?  His total lack of self-awareness.  Trying to impress isn’t the same as trying to connect. 
  • Desperado Diane:  She is a living, breathing country and western song.  She would have met with me sooner, but there’s been a series of catastrophes.  The details of the tragedies include crying, loving and leaving – a very familiar refrain.  But the good news, she shares as she sniffs, is that she’s put all that behind her now and is ready to get serious about her career.  Desperado Diane’s fatal flaw?  Oversharing.  And if she’s like that with me during our first meeting, I don’t want to hear the chorus to her verse.
  • Mentor Me Mandy:  She starts strong.  Her tone is conversational but not overly casual.  She is prepared but not assumingly personal.  She knows something about what she wants and can reasonably articulate her strengths.  Where does it go wrong?  Every time we meet, we repeat that same conversation.  Mentor Me Mandy’s fatal flaw?  Starting strong and then failing to make an actual ask.  Always have the courage to ask for what you want! 

Fortunately, I occasionally hear from Powerhouse Pat.  Who is Powerhouse Pat?

What to Do

Powerhouse Pat is the standout superstar in a cast of mediocrity.

Pat is prepared.

Pat is articulate.  Focused.  Pat has clear priorities.  Simple and precise talking points.  Examples of desired outcomes and impacts.  And a well-thought-out series of questions and asks.  

How can you show up as Powerhouse Pat and increase your odds of a successful mentoring relationship?  Invest as much thought in crafting your conversations as you would in preparing for a job interview.  Your message matters.  Your message is your tool to make a great first impression.  To differentiate yourself.  And to create commitment to realize results from your mentoring relationship.


Success begins with your story.  And, when you change your conversation, you change your results. 

For more on mentorship, check out Questions to Ask a Mentor About Career Path

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