Storytelling as a Mentoring Tool

By Kelly Vandever


Storytelling as a mentoring tool has been around forever… well, I say that because there’s a Biblical record of the prophet Nathan telling Kind David the story of two men, a rich dude and a poor dude, and about the rich dude took something precious from the poor dude which enraged David… and then Nathan dropped the moral of the story on David, that he was the rich man.  The story was the vehicle to demonstrate for David why he was in the wrong… and if you know the story, you know he was DEFINITELY in the wrong – like adultery and murder wrong!


God told Nathan to take the storytelling approach.  God knew David wouldn’t have taken the message to heart if Nathan had said, “King David, you’re a horrible person.  Basically you murdered a guy so you could steal his wife and not get caught having impregnating her while her husband was away fighting a battle for you.” The natural human reaction to being called out is to get defensive and rationalize and justify our actions.  The story helped make the point, evoke the emotions of right and wrong, and layout in a visceral way how truly wrong David was. The story laid out the truth in a way that David couldn’t argue with.


(Read more about David’s particular sinsand how God told Nathan to coach Danielin 2 Samuel Chapter 11 & 12.)


While hopefully, you don’t have to deal with adultery and murder in your workplace, stories can be a great way to instruct and mentor people by engaging the emotions and helping people feel in a tangible way why certain types of behaviors in the workplace are desired and other behaviors don’t fit with the organization’s values and purpose.


Storytelling as a Mentoring Tool in the Workplace


Sharing personal and work stories help us to fast track getting to know each other as people and help illustrate how we came to learn important lessons, particularly lessons about soft skills and emotional intelligence.  Like the story with Nathan and David, stories lower our guards and help us to see from a different perspective.


But many people struggle with finding stories and know how to tell them.


In my workshops, we cover several ways to engage in storytelling.  Below are several exercises designed to help colleagues and mentor/mentees to get to know one another and have conversations about important ideas.  Feel free to try these techniques for yourself.  Or contact meif you’d like to have me or one of my coaches come work with you and your team.


Storytelling Exercises:


Personal Story Generator– This exercise is designed to help you uncover stories you didn’t even know you had and tell them in a meaningful way.  I learned this technique from the amazing Max Dixon.  The exercise starts by identifying different roles you’ve played in your life, then pairing up randomly chosen roles with trigger words. These trigger words activate memories of events that happened related to your roles.  We then use the hero’s journey framework to craft the story into an engaging format.


First Bosses– Our first experiences in the workforce often forms a lot of our opinions and work habits.  In this exercise, we use a list questions to explore where your colleagues are coming from.  (Of course, this could be awkward if you are an employee’s first boss!)  Example questions:  Tell me about your first couple of bosses in our industry.  What do you remember about them?  What did you like about them?  What drove you nuts about them?  What did you learn from them?  What’s something you do today that was influenced by your experience with your first couple of bosses?


That Reminds Me of the Time…– Have you ever been to a cocktail party or with a group of friends and noticed that after one person tells a story, usually that person’s story will triggers someone else to tell a related but different story, and before you know it, multiple stories have been told?  This exercise is built on the same principle. The group leader will start by telling a story that has some sort of significance and encourage others to tell their stories.  Then the group can reflect together on their goals and values based on what they’ve heard during the session.


When a Leader Speaks– Identify an issue that you think is important for the organization or your mentee to get right and share why you think it’s important.  Ideally, tell a story about this issue from your own history.  If possible, tell a story where you’re not the “hero.”  By that I mean two things: either (1) make someone else the hero of the story (like the person who taught you an important lesson) or (2) tell a story where you don’t look so good.  Tell them about how you made a mistake and the lesson you learned the hard way from that mistake.  Ask others or your mentee about their experiences with this important issue and ask them how they feel about the organization relative to this issue. Ask them for their help and commitment to getting the issue right.


Let’s Talk Business– There are often hidden talents in our midst. These questions help people talk about what they’re good at and encourage them to share where they struggle. The cool thing is, as humans, we want to be helpful.  If the struggling person is willing to share, their colleagues will be eager to offer their insights.  Everyone wins.  Sample questions:  What’s the hardest job-related problem you’ve had to work through?  (If one doesn’t stand out above all others, what was the latest tough problem you worked through?)  What’s something that you’re stumped on right now?  What have you tried?  What do you plan to try?  Would you welcome suggestions?  What’s something you tried that turn out way better than you expected?


Keep the Ball Rolling


Stories have the power to open up discussions by engaging the emotions and helping us to let our guard down.  They can be especially helpful in a mentoring and leadership capacity.


Take some time to remember the early lessons you learned that formed the person, employee and leader you are now.  Look for ways to share those stories to help promote your values and encourage your team.


Again, if you’d like some help with encouraging people to tell their stories, contact meand we’re happy to help you and your team grow together.




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