How to Mine the Year’s Experiences for Leadership Stories

Look back on any given year, and you will see one filled with a wealth of different experiences: some of them forgettable, some memorable, and some truly transformational in terms of the impression they’ve made on you. If an experience is sticking with you, floating into your consciousness again and again, there is likely a reason for that and, even more likely, there’s a leadership story you should be developing and telling about it.

When we recount experiences with others, we do so most naturally through stories. Some of those stories are told purely for entertainment purposes. Other stories, however, are shared for more strategic reasons.

By “strategic reasons,” I don’t mean that the intent is overly calculated or manipulative: on the contrary. I mean that, in telling the story of an experience, you genuinely do so to have a positive impact on an audience. You are sharing the story of an experience for the benefit of others, not you. More specifically, you tell that story to shape the way the audience thinks and feels about a particular challenge or opportunity they face and – thanks to the relevant learning and understanding gleaned from your own experience – help them see how they can best address it. This is the difference between social storytelling (for entertainment) and strategic storytelling (for enlightenment, persuasion and inspiration).

Dissecting an Experience for a Leadership Story

To determine if an experience would make for a strong leadership story, you need to unpack it, peeling back the layers of the onion surrounding that experience by asking some key strategic questions. Starting with the experience in mind, I ask:

  • Did I learn anything profound or meaningful from that experience, or is there a strong message or idea inherent in and connected to it? If yes…
  • Could that lesson, message or idea be effective in shaping thoughts and feelings in others and, more specifically, what thoughts or feelings might they shape? If yes…
  • Could those thoughts and feelings help inspire a specific action or motivate a desired change in behaviour in others and, more specifically, what actions or behaviours might they be?

If I have a solid answer for all of the questions above (especially the first one), then I have a potentially strong story for my leadership storytelling library. I just need to find the right time, situation or audience with whom to share it.

A Leadership Storytelling Example

One of this past year’s most memorable experiences was when I was invited to come back to my prep school (Western Reserve Academy) to talk to the student body about storytelling. This was a huge honour for me, and I was thrilled to be asked. However, I was also more nervous about this one talk than I’d been for any other in my career. I knew how tough a crowd of teenagers could be and remembered how sullenly and cynically I had sat through guest speakers when I was a student at WRA. Adding to my nerves was the fact that I had several of my dearest school friends coming to watch me speak, and I wanted desperately to make them proud.

speaker in a lecture hall

As the months leading up to this talk dwindled down to weeks, I started to methodically and tenaciously spin myself into the ground with anxiety. The more I worked on my talk, the more certain I became that it was crap, that I was crap, and that this one speaking opportunity would open up the world to those truths. I was riddled with insecurity and frozen with fear, unable to produce anything substantial as I tried to prepare.

But about two weeks before the talk, I had a quiet conversation with my ego and anxiety. I told myself that being nervous meant I cared and that I held myself to high standards. I also reminded myself that the organizers at WRA had seen examples of my talks and wouldn’t have invited me to come speak if they didn’t think I would do a good job of it. I also remembered that, while I certainly have my weaknesses, public speaking is typically a strength for me, and I usually got very good feedback on my keynotes. As a result of this self-pep-talk, I changed my attitude about my speech and changed my approach to it. And while it wasn’t perfect, it was certainly not the disaster I had originally envisioned, and I think the students genuinely enjoyed it.

So, taking that experience and unpacking it per the line of questioning above:

  • Is there a learning, message or idea gleaned from my experience? — Yes, to trust and believe in my own skills, experience and capabilities
  • What thoughts and feelings could my message shape in others? — To logically understand that, if others believe in you, there’s a good reason for it. To feel less insecure and more self-confident (without getting cocky).
  • What action or change in behaviour could those thoughts and feelings inspire — To throw yourself into it, make the most of this opportunity, and enjoy the experience.

How to Take Storytelling Stock of the Past Year

As you head into the Holiday Season and, hopefully, a bit of a break from the never-ending emails and meetings, I encourage you carve off some quiet time to reflect on the past year. Take stock of the experiences you’ve had during it, and see if there are some leadership stories you can strategically harvest from them. More specifically, I encourage you to:

  1. Flip through this past year’s calendar to jog your memory of all the different experiences you’ve had, personal and professional.
  2. Make a list of the most memorable and/or transformational experiences (e.g., maybe seven or eight of them).
  3. Take that list and unpack each experience per the line of thinking and questioning outlined above.
  4. And if an experience elicits solid answers for those questions, make some time to develop a story around it, thinking about the content of that story and mapping out the plot for it.
  5. Then practice telling that story a few times to get comfortable with it, setting it into your consciousness, and having it at the ready when the right situation for it pops up.

Make no mistake, many of the experiences you’ve had might be insubstantial, forgettable or pure entertainment and nothing more. But I have no doubt that some of those experiences will make you pause and relive it in your mind, as well as your heart. If this happens, make note, and then make time down the road to turn that experience into a strong leadership story for your library.

We live by stories. We also live in them. We are living in the stories that are planted in us early and along the way, but are also living in the stories we plant in ourselves.


– Ben Okri, Nigerian Storyteller


Tagsleadership storiesleadership storytellingstorytelling library

© 2024 BB&Co Strategic Storytelling All rights reserved.
Site by Sparkjoy Studios. | Log in