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Once Upon a Business...The Role of Storytelling in Leadership, Management, and Entrepreneurship

The Silicon Valley Junto -- an intellectual discussion society that Chris and I run -- met a few weeks ago around the topic Once Upon a Business...The Role of Storytelling in Leadership, Management, and Entrepreneurship.

David Cowan kicked it off with an oral telling of a story he recounted on his blog: How do you get to Europe on an expired passport?" It's an awesome story (most disastrous travel adventures are!) and David did a masterful job telling it. Since that meeting I've been thinking about how I can improve my own storytelling techniques. In my speeches this past month I always started with a story and it seemed effective. But I know I can improve.

So I recently re-read this e-book / PDF on storytelling techniques in the workplace. Below are a few of the tips.

To be a good story it should:

  • Be brief and simple
  • Be told from the perspective of a single character
  • Describe a dilemma that is familiar to the audience
  • Have a degree of strangeness or peculiarity to capture the audience’s interest and stimulate the imagination
  • Be at the same time plausible and oddly familiar
  • Be true (or have an element of truth)
  • Have a happy ending (or give hope)
  • Be told with a bit of flair and passion.

How to tell a good story:

  • Pretend that you are confident - don't make apologies as you start, either with your body language or your words.
  • Relax, breathe and play - this is meant to be fun!
  • Don’t memorize it. Tell it with your own words and your own images.
  • If you get stuck, keep going. There are no mistakes, because no one knows what you were going to say, so they can’t tell if you’ve messed up. Think on your feet and improvise - sometimes you will stumble on real gems.
  • Keep your stories short (10 minutes or less).
  • Pay attention to pacing. Use moments of silence.
  • Take time to finish well. Don’t rush through the punch line.

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