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.

Is Love the Killer App? Do Nice Guys Win?

The Silicon Valley Junto, the Bay Area’s preeminent intellectual discussion society for business and technology executives, convened this quarter to discuss: Love is the Killer App: The Soft Heart in Business. Do nice guys finish first?

Chris Yeh and I started the Junto to continue the tradition of Ben Franklin, a remarkable guy, who in 1727 hosted 12 of his friends on a weekly basis to discuss the issues of the day. The Silicon Valley version attempts to bring our smartest friends into a room over pizza once a quarter to talk about something other than web 2.0. Past topics have included Americanism, humor, and happiness.

"Love is the Killer App" is the name of Tim Sanders book, which I just read, and enjoyed quite a bit. You can find my rough summary here.

After participating in both the Palo Alto and San Francisco discussions, I can safely say that I think compassion and love in the workplace — if defined as a genuine sense of caring and a proactive drive to help others out selflessly — is a killer app. Here are some of my notes:

  • Remember the Buddhist loop — to be selfless can be selfish.
  • Compassion will be beneficial in the long run, just remember the long run may be 20 years.
  • Yes, assholes sometimes win in business. Life’s not fair. But most highly effective CEOs lead with warmth.
  • With an increase in transparency thanks to the internet, nice guys should win more.
  • To show love in the workplace means you will share your knowledge and network.
  • How can you be more compassionate in the workplace?
    • Actually listen to people, and care about what they say. Everyone yearns for respect.
    • Understand people’s responsibilities — what are they trying to get done everyday
    • Look to help others — "Let me know how I can help you"
    • Care about their life outside work
    • Look for the best parts of someone and compliment it. Reinforce someone’s strengths.
    • Most important: be genuine. It’s gotta come from the heart.
  • It takes 100 positive interactions / actions to make up for one negative interaction.

What’s your experience been? Are the successful people you know (by traditional definitions) compassionate and "nice"? Or does the hard ass win more often? How do you express compassion?

Here are Susan Etlinger of the Horn Group’s thoughts on the Junto.


Funny Business: Using Humor to Thrive in the Professional World

Each quarter the Silicon Valley Junto, a discussion forum for business and technology executives that Chris Yeh and I run, gathers to discuss an intellectual topic that’s not directly related to business or technology. It’s an invitation-only lunch held on the peninsula and in San Francisco.

Our topic this quarter was: Funny Business: Using Humor to Thrive in the Professional World.

At the Trinity Ventures office in Menlo Park about a dozen super interesting people gathered to analyze this very serious issue. In San Francisco, at the North American headquarters of Comcate, Inc., a dozen people from slightly different backgrounds (more women, more non-profit heads) tackled the same topic.

Check out the notes from the meeting for the insights we collectively gathered. If you want them in more organized fashion you’ll have to wait for the e-book on humor Chris and I are writing. Here’s Tim Taylor’s useful post about the meeting, and Jackie Danicki’s post.

Here are photos from the two meetings on Flickr.

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Be Funny: Humor for the Businessperson

Some day, Chris Yeh and I will start a secular church and a political party (economically conservative and socially liberal). But for now, we’re sticking to the Silicon Valley Junto and …e-books.

We have two e-book ideas. The first is on humor and business. We think humor is really important. People who can integrate belly-laugh quality humor in their daily business lives are in a class of their own, I think. So Chris and I want to publish a low-cost, PDF-style e-book that can make funny people funnier and dull people manageable. Hell, we’re even throwing in a situational matrix. It will probably be several months until this is done — since both of us really don’t even have time to do this — but so long as Chris’ kids require tuition money, we all have to chip in somehow.

Go add your ideas, thoughts, and examples on this public wiki so we can make it good. Password: humor

Incidentally, I just heard this NPR piece on humor in politics, in which former senator Alan Simpson says:

"You show me a humorless person and I’ll show you a guy I can always whip in a debate."

"My mother always taught me humor was the universal solvent against the abrasive elements of life."

Conversation: The Greatest, Most Lasting, Most Innocent, Most Useful Pleasure of Life

I practically drooled over Russell Baker’s piece (free, print-length) in the New York Review of Books on the new book Conversation: A History of a Declining Art. An excellent conversation can often be elusive when everyone seems so short on time, so full of one-liners from talk radio. We must keep searching…For a good conversation is among the greatest pleasures in life.


Both participants listen attentively to each other; neither tries to promote himself by pleasing the other; both are obviously enjoying an intellectual workout; neither spoils the evening’s peaceable air by making a speech or letting disagreement flare into anger; they do not make tedious attempts to be witty….

Typically, Michael Oakeshott, the late British philosopher, thought conversation should have a distinctive lack of purpose. Conversation "has no determined course, we do not ask what it is ‘for,’" he said. It is "an unrehearsed intellectual adventure." As with gambling, "its significance lies neither in winning nor in losing, but in wagering."

…Montaigne finds a sharp conversational exchange physically and mentally exhilarating. Conversation, says Swift, is the "greatest, the most lasting, and the most innocent, as well as useful Pleasure of Life." Dr. Johnson thinks "there is in this world no real delight (excepting those of sensuality), but exchange of ideas in conversation."Montaigne speaks like a man for whom conversation is an exhilarating workout at the intellectual gym. Conversation, he said, was "the most fruitful and natural exercise of our mind" and "the most delightful activity in our lives."