Effective Leadership: Yippee Ki Yay! Cowboy Wisdom in the Business World

The business wisdom of Will Rogers

A friend sent me an e-mail the other day with some quotes from Will Rogers. My father-in-law used to say things like, “Let’s mount up!” when we were supposed to get in the car to go to dinner, so it struck a chord with me. After rereading it today — it’s one of those e-mails that I couldn’t seem to delete — I realized that many have business implications. I hope you do too.

1. “Never slap a man who’s chewing tobacco” and its close cousin, “Never kick a cow chip on a hot day.” Business translation: Think about unintended consequences before you act.

2. “Never miss a good chance to shut up.” I’ve had much better results (a) getting to know people and (b) learning things by asking questions rather than talking. The other day I actually said to a guy, “OK, enough about you; let’s talk about me!” after he droned on for about 20 minutes.

3. “Always drink upstream from the herd.” Have you ever found yourself hanging around the water cooler with a bunch of people with lots to bitch about but no solutions? Head upstream!

4. “Good judgment comes from experience, and a lot of that comes from bad judgment.” True leaders aren’t afraid of making mistakes, and failing fast is a good skill set. An old boss from many years ago said, “You’ll never get rich running scared! Make some mistakes!”

5. “If you’re riding ahead of the herd, take a look back every now and then to make sure it’s still there.” The other day, I met with a bright CEO who was a great strategic thinker. His challenge? Slowing down so that everyone else could catch up. In business, the whole team needs to get across the goal line.

6. “If you find yourself in a hole, stop digging.” You’re running a company or division and your results stink. Do you dig faster or dig elsewhere? It’s not always an easy decision. Consider getting some fresh eyes on the problem.

7. “There are three kinds of men: the ones that learn by reading, the few who learn by observation and the rest of them have to pee on the electric fence and find out for themselves.” (Note: There are probably three kinds of women as well. …) A few years ago while skiing in Whistler, British Columbia, some friends and I saw a young Australian guy named Angus jump off a very large rock. The result? Big-time yard sale. (By the way, I know his name because I helped him collect his gear and limbs.) We then watched his three buddies all do the same thing with identical results; I guess the fourth guy must have been dumbest. Experiential learning is great, but there’s a lot to learn from observation, and it’s much less painful (this is often called “best practices” in the business world).

8. “Long ago, when men cursed and beat the ground with sticks, it was called witchcraft. Today it’s called golf.” No business application, but because I golf about as well as I sing, I liked it.


Todd Ordal is President of Applied Strategy®. Todd helps CEOs achieve better financial results, become more effective leaders and sleep easier at night. He is a former CEO and has led teams as large as 7,000. Todd is the author of, Never Kick a Cow Chip On A Hot Day: Real Lessons for Real CEOs and Those Who Want To Be(Morgan James Publishing, 2016). Connect with Todd on LinkedIn, Twitter, call 303-527-0417 or email [email protected].

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