10 great leadership lessons from my all time favorite movie Butch Cassidy & the Sundance Kid. A great script and two legendary actors in their prime play out some great leadership lessons.

1. 10 Powerful Leadership Lessons From,
Butch Cassidy and the Sundance Kid
By Andrew Wood

2. #1 Your reputation always precedes you!
Butch Cassidy, played by Newman, is about to walk in on the Sundance Kid,
who’s playing cards in a dark and dusty saloon. He’s beating the man he’s
playing with badly, and the man has accused the Kid of cheating. He tells
Sundance to leave the money on the table and leave town. Sundance insists he
wasn’t cheating, just as Butch Cassidy walks in on the scene. Butch tries
desperately to talk the Kid into leaving, but he insists again that he wasn’t
cheating and that the only way he’s leaving is with the money and only then if
he’s asked to stay.
Butch approaches the man, who is standing, ready to draw, and cautiously and
inquires, very politely, what he would think about maybe asking them to stick
around. The man, astonished, pushes Butch away, at which point Butch turns to
the Kid and says, “Sundance, I can’t help you.”

3. #1 Continued…
The man, instantly recognizing his name as one of the fastest guns in the west,
immediately starts backtracking and eventually moves aside and asks them to
stick around. Cassidy gathers all the money into his hat and says, “Thanks, but
we’ve got to get going.” As the kid walks out of the saloon, the man yells at
him, “Hey, Kid, how good are you?” at which point Sundance wheels around
and shoots the guy’s gun out of his holster, hitting it three or four more times
as he sends it spinning across the room. Then he calmly spins his pistol, puts it
back in his holster, and walks out into the sunlight. This is a classic case of
allowing your reputation to talk for you.
Your reputation—good, bad, or indifferent—almost always precedes you. It
precedes you in business, in sports, and everything you do in life.

5. #2 Allow other members of the gang to take credit
There’s a great scene in Butch Cassidy and the Sundance Kid where Butch and Sundance
come back to their gang’s mountain hideout, Hole in the Wall, after a long absence only to
find Harvey Logan has taken control of their gang. Butch insists it’s his gang, not Logan’s.
When challenged as to the authenticity of the statement, he turns to News Carver and
says, “Read ’em a clipping, News." News proceeds to take a sheaf of newspaper clippings
from his saddlebag and selects one from the Salt Lake Herald: “‘Butch Cassidy’s Hole in the
Wall gang…’”
“That’s me,” says Butch, and continues a monologue as to why he is the best person to lead
the gang while News continues reading the article out loud. “You can shut up now!” yells
Butch. “No, not till I get to the good part,” says News.
“‘Also known to have participated in the robbery were Flat Nose Curry and News Carver’—I
just love to read my name in the paper, Butch.”
Recognition is such a key component of any relationship, business or personal.

7. #3 Surprise is always a great strategy
Undeterred by Butch’s impassioned speech as to why he should remain leader of
the gang, Logan challenges Butch to a fight —“Guns or knives?” he barks.
Butch replies that he doesn’t want to shoot with him, whereupon Logan pulls out
a giant knife, takes his shirt off, and crouches for attack.
Butch, blue eyes blazing, strolls up to him casually, smiling, shaking his head, and
waving his hands in the air, saying, “No, no, no, not until me and Harvey get the
rules straight.” The astonished Logan stands up, looking at the smiling Butch in
disbelief, and says, “Rules in a knife fight?” Butch then plants a thunderous kick to
his groin, doubling the hulk of a man over.
“Well,” says Butch, “if there aren’t going to be any rules, someone get the fight
started.”

8. #3 Continued…
Sundance quickly obliges, with a one-two-three count, and Butch
punches the bent-over Logan in the head, knocking him out cold.
Butch just dusts himself off and walks triumphantly back toward the
rest of the gang. This classic scene has so many real-world
applications. How many times have we felt bound by rules, both real
and imaginary?
Constraints that we let dictate our every action without ever
questioning their validity, which in many cases are simply are not
real.

10. #4 Concentrating force can be the answer
There is a classic scene in the movie where they hold up the Union Pacific train
for the second time, only to find the safe in the boxcar far larger and stronger
than the first. They add a few extra sticks of dynamite, blowing the car and it’s
contents to kingdom come, causing Sundance to quip, “Think you used enough
dynamite there, Butch?” In real life, the Wild Bunch did indeed use brute force
to rob a train; only they blew up the tracks so they wouldn’t need to actually
jump on the train to stop it. While force is never usually the best choice to solve
any problem, it’s a proven solution when other options have failed.
Marshall all your troops and talents to the weakest spot in your current
challenge.

12. #5 Never underestimate your competition
“Who are those guys?”—a phase uttered many times throughout Butch
Cassidy and the Sundance Kid as they are relentlessly pursued by a
superposse. Each new surefire scheme to lead their pursuers astray fails,
as the people tracking catch on and get right back on their trail.
How many times have we underestimated the competition? From missing
a place on a high-school team to losing out on a date, a place in college,
or a job? To finding your loyal employee has jumped ship or that your
business is in a sudden cash-flow crunch because you competitor just
slashed prices?
Never underestimate your opponent, whomever they may be. Always
assume they are smarter and stronger than you think.

14. #6 Take time out to enjoy life and re-charge
You cannot maintain peak performance and creativity without taking time
off to reflex and enjoy the fruits of your labor.
It’s good to have your own “Hole in the wall” where you can stimulate
your body and mind with sights, sounds and activities never found in the
course of a normal work week.

16. #7 Hire or partner with the best people
Why can’t Butch Cassidy and the Sundance Kid shake the posse that’s
relentlessly tracking them?
On account of Mr. E. H. Herriman, owner of the Union Pacific Railway, who
resents the way the two outlaws have been picking on his trains and robbing
him. In response, he has put together the best team of lawmen and trackers
ever assembled. Yes, he actually did this!
Likewise once in South America, our two lovable outlaws used the charm
and beauty of Etta Place, as cover and to gain access to bank vaults. She also
spoke Spanish.

18. #8 When market conditions change
so must you
When the competition gets too hot or the soils of success too hard to
get it’s time to look for new products, new markets or both.
While Butch and Sundance tried career change first “Payroll guards”
was never really a good career fit. They did, however, find great
success in robbing the banks of South America.

20. #9 There comes a time when you must
have the courage to take massive action
Butch and Sundance are trapped on a rock ledge, several hundred feet above a raging river,
having been pursued relentlessly by a posse for several days. They sit on the ledge and
consider the potential options. They could give up, but they don’t fancy going to jail. Their
pursuers could go for position and pick them off one at a time or pin them down and
starve them out. They could also get a rock slide started. Butch asks Sundance what else
they could do. “They could surrender, but I wouldn’t count on it” comes his sarcastic reply.
Butch suddenly jumps up and says, “I know; we’ll jump!” “The hell we will,” says Sundance.
But after some tense back-and-forth, jump they do, holding a belt since Sundance can’t
swim. Our two lovable outlaws survive and float down the river away to safety.
How many opportunities did we miss in life by standing on the edge and worrying what the
consequences are? If we simply have the courage to jump more often, how much more
exciting and rewarding could our lives be?

22. #10 Remain optimistic
Holed up in a small room, exhausted, shot up and with an entire regiment of the
Bolivia army surrounding them Butch and Sundance banter back and forth. Keenly
aware of the gravity of their situation Butch keeps the conversation upbeat,
repeating a suggestion from earlier in the movie, “Next time I say let’s go to
Australia, let’s go.”
Suddenly Butch looks alarmed. “Wait a minute; you didn’t see Lavore’s out there did
you?” This in reference to the Marshal who has been relentlessly pursuing them.
“Naw,” says Sundance.
“Good,” says Butch, “For a minute there I thought we were in trouble,” as they
stumble out into the plaza guns blazing.
Whatever challenge you face, facing it with humor, optimism and both guns
blazing is the way to go!

23. Andrew Wood is the co-author of Cowboy
Wisdom- Classic Lessons in Leadership
and Life. Despite being born in Oxford,
England, Wood always had a love of
everything Western and studied the
biographies of all the West’s famous
characters.
Partnering with world-renowned horse
trainer and former rodeo cowboy, Pat Parelli
the two mix their experience of building
multi-million dollar companies with classic
lessons from famous Western movies. The
result is a thought-provoking, insightful and
entertaining look into the leadership and life
skills that matter.
www.classiccowboywisdom.com
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