What Every Executive Can Learn From A Real Cowboy

It’s much more than what size hat to wear and how to walk cool.

What Every Executive Can Learn From A Real Cowboy
[Image: Flickr user Terry Pratt]

What do you do when you’re the CEO of a company fast approaching a value of $1 billion within just three years? What about when your executive team is asking pressing questions about the business strategy and how the company plans to grow and evolve? What do you do when your leadership team is moving as fast as they can but would be more effective if they had a streamlined process? You invest time to create an opportunity for the entire organization to reflect and connect around the purpose of the company and its operating values, working together to articulate a clear strategy for tomorrow–the goal being that you leave the team with an experience that challenges, informs, and inspires them.


I recently returned from three action-packed days on a cattle ranch in Wyoming where my company, Bulldog Drummond, played the role of protagonist, guide, and coach for an executive summit that we designed for a team of 14 executives. They arrived with many challenges; frustrated by the pace of business and the fact that they had to take time out of their already jam-packed schedules.

Carve out time to reflect and plan.
We worked side by side with the CEO to design a combination retreat and executive therapy session for three days of executive detox focused on overcoming the biggest strategic roadblocks for the business while simultaneously building a long-term strategy to prepare the business growth for $3B. The team arrived on day one tired and testy, and departed three days later informed, empowered, and energized, describing the session as the best time they’d spent with the company to date. The reality is that most executives and their teams don’t spend enough uninterrupted time thinking about the business. It’s imperative to carve out time for planning and reflection throughout the calendar year, not just during a crisis.

The “Ranch Challenge” started with dinner and beers on a deck overlooking a river and a golden Wyoming sunset. The team played poker with a vengeance and slept like babies. With instructions to be up with the sun, everyone was given clear directions about a rigorous hike up a challenging peak and armed with a customized journal that included questions about personal life goals, purpose, values, and time priorities. As we hiked the peak, we stopped every 20 minutes and the team was individually sent off to find a quiet space, sit down, and answer a section of the journal. The cynics who thought the exercise was too touchy-feely at the start were the first to express how much they discovered about themselves and how in dire need they were to get a better grasp on their lives.

Use your vision, mission, and values as your compass.
After the morning hike, we dug deep into the company’s vision, mission, and values, and we looked at the problems that needed to be solved. While I won’t get into the details or methodology, I’ll tell you that at the toughest part of a long first day while mapping the realities of the rapidly growing business and laying out the problems, tensions were high and the team was drained. Pride and ego were the internal unspoken enemies, and the lack of forward planning and clear communication were central issues holding the team back from being world class. But grounding the conversation around the company vision clearly created a framework for a 2014 and 2015 mission.

Work hard and ride like a cowboy.
The strategic planning involved rigorous debate and a lot of mental energy—so to break up the summit, we worked with the ranch’s outfitter to help relieve stress and give the executive team a taste of the skills needed to operate a 200,000-acre cattle ranch. We also invited a team of expert sharpshooting cowboys to teach the team to shoot with antique-replica pistols, rifles and double-barreled shotguns. With moving targets and the responsibility of loading our own guns, that natural competitive spirit kicked in and everyone competed to be the best.

Shoot with precision and timing.
While the executive team was competing and trash-talking about my English marksmanship skills, I decided to listen to Big Pete, the sharpshooting 70-year-old cowboy who told me that if I shoot precisely and deliberately, the timing will take care of itself. I listened carefully, and while I was horrendous during the practice rounds, I cleaned everyone’s clock with timing and accuracy, receiving a perfect score. The lesson we used in our afternoon strategy session was twofold: Precision and timing are fundamental ingredients for playing the game and winning.


Ride for the brand.
Throughout the three days, the ranch became more than a place where we stayed. It was a space to observe passionate and talented people run a world-class operation. On the last night, we were trucked to a bend in the river at sunset to cook and eat the best barbecue ribs and beans you’ve ever tasted. While we listened to a cowgirl and cowboy duet sing about the land and life they both loved, their passion came through about the importance of love, neighbors, and friendship. One of the songs was, “He Rides for the Brand,” which struck every member of the team. It was a friendly reminder that no matter the adversities and challenges you face, you ride for the “brand” and the team you steward and manage.

Master simplicity
As I reflected on the $1 billion challenge we came together for, it was an inspiring process to watch the cowboys, masters of their craft, make their roles look effortless. They manage the land and animals with care, operate with deliberate focus, efficiency, simplicity, and passion. We can all take a page out of the cowboy book of management as we think about how we lead and inspire our teams.

About the author

Shawn Parr is the Guvner & CEO of Bulldog Drummond, an innovation and design consultancy headquartered in San Diego whose clients and partners have included Starbucks, Diageo, Jack in the Box, Taco Bell, Adidas, MTV, Nestle, Pinkberry, American Eagle Outfitters, Ideo, Sony, Virgin, Disney, Nike, Mattel, Heineken, Annie’s Homegrown, Kashi, The Michael J. Fox Foundation for Parkinson’s Research, The Honest Kitchen, and World Vision.