Reflections on Horseback: Five Days in the Bradshaw Mountains with Gentleman Jack

For several years now I have been involved in a springtime horseback trail ride in the Bradshaw Mountains of Arizona. This annual ride includes about 140 to 150 riders, all male, and about 25 to 30 wranglers and other employees. The ride lasts five days, starting with a noon-time parade out of Wickenburg, Arizona, on Monday. We ride five and a half hours on Monday, about nine and a half hours on Tuesday, take a day off on Wednesday, ride about nine hours on Thursday, and three to four hours on Friday. We come back into Wickenburg about noon on Friday to another parade with well-wishers and on-lookers lining the streets.

A typical annual ride covers about 100 miles. Every night we sleep under the stars on metal cots with cowboy bedrolls. After enough successful rides, and assuming you are not a jerk, you are invited to become a full-fledged Trail Ride member. Fortunately, I was added to the rolls after the 2023 ride year.

Riders come from a range of occupations including teachers, ranchers, surgeons, commercial truck drivers, government workers and retired entrepreneurs. We even have riders who come from abroad each year. On the trail we are all the same and expected to follow the rules of good horsemanship and to be considerate to and helpful of other riders. Hot meals are provided for breakfast and dinner, but lunches are “brown-bag†and eaten out on the trail.

The trail is considered challenging, even treacherous, especially for those who are not accustomed to demanding trails like these. The new rider return rate is only about 20 percent. For most riders it is a one and done experience. At the same time, we have riders with 50 successful rides under their belt.

Being in the saddle for the better part of five days gives you a lot of time to think and I want to share with you some of my reflections and their applications. But first, I want to introduce you to Gentleman Jack, who was my steed for this year’s ride.

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He stands 16 and a half hands tall and weighs 1400 pounds. By way of comparison, the average quarter horse is a little over 15 hands tall and weighs 950 to 1,000 pounds. Gentleman Jack is a big horse. Don’t make a habit of letting him step on your boots. Trust me.

Reflection #1: Check Your Cinch

A cinch is a piece of equipment used to keep the saddle in place on a horse. Having a tight cinch is critical to safe riding; a loose cinch allows the saddle to move around on the top of the horse and even slide down the horse’s side.

Cinches typically loosen with riding because the chest of the horse decompresses as you ride and in hot weather, the sweat of the horse loosens the cinch. To have a successful day-long ride you often need to stop, get off your horse, examine the cinch and tighten it if necessary. On a long ride, you may tighten your cinch by three notches.

Bad things can happen if your cinch is loose. One rider in our group, a rookie rider, allowed his cinch to loosen and as a result his saddle slid off the horse. The rider also came off the horse, slid down a rocky mountain side and suffered significant injury. His ride was over for the week. Fortunately, he had no concussion or broken bones, but he did suffer significant lower back soft tissue damage. To be sure, these consequences were bad enough, but they could have been disastrous.

There are many parallels in our business lives. For example, if we are responsible for overseeing others, we may think we are going a great job. In fact, managers typically rate their own managerial performance about 15 percentage points higher than do their employees.

A 180-degree upward feedback survey is a great way to “check our cinch†and to determine if we are giving our employees the support they need, and the respect and the recognition they deserve. Such a check-in can tell us what adjustments are needed to maximize their engagement and the team’s performance.

A loose cinch can lead to injury or even death. It requires ongoing examination and at times, adjustment. Examining our own performance, especially in terms of how we relate to others is like checking one’s cinch. Sometimes we realize, before it is too late, that adjustments are needed.

Reflection #2: Hydrate

We all understand that hydration is a matter of life and death in any climate. But on a day-long horseback ride in the desert mountains of Arizona, with low humidity and the sun beating down on you, it takes on outsized importance.

To my own discredit, in the hustle and bustle of getting ready for Tuesday’s day-long ride, I forgot to pack my two bottles of water in my saddle bag. I tried to make up for this by drinking a lot of water at the lunch break and after the day-long ride.

But I still woke up twice during my Tuesday evening sleep needing to leave my warm sleeping bag tucked into my cowboy bedroll, so that I could walk off episodes of cramps. My legs felt like they were literally on fire! Walking off cramps in an empty field dressed only in my long underwear in near freezing temps at 3 am in the morning was not fun. Lesson learned!

On last year’s ride I also witnessed the effects of dehydration. At an evening meal, a man at the other end of the picnic bench slumped over in a heap. Everyone suspected a heart attack. Medics rushed in, as did a few physicians sitting nearby, and he was taken by a deputy sheriff’s car to the hospital.

As it turns out, it was not a heart attack. He was simply suffering from dehydration. And guess what? This heaped-over man was a medical doctor.

Water is a source of life and necessary for good bodily function. But what about our own day-to-day functioning as leaders of others? Don’t we need the nourishment that mentoring, coaching, and training can provide?

Just as water intake fights off the night-time cramps that accompany trail rides, our ongoing leadership development may fend off the defection of talented staff and help us attract the new employees needed for business growth. Being placed into a leadership role should never mark the end of our development as leaders. Partaking of ongoing, even career-long development and growth, is essential to sustaining our own success and the performance of the teams we oversee.

Reflection #3: Keep up with the Pack

Our 100-mile trail ride is supposed to be nose-to-tail horseback riding. Riders are taught to keep their horse about four-to-five feet behind the horse in front of them.

Why not allow for larger gaps?

One reason is that there are a lot of twists and turns on the trail and, believe it or not, riders who do not keep up can get lost. This happened this year when riders who fell behind after crossing a shallow river took a wrong fork in the road and got lost. The whole trail ride had to stop so that a search party could go back, find them and get them back on the trail.

The more prevalent reason for not allowing gaps to develop has to do with the nature of horses, who are pack animals. If you allow a large gap, say 20-30 yards to develop, your horse will eventually start trotting to catch up with the pack.

For most riders, and particularly those who don’t know how to “post†while riding, a trotting horse means a lot of up and down pounding in the saddle. And it is not just the one rider who experiences this. When you let a large gap develop, you are creating an unpleasant experience for the other riders behind you whose horses are likewise trying to catch up, while at the same time making yourself unpopular trail hand.  

The goal is a nice steady ride, an orderly ride, with riders following the instruction and example of more experienced riders, to the benefit of all. The same is true in organizational life. When we don’t keep up, when we don’t pull our weight, others suffer the consequences. Deadlines are missed, customers are angry, co-workers grumble.

My global research reveals that of the most important things managers universally want from their employees, 50% has to do with personal values and work ethic – being honest and trustworthy, hard-working, committed and loyal, dependable, and cooperative and supportive.

Does that describe us? Are we what our bosses want us to be? Even if we are the top boss, does our behavior serve as the standard for others?

Reflection #4: Don’t Become Over-Confident

Some of the trails we ride are very open, for example, dry riverbeds or washes, like riding on a beach. Other paths are much more challenging and involve climbing up or down a rocky mountainside, brushing up against all manner of rough vegetation, even riding along narrow passages on the side of a cliff. Riders must stay vigilant of their horse, the path, other riders, and other horses.

This is true even for experienced riders. One man this year, an experienced horseman, in fact an owner of a dude ranch, illustrates this point.

As we approached the end of a long day of riding, along a narrow passage with rocks mounded up on one side and a shallow cliff on the other, and while he was distracted talking to others, his horse mis-stepped and rolled over the cliff. The rider also rolled over the cliff, landing on rocky ground, with the horse rolling over on top of him. The horse came out okay. But the rider suffered four broken ribs and had to be helicoptered out to the hospital.  

One of his wranglers had warned the rider not to ride an untested horse. But the man was confident the horse would finish the week-long trail-ride without incident. To add insult to injury, he laid down a $600 bet that his horse would finish the ride.

As leaders we hear a lot about the importance of exuding confidence. But it is often over-confidence that leads to mistakes and regrets. This rider, an excellent rider and easily one of the most popular men on the trail ride, would have benefited by listening the advice of a trusted employee. But he didn’t and I am sure he gave a lot of thought to that while recovering in his hospital bed.

Reflection #5: Don’t Start a Rodeo

Normally you think of a rodeo as a good thing because it involves trained riders engaged in highly competitive events in front of enthusiastic audiences. But, in the context of this trail ride, a rodeo is not a good thing. A “rodeo†happens when you mismanage your horse in a way that unleashes chaos and puts you, your horse, and other riders and other horses in danger.

I barely avoided starting a rodeo on my first ride. I rode too close to a dried-up piece of driftwood that was on the ground with its dead branches pointing up. One branch almost lodged between my boot and the inside of my stirrup. Eventually that branch would have poked the underbelly of my horse, which of course, the horse would not have liked. I avoided the rodeo by quickly and luckily maneuvering the branch out of my stirrup.

This year one rider did create a rodeo. At the end of the day’s ride, we are to dismount and give our lead rope to one of the wranglers who will tie it off on the picket line. One inexperienced rider instead tied his lead rope to a saddle stand. That was a bad idea. The horse broke loose, bringing along one of the stand’s steel rods, and started trotting down the picket line. The horse was stopped but not before another rider was injured by the trailing rod. Fortunately, the injury was not serious. But it is easy to see how the situation could have produced serious consequences for other riders and horses.

How can we create a rodeo along the picket line of our own business? One way involves improperly sharing information about another member of the team in a way that is not helpful, but in fact harmful. It can destroy team cohesion and if done by a leader it can seriously damage their sense of being trustworthy.

Another way is when we experience some unfortunate event, for example, a customer service mistake, and immediately place blame on another before gaining an understanding of the larger context. Psychology tells us we often explain away our own mistakes while failing to give another the same benefit of the doubt. Being overly quick to anger and overly quick to judge can start a rodeo.


Five days with Gentleman Jack in the Bradshaw Mountains of Arizona gave me a lot of time to observe and reflect. Staying safe and performing your best while on horseback depends on checking your cinch, staying hydrated, keeping up with the pack, not being over-confident, and not starting a rodeo. The same is true for leaders in organizational life. We need to check on how others are responding to our leadership, keep developing our own skills and abilities, pull our fair share and more, stay humble, and focus on ensuring our teams are working smoothly. And we need to do this consistently. This is a proven formula for success. Happy Trails!

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