The Thriving Lawyer: Why Cowboy Leadership Works

Let me be clear, I am not saying that people are horses, or like horses. What I am suggesting is there are certain universal principles in training. In working with my equestrian trainer to train my youngster (a very large horse with a mind of his own), I’ve experienced firsthand the magic of training like a cowboy. Or perhaps it’s better said, leading like a cowboy.

When you think “cowboy,” you may imagine a rodeo cowboy on a bucking bronco. That’s not what I am talking about. Or at the very least, that image portrays exactly what we’re trying to avoid: resistance and misalignment. Once you accept that you cannot force another to do anything, then cowboy leadership makes perfect sense. The cowboy creates the circumstances for the horse to succeed.

Let’s start with creating safety. No one learns well when they are in fight-or-flight mode. While in these modes, the objective is to survive. Horses flee when they are afraid. They “high-tail it” out of there––their legs are their survival. They cannot learn when worried about their safety.

To feel safe, horses must learn that certain stressors such as noises, motion and wind are not life-threatening. Cowboys, as trainers, teach by patiently and deliberately exposing horses to “scary” stimuli in appropriate doses and ask them to stay focused on the task. They do so because the cowboy offers them security. The cowboy and the horse develop a trusting relationship built on more than the daily carrot and “good boy” snuggle. Critically, the relationship is built on consistency and the fact that the cowboy does not “overface” the horse, meaning that the cowboy accurately judges the horse’s capacity and development as well as that day’s emotional state when pressing for performance. Only then can the cowboy provide a learning experience that may be a stretch, but not overwhelmingly so. The cowboy breaks tasks down for the horse and the horse develops confidence. Confident and relaxed horses perform well.

Now put safety, overfacing, relaxation and confidence in the context of training an associate. What we’re really talking about is a healthy culture in which associates feel supported in doing their work, the expectations are reasonable and appropriate given experience, and colleagues are respectful. Like the cowboy, the partner breaks down the assignment for the associate based on the associate’s experience. Consider whether a first-year associate feels safe or overfaced when asked to argue a motion or draft and present a memorandum on complex issues to a client. Think about what it’s like for the associate who delivered poor work product and senses the partner’s anger. Surely the associate does not feel safe.

At the same time that you create safety, you establish black-and-white boundaries for the associate. With a horse, aggressive or playful behaviors such as biting, kicking out or turning its rump (a sure sign of disrespect and even anger) are unacceptable to the cowboy. Call this “setting expectations.” The workplace analogy most definitely includes harassing and rude behavior. Consider also what the horse world refers to as “evasions” and the human world calls “passive-aggressive” behaviors. For a horse, it’s a head toss, bolting across the arena or lackluster foot-dragging gate that says, “I’m trying to avoid hard work.” In the workplace, the behaviors include omissions such as failing to show up for a meeting or “ghosting” email, texts and calls. Other loathsome behaviors include failure to proactively inform the partner that a deadline will likely be missed before being asked or waiting to be reminded to fulfill obvious responsibilities. So yes, the concept of evasions applies in the workplace. And, where there is evasion, learning and performance are poor.

Eight Tips for Creating the Circumstances for Success

So how does a lawyer become a cowboy leader, implementing this framework daily? Apply these tips to cowboy up!

1. Recognize you are a leader. It’s not just practicing law; you need to allocate the necessary time and energy to leading your team.
2. Create safety even if you’ve been let down or ghosted. Keep your anger and frustration to yourself by focusing on improving the associate’s performance and client deliverables.
3. Don’t overface. Consider whether the task is at the appropriate level for the associate. If not, modify it. Just like a cowboy breaks down an exercise for a horse, create a work plan that anticipates needs for guided improvements.
4. Let the associate struggle only so long as progress is being made. The partner will likely need to balance the imperative to avoid overfacing with the desire for the associate to wrestle with the problem in order to learn. More frequent guidance will help the partner both provide input and ensure progress. Sufficient time to learn is essential.
5. Clarify and reinforce expectations. This includes expectations for communication, meetings, a work plan and how to best reach you with questions. Work in enough time for missteps particularly until you’ve developed trust in the associate’s reliability and competence.
6. Take advantage of every training opportunity. Talk about the little problems before they become big problems. This doesn’t mean you nag or micromanage. But it means that you call out failures to meet expectations with curiosity, compassion and a problem-solving mindset.
7. Separate your feelings from your leadership. Don’t let your like or dislike for an associate affect how you train, mentor, set expectations and maintain boundaries.
8. Nurture a learning mindset. Be the teacher by good example. Express curiosity about solving a problem. Demonstrate and teach critical thinking skills.

Follow these tips and you’ll create an environment where associates are chomping at the bit to work for you.