From Amateur to Pro: Embracing the Path of a Practicing Leader

Estimated reading time: 11 minutes

I had a, “I’ve been thinking about this all wrong,” moment the other week.

After reading and loving, The War of Art, I immediately read Steven Pressfield‘s next book, Turning Pro. In that book, Pressfield describes the difference between an amateur and a professional leader. Specifically, professionals have a practice. As part. of their practice, they get up, go to a set place, at a set time, and do their work.

He writes, “A practice may be defined as the dedicated daily exercise of commitment, will and focused attention, aimed on one level at the achievement of mastery in a field, but on a loftier level, intended to produce a communion with a power greater than ourselves.”

As he continued describing the elements of a practice for creating art, it occurred to me that leadership followed many of the same rules. The implications of this realization are that someone who practices leadership can be more successful in any leadership role than someone with technical or subject area expertise.

The Practicing Leader is a Warrior

As we start to view leadership as its own discipline, requiring a practicing mindset, it means that most senior leadership roles are being filled incorrectly. Rather than looking at someone’s technical abilities, length of tenure, or other pre-requisites, perhaps we should be looking at their results, team engagement, and character.

The results we feel are ones that permeate so much of my LinkedIn field. Arrogant bosses, narcissists and egomaniacs in Senior Leadership roles at the top of large organizations cascade misery throughout their organizations. When this happens, employees stay in misery and low productivity, or leave looking for better organizations. When employee engagement and low and turnover is high, management in supervisory roles are almost always the reason.

Understanding leadership as a practice in itself means understanding the qualifications for senior leaders totally differently than we do today.

Characteristic #1: The Practicing Leader has Intention

In Turning Pro, Pressfield writes, “Our intention…is to get better, to go deeper, to work closer and closer to the bone.”

The Practicing Leader has a leadership philosophy, which serves as their intention. She proactively decides what her team needs from her to be successful and puts that into place. She wants to be a leader to make a difference or to improve something. The Practicing Leader understands that leadership is not about her, but about the people she leads.

Characteristic #2: The Practicing Leader has as a Warrior Mindset

Pressfield explains, “The Sword Master stepping onto the fighting floor knows he will be facing powerful opponents. Not the physical adversaries whom he will fight, though those indeed serve as standards for the enemy. The real enemy is inside himself.”

The Practicing Leader is self-aware. He solicits others for feedback. He has a thick skin and does not take feedback personally. The Practicing Leader knows who he is because he has defined his values. He meditates and takes care of himself to continue to practice leadership and service for years to come.

The Practicing Leader is not deterred by obstacles or failure. He looks for new ways to accomplish goals and protect his team. He leaves nobody behind.

Characteristic #3: The Practicing Leader is Humble

Steve Pressfield writes, “We come to a practice in humility. We may bring intention and intensity to our practice. In fact, we must. But not ego. Dedication, even ferocity, yes. But never arrogance. The space of the practice is sacred.”

One test I have come across to understand the humility of a leader is their motivation for leadership. If ego is motivation, then leadership is not the right fit for that person. You call tell this by learning if the leader wants to “Be something” or “Do something.” If they want to be something, it is probably more ego.

Being a “Boss” in business is about ego. Characteristics of most bosses is status (Do as I say!), arrogance (What can I learn from someone like you?), and a lack of self awareness (Everybody loves me!). The character Michael Scott from the sitcom The Office comes to mind.

Additionally, modern attention seeking politicians fall into this category as well. These are the people who enjoy the trappings of the job, seeking fame, not better policy.

Pressfield writes, “My beef with American culture is that almost every aspect, including the deliberations of the legislature and the judiciary, has been debased to pander to the culture of amateurism. The promise that our products and politicians proffer is the promise one might make to an infant or an addict. I will get you what you want and it will cost you nothing.”

Sadly, we do the same with some people in Senior Leadership roles. We promote bosses and politicians and then wonder why we get amateur results.

Characteristic #4: The Practicing Leader is a Student

According to Pressfield, “Even the peerless sword-master Miyamoto Musashi. Entered the fighting square to learn as much as to teach.”

The Practicing Leader always has more to learn. She approaches her team as a student and a servant, learning and synthesizing information to make life easier, more focused, and more productive. She goes to where the work is, and does not turn her office into an ivory tower.

The Practicing Leader is a voracious reader, getting her hands on all the information she can to be a better as a professional. She learns from everyone around her, regardless of title, and strives to nurture and develop more practicing leaders.

Characteristic #5: The Practicing Leader Practices for Life

Finally, Pressfield explains, “Once we turn pro, we’re like sharks who have tasted blood or renunciants who have glimpsed the face of God. For us there is no finish line. No bell ends the bout. Life is the pursuit. Life is the hunt. When our hearts burst then we’ll go out, and no sooner.”

The Practicing Leader views leadership as a lifelong endeavor. As long as there is a worthy cause requiring the power of collective thinking, the leader will answer the call.

Examples

To illustrate that practicing leaders exist and the benefits of approaching leadership this way, there are three case studies worth focusing on: Ted Lasso, Vince Lombardi, and Richard Branson.

Example #1: Ted Lasso

I’ve written in the past about Ted Lasso, one of my favorite television shows.

The Apple TV+ series is about a college football coach who is hired to manage a Premier League soccer team in England.

It is a running joke in the show that Lasso knows nothing about soccer. However, he knows about leadership.

Just look at Lasso’s first press conference and the question here gets from journalist Trent Crimm: “I just want to make sure I have this right: You’re an American, who has never set foot in England, whose success has only come at the amateur level, a second tier one at that and is now being charged with the leadership of a premier league football club, despite clearly possessing very little knowledge of the game…Is this a joke?”

Now, just 2 years later, Trent Crimm is writing a book about Ted Lasso’s coaching style. He describes Lasso’s leadership, which we witness him practicing throughout the series, like this: “Slowly but surely building a club wide culture of trust and support to thousands of imperceptible moments.”

SPOILER ALERT (Skip this paragraph if you haven’t watched the finale): At the end of the series, Lasso becomes a successful soccer coach.

If you looked at Lasso’s traditional resume, he had no business coaching in the Premier League. However, his success skyrocketed when he found a tactic that supported the culture he built as a leader.

While Ted Lasso is, of course, a hypothetical character, there are more examples of leaders who have excelled even in areas where they have no experience or expertise because they practice leadership.

Example #2: Vince Lombardi

Vince Lombardi was a practicing leader
Vince Lombardi by Daniel A. Moore Credit: Smithsonian National Postal Museum

In 2014, Ian O’Connor wrote a detailed article on Vince Lombardi for ESPN The Magazine called, The Gospel of St. Vince. O’Connor describes the legend of Vince Lombardi who is best known for winning Super Bowl’s I and II. In fact, professional football’s championship trophy is named for him.

But, it wasn’t only Lombardi’s accolades as a football coach that stood out. Lombardi’s first coaching job was at St. Cecilia’s High School in New Jersey. In addition to coaching football, Lombardi also coached basketball.

However, Lombardi didn’t know the first thing about basketball. As the story goes, he went to the library and read old manuals on basketball to become more familiar with the game.

In the documentary, Vince Lombardi a Football Life, we hear from Mickey Corcoran, one of his players on that team who said, “He didn’t know much about basketball but he knew about people. He was a master psychologist…He just made me want to play harder.”

Lombardi coached basketball at St. Cecilia’s for eight years. He finished 105-57 and he won the only state basketball championship in the high school’s history.

If leadership is technical, how did Lombardi pull it off? How did he post a 65% winning record and win a championship in a sport he learned overnight?

Lombardi on Being a Practicing Leader

In his own words, Lombardi said, “I think coaching is teaching, see? So I don’t think there is any difference whether you teach on the football field or whether you teach in the classroom, right? They are both exactly the same. It’s a question of a good teach puts across what he must put across to his pupils whether it is done on a football field or done in a classroom, it is one of the same thing.”

While Lombardi knew a lot about the technical side of football to the point of obsession, he still identified not as a football coach, but as a teacher. He too viewed leadership as a practice, which is why he was successful not only as a football coach, but as a basketball coach.

Example #3: Sir. Richard Branson

Richard Branson is a practicing leader
Photo of Richard Branson Credit: Virgin

Sir Richard Branson is the founder of the Virgin Group. Virgin now has business in entertainment, health and wellness, music, finance, technology, travel, and space travel.

Branson has been massively successful in almost all of these business areas, which at first glance seem to have nothing to do with one another.

All the while, Virgin has a global presence, but no central headquarters, no management hierarchy, and minimal bureaucracy. In his book Losing My Virginity, Branson discusses his leadership style and practice. He encourages his teams to have fun, not worry about failure, and always think about the customer.

One of my favorite of his quotes is “I’ve never gone into business to make money. Every Virgin product and service has been made into a reality to make a positive difference in people’s lives. And by focusing on the happiness of our customers, we have been able to build a successful group of companies.”

Conclusion – Becoming a Practicing Leader

There needs to be a fundamental shift in our understanding of leadership. Leadership is not defined as getting results via leadership, or simply as a means to an end. Instead, it is the idea that I understand leadership, so I get results.

Becoming a practicing leader is work. For some people, managing people is excruciating. For these folks and others that excel in vital technical areas, there should be a compensation ladder on-par with Senior Leadership that does not require them to manage people.

Today, leadership development is viewed as a series of tasks. We describe how to set an agenda for a meeting, how to conduct 1:1’s, and how to hire and fire. Those skills are all important, but they are not leadership skills. They are management skills. To take it to the next level, aspiring leaders must start and stick with a leadership practice. Leadership development and leadership coaching must rise to this calling and develop the programs to nurture practicing leaders.

If you are new to a leadership role, I encourage you to adopt the mindset of a practicing leader. Understand the characteristics of a practicing leader and develop yourself as one. Solicit the help of leaders you admire, mentors, and team members.

Key Takeaways

Leadership should be seen as a practice requiring commitment, intention, self-awareness, humility, and a continuous learning mindset. By shifting our focus from technical expertise to these qualities, we can cultivate effective leaders who achieve results, foster team engagement, and make a positive impact.

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“Be curious, not judgmental”

Like some of you reading this post, I used to watch a lot of television, but I have cut most of it out over the last few years. The main exceptions are if my wife and I get into a show together and watch one episode per night or watching live sports. During the pandemic, this pattern really has not changed, as I have enjoyed spending time reading and playing with my son.

Not only can watching television be a big time waster, it can also be a source of stress, especially 24 hour news channels, which I actively avoid. Furthermore, I have often worried about Hollywood’s glorification of rude jerk personalities, like Dr. House and Ari Gold from Entourage. One of the final straws which led me to limit my TV-watching was the juxtaposition of the optimistic portrayal of public service through shows like The West Wing in the early 2000s, to the ultimate in cynicism shown through political dramas like House of Cards, which premiered around 10 years later. Every time I would turn on the television, I would see more glorification of the “love-able jerk” characters, which just does not align with my values.

But then much to my surprise, in walks Ted Lasso. If you have not seen the show, Ted Lasso is on Apple+ and I highly recommend it.* In short, it’s the story of an American college football coach who is hired to coach a premier league soccer team in England. Without giving too much away, the Ted Lasso character, played by Jason Sudeikis, is optimistic and resilient, the ultimate “good sport.” Every Friday, I excitedly wait for the next episode, sometimes using the excuse of my son rising early to get my early morning fix before starting the rest of my day.

A recent episode had a moment in it that taught a very important lesson and made me reflect and go deeper.

Take a look:

Instantly, the story and the quote, “Be curious, not judgmental,” struck me both intellectually and emotionally. I started to consider how often I rush to judgment, and whether doing so was actually serving me well, or limiting me when trying to reach my goals.

Our minds are meaning-making machines, constantly making assumptions, judgements, and looking for patterns. This is not an inherently bad trait – it kept humans safe as we evolved for a very long time. However, interpersonally these same tendencies may not serve us as well. Our internal narratives can be filled with bias, can be self-destructive, or can result in hurting someone else. At the end of the day, our judgments can be the lens through which we understand the world and that lens is foggy at best, opaque at worst.

So what would happen if we replaced our judgments with curiosity? What would that world look like? And what would a workplace like that feel like?

These are all questions that have been on my mind since reflecting on this powerful quote by way of Ted Lasso. I have found that I need to check myself all the time to try be more curious rather than judgmental. In doing so, I have found that it is amazing how many of my assumptions are actually wrong. I’ve also learned that being curious is much more enjoyable, light, and energy-saving than being judgmental.

The more we learn about something, the more we open ourselves up to different points of view, and the more we question, the more truths and wisdoms we will learn. Leaders must continue to pursue truth and wisdom as the world continues its fast pace of change. It serves leaders to be curious, to not judge, and to not rely on what has worked in the past.

How will you be curious, not judgmental?

The practicing leader quote - be curious not judgmental Ted Lasso

Leadership Lessons Learned

We all have so much to learn and being judgmental can shut us off from truth and wisdom. “Be curious, not judgmental“.

*Note: Ted Lasso is rated TV-MA for those who may want to screen before watching with families and young children.

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