systems thinking

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

/ Jonathan Sachs

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.

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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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How To Lead Middle Managers

/ Jonathan Sachs

Imagine for a moment that you owned a community swimming pool.

As the owner of the pool, you are responsible for making sure your customers swim in clean water and do not drown. Now you can’t be at the pool all day because you have other responsibilities. For example, you have to go make sure that you are signing up new pool members, going to the wholesale store to stock the snack bar, and fixing things around the pool when they break. In that scenario, you will need someone to watch over the pool and keep it safe. Would you trust that responsibility to someone who can’t swim? How about hiring someone who can swim but is not a certified lifeguard?

In this case, you would hire a trained and experienced lifeguard. If your pool is known for being unsafe, you are negligent and likely out of business.

Yet, businesses do things like this every day. They often make people “lifeguards” in their company without training to help them do their job well.

Most businesses don’t have literal lifeguards. With this analogy, I am referring to “Middle-managers.” Like the lifeguard, middle managers play a critical role in the success of the company, yet are often under-resourced to do the job well.

Middle Managers are often caught in the middle of expectations and demands from individual contributors and senior leaders.

The Important Role of Middle-Managers

Middle managers serve a vital role in most organizations. As the leader closest to the work, these managers are often responsible for making sure the business opens on time, is staffed correctly, and meets sales targets. They manage the requirements and expectations of both individual contributor employees and senior leaders. High performing individual contributors usually fill these leadership roles with no training or context to be successful in their new role.

Furthermore, these leaders are the most important for employee engagement. They lead individual contributors who are the biggest part of an organizations’ workforce. Individual contributors often decide to leave or stay at an organization due to their interacts and relationships with their direct supervisor.

In fact, middle managers are often responsible for being “The CEO” of their part of the business. They must navigate and drive results in revenue generation, operational efficiency, customer satisfaction, and employee engagement. In addition, they are also delegated additional responsibility or instruction from senior leadership about how to do to their jobs. Most compliance and reporting functions are delegated for at least preparation among middle managers.

Businesses Under Value These Leaders

According to a recent article from McKinsey, middle managers are often undervalued and underutilized in organizations. Despite functioning as a crucial link between top management and front-line employees, middle-managers often face significant challenges, such as conflicting demands and unclear responsibilities. The McKinsey article recommends that organizations should invest in developing middle managers’ skills and providing them with clear expectations and support to enable them to become effective leaders who can drive organizational success.

The article also suggests several strategies for empowering middle managers, such as creating a culture of feedback and recognition, providing opportunities for professional development, and fostering a sense of ownership and accountability. By investing in middle managers, organizations can unleash their potential and improve overall performance.

Five Ways to Engage Middle Managers

The article from McKinsey suggests numerous ways to better engage middle managers. In my experience, I have used several additional tactics to help these leaders be successful.

1. Give Them a Real Orientation

Many people entering a middle manager role have never held a leadership role before. Making sure they have an immersive multi-day orientation is important. Give them opportunities to learn systems and mechanics as well as the basics of leadership.

2. Clearly Define Their Role and Your Expectations

These leaders have the most scrutiny of living the organization’s values and achieving results. Make sure you clearly communicate your expectations of them in as clear language as possible. Spend time with them and let them know that they are vital to the organization achieving its goals. Be accessible to these leaders. After-all, they are your “Lifeguards”. Without them, your business does not work.

3. Develop Middle Managers to be Leaders

While we call these roles, “Managers,” in today’s business environment, organizations need them to lead. Since they are the leaders closest to the work or the customer, how they manage their business unit has a disproportionate impact on organizational results. Spend time with these managers to coach them. Ask them questions about what made them want to be a leader and how they want to lead with intention. Answer their questions when there is a new initiative and they are struggling with understanding its purpose.

4. Engage in Skip Level Meetings

Skip level meetings is a standard practice for me. A skip level meeting is when you have regular check-ins with the people who report to the person who reports to you. I always try to be aware if I, as a senior leader, am being managed. It’s important to know if a middle manager is indeed as skilled as they say they are or if they are making the teams they lead miserable. Regular skip-level meetings are an effective strategy to create more social bonds with your employees and have you finger on the pulse of the business.

5. Cut Red Tape Where You Can

There are a lot of well-intentioned people who create a lot of initiatives that get “pushed down” to middle managers. Too many of these initiatives from silo-ed units can crush middle managers, often overburdening them with tasks like data collection and reporting. This can lead to dissatisfaction and burnout. In addition complicated and dysfunctional processes can create unnecessary delays in addressing the needs of middle managers. When you identify red tape that is either inefficient or downright wasteful, fix it or eliminate it to make middle managers’ lives easier.

We Must Do Better

Middle managers are vital leaders in most organizations. Despite that, they are usually undertrained and under-resourced to do their jobs effectively. They deserve more than “Sink or swim.” They deserve to be guided and prepared for the awesome responsibility that is leadership.

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Key Takeaways

Middle managers play an essential role in organizations, however they are are often undervalued and underutilized. Organizations should invest in their professional development to empower them to drive organizational success. There are several important strategies for engaging middle managers, such as clearly defining their roles and expectations, developing them as leaders, and cutting red tape.

Team Accountability Isn’t What You Think it is

/ Jonathan Sachs / 1 Comment

The idea of team accountability is important, but often misunderstood. Many organizations struggle to hold people accountable. Leaders must have a good understanding of accountability to be an effective leader.

Gone are the days of rewards and punishments to drive team accountability. When most leaders discuss “holding people accountable,” they usually mean terminating low performers or punishing them in some other way. Accountability, by this definition, does not work. Instead, it becomes a recipe for turnover and disengagement.

When Accountability is Confused with Punishment

When I speak with leaders, especially leaders in middle management, there is frequent frustration around team accountability. What they tend to talk about as we unpack accountability is dissatisfaction about politics, treatment, and behaviors. Other leaders want to tie accountability to performance, similar to how General Electric CEO Jack Welsh used “Stack rankings” in the 1980s. In this model, the bottom 10% of performers would be fired at years’ end.

Tying team accountability only to outcomes is problematic because it discourages appropriate risk-taking. In addition, even high performers miss targets for legitimate reasons. While there needs to be recognition that the person did not meet their goals, punishing them is usually unwarranted. Tactics like “Stack rankings” are ineffective due to their short term orientation and punitive nature. “Stack rankings” only served to create a cut-throat and disengaged culture.

So that brings us back to the middle manager definition of team accountability. What they refer to when they describe a lack of accountability is witnessing inconsistent treatment based on favoritism, rude behavior, or a lack of performance among their peers with no obvious consequences. Using that as a starting point helps us to better understand how effective leaders understand team accountability.

Working-Definition of Team Accountability

With these leaders in mind, my personal working definition of team accountability involves two aspects: Empowerment and Transparency.

Team Accountability is really about empowerment and transparency

An organization cannot have accountability without empowerment. If leaders are not able to creatively and uniquely develop strategies and tactics to achieve their goals, accountability is not possible. There must be space for leaders to maneuver in an organization. This means that senior leaders need to set clear performance goals and expectations for behavioral standards that all team-members must follow. Leaders should have plenty of room to achieve their goals within those well-defined boundaries without being micromanaged. Creating a clear boundary like this simultaneously encourages mid-level leaders to think more like owners of their book of business, rather than managers executing someone else’s playbook.

Effective leaders use transparency as the other powerful tool in creating a sense of team accountability. By publishing relevant data regularly, it becomes abundantly clear who is high performing and who is not. In these instances, the healthiest cultures will see high performing leaders helping lower performing leaders. Further, the leaders who are struggling are aware of it and are given additional help and support.

When empowerment and transparency occur together, there is rarely a need for punishment. Everyone in the organization understands the expectations and whether they and their teams are meeting those expectations. In these cases, the conversations around accountability almost disappear. This is because often these organizations are achieving their goals and because the organization’s expectations around performance and behavior are communicated openly and repeatedly.

Using Accountability in your Leadership Practice

When a leader defines accountability as the sum of empowerment and transparency, they can achieve incredible results. I know this from personal experience. I once inherited a team that was low performing and high-drama, often asking for accountability for other team members. When we introduced clear boundaries for empowerment and transparent weekly data reporting, we never heard about accountability again.

The desire for accountability is usually a symptom of under-defined expectations and a lack of transparency. Using this model, leaders can have an immediate impact of getting the team focused on what matters most: Driving results and growing the organization in a way that supports and empowers the employees of that organization.

Key Takeaways

Team accountability is the sum of a culture that has empowerment and transparency. Clearly defined goals and behavioral expectations, coupled with transparent reporting, help to create clarity and focus on results.

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Why Leaders with a Transactional Style Don’t Achieve Transformational Results

/ Jonathan Sachs

Transformational leadership is a leadership approach that seeks to inspire and empower others, rather than simply trying to control them. This approach can produce dramatic results for an organization by generating high levels of commitment, creativity, and productivity from its followers. Transformational leadership has two dimensions: (1) their level of warmth or concern for the people they lead and (2) their level of intellectual stimulation or use of new ideas in relation to the people they lead.

On the other hand, a transactional leadership approach focuses more on maintaining order and getting work done through a system of rewards and punishments. It does not create a sense of loyalty among employees because they are not offered much beyond compensation.

Richard Branson, the Founder and CEO of the Virgin Group, is a transformational leader because he is interested in fostering leadership skills and creativity among his employees. He seeks to inspire others, rather than simply control them. For example, when Richard’s Virgin Atlantic Airlines was struggling financially during the global recession of 2009, instead of firing workers or hiring consultants like other CEOs might have done under similar circumstances, he flew to London and he spent the next few weeks checking in on every aspect of his company, asking employees for their ideas on how to save the business.

Transactional leadership focuses more on maintaining order and getting work done through rewards. There are many examples of transactional leadership in business. One example is a CEO who assigns employees tasks and then closely monitors their performance on those tasks, specifically to determine if they will be able to keep their jobs or not. This CEO uses rewards and punishments in order to achieve results, and often, their actions benefit themselves more than the employees.

As you can see in the example above, transactional leaders are inherently more short term focused and are oriented towards immediate results. This can lead some transactional leaders to prioritize a short term benefit at the detriment of longer-term goals. Simon Sinek shares the example of publicly traded companies who go through rounds of layoffs to make quarterly numbers. While the companies may “make their numbers,” they do so at the cost of psychological safety and long term profitability.

True organizational transformation, like pursuing excellence in customer service, operations, or innovation, involves focus, discipline, leadership, and time. There is no “Get rich quick scheme” in transformational leadership.

Organizations that pursue transformational goals need transformational leaders. These are leaders that set a bold vision and build high-performing teams, follow principles that promote psychological safety, and empower people to achieve their vision.

There is a still a role in organizations for transactional leaders, which is a topic for it’s own post, but they are fundamentally ill-equipped to achieve bold and lasting organizational transformation. Creating bold transformation actually requires the leader to release control by empowering others and trusting that people are doing the right things even when you cannot measure it.

Transformational leadership offers a vision that gets people energized and committed to achieving organizational goals.

Transformational leaders embody the principles of psychological safety by creating an inclusive environment where all employees feel valued, regardless of their position in the company hierarchy. Having transformational leaders in leadership roles will help organizations achieve their full potential. These are the individuals who will leave a powerful legacy by creating meaningful and impactful change.

KEY TAKEAWAY: Transformational leadership is a powerful way for leaders to motivate and inspire their followers. In contrast, transactional leadership can be used as a tool by those in power who want to maintain control over followers through incentives or punishments—but these tactics do not provide long-term results. To achieve real transformation, leaders need to be transformational leaders. A transactional leader will not be able to truly achieve transformational goals.

Legends never die

/ Jonathan Sachs

Remember kid, there’s heroes and there’s legends. Heroes get remembered but legends never die, follow your heart kid, and you’ll never go wrong.

Babe Ruth’s Ghost from The Sandlot

Over the 4th of July, I turned on one of my favorite movies, The Sandlot, which is a story about friendship, community, and baseball. I have probably seen this movie hundreds of times, mostly wearing out the VHS tape at my parent’s house when I was a child.

One of my favorite scenes in the movie happens when Babe Ruth’s ghost visits one of the main characters in the movie, Benny “The Jet” Rodriguez in a dream. The ghost leaves Benny with these words, “Remember kid, there’s heroes and there’s legends. Heroes get remembered but legends never die, follow your heart kid, and you’ll never go wrong”.

Heroes, of course, are people. We look up to them, we learn from them, and we follow their example. But like all people, they are mortal and will eventually pass away.

Legends, or stories, however, are different. It brings our memories to life and they create powerful feelings of interconnectedness.

This difference between heroes and legends has become even more clear to me recently. A few months ago, I bought an ancestry DNA kit and have used it to build out my family tree. It is a wonderful exercise and one I recommend for everyone who wants to learn more about their heritage. Through ancestry, I was able to map back three generations. But what are simply names in census data can “come to life” once again through stories.

For example, my great grandfather, Herman Sachs, was a talented painter. Before he passed away, my grandfather, Arnie Sachs, told me a story that Great-Grandpa Herman asked him one morning what color he wanted his room to be painted. My grandfather answered smartly, “knotty pine,” and when he arrived home his room looked like the inside of a tree!

When I think of that story, in a way it brings my Great-Grandpa Herman back to life, in a way. He has become more than a name now for me. The story gave me some color-commentary, an indication of his personality and talent. The “legend” gives me a lens into who he was and it is a story I will pass down to my own son, Aaron. Stories like this one makes me realize that for so many of my other relatives, I have only names, a small piece of who they were without the legend. While it is hard for me to remember most of their names, Great-Grandpa Herman’s is one I will always remember.

As leaders, the stories we tell (and are told about us) are powerful influences on how we accomplish our goals. Stories that we tell can help us contextualize the direction we set, and can be used to cement that direction to our teams’ collective memory. Stories that are told about us can either inspire confidence, faith, and trust, or they can work against us. That is why leading by example is so important, as those are the stories the team tells each other about us when we are not present.

The more leaders can integrate storytelling into their presentations and other methods of communication, the better their teams will be able to follow and spread the important messages. A good story has an exponential effect when it is told multiple times to better reinforce and embed it into the culture.

If you are a leader, the legends you tell will endure as part of the fabric of your organization. Further the legends that are told about you will be your legacy.

Knowing the power of the story and its enduring capabilities, what will you do next?

KEY TAKEAWAY: Storytelling is an important tool in a leader’s toolbox. It can help them spread the message and create a positive team culture. It can also work against them if they are not leading by example.