Why are there bad leaders and coaches?

James McGrath
6 min readJan 27, 2021

Access to rare influential leaders and coaches has created a seemingly unfair benchmark that we all apply to our everyday interactions.

Photo by Markus Spiske via Unsplash

One of the consequences of the Information Age and access to basically unlimited content is increasing expectations. These expectations are often highlighted in the teen depression statistics stemming from an Instagram fueled facade of what kind of life is possible or expected, the success stories and after-photos from diets that camouflage the discipline and work required for results, and in overall consumer preferences of the 21st century. The concept of increasing expectations is not new or different. But it is a concept that is seldomly applied to the really personal interactions that govern our lives. Leadership, coaching, management, and mentorship.

**Note that I am using leadership, coaching, management, and mentorship interchangeably for this piece as the thesis can be applied to each with just subtle differences**

Digital technologies like podcasts and platforms like Medium or Substack have given us unprecedented access into the minds of truly great and inspiring leaders, mentors, and coaches, which in turn has evolved our expectations of what a leader or a coach can and should be. Take Jocko Willink for example, ex-Navy SEAL commander, founder of a leadership consulting firm, author, entrepreneur, and in the ears of thousands of people worldwide through his podcast, Jocko Podcast, along with regular appearances on The Joe Rogan Experience and The Tim Ferriss Show (two of the top podcasts out there). Jocko is unique in the sense that most people haven’t lived the heightened experiences that come with being deployed to a war zone or commanding a platoon of Navy SEALs. Part of his intrigue is his ability to extrapolate lessons and insights from his experiences and make them applicable to the average listener's reality at scale. Current technologies have given somebody like Jocko the ability to reach not just his sphere that he would interact with daily or the 100 people in a crowd that would come to hear him speak, but millions of people digitally at differing moments from vastly different walks of life. And if the message is truly moving, informative, applicable, or resonates with the listener (since we are talking about the best of the best in podcasting, the chance is greater), the reader/ listener can apply the knowledge or personal lessons to their existence. This is a form of life coaching whether we realize it or not. Over time the exposure to great leadership through stories, examples, and anecdotes raises our personal benchmark of what we consider a great leader or coach to be, oftentimes unknowingly.

Photo by Jukka Aalho via Unsplash

There are very few people, if any, who can inspire, lead, or coach effectively everyone they come across. This is one of the primary roots of disconnect between our expectations versus reality. “Good” leadership, coaching, managing, and mentorship are often very subjective with approaches, tenants, values, and requirements differing drastically from person to person. What I believe is good leadership typically differs from what you believe good leadership to be. The great equalizer in this equation is choice. Choice enables people to seek out what inspires or moves them. Where does this choice come from? According to PodcastInsights, there are over 1,500,000 podcasts worldwide, and according to Techjury, over 31.7 million bloggers are producing original content. That is the choice, and it is not even including the millions of influencers making their mark across social media. The scale of accessible content is so great that there is something for everyone. It could be Jocko sharing war stories of brotherhood and tragedy, or Adam Grant on WorkLife dissecting office culture and management, or Steve Kerr and Pete Carroll breaking down how to become a champion in the premier competitive arenas on Flying Coach, to name a few. It makes sense that people gravitate toward what inspires them, which is possible digitally in an internet era, but largely not possible when interacting with bosses, coaches, or mentors in daily life. The latter typically “assigned” to us by organizations or networks.

“It is also the fate of leadership to be misunderstood. For historians, academics, writers, and journalists to reflect great lives according to their own subjective canon” — Nelson Mandela

That is not a criticism of today’s leaders. It is typically an unfair ask for leaders, bosses, and coaches to tailor their approach to an individual level without deeply understanding the individual. And according to the social brain hypothesis the biological limit (due to cognitive constraints) of “coherent face-to-face” relationships a person can have is only 150, which doesn't account for the depth of relationship needed to effectively mentor or coach someone. The true number is likely much smaller. It is also worth pointing out that most people would “spend” their 150 relationships on family and friends as opposed to inorganic coworking or mentor relationships.

To Recap:

  • “Good” leadership, coaching, management, and mentorship is subjective
  • Individuals can’t meet these subjective requirements without deep understanding
  • Digital technologies give us the choice to meet these requirements
  • We compare our digital experiences to our actual experiences
  • Our actual experiences typically suck
Photo by KOBU Agency via Unsplash

The discussion around quality leadership and coaching is often polarized largely around generational boundaries. The narrative of the “coaches” (Baby-Boomers, Gen X, Older Millenials) is that young people are entitled, lack humility, closed-minded, and are deficient of the drive to push through difficult situations or walk uphill both ways to school. The narrative of the “coachees” (Younger Millenials, Gen Z) is that our leaders are stuck in their ways (hierarchical approach), inept, and void of empathy. These narratives are certainly reductionist and shouldn’t be applied broadly, but they possess undertones that resonate with most people. We have all had those thoughts at work, in athletics, and even in familial relationships. But these viewpoints are scapegoats used to put people in categories. Additionally, according to the Generation Differences Chart below, all of our preconceived notions might not even be correct:

Millenials… “Will test authority but often seek out authority figures when looking for guidance”

Gen X when mentoring… “They work with you, not for you”

So what? The consequences of our increased expectations are real and tenuous. They sow discontent into the relationships that are supposed to guide us forward to a happy life. It is important to realize that the causes of these emotions aren’t generational differences and that most people have and will assume both roles many times throughout their lives. To overcome the unsatisfactory feelings, it will take mindful commitments from both parties. The “coachees” must develop an awareness that the reasons their coaches can’t live up to their expectations might be as much about their standards as it is about the coaches themselves. And the “coaches” need to realize that they cannot effectively coach everyone and must invest their efforts into creating a few deep and meaningful relationships… because we are all not Jocko Willink.

James McGrath

Most of me believes that having underwhelming mentor and coaching relationships is an inevitable consequence of society and humans. I would trend toward powering through the bad with the goal of finding one or two good ones and calling it a day. Thank you for reading.

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