Leadership Lessons from “The Holdovers”: Navigating Relationships in the Face of Adversity

Summary: In cinematic storytelling, “The Holdovers” offers a rich tapestry of lessons on leadership and relationships. This movie serves as a compelling case study for understanding the intricacies of leadership amidst adversity and the profound impact relationships can have. Let’s explore the dynamics of teamwork, resilience, and the transformative power of authentic connections.

Dear Dr. Sylvia,

I went to HR to complain about how my boss talked with me and his team.

For example, he keeps telling us that “he is in charge” and that “he will not accept any whining and complaining about the extreme amount of daily work.”

In other words, when we explain that some deadlines are impossible and the why behind the various situations, he shrugs and says, “The meeting is over; figure it out.”

The head of HR said, “That is who he is, and he will never change. I suggest you accept it.”

Everything is based on relationships. That is how we help to change ourselves and others.

Most importantly, you believe relationships can be the golden ticket to profound personal change.

Therefore, I wonder if you live in La La Land. Sorry to be so direct, but are you right, or is the VP of HR right?

I need to decide if I want to stay in my job, which pays well, or find a more compassionate leader.


LtL (Looking to Learn)

Dear LtL,

My initial response to who is right is we both are.

Firstly, from my years as an executive coach, I believe the opportunity to change comes primarily through relationships. However, many are tone-deaf and stay in their small, dark rooms, determined not to change.

I will discuss this further using the Oscar-nominated film “The Holdovers.”

Rather than guns and car crashes, it is about three individuals who begin a new level of personal change from their time together.

To fully grasp the leadership insights embedded in the film, it’s essential to outline the plot and characters of “The Holdovers.”

A crabby, unhappy teacher, played by Oscar-winner Paul Giamatti, must “babysit” a boarding school student, played by talented newcomer Dominic Sessa. The student, from a wealthy family, is stuck at school while his mother and stepfather vacation without him over the winter holidays. It is a depressing and challenging time. Neither wants to be there.

Ultimately, the two disaffected individuals grapple with their time together. Add the head cook, Da’Vine Joy Randolph, also an award winner who is there to supply their meals. Her son, killed while serving in the military, left her in emotional pain. And she expresses her deep mourning in a way we can all relate to.

The Power of Diversity in Leadership

One of the most prominent themes in “The Holdovers” is the strength that emerges from diversity.

The characters in the film represent a spectrum of talents, experiences, and perspectives, mirroring the real-world complexities of modern organizations.

In short, an aging professor, a privileged teen, and a grieving mother showcase how to harness their different strengths. Here, they eventually overcome the sense of aloneness and disappointment.

Building trust takes time and determination.

Trust is the bedrock of effective Leadership, and “The Holdovers” vividly illustrates the delicate process of trust-building in a high-stakes environment.

We see how trust builds. As it is everywhere, it developed through one truth at a time.

Initially, truth is absent. The three, as most employees, stay behind the curtain of safety.

In my team building offsites, trust is always one of the main elements everyone yearns for at work. The big question is how to take the risks of being honest and authentic in front of others.

Telling the truth is NOT spilling your guts.

Here, we watch the cultivation of trust by several moments of truth-telling. It is not elegant. It isn’t easy and can be divisive.

Initially, as I said, I was absent. It often takes moments of frustration and fear to lead to the truth.

Truth is the critical factor in developing trust. Truth is pivotal in fostering all relationships, including cohesive and resilient teams. And might I add, it takes time to grow, even in family systems.

The Role of Communication in Leadership

Effective communication is a cornerstone of successful leadership. The film provides numerous instances where the characters must navigate communication challenges to achieve their common goal.

There is an art to communication under pressure.

In other words, telling the truth without “spilling your guts” is an art form that substantially impacts team dynamics, all human dynamics.

Leadership in the face of adversity demands resilience and adaptability.

“The Holdovers” presents a compelling narrative arc wherein characters confront unforeseen challenges.

The film portrays the importance of resilience, the ability to adapt to changing circumstances, and the role of these qualities in shaping successful leadership.

The depressed teacher, the abandoned student, and the angry head cook become allies. They do not know they are there to help each other grow and change. They do it anyway.

Authentic Leadership is vital now more than ever.

Authenticity is a quality that resonates with audiences and team members alike. Authenticity often hides under the covers. We mostly favor playing it safe and being superficial.

For example, it took the student to start the ride to truth and trust. His authenticity led the teacher and cook down the path to unveil their more profound inner thoughts.

Subsequently, leadership is about giving orders and leading by example.

Being honest and listening to others is difficult in a world of sound bites and debate.

We can learn essential lessons from leadership failures.

Not every leadership decision in “The Holdovers” leads to success, and that’s a crucial aspect of the narrative. Analyzing these failures provides valuable lessons on the consequences of poor leadership choices and the importance of learning from mistakes.

In the same vein, the success of any mission, whether in a fictional film or real-life scenario, hinges on the team’s cohesiveness. The three main characters in “The Holdovers” foster unity through their truth and openness with each other.

“Knowing you has changed me for the better” from “Wicked.”

In conclusion, the key leadership lessons extracted from “The Holdovers” include the ability for each individual to see, hear, and feel aspects of their lives differently. It emphasizes the applicability of these lessons in real-world leadership scenarios, urging us to reflect on our leadership styles and relationships within our professional and personal spheres.

In my book, “Don’t Bring It To Work,” there are many examples of how we can help each other change.

In addition, I have added one of my favorite songs about how we come into each other’s lives for a reason. Please enjoy.

To your success,

Sylvia Lafair

PS. I respond deeply to truths told by my students. We are teachers for each other. I am awestruck by those courageous enough to speak up and be heard. And that means even if it is uncomfortable. What about you?

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Sylvia Lafair

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