Discovering the Humanity Behind Leadership

If you are a leader—or aspire to become one—take a moment and ask yourself: Why? What motivates you? 

For many, the answer boils down to one of two reasons: individual success (and money) or helping others succeed. Here’s the hard truth: you can’t truly pursue both simultaneously. You might convince yourself that you’re balancing these goals, but those you lead will always know the truth. If you’re in it for yourself, your team will see it, feel it, and react accordingly. If you’re genuinely in it for others, they’ll know that too. 

Leadership isn’t for the faint of heart. In fact, it can often be exhausting. People are complex, unpredictable, emotional, and yes, sometimes downright irrational. And that’s okay—because so are you! This is why great leadership can’t be outsourced to technology or automated through AI. 

As a husband and father, I often tell my wife that some days, working in HR feels like managing an adult daycare. “You woke up today and decided to do what?” The difference between these individuals and my children is that I have no choice but to love my kids. 

Over my career, I’ve learned this simple truth: the most important thing any organization or individual can do is cultivate great leadership. 

Think about it: if you work for a great leader, you work in a great place. If you work for a terrible leader, you work in a terrible place. As a leader, you’re always building something—either an environment where people thrive or one where people can’t wait to escape. Remember, you’ll likely spend more time at work than with your own family. So, wouldn’t you want to be the kind of leader who makes people’s days better and sends them home at night filled with purpose? 

Delegation in Leadership: Why Accountability Cannot Be Outsourced 

One of the most important lessons I learned early in my leadership journey is that it comes with three distinct truths. As a leader, you have authority, responsibility, and accountability. 

Every day, leaders must make decisions about delegation, because no one can effectively lead without empowering their teams to accomplish the work. Delegation often requires giving team members some of your authority so they can drive outcomes—whether it’s leading a meeting, managing a project, or stepping up in your absence. 

I once worked with a great leader who reminded me that if I couldn’t figure out how to delegate, the company was overpaying for both me and someone else to do the same job. However, one thing you can never delegate is accountability. 

If you’ve ever listened to Jocko Willink, you know that regardless of what happens, the leader is always the most accountable. The same leader who taught me the value of delegation also remembered every employee’s birthday, their children’s names, and their partners’ names. While he understood the importance of accountability, he also recognized that fostering accountability required humanity. 

Accountability Meets Humanity: A Tale of Two Leaders 

Two leaders taught me the power of human connection in very different ways. 

The first was a gruff, no-nonsense leader I supported as a human resources business partner. He seemed incapable of warmth, yet his team adored him. For the longest time, I couldn’t understand why. 

Then, I ran into him at the airport while traveling with my wife and youngest daughter, who was a toddler at the time. Exhausted from the trip, she walked up to him, and he instinctively scooped her up with a gentleness that caught me off guard. He held her the entire time we waited to board the plane. 

In that moment, I no longer saw him as scary but as a father—human and relatable. Over time, I realized what his team already knew: he was fair, consistent, and fiercely protective of his people. That small act of vulnerability changed how I viewed him and taught me that leadership isn’t about being perfect; it’s about being real. 

The second leader was my first boss. After hiring me, he admitted one evening over dinner with our wives that I hadn’t been his first choice for the job. The other candidate had fallen through, and after praying about it, he decided to take a chance on me. 

At first, his honesty stung. My initial motivation came from wanting to prove him wrong. But as time passed, I grew to respect his quirky openness, and our relationship deepened. By the end, I believe he’d say I was one of his best hires—and he became one of my favorite leaders. 

Both leaders taught me that leadership isn’t about authority—it’s about connection. 

Shaping Influence Through Human Connection 

If I asked you to list ten things about your favorite employee, you’d probably rattle them off effortlessly: their partner’s name, their alma mater, their favorite sport, and more. 

Now think about a challenging employee. Can you name three things about them? Are they married? Do they have kids? You might guess correctly by accident, but if you can’t recall anything meaningful about them, the problem isn’t them—it’s you. 

I’ve seen leaders struggle to influence their teams because they failed to connect on a human level. Influence isn’t a byproduct of authority; it’s the result of trust, and trust comes from connection. Leaders who take the time to know their people create cultures where everyone feels valued—and that’s where influence thrives. 

Coaching Kids’ Softball and What Billy Beane Taught Me 

Coaching my oldest daughter’s 7- and 8-year-old softball team has been one of the most rewarding experiences of my life. It also showed me that leadership at work and on the field aren’t all that different. 

Each player brought unique strengths and challenges. Some were naturals; others struggled to grasp the basics. My responsibility as a coach was to connect with each of them, understand their potential, and help them grow. I did this by listening, being the goofy coach, and getting to know them individually. 

The most rewarding moments weren’t the wins but the personal victories—like watching a player finally hit the ball or seeing the team rally around a teammate who caught a fly ball. Every player mattered. 

This reminded me of Billy Beane in Moneyball. He didn’t build a winning team by seeking perfect players. Instead, he focused on undervalued strengths and created a system that allowed everyone to contribute. Leadership is no different. Success isn’t about finding perfect employees—it’s about building an environment where everyone’s best qualities can shine. 

Leadership Doesn’t Mean You Are Better 

Many leaders strive to project an aura of absolute control and credibility. They want to appear as if they know more about everything than those who report to them. But if that were true, what would be the point of having a team? 

One valuable lesson I learned from my father, who was also an attorney, is that you should never practice law—or leadership—in a vacuum. There is always value in gathering facts, consulting with those who have greater expertise, or simply listening a little longer. As the saying goes, “To be right too early is to be wrong.” 

Leaders who focus solely on winning every debate or looking like the smartest person in the room often stifle team dynamics. They drive the best ideas underground, leaving their teams disengaged and their potential unrealized. 

Malcolm Gladwell illustrates this idea in Blink when he discusses "contempt." People can quickly sense when a leader believes they are superior. Few things erode trust faster than a leader operating with arrogance. While employees are required to respect a leader’s position, genuine leadership inspires respect for the person. 

Too often, leaders introduce themselves with their title first: “Hello, I’m so-and-so, Vice President of Whatever.” What they forget is that their success depends on the very team they lead. Leadership isn’t about proving you’re the smartest in the room; it’s about creating an environment where everyone’s intelligence, ideas, and contributions can thrive. When leaders trade arrogance for authenticity, they unlock their team’s full potential—and in doing so, they elevate their own. 

Culture Doesn’t Come from a Handbook 

Too many leaders miss the most critical part of their role: accountability for their team’s success. Some think their only responsibility is to deliver results, ignoring that leaders only succeed through their teams. 

I’ve often seen leaders try to delegate their leadership accountability to HR. Frankly, my approach has always been that if I have to manage your team for you, then we need one less manager. 

In an ideal world, organizations wouldn’t need policies or handbooks. People would act with honesty, fairness, and consistency. But the world isn’t perfect. Leaders often hide behind policies, creating blanket rules to avoid having difficult conversations with one or two individuals. 

When leaders are fair, consistent, and trustworthy, they create environments where policies become less about control and more about guidance. Employees work harder for leaders they believe in—not because they have to, but because they want to. 

Why? Because great leaders build great cultures, and great cultures don’t need to micromanage behavior. 

Leading With Humanity 

Leadership isn’t about being perfect or invincible—it’s about being human. It’s about connecting with people, understanding their strengths, and inspiring them to bring their best selves to work every day. 

If you choose not to engage, you’re still making a choice—but it’s likely not the result you want. Leadership requires trust, fairness, and authenticity. When you lead with humanity, you create a workplace where people don’t just show up for a paycheck—they show up with purpose. 

The beautiful thing about leadership is that it’s a choice. If you don’t like the leader you are, you can change. Start today. Invest in relationships. Be vulnerable. Watch as your leadership transforms—not just your team but also yourself. 

Michael “Keith” Cutter is the Vice President of Talent Strategy at Delek US Holdings Inc., a downstream energy company. A licensed attorney in Texas, Keith has over 15 years of experience in human resources and labor relations. Passionate about culture and leadership, Keith has led strategic initiatives in talent management, diversity, and organizational development, primarily in the oil and gas industry.


 
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