Empathy Is a Strategic Advantage

Book Inspiration: Wisdom Takes Work – Ryan Holiday

There’s a line from Tennyson that Ryan Holiday uses to open the final section of Wisdom Takes Work, “Knowledge comes, but wisdom lingers…,"That line stuck with me.

In leadership and in life, knowledge may sometimes feel like it’s simply acquired through process. We can read, study, attend, watch, and accumulate information.

But wisdom is entirely something else. It's application, growth, and accumulation over time. It’s slower, it’s harder, and it tends to show up only after experience, reflection, and likely some difficulty along the journey.

Throughout the book, Holiday simplifies the path to wisdom into two starting points that sit in opposition: humility and conceit. From conceit, our perspective narrows. We become more certain, more rigid, and less open to learning.

From humility, something different happens. We become open. We begin to see more clearly, and from that openness, we can develop empathy.

Empathy, in that sense, is not just a trait, it is a byproduct of humility; and over time, it becomes something more: A strategic advantage in how we lead, decide, and understand the world around us.

Empathy Is a Strategic Advantage 

In my more formative professional years, one of the most practical and often overlooked expressions of wisdom in leadership is empathy. Empathy was often strictly associated with a customer service standard. More negative constructs may view empathy as softness or timidity. 

I have come to view empathy as a strategic advantage for leaders. It gives us the ability to see a situation clearly, not just from our own vantage point, but from the perspectives of others involved. This gives us access to insights that help us understand motivations, constraints, fears, and incentives that may not be immediately visible. 

This is where emotional intelligence becomes central to leadership. Daniel Goleman’s framework breaks this into four components:

1. Self-awareness  

2. Self-management  

3. Social awareness  

4. Relationship management

   
   

Empathy sits at the center of this model. Without it, the rest begins to break down. 

My Early Misconception: Leadership as Accumulation

Early in my leadership journey, I viewed achieving a City Manager or CEO role as the accumulation of experience. I believed it was something earned through navigating difficult moments:

• Managing millage campaigns

• Leading through crises like the 2014 “100-year” flood event across metro Detroit

• Working positively through conflict and pressure during public engagements

I saw leadership as a summit, and at that summit, I believed I would arrive at a kind of clarity; that perspective would come naturally with the role. That being “at the top” would allow me to see more clearly.

But over time, I’ve come to realize that attaining the role is not the end. It didn’t automatically grant perspective (it turns out it requires endless effort).

Perspective is not a function of position. It is a function of how you think.

The Turning Point: Seeing My Blind Spots

Before I pursued and accepted my first promotion, a mentor gave me direct and honest feedback about my emotional intelligence. She encouraged me to complete an assessment. That assessment helped me see my blind spots including an ultra low score of social awareness (empathy).

But seeing them was only the beginning. Acting on them required something else, openness, vulnerability, and a willingness to acknowledge that how I understood myself was not always how others experienced me.

That EI process became a foundation for something much more important than technical competence—humility. And humility, in my experience, was the gateway to leadership through empathy.

From Humility to Empathy to Better Decisions

That early work shaped how I approached leadership going forward, creating a positive feedback loop. It became a launching point for the leadership expectations I would later define and hold myself accountable to.

• Leading with humility creates openness.

• Openness creates the ability to understand others.

• Understanding others creates better perspective.

Better perspective leads to better strategy and a long-term mindset. When leaders operate with empathy:

• They see second- and third-order impacts

• They better accept and understand resistance—not as obstruction, but as information

• They weigh both short-term and long-term consequences more effectively

Without empathy, decision points become narrower, more reactive, with less positive endurance.

Lincoln and the Practice of Empathy

Ryan Holiday illustrates this through anecdotes on the life of Abraham Lincoln.

During the Civil War, when Union forces captured Confederate envoys traveling to England, the situation carried significant diplomatic risk. Mishandling it could have drawn Britain into the war, Lincoln did something simple, but powerful.

He asked his Secretary of State to write the argument from Britain’s perspective. He then wrote the American perspective himself.

In doing so, he created space to see the issue more clearly, including the weaknesses in his own position, and sided with his Secretary of State—ultimately choosing not to detain and punish the diplomats. His comments afterward to his cabinet perfectly illustrate a humble leader:

“Presidents and kings are not apt to see flaws in their own arguments.”

That exercise in empathy helped de-escalate a situation with England that could have significantly complicated things for the North during an already difficult time. 

Closing: Empathy in Practice

Empathy is not instinctive for most leaders, especially in high-pressure and political environments where speed, trade offs, and decisiveness are valued. The practices below require discipline and consistent effort. The next time you’re facing a big decision or moment, consider incorporating these into your process:

1. Pausing before reacting

2. Asking better questions

3. Actively seeking opposing viewpoints

4. Being willing to revise your thinking

It also requires internal work of managing the ego, regulating emotion, and staying open with self-confidence when challenged. These may appear simple, but they are difficult to execute consistently, which is why emotional intelligence, empathy, and humility are not “soft skills,” but core leadership capabilities.

Empathy is not a deviation from strong leadership; it is what makes strong leadership possible.