Why Serious Leaders Read and Why It Separates the Good from the Great

In my leadership journey, which continues to this day, many factors have contributed to the successes I have achieved. Leadership training, EQ team building, mentors, mentoring, failing, and learning from your failures.  All of these contribute to a leader’s portfolio and to their long-term success.

Leadership is not a destination; it’s a continuous process. Training, emotional intelligence, mentorship, failure, and recovery all shape effective leaders over time. Each contributes to a leader’s professional “portfolio.”

But there is one discipline that consistently separates competent leaders from exceptional ones—and too often goes undervalued:

Reading

Not casually. Not occasionally. But deliberately and consistently.

The oft-quoted line, “Not all readers are leaders, but all leaders are readers,” may or may not belong to President Harry S. Truman. Attribution aside, the insight holds. Leaders who do not read deprive themselves of one of the most efficient tools for expanding judgment, perspective, and strategic depth.

In my career across government and the private sector, I’ve seen capable leaders plateau simply because they stopped learning. In more than a few cases, I even bought books for supervisors, knowing deep down they would never open them.

That choice has consequences.

Reading as a Leadership Multiplier

Reading is not a passive activity. For leaders, it is force multiplication. The “how to do it” kind of books. A little selfish promotion, but books like my first two, “The Art of Ronin Leadership,” and “The Art of Executing Ronin Leadership Strategies.” However, there are many other wonderful books on leadership written by accomplished leaders who detail their journeys and what worked and didn’t work for them as they are building teams and strategies while dealing with the inevitable

The right books accelerate experience you don’t yet have, expose blind spots you didn’t know existed, and help you avoid mistakes others have already paid for. This is not theoretical. It is practical leadership development at scale.

Three categories of reading stand out for executive leaders.

Leadership Books: Codifying Hard-Won Lessons

Leadership books, especially those written by experienced practitioners, offer frameworks forged in real environments: staffing challenges, budget constraints, political friction, and organizational resistance.

These books are not about abstract theory. They are about execution.

They show how leaders built teams, made decisions under pressure, recovered from failure, and sustained momentum over time. Whether the lessons resonate immediately or sit dormant until needed, they compound over a career.

Leaders who dismiss these resources as unnecessary are not signaling confidence—they’re signaling stagnation.

Biographies: Learning from Failure at Scale

Biographies may be the most undervalued leadership tool available.

Yes, they chronicle success. But the real value lies elsewhere: failure. Poor decisions. Blind spots. Miscalculations. Public consequences.

Consider President John F. Kennedy.

In 1961, the Bay of Pigs invasion was a strategic disaster—poor intelligence, flawed assumptions, and overreliance on military advice led to international humiliation. Kennedy could have doubled down or retreated from decision-making altogether.

Instead, he adjusted his approach to leadership.

One year later, during the Cuban Missile Crisis, Kennedy structured decision-making differently. He formed a small, trusted advisory group—ExComm—that encouraged dissent, debate, and alternatives. Rather than defaulting to military escalation, he chose a naval blockade.

That decision likely prevented nuclear war.

The difference between those two moments wasn’t luck. It was learning.

As a senior leader at Microsoft Global Security, I adopted a similar model, forming my own “kitchen cabinet” beyond direct reports to pressure-test strategy and execution. The concept didn’t come from instinct alone.

It came from reading history.

Stoicism: Mastering What You Can Control

Beyond tactics and history, leaders benefit from philosophy—particularly Stoicism. I am a big fan of this one. Stoicism is a branch of philosophy that emphasizes focusing on what you can control and remaining calm during storms

Stoicism emphasizes four core virtues:

• Wisdom
• Justice
• Temperance
• Courage

These are not abstract ideals. They are leadership fundamentals.

Stoic thinkers such as Epictetus, Seneca, and Marcus Aurelius focused on one essential principle: control what you can; accept what you cannot.

Few examples illustrate this better than Admiral James Stockdale. Shot down over Vietnam in 1965, Stockdale endured more than seven years of captivity and torture. He later credited his survival not to optimism, but to Stoic discipline, particularly the teachings of Epictetus.

Stockdale couldn’t control his imprisonment. He could control his mind.

Epictetus was born a slave, and his master purposely shattered his leg to see how long it would take to break. Epictetus had a permanent limp for the rest of his life; however, his entire philosophy centered on what you can control. He couldn’t control his abusive master. But he could control his mind and not let things out of his control affect his behavior or resolve.

While few leaders will face extreme circumstances, the lesson is universal. Pressure, uncertainty, and adversity are constants in leadership. Emotional discipline is not optional; it is decisive.

The Executive Imperative

Reading is not about appearing thoughtful. It is about becoming effective.

Leaders who read consistently:

• Make better decisions under pressure
• Learn faster from failure—both their own and others.’
• Build perspective beyond their immediate environment
• Develop emotional and strategic resilience

If you want to lead people and programs responsibly, reading is not a hobby. It is a professional obligation.

Read. Reflect. Apply. Repeat.

That is how leaders grow.