As a coach, my role extends far beyond teaching the mechanics of the game. My calling is to be a transformative force, helping individuals move from where they are to where they could—and should—be. The word “coach” originally meant a vehicle that transported people, and I see my role similarly: guiding others along their journey, not just in sports, but in life.

To be effective in this, I must continuously examine and refine who I am, ensuring that my coaching comes from a place of conviction and compassion.

For me, this journey involves confronting my own tendencies. One of my ongoing struggles is arrogance. My confidence, often rooted in past achievements and the belief that I can replicate or surpass those successes, sometimes crosses into the realm of arrogance. This usually happens when I feel disrespected—when I perceive that my abilities or contributions aren’t valued. In those moments, my pride swells and I find myself leaning into arrogance as a defense mechanism.

But I know this is not the path to true leadership or effective coaching.

My constant prayer is for humility. Humility isn’t about diminishing my worth or abilities; it’s about recognizing the worth of others and valuing them as much as, if not more than, myself. This month, my core focus is on humility. It’s the value guiding my interactions and decisions, both on and off the field.

In September, as I guide my players through our assessment phase—a period where we evaluate and stretch ourselves to become more athletic and innovative—humility is the anchor that keeps us grounded.

The assessment phase, spanning August through October, isn’t just for my players; it’s for me as well. As they experiment with new techniques and push their limits, I, too, am reflecting on how I can better serve them. This phase reminds us that growth requires a willingness to step back, reassess, and sometimes, admit when we’re wrong or need help. It’s a humbling process, but one that is necessary for transformation.

Arrogance, while it may stem from confidence, ultimately blinds us to the needs and potential of others. Humility, on the other hand, opens our eyes to the value in every individual we coach. It allows us to be not just instructors, but mentors who guide with a sense of empathy and understanding. True coaching, after all, is about nurturing the whole person—their mind, body, and soul.

To that end, here are three questions for reflection, both for myself and for anyone in a coaching or mentoring role:

1. What areas of my life do I need to assess to ensure I’m leading from a place of humility rather than arrogance? Reflect on moments where you’ve felt disrespected or undervalued. How have you reacted, and what can you learn from those reactions?
2. Beyond physical skill training, what mental or emotional areas do I need to develop to become a more holistic coach? Consider what biases or preconceived notions may be influencing your coaching style. How can you challenge those to foster a more compassionate approach?
3. How can I better support the growth of others by focusing on their needs rather than my own achievements or expectations? Identify one practical way you can prioritize the well-being and development of those you coach this month.

In this season of assessment, my commitment is to lead with humility. I want to inspire my players not just to improve their skills, but to grow as individuals who value others. By doing so, I believe we can create a culture where everyone, including myself, becomes a better version of who they are meant to be.

Coaching is a journey—not just for those we lead, but for ourselves. And it’s one that requires us to continually assess, adjust, and grow with a spirit of humility and grace.

Remember: Intelligence tops being smart.

For more information, visit L.E.A.D. Center for Youth today.

C.J. Stewart has built a reputation as one of the leading professional hitting instructors in the country. He is a former professional baseball player in the Chicago Cubs organization and has also served as an associate scout for the Cincinnati Reds. As founder and CEO of Diamond Directors Player Development, C.J. has more than 22 years of player development experience and has built an impressive list of clients, including some of the top young prospects in baseball today. If your desire is to change your game for the better, C.J. Stewart has a proven system of development and a track record of success that can work for you.

As the calendar flips to September, I am committing this entire month to focus on humility—something I do annually. My middle name is James, and this particular month holds deep significance for me, not just because of the commitment to humility, but also because my favorite Bible verse, James 4:10, speaks directly to it: “Humble yourselves in the presence of the Lord, and He will exalt you.”

This verse is a constant reminder that there is no exaltation without first embracing humility. Born on April 10, the fourth month and the 10th day, the symbolism of humility holds personal resonance in my life.

Humility, to me, is not about thinking less of myself but rather thinking of others more. It’s the foundation upon which all my other core values stand, and each September I return to this value, renewing my commitment to it. Throughout the year, I focus on a core value for each month, but September is when I intentionally root myself in humility.

True humility extends beyond grand gestures; it lives in the small, daily acts that show we value others. In baseball terms, it’s like rounding the bases by doing the simple things: saying, “Please” and “Thank you,” listening with empathy, and speaking truthfully from a place of care and understanding. These small acts, while easy to overlook, make a profound impact and demonstrate humility in everyday life.

Several years ago, I was leading a project where I held the position of authority. My team looked to me for direction, but I quickly noticed that one of my colleagues had an incredible idea that could lead to success for the entire group. Instead of taking ownership of the idea, I humbled myself, gave them the credit, and encouraged them to present it.

The success that followed wasn’t mine—it was shared. That experience taught me that leadership isn’t about who gets the praise, but about creating space for others to shine. True humility is recognizing when to step back so others can step forward.

As you reflect on your own journey, here are four questions to ask yourself, formatted like rounding the baseball bases:

First Base:
Do I genuinely acknowledge and appreciate the contributions of others, even when they outshine my own efforts?

Second Base:
When I listen to someone, am I focused on understanding their perspective, or am I simply waiting for my turn to speak?

Third Base:
Do I speak from a place of honesty and truth, even when it might be uncomfortable or less flattering to my ego?

Home Plate:
When I succeed, do I give credit to those who helped me, or do I seek praise and recognition for myself?*

Humility isn’t always the easiest path, but it’s the most rewarding. Let’s all commit this September to cultivating a deeper sense of humility in our lives—by thinking more of others and allowing the Lord to do the exalting. And for me, this is not just a September tradition; it’s a core value I return to every year, with each month bringing a new focus.

Remember: Intelligence tops being smart.

For more information, visit L.E.A.D. Center for Youth today.

If you found this inspiring and thought-provoking, or if you have any questions, comments or concerns, add me on Discord and let’s go deeper.

C.J. Stewart has built a reputation as one of the leading professional hitting instructors in the country. He is a former professional baseball player in the Chicago Cubs organization and has also served as an associate scout for the Cincinnati Reds. As founder and CEO of Diamond Directors Player Development, C.J. has more than 22 years of player development experience and has built an impressive list of clients, including some of the top young prospects in baseball today. If your desire is to change your game for the better, C.J. Stewart has a proven system of development and a track record of success that can work for you.

As a baseball coach, I often hear the phrase, “Development is important.” It’s a well-worn sentiment in our sport, but what does it truly mean? To me, development isn’t just about improving skills; it’s about embracing the art of athleticism, especially when you don’t fundamentally know how to do something.

Athleticism, in its purest form, is about figuring out how to get things done, even when you’re outside your comfort zone.

That’s why I believe August, September and October arae crucial months for our hitters. These three months form the perfect period to assess, evaluate and, most importantly, to experiment. This is when they should try new things, test different approaches, and find out what works and what doesn’t. This is the time to be athletic in its truest sense.

Why Fall is the Best Time to Experiment

In the fall, there are fewer competitive pressures—no standings to worry about, no championship games to prepare for. This makes it the ideal time for players to break away from the norm and try something new. They can explore different batting stances, experiment with a high leg kick to generate more power or even take a shot at switch-hitting. It’s about allowing them the freedom to fail, learn and grow.

Trying new things is essential for athletic growth. By experimenting, hitters can better understand their strengths and weaknesses. They can push their boundaries and discover what they are truly capable of. This isn’t just about finding what works; it’s about learning what doesn’t, and why. This process is crucial for their development as well-rounded, adaptable athletes.

The future of baseball lies in creating athletes who are not only skilled, but also adaptable and resilient. By giving them the freedom to experiment in the fall, we encourage them to become thinkers, innovators and problem-solvers.

Building Better Habits in the Winter

Once hitters have spent the fall experimenting and learning, they can go into the winter months—November, December, and January—with a clearer understanding of their game. This is when they can start to build solid habits based on what they’ve learned. The offseason becomes a period of refinement.
With fewer games, players have more time to focus on their training without the pressure of immediate results. They can hone in on the techniques that showed promise in the fall, reinforcing the muscle memory and mental toughness needed for success.

Moving Beyond Wins and Losses

It’s important for coaches to understand that fall isn’t about wins and losses; it’s about growth. Too often, we get caught up in the scoreboard, but true development happens in the spaces between the games. If we allow our players three months to just be athletic, to explore and take risks, we set them up for long-term success. When spring and summer roll around and the games start to count, they’ll be more prepared, more adaptable, and more confident in their abilities.

Embracing the Future of Baseball

The future of baseball lies in creating athletes who are not only skilled, but also adaptable and resilient. By giving them the freedom to experiment in the fall, we encourage them to become thinkers, innovators and problem-solvers. This mindset will serve them not only on the field but in life as well.

So let’s make the most of August, September and October. Let’s encourage our hitters to try new things, to fail forward, and to embrace the art of athleticism. The habits they form during this period of exploration will shape their success in the seasons to come.

Let’s commit to development—not just in words, but in practice. Our future generation of elite baseball players deserves nothing less.

For more information, visit L.E.A.D. Center for Youth today.

If you found this inspiring and thought-provoking, or if you have any questions, comments or concerns, add me on Discord and let’s go deeper.

C.J. Stewart has built a reputation as one of the leading professional hitting instructors in the country. He is a former professional baseball player in the Chicago Cubs organization and has also served as an associate scout for the Cincinnati Reds. As founder and CEO of Diamond Directors Player Development, C.J. has more than 22 years of player development experience and has built an impressive list of clients, including some of the top young prospects in baseball today. If your desire is to change your game for the better, C.J. Stewart has a proven system of development and a track record of success that can work for you.

As August rolls around each year, I find myself returning to one of my core values: excellence. To me, excellence isn’t about going above and beyond every single time; it’s about meeting expectations. It’s about doing what’s required and doing it well, consistently.

When I talk about excellence with my players, I emphasize that excellence is within their reach if they commit to understanding what’s expected of them and execute accordingly.

A crucial part of this process is encouraging my players to ask the right questions—the “Should Ask Questions.” These are not the typical inquiries you might expect from an athlete. Instead of asking, “How many reps do I need to do?” or “What drills will we be running today?” they should be asking deeper, more thought-provoking questions that get to the heart of their development and role within the team.

What Are ‘Should Ask Questions?’

“Should Ask Questions” are questions that help players understand the bigger picture, the strategy, and their place within it. These questions are designed to help them grasp not just the “what” and “how,” but also the “why.”

For example:

• “What is the purpose of this drill, and how does it relate to our game strategy?”
• “What does success look like for my position?”
• “How can I contribute to the team’s goals beyond just my individual performance?”

These questions are powerful because they encourage players to think critically about their roles and the expectations set upon them. When players understand the “why” behind their actions, they are more likely to execute with precision and purpose, leading to a more significant impact on the field.

The Path to Execution and Impact

To meet expectations and truly embody excellence, players need clarity. Clarity comes from understanding what is expected of them—not just in terms of physical performance, but also in terms of attitude, effort, and adaptability. The right questions can illuminate these expectations and help players align their actions with the team’s objectives.

Encouraging players to ask these questions fosters a culture of curiosity and continuous improvement. It shifts the mindset from merely completing tasks to understanding and mastering them. When players are curious, they are engaged. When they are engaged, they are more likely to put in the effort required to meet and exceed expectations.

Creating a Culture of Excellence

As coaches, it’s our responsibility to create an environment where excellence is the norm. This starts with clear communication about expectations. However, it doesn’t end there. We must also model the behavior we want to see, demonstrating our commitment to excellence in our preparation, communication, and actions.

By fostering a culture where “Should Ask Questions” are encouraged, we empower our players to take ownership of their development. We move away from a top-down approach where coaches dictate every action to a collaborative environment where players feel invested in their growth and the team’s success.

Excellence is not an unattainable ideal; it’s a choice we make every day to meet expectations and fulfill our roles to the best of our abilities. For my players, embracing excellence means asking the right questions, understanding their purpose, and committing to executing with intent and focus.

As we continue through August, let’s remind ourselves that excellence starts with clarity, curiosity, and a commitment to meet expectations—both ours and those of our teammates.

Let’s strive for excellence, one question at a time.

For more information, visit L.E.A.D. Center for Youth today.

If you found this inspiring and thought-provoking, or if you have any questions, comments or concerns, add me on Discord and let’s go deeper.

C.J. Stewart has built a reputation as one of the leading professional hitting instructors in the country. He is a former professional baseball player in the Chicago Cubs organization and has also served as an associate scout for the Cincinnati Reds. As founder and CEO of Diamond Directors Player Development, C.J. has more than 22 years of player development experience and has built an impressive list of clients, including some of the top young prospects in baseball today. If your desire is to change your game for the better, C.J. Stewart has a proven system of development and a track record of success that can work for you.