Why the ‘Should Ask Questions’ are so important

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.