Most leaders focus on the next decision.

The strongest leaders understand the next five consequences.

The 2326 Group helps executives, founders, and leadership teams navigate complexity through 4th & 5th Order Thinking.

A middle-aged man wearing glasses, a white shirt, and a blue blazer, speaking during a presentation. His hands are visible, gesturing as he talks. The background features a wooden wall and a projection screen.

How Tony Helps

Military Precision.
Executive Perspective.

After leading teams in high-stakes military environments and contributing to strategic planning efforts at the Pentagon, Tony Caldwell discovered a pattern:

Organizations rarely struggle because of a lack of effort. They struggle because complexity outpaces leadership capacity.

Today, Tony helps executives and leadership teams anticipate consequences, navigate complexity, and build organizations designed for long-term success.

A diagram illustrating a decision-making process with a series of ordered steps, including categories such as First Order, Second Order, Third Order, Fourth Order, and Fifth Order, each associated with specific impacts like immediate, team, system, cultural, and strategic impacts.

The Framework

4th & 5th Order Thinking

4th & 5th Order Thinking helps leaders understand the ripple effects decisions create across teams, systems, culture, and long-term strategy.

The goal isn't to predict the future. It's to make better decisions by seeing farther than everyone else.

This framework serves as a foundational element of Tony's coaching, consulting, and leadership development engagements.

Trusted by Leaders
who Think Differently

5-Star Reviews

Tony helped me quickly clarify my priorities and articulate what I was looking for. That clarity allowed me to move forward with confidence and take decisive action.

His approach is direct, grounded in experience, and focused on how you think as a leader. The impact was immediate and lasting.

-Manuel Rodriguez

Tony’s sessions on 3rd and 4th order thinking, a framework he developed as an Army officer at the Pentagon, reframe how you evaluate business decisions, not just for immediate results but for the ripple effects that play out over years.

-Daniel Arthur

Tony has a way of making everyone feel comfortable while sharing valuable insights on a wide variety of topics. His presentations are engaging, down to earth, and full of practical takeaways. Highly recommend Tony and The 2326 Group!

-Summer Berry

Tony adds to his experience from a career in the Army and the corporate world a unique ability to ask insightful questions of someone who may be stuck. This gets his clients to dig deeper to find the true obstacles then figure out for themselves how they can overcome them. Anyone who is struggling to get to the next level would benefit from working with Tony.

-C. Lassere

Better Decisions Start With Better Questions.

Whether you're developing leaders, preparing for growth, or navigating organizational change, The 2326 Group can help.