Something often happens between the end of a leadership workshop and Monday morning.
The room was engaged. People took notes. The ideas were sensible and useful. Then everyone returned to work, a difficult conversation arose, pressure increased—and they handled the situation much as they always had.
Jeff Sesol has been watching that pattern for more than three decades.
Before founding Pull the Chute in 2021, Sesol built and operated several companies, including FreeDrive, an early web-based storage business, and SonMedia, an internet-safety platform for parents. Across those experiences, he observed that leaders rarely failed because they had never heard of trust, communication or accountability.
Most could describe what good leadership looked like. The difficulty was consistently practicing it when circumstances became uncomfortable.
That observation became the premise behind Pull the Chute: leadership development should not merely transfer knowledge. It should change behavior.
Leadership Development as a System
Pull the Chute is an Illinois-based leadership-development company serving organizations across the United States and the United Kingdom. It provides corporate leadership development, executive coaching and peer leadership groups, but its approach is designed as an integrated system rather than a series of disconnected services.
The process combines assessment, senior-leadership alignment, cohort development, individual coaching, real-world application, reinforcement and measurement. The goal is to create a shared leadership language that moves through the organization and becomes visible in everyday decisions and conversations.
The system is organized around six connected pillars: trust, communication, accountability, people development and empowerment, culture, and intentional leadership growth. Self-awareness runs through all six because Sesol believes leaders must first understand how their own behavior affects the people around them.
“Leadership is not about you,” he says.
Whether someone has led well is ultimately a question about the people around that leader. Have they developed? Are they making stronger decisions? Can they accept greater responsibility? Are they more capable because of the leadership they experienced?
Starting at the Top
The first practical implication of the Pull the Chute model is where the work begins.
Organizations frequently send middle managers to training while senior leaders remain outside the process. Sesol believes that approach limits the likelihood of lasting change.
Senior leaders establish the behavioral norms everyone else follows. Employees watch how executives respond to bad news, whether expectations are clear, how consistently standards are applied and what behavior is tolerated when performance pressure rises.
Lasting culture change cannot simply be delegated downward. Senior leaders must model the behavior they expect throughout the organization.
From there, the work can expand through cohorts of managers and emerging leaders. Group sessions provide a common framework, while individual coaching connects that framework to the specific decisions, relationships and challenges each leader faces.
Participants do not work only with hypothetical case studies. They apply what they are learning to current situations: an employee who is underperforming, a conversation they have been postponing, a decision that has become bottlenecked or a team struggling with trust and accountability.
The work continues long enough for new behavior to be practiced, tested and reinforced under real conditions.
What Gets Measured
Traditional leadership programs often rely heavily on participant satisfaction. Did people enjoy the session? Was the facilitator engaging? Would participants recommend the program?
Pull the Chute asks different questions.
Are conversations inside the organization more direct and productive? Are expectations clearer? Is accountability maintained when something goes wrong? Are managers solving every problem themselves, or are they developing employees capable of taking ownership? Are decisions being made at the appropriate level? Are difficult issues reaching senior leadership early enough to be addressed?
The company also looks at broader organizational consequences. Is employee retention improving? Are teams better aligned? Are leaders spending less time resolving preventable problems? Can employees explain how their work contributes to the organization’s priorities? Is the culture becoming something capable people want to be part of?
Not every result appears immediately, and not every outcome can be reduced to a single number. Behavioral change often becomes visible through repeated moments.
A manager gives clear feedback instead of allowing frustration to accumulate. A leadership team challenges one another without damaging trust. An executive stops rescuing employees and begins coaching them to make decisions. A problem is raised early instead of being hidden until it becomes a crisis.
Individually, those moments may seem small. Over time, they change how an organization performs.
Closing the Knowing-Doing Gap
Sesol believes the real test of leadership development is what happens after the session ends.
Can a leader remain intentional when the quarter is difficult? Can a manager have an honest conversation while still treating the employee with respect? Can senior leaders hold one another accountable rather than placing responsibility only on people below them?
Pull the Chute is designed to close that knowing-doing gap through sustained practice and accountability.
Sesol has extended his leadership work through two books—Pull the Chute: Taking Your Business to New Heights and The New Leadership Landscape: Redefining a True Leader—and the weekly Pull the Chute Podcast, co-hosted with communications coach Janna Landry. Partner Bob Cotton leads the company’s work in the United Kingdom.
Yet Sesol’s definition of success has become increasingly personal.
“I used to think success was measured by the businesses I built,” he says. “Today, I think it’s measured by the people who are better because I was part of their journey.”
That belief shapes what Pull the Chute measures at the end of a year.
The question is not simply whether leaders completed a program or learned new terminology. It is whether they communicate differently, make stronger decisions, develop more capable people and build an organization that performs better because of how they lead.