Most leadership programs begin with a curriculum. Jeff Sesol begins with a question:
Are the people around you better for having been led by you?
That question, he argues, exposes a gap much of the leadership-development industry fails to address. Organizations invest in workshops and certifications. Leaders leave with new information and good intentions. Then pressure arrives, an employee underperforms or a difficult quarter unfolds—and familiar behavior returns.
“Leadership is not about you,” says Sesol, founder and CEO of Pull the Chute, an Illinois-based leadership-development company serving organizations across the United States and the United Kingdom.
A leader’s knowledge, experience and individual performance matter. But Sesol believes leadership is ultimately measured by what happens to the people around that leader. Do employees become more capable? Are managers making stronger decisions? Can people discuss problems honestly? Does accountability improve? Can the organization perform without every decision returning to the same person?
Closing the Gap Between Knowing and Doing
Most leaders already know that trust, communication and accountability matter. They understand that difficult conversations should not be postponed and that employees need clarity, feedback and opportunities to grow.
The problem is rarely a lack of information. It is consistently applying that information when the pressure is on.
Pull the Chute was built to operate in that gap. Its engagements unfold over months and are incorporated into the organization’s working rhythm. Leaders apply what they are learning to actual employees, decisions and organizational challenges. Group development is reinforced through individual coaching, practical commitments, follow-up and measurement.
The company describes its approach as a leadership-development system rather than a collection of workshops or disconnected coaching engagements. The process combines assessment, senior-leadership alignment, cohort development, individual coaching, real-world application, reinforcement and measurement.
The Pull the Chute 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.
Sesol believes leaders cannot meaningfully change a team or culture until they understand how their own behavior affects the people around them. That is why leadership begins with the person in the mirror.
A leader may believe they are being decisive while employees experience them as dismissive. A manager may think they are protecting standards while discouraging initiative. An executive may believe they are supporting a team while continuing to make every important decision personally.
Intent and impact are not always the same.
Start at the Top
One of the defining features of Pull the Chute’s model is where the work begins.
Organizations frequently invest in developing middle managers while leaving senior-leadership behavior largely unexamined. Sesol believes that sequence works against lasting change.
Senior leaders establish behavioral norms whether they intend to or not. Employees watch how executives respond to bad news, whether standards are applied consistently, which behaviors are rewarded and what the organization is willing to tolerate.
Lasting culture change cannot simply be delegated downward. Senior leaders must model the behavior they expect throughout the organization. From there, Pull the Chute expands the work through cohorts of managers and emerging leaders, creating a shared leadership language across organizational levels.
Built from Experience
Sesol developed his leadership philosophy through more than three decades of building and operating companies. His entrepreneurial career includes FreeDrive, an early web-based storage company, and SonMedia, an internet-safety platform for parents.
Across those experiences, he observed that even a sound strategy or promising product could be undermined by weak leadership execution. Growth stalled when communication broke down, accountability became inconsistent, decisions bottlenecked at the top or capable employees stopped believing they could grow inside the organization.
“I used to think success was measured by the businesses I built,” Sesol says. “Today, I think it’s measured by the people who are better because I was part of their journey.”
That realization became Pull the Chute, which he founded in 2021.
The company’s name comes from a skydiving experience on Sesol’s 40th birthday. At approximately 5,500 feet, he pulled the chute. The speed and chaos changed immediately. He could see his direction and focus on the landing point.
The image stayed with him because it reflected what he had observed in business. When leaders feel pressure, their instinct is often to move faster or take greater control. What they may need instead is a deliberate pause—a chance to confront reality, examine their assumptions and make an intentional decision before it is too late.
Measuring What Matters
Pull the Chute measures success differently from programs built around attendance or participant satisfaction.
The questions Sesol considers meaningful are behavioral. Are conversations inside the organization changing? Are leaders addressing problems earlier? Has accountability become clearer? Are managers developing employees instead of creating dependence? Are decisions being made at the appropriate level? Is the culture becoming something capable people want to remain part of?
The changes may appear small: a manager finally having an avoided conversation, a senior team learning to challenge one another without damaging trust or an executive allowing someone else to take responsibility for an important decision.
But those moments accumulate. They produce clearer communication, stronger accountability, more capable employees and better organizational execution.
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.
For Sesol, leadership still returns to the question that began the work:
Are the people around you better for having been led by you?
Pull the Chute was built to help leaders make the answer visible—in their people, their culture and their company’s performance.
