Most leaders Jeff Sesol works with already know what good leadership is supposed to look like.
They understand that communication matters, trust can disappear faster than it is built, and accountability begins with clear expectations. They have attended seminars, read books, and returned to work with frameworks they genuinely intended to use.
Then pressure arrives.
A difficult quarter forces hard decisions. A valuable employee begins underperforming. Conflict develops within the leadership team. A conversation everyone knows needs to happen gets postponed again.
In those moments, leaders often return to familiar behaviors—not because they lack knowledge, but because knowing what to do and consistently doing it are two different things.
That is the problem Sesol built Pull the Chute to address.
Founded in 2021, the Illinois-based leadership-development company is designed to close the gap between what leaders understand and how they actually behave, especially when the pressure is on.
“Leadership is not about you,” Sesol says.
His definition of leadership is not based primarily on a person’s title, accomplishments, or individual productivity. It begins with a different question:
Are the people around you better because you led them?
For Sesol, that is the measure of leadership that matters most.
A System, Not a Stand-Alone Seminar
Pull the Chute offers executive coaching, leadership groups, organizational-development programs, workshops, and speaking engagements. However, the company’s primary distinction is not a single presentation, coaching method, or collection of leadership concepts.
Pull the Chute is a leadership-development system.
A workshop can introduce valuable ideas and create momentum. A speaker can inspire leaders to examine their behavior. A coach can help an executive work through an immediate challenge. Each can play an important role.
But lasting behavioral change requires those experiences to be connected through a sustained process of assessment, application, coaching, accountability, and reinforcement.
That is why Pull the Chute’s organizational engagements unfold over months rather than ending after a single event. The work begins by understanding the organization, its goals, its leadership challenges, and the behaviors that may be limiting performance. Senior leaders align around what needs to change, and development then moves through leadership cohorts supported by individual coaching and real-world application.
Participants do not simply discuss leadership in theory. They apply what they are learning to actual conversations, decisions, performance issues, and organizational challenges. They return to the group to examine what happened, receive feedback, and determine what they need to do differently.
Over time, new leadership behaviors begin to replace established habits.
The Six Pillars of the Pull the Chute System
The Pull the Chute system is organized around six connected pillars:
- Trust
- Communication
- Accountability
- People Development and Empowerment
- Culture
- Intentional Leadership Growth
These pillars are not intended to operate as six independent topics. Together, they create an architecture for how leadership is experienced throughout an organization.
Trust determines whether people feel safe enough to speak honestly, raise concerns, admit mistakes, and challenge an idea without fearing retaliation.
Communication determines whether expectations, priorities, decisions, and feedback are clear enough for people to act confidently.
Accountability ensures that commitments have meaning and that leaders hold themselves to the same standards they expect from others.
People development and empowerment move leaders away from solving every problem themselves and toward building the judgment, confidence, and capabilities of the people around them.
Culture reflects the behaviors an organization rewards, tolerates, reinforces, and repeats—not simply the values it publishes.
Intentional leadership growth recognizes that leadership development cannot be left to chance. It requires reflection, practice, feedback, and a willingness to confront behavior that may have contributed to the problem.
Self-awareness runs through every pillar. Before leaders can strengthen an organization, they must understand how their own behavior affects the people around them.
Leadership Begins With the Person in the Mirror
Organizations often send middle managers, supervisors, or emerging leaders to training without first addressing the behavior of senior leadership.
Those managers may return with useful ideas, but they are still operating within a culture shaped by the people at the top.
Senior leaders establish organizational norms whether they intend to or not. What they reward, tolerate, question, ignore, and reinforce sends a message throughout the company. How they respond when something goes wrong often influences the culture more than anything written in a mission statement.
For that reason, Pull the Chute begins with senior leadership.
That does not mean positive change can only come from the top. It means lasting organizational change is difficult to sustain if the people at the top are not modeling and reinforcing it.
The process asks leaders to look in the mirror before diagnosing everyone else:
What am I doing that may be contributing to this problem?
What behavior am I tolerating?
What conversation am I avoiding?
Have I made my expectations clear?
Do people feel safe telling me the truth?
Am I developing my people—or making them dependent on me?
Without that self-examination, leaders can use every new concept to identify what other people need to change while avoiding the changes required of themselves.
The Meaning Behind the Name
The Pull the Chute name comes from Sesol’s first skydiving experience on his 40th birthday.
At approximately 5,500 feet, he pulled the parachute. The chaos and speed of the free fall stopped. His direction became clearer, and he could see where he was going to land.
The experience became a metaphor for what leaders must sometimes do when pressure is building and events are moving quickly.
Pulling the chute does not mean avoiding a decision or becoming passive. It means interrupting an automatic reaction long enough to assess what is happening, choose an intentional response, and redirect before the organization moves further off course.
For Sesol, that pause is often the difference between reacting to a situation and truly leading through it.
Built Through Experience
Sesol developed his leadership philosophy through more than 30 years of building and leading companies.
His entrepreneurial experience includes FreeDrive, an early web-based storage company, and SonMedia, an internet-safety platform created for parents. He later served as vice president of operations and revenue at Jaymie Scotto & Associates.
Across those experiences, he repeatedly reached the same conclusion: strategy, technology, product, and process can take a company only so far. Eventually, the constraint becomes leadership.
Organizations can have sound strategies and still struggle because leaders avoid necessary conversations. They can recruit talented people and lose them because of the accumulated effects of poor management. They can publish strong values and undermine them by tolerating behavior inconsistent with those values.
Those observations eventually became the foundation of Pull the Chute, which now works with leaders and organizations across the United States and the United Kingdom.
Sesol has written two books on leadership—Pull the Chute: Taking Your Business to New Heights and The New Leadership Landscape: Redefining a True Leader—and co-hosts the weekly Pull the Chute Podcast with communications coach Janna Landry.
Measuring What Actually Changes
Leadership development is frequently evaluated by asking participants whether they enjoyed a session, found the material useful, or would recommend the program.
Sesol believes those measures are insufficient.
A leader can enjoy a program without changing how they lead. The more important questions are behavioral:
Are difficult conversations happening sooner?
Are expectations clearer?
Are leaders addressing problems before they become crises?
Are managers holding their people accountable while accepting accountability themselves?
Are decisions being made at the appropriate level, or does everything still bottleneck with the CEO?
Are employees becoming more capable and confident, or are they still dependent on senior leaders for every answer?
Do people feel safe telling leadership what leaders need to hear—not merely what they want to hear?
These changes take time to become visible. They may appear when a leadership team handles a difficult quarter differently than it would have a year earlier, when a manager finally addresses a performance issue, or when employees begin making sound decisions without waiting for the CEO.
Over time, those behavioral changes can contribute to stronger retention, faster decision-making, improved execution, fewer unresolved conflicts, and a deeper leadership bench.
Developing People, Not Dependence
Sesol believes one of the most common leadership mistakes is trying to become the hero of every situation.
Leaders answer every question, solve every problem, and step in whenever something becomes difficult. Although that behavior may initially appear helpful, it eventually creates dependence and turns the leader into an organizational bottleneck.
Leadership requires something more difficult: building the capability of other people.
A leader’s legacy is not simply what the company accomplished while that person was in charge. It is what the organization and its people remain capable of accomplishing when that leader is no longer in the room.
“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.”
Pull the Chute is the system Sesol built around that conviction: helping leaders turn what they know into how they lead—and helping organizations grow by growing their people.
