There is a moment in the life of many companies, a terrifying, silent point of acceleration when the thrill of the initial launch gives way to the dizzying reality of a business in freefall. It is not a fall caused by a lack of vision or a failing product, but by the founder’s own grip. Clinging too tightly to every decision, every task, every thread of control, they become the very anchor that is dragging their creation down. They are exhausted, their best people are leaving, and the growth they dreamed of has stalled. This is the moment they need to pull the chute. This is the moment they need Jeff Sesol.
Jeff, an award-winning leadership coach, best-selling author, and the voice behind the “Pull the Chute” podcast, has built his life’s work around this critical juncture. He is a sort of first responder for businesses teetering on the edge of their own potential, a calm presence who arrives not with a complicated new strategy, but with a deceptively simple philosophy: Grow your employees, and you will grow your business. He is the architect of a methodology designed to cure what he calls “Founder’s Syndrome,” the top-down, command-and-control style of leadership that inevitably becomes a bottleneck.
He operates in the space between a company’s ambition and its culture, a place often littered with good intentions and poor execution. It is a silent crisis playing out in cubicles and corner offices, reflected in stark numbers: nearly half of all employees are unhappy at their jobs, and a staggering 79 percent of people leave their jobs because they feel unappreciated, while only 12 percent leave for more money. Jeff Sesol’s work is to mend this disconnect. He teaches leaders the art of letting go, of trusting their teams, and of transforming a culture of ownership from a singular noun into a plural one. He guides them to the point where their employees stop thinking of it as the founder’s company and start saying, with genuine conviction, “this is my company too.”
The Architect of Trust
To understand Jeff’s philosophy, you must first understand the soil it grew in. Raised in a family that prized hard work, resilience, and an insatiable curiosity, he learned a foundational lesson early on. “Success wasn’t just about what you achieved individually,” Jeff recalls, “but how you lifted up the people around you.” While his formal education was traditional, his real classroom was the business world itself, a dynamic landscape where he moved between the structured halls of large corporations and the scrappy, agile environments of entrepreneurial ventures.
In this diverse ecosystem, Jeff became an observer, a student of organizational dynamics. He saw a clear, recurring pattern. Some companies would flare brightly for a moment and then burn out, while others demonstrated a steady, enduring capacity for growth. The difference was not in their products or their marketing budgets. “The companies that thrived over the long haul always had one thing in common: they grew their people,” Jeff says.
“That shaped my core philosophy. When you create an environment where employees feel supported, trusted, and developed, the business naturally follows.”
This was not an abstract theory; it was a tangible reality he witnessed again and again. Jeff saw how investing in an employee’s skills and goals created a ripple effect, boosting not just morale but also innovation, productivity, and the bottom line. The idea became his mantra, the central axis around which his entire career would pivot. The fastest way to elevate a business was not to focus on the business at all, but on the people within it.
The Founder’s Syndrome Epidemic
The inspiration for Pull the Chute was not a single event, but a slow burn of observation, a growing frustration with seeing the same story play out in too many promising companies. He watched brilliant, passionate founders become the biggest obstacle to their own success. They were stuck in a self-perpetuating loop of control, micromanaging every detail and making every decision, convinced that no one else could do it right. “That approach might work in the early stages,” Jeff notes, “but it doesn’t scale.”
The defining moment, the one that crystallized his mission, came not in a boardroom but in a candid conversation. “A business owner admitted he didn’t trust his team to make decisions,” Jeff remembers. “That was the lightbulb. If you can’t trust your people, you can’t grow.” In that single confession, he saw the entire problem encapsulated: a fundamental breakdown of trust that was suffocating potential.
Pull the Chute was born from that insight. The name itself is a call to action, an urgent plea for leaders to act before it is too late, to slow down, reset their trajectory, and deploy a new system that relies on the collective strength of the team. To work on their business, not in their business. The goal is to create a culture where employees are not just passengers on the journey but are co-pilots, empowered to take ownership and help navigate the direction of the business. The results of this shift can be dramatic.
One tech startup Jeff worked with, a company mired in the founder-controlled loop, managed to triple its leadership capacity in just six months. The method? Simply distributing the act of decision-making. “The founder went from exhausted to energized,” Jeff reports, “and the company broke through a growth ceiling it had been stuck under for years.”
From ‘My Company’ to ‘Our Company’
Making this cultural shift is delicate work. It requires rewiring the instincts of both leaders and employees. For leaders, the process begins with awareness. They must first see themselves as the bottleneck. From there, Jeff guides them through a series of intentional, practical steps: effective delegation, genuine empowerment, and open, consistent communication. It is about building new structures and habits that make it safe for leaders to let go and for employees to step up.
For employees, the focus is on building confidence and providing clarity. “When people understand the vision and feel trusted to contribute,” Jeff explains, “they naturally step into ownership.” Over time, the language within the company begins to change. The divisive “they” of management gives way to the inclusive “we” of a unified team. The possessive pronoun shifts from singular to plural.
Jeff offers a powerful example of a manufacturing client whose founder was the central hub for every daily decision, a classic case of Founder’s Syndrome. After undergoing the Pull the Chute coaching, the founder made a conscious effort to shift responsibility to his operations team. The results were staggering. Within a year, not only had productivity increased, but the newly empowered employees began to proactively identify and suggest new efficiencies. Their on-the-ground insights, now valued and acted upon, saved the company over half a million dollars annually. “That’s the power of shared ownership,” Jeff states. It is not just a feel-good concept; it is a powerful engine for innovation and financial growth.
Breaking the Habits of Command and Control
At the core of Jeff’s work is the delicate process of breaking deeply ingrained habits. He finds that most leadership challenges boil down to two common, destructive behaviors: the tendency to micromanage and the avoidance of difficult conversations.
“Micromanagement comes from fear of losing control,” he says. His approach is to coach leaders to reframe their role. Instead of managing tasks, they should be defining outcomes. He teaches them to replace the impulse for control with the practice of trust by setting crystal-clear expectations and then measuring results, giving their teams the autonomy to figure out the “how.”
The second challenge, avoiding tough conversations, is often disguised as kindness. “Many leaders think they’re being ‘nice’,” Jeff observes, “but in reality, they’re withholding valuable feedback.” This creates a culture of ambiguity where employees never know where they truly stand, and mediocrity is allowed to fester. He provides leaders with practical frameworks for having constructive, honest conversations that are designed to build people up rather than tear them down.
The impact of breaking these two habits alone can be transformative. He recounts the story of a service company plagued by high employee turnover. The issue was not pay or benefits; it was management. Once the company’s managers learned how to provide clear, constructive feedback and trust their teams, the culture shifted dramatically. “Employee satisfaction shot up,” Jeff says. “Within a year, turnover dropped by 40%, which in turn saved the company hundreds of thousands in rehiring costs.”
The Flywheel of Influence
Jeff’s mission extends far beyond one-on-one coaching sessions. He is a prolific communicator, leveraging multiple platforms to amplify his message. His role as a best-selling author allows him to distill his philosophy into structured, scalable frameworks. His podcast, “Pull the Chute,” offers a more informal, accessible medium, featuring real conversations with leaders who are navigating the very challenges his listeners face.
“Each platform reaches people in a different way,” he explains. Coaching is deeply personal and tailored. His books provide the foundational architecture of his ideas. The podcast offers practical, in-the-moment insights. “Together, these roles create a flywheel,” he says. “They reinforce each other and broaden the impact of our mission: growing people to grow companies.” This multi-pronged approach has established him not just as a coach, but as a central thought leader in the movement towards more human-centered, effective leadership.
The Power of the Five-Minute Huddle
A common concern among leaders of small or mid-sized companies is the perceived cost of investing in their people. They see the value, but they believe they lack the resources for elaborate training programs. Jeff is quick to dismantle this misconception.
“Start small,” he advises. “You don’t need a massive budget.” He suggests simple, high-impact, low-cost actions: hold regular one-on-one meetings where the primary goal is to listen to an employee’s goals and challenges; offer cross-training opportunities to expand skills and prevent silos; and, most importantly, create consistent rituals of recognition. “Recognizing and celebrating wins-even small ones-sends a powerful message: we value you, and we’re investing in your growth.”
One of his favorite examples is a mid-sized logistics company that implemented weekly five-minute “recognition huddles.” It was a simple, zero-cost addition to their routine. But the effect was immediate and profound. “Employees felt seen and valued,” Jeff says. “Engagement rose so sharply that productivity improved by 25% in just one quarter.” It is a powerful testament to the idea that the biggest returns often come from the smallest, most human investments.
Slowing Down to Go Fast
As Pull the Chute continues to grow, its vision is becoming increasingly global. Jeff has brought on Bob Cotton from the UK as a partner to spearhead international expansion. He has also formed a strategic partnership with John Zettler of Fair Winds Training in Canada to create TheExecutiveCoachNetwork.com, a collaborative entity designed to merge educational and coaching skills for emerging leaders. He is also at work on his next book, which will offer even more practical tools for leaders looking to build people-centered cultures.
For a man so focused on helping leaders manage the relentless pace of business, his own life is a study in deliberate balance. “Family time grounds me,” he shares. Spending time with his wife of 44 years, the families of their three daughters, including seven grandkids, along with reading and daily journaling, are non-negotiable rituals that keep his mind sharp and his ideas flowing. “These rituals keep me recharged so I can show up fully for the leaders I coach,” he says.
It is this personal commitment to balance that gives his final piece of advice its profound authenticity. His personal mantra, he says, is the very principle upon which his company was built: “Slow down to go fast.” It sounds like a paradox, but in Jeff Sesol’s world, it is the fundamental truth of sustainable success. It is the act of pulling the chute by pausing, listening, and investing in people that allows a company to stop its uncontrolled freefall, land safely, and then begin to soar faster and higher than ever imagined.
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Also Read: Beyond Growth: Building Companies by Growing People with Pull the Chute
