Born to Succeed Insights

“Win By Laughing©: Culture by Intention.” Is Your Team In Need of A Culture Reboot?

Executive Leadership Coach Jill Bornstein, ACC and Corporate Comedy Coach Christine O’Leary launch “Win by Laughing©” to help teams have a culture reboot to better connect and perform for success.

Remote work may be the new normal, but leadership coaches Christine O’Leary and Jill Bornstein, ACC believe in-person interaction is both necessary and should take center stage — now more than ever. Enter their one-day program, Win by Laughing©: Culture by Intention, the executive and team culture reboot that ensures enhanced community, better productivity, and a shared business vision through the universal cure-all, laughter. They aim to infuse humor and joy into the workplace for an overall win-win.

Award-winning Stand-Up Comedian and Corporate Coach, Christine O’Leary, knows the power of funny. With years of teaching sold-out comedy classes and schooling executives worldwide, Christine has seen laughter connect colleagues and breed positivity, inside the office and out. Her training has helped companies achieve optimized truth, trust, and intention around their culture.

Jill Bornstein, ACC, Executive Coach and Builder of High Performing Teams, facilitates success through a series of upbeat culture-building strategies and team accountability. In short, she assists leaders and teams with meeting important challenges and achieving exciting goals. Her focus is to help CEOs and beyond make healthy changes to create a cohesive culture, spurring positive results. Additionally, she motivates executives to prepare for what’s to come, prompting her leadership coaching firm’s name, Upnext. With their common charge, the dynamic Christine-Jill tag-team joined forces to carefully craft and launch Win by Laughing: Culture by Intention.

Christine and Jill cite 8 reasons for leaders and their teams to gather in person: 1) Communicates the team’s importance by making the investment to get together 2) Sparks new ideas faster 3) Lessens feelings of isolation 4) Strengthens connections to sustain colleagues until the next team
in-person event 5) Provides networking opportunities 6) Offers strategic perspective
7) Reboots and engages an organization’s culture 8) Allows for laughter to build a joint path forward. Time is money, so the goal of the one-day session is for colleagues to create deeper connections quickly. The need for change within today’s corporate cultures is clear: culture by default is out; culture by intentional development is in.

People don’t leave companies; they leave broken organizational and team cultures that haven’t had a fresh look since Covid forced us to work differently. That’s a hurdle organizations face and where Win by Laughing comes in,” said Bornstein.

The innovative Win by Laughing program enables teams to improve collaboration, interpersonal dynamics, and the development of intentional culture — all for the better. Initially, the Organization CEO, Division President, Executive Team Leader, or Director will deliver an ice-breaking comedy “set” Christine helped them develop and hone. Hence, humor is the backdrop from with the truth about the current culture springs forth.

Comedy is a way to tell the truth, solve a problem, and sell the material with a feeling. It’s liberation and freedom and can help professionals up their game in any career. Our program helps people to excel by literally lightening up through laughter, our shared ground,” said O’Leary.

Once the team has “truthed up,” Jill assists with the reset via establishing trust and a deeper team connection. She guides the group through a values examination, behaviors expectations, and the alignment of working norms. The session will conclude with a group comedy experience, propelling them joyfully and jointly forward to harness greatness, both individually and as a corporate team.

Our firm’s Team Day led by Jill and Christine was unique, highly interactive, and nothing short of transformative. Their morale and business boosting tactics — peppered with savvy guidance, joyful community building, and truth-telling comedy — made for a fulfilling and fun experience. Attendees became bonded and recharged having forged personal and professional connections: they came away feeling appreciated, happy, and less isolated. The Win by Laughing program was a resounding success, spurring a newfound comradery that’s made a marked difference in performance, leadership development, and the bottom line,” said David McInnis, President & Founding Partner, Willard Powell, Inc.

Win by Laughing sessions can be held for half or full-day time periods, depending on the depth of laughter and culture reboot needed. For details, contact “Joy Junkie” Christine O’Leary at or High Performing Team Culture Builder Jill Bornstein, ACC at to get your Win by Laughing: Culture by Intention program booked. Professional revelry, reinvention, and reconnection guaranteed.


Photo caption: (from left) Corporate Comedy Coach Christine O’Leary and Executive Leadership Coach Jill Bornstein, ACC announce the launch of a joyous, truth-finding one-day company culture reboot program, Win by Laughing: Culture by Intention. For details and bookings, email or Photo Credit Ann Charles Photography.

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