Lessons Learned – The Impact of Bailey Webb’s Undercover Boss Experience

Lessons learned are experiences distilled from past activities that should be actively taken into account in future actions and behaviors. Generally, lessons are documented and shared at different levels in an organization.

Usually, these documents are stored on a centralized repository and easily accessible to other project teams through keyword search.

1. Don’t be afraid to ask for help.

Bailey Webb’s life changed after an episode of Undercover Boss went live. A junior nursing major at Morehead State University, Webb was chosen to train ice cream servers and cashiers for Dippin’ Dots at Kentucky Kingdom. Dippin’ Dots CEO Scott Fischer filmed the episode to see firsthand what his employees needed. After the episode aired, Fischer gave Bailey $20,000 for living expenses and created the Devin Webb Foundation in memory of her brother, who died due to undiagnosed heart disease.

Appalachian State football alumnus Jeff Dudan, founder and chief executive officer of AdvantaClean, is scheduled to appear on the season finale of Undercover Boss Sunday, May 29. Dudan played tight end and fullback for the Mountaineers from 1989-90, earning honorable mention All-Southern Conference recognition both seasons.

2. Don’t be afraid to speak up.

The summer before Bailey Webb’s senior year at Morehead State University, she took a job at Kentucky Kingdom in Paducah to help pay her college tuition. Little did she know that her summer job would lead to an appearance on Undercover Boss and a new life for her family. During her episode, Dippin’ Dots CEO Scott Fischer worked alongside the junior nursing major to learn about her family’s struggles, including the loss of her brother, Devin, to an undiagnosed heart condition. Upon her return, Fischer awarded Bailey with $20,000 for living expenses and established the Devin Webb Foundation to support families dealing with similar hardships.

3. Don’t be afraid to fail.

During her summer job at the Kentucky Kingdom amusement park working at Dippin’ Dots ice cream stands, Bailey Webb made an impression on CEO Scott Fischer who later invited her to appear on his show Undercover Boss. While she originally turned down the opportunity, a change in her mindset and focus allowed her to learn and grow from the experience. A former Mountaineer tight end and fullback, she is the author of the new book Breaking Cover: How to Make a Difference in Your Life No Matter What.