To provide new insights, tips and tools for a better understanding of how to facilitate better communication and team-building skills between millennials and baby boomers. The results will lead to new perspectives on:

  • How to lead
  • How to communicate
  • How to improve inter-generational understanding
  • How to build relationships
  • Connecting and leading across generations
  • Improving inter-generational understanding and outcomes


  • Millennials and baby boomers
  • Individuals with hiring, supervising and coaching responsibilities
  • Baby boomers who supervise female millennials
  • Millennials trying to better understand and communicate with female baby boomer management
  • Any generation or gender interested in improving inter-generational understanding and outcomes for women

When Stilettos & Sneakers presented to our women’s leadership group, they helped us validate a model of leadership defined by women from the perspective of not one but two generations. Together, we reassessed the meaning of both failure and success. It was a very moving and transformational experience.” – Mary Ruiz, Past President International Women’s Forum Florida Suncoast Forum


At this time, all workshops will be presenting virtually using a ZOOM format.


Stilettos and Sneakers discuss leadership and inter-generational understanding through eight topics. Three topics can be handled per workshop. The topics to choose from are:

  • Hard Skills and Soft Skills
  • Relationships
  • Self-Confidence
  • Public Failure
  • Private Failure
  • Nontraditional Women
  • Life Choices
  • Extended Italian-American Family

Key Takeaways

  • Unveil and discuss implicit biases resulting in less pre-judging of other generations.
  • Participants will be more open to new thinking, ideas, and a greater understanding of different generational leadership styles.
  • Participants will leave more informed, empowered with an understanding and appreciation of the leadership and working styles of each generation.