David Stillman: Generational Speaker

    David Stillman helps organizations bridge generational gaps, understand changing workplace expectations, and strengthen communication, leadership, and collaboration across age groups and career stages.

    David Stillman - Image 07 (October 26, 2026)

    Quick Facts:

      • More than 20 years of experience in generational topics.
      • Co-author of When Generations Collide and The M-Factor.
      • Co-author of Gen Z @ Work with Jonah Stillman.
      • Media commentary across major national broadcast and print platforms.
    • Formats:
    • Keynote presentations.

    • Audiences:
    • Business leaders, HR professionals, managers, employee teams, professional associations, and organizations navigating a multigenerational workforce.

    • Outcomes:
      1. Recognize how generational experiences can influence workplace expectations.
      2. Identify communication approaches that support understanding across age groups.
      3. Explore ways to strengthen collaboration and engagement across career stages.
    Reading time: 8 min
    Reviews: (0 reviews)
    • Travels from: Excelsior, MN
    • **Fee range: $20,001 - $35,000

    Keynote Topics

    With the recent Coronavirus pandemic, businesses, families, and communities at large have been changed forever. No longer is the goal to return to life as we knew it, but instead to navigate the best path forward.

    “The Generations In A New World” is an uplifting conversation around what has changed and what has not for each generation. A combination of primary data, case studies, and first hand stories explain the traits that each generation can bring to the table as we repair our world. In addition, areas of concern with each generation are discussed so that we can all be more aware of how to help each other.

    Our global study of the generations in this new world reveals that each generation has been changed in unique and different ways.

    Results include

    • Baby boomers rage against age.
    • Gen Xers becoming the sandwiched generation.
    • Millennials new outlook on loyalty.
    • Gen Z’s struggle to gain social capital.
    • David Stillman and Jonah speak together or separately.

    Believe it or not…there’s life after the Millennial generation. A new generation is starting to hit our workforce, yet no one has been talking about it. Until now.

    Are you ready for GenZ? Don’t be surprised when you find they are nothing like the Millennials and the time to get to know them is today. The leading edge of GenZ has entered their 20s. While they might just be your intern for now, you need to know that they are your future workforce and marketplace.

    Best selling author and generations expert David Stillman offers insights into the next generation – and even better, he’s bringing one along! The first GenZ speaker to hit the circuit.

    That’s right, the first GenX and GenZ (father-son) speaking combo with David Stillman can help you get ahead of the curve. No more speculating about the latest generation, here’s your chance to get the straight scoop from two experts, and have fun doing it!

    Based on the results of a national Gen Z research study, GenZ@Work, audiences will get fresh insights on what makes this newest generation tick. Who are they? What are their expectations around careers and the workplace? How have changes in parenting styles shaped them in new ways? What’s it going to take to get this generation in the door, on board, and up to speed?

    You Will Learn

    • Who are the primary generations in the workplace and marketplace today?
    • What makes Generation Z unique?
    • How has the influence of parents shaped this dynamic generation?
    • What’s it going to take to recruit, retain and manage them?
       
       

    You may think you know the generations, but the Baby Boomers, Generation Xers and Millennials are carving out new territory as they evolve. Now comes the latest twist—the arrival of Generation Z in the workplace and marketplace. Just when you think you’ve bridged all the gaps, it’s time to learn about what happens when generations continue to collide.

    In Generations 2.0, you will learn from David Stillman where all the generations are in their careers today and what they need to be successful. Where are the big generational issues on the horizon for leaders, managers, and individuals? And what’s going to happen when a whole new generation arrives on the scene — Gen Z?

    This energizing, fresh, and funny update on Generations 2.0 will help you identify the gaps creating mayhem in your workplace and marketplace, apply smart solutions to help you navigate multigenerational minefields, and ultimately, look at the generations in a whole new way.

    David Stillman multimedia presentations are always entertaining and thought-provoking. Known for customizing his material for every client, David can focus his generational insights in three distinct areas.

    Workplace: recruiting, retaining, communicating with 4 generations
    Marketplace: customer service and sales for 4 generations
    Giving: how to attract and retain 4 gens of donors and volunteers
     
    You Will Learn

    • What are the hot generational trends hitting the workplace and marketplace today?
    • How is the arrival of Generation Z going to shake things up?
    • What does each generation need to be successful?
    • How can you bridge the gaps more effectively whether you are a leader, a manager or an individual contributor?
       

    Talent Short Bio

    David Stillman is a generational expert, keynote speaker, and author with more than 20 years of experience helping organizations understand generational differences.

    He is the co-author of When Generations Collide and The M-Factor: How the Millennial Generation Is Rocking the Workplace. He also co-authored Gen Z @ Work with his son, Jonah Stillman, exploring seven key traits of Generation Z and their workplace implications.

    David’s commentary has appeared on CNN, CNBC, the TODAY show, and NPR, as well as in publications including The New York Times, Fast Company, and The Wall Street Journal.

    Drawing on his generational expertise and creative communications background, David helps leaders and teams examine workplace expectations, improve communication, and build more effective relationships across generations.

    David Stillman is a generational expert, keynote speaker, and author who helps organizations bridge generational gaps and strengthen collaboration. For more than 20 years, business executives, policymakers, and media outlets have turned to him for perspectives on how different generations approach work, communication, and leadership.

    David’s work explores the experiences and expectations that influence people across age groups. He helps audiences recognize where misunderstandings can arise and consider how greater awareness can improve working relationships. His presentations connect generational insights with practical questions facing leaders, from communicating expectations to engaging employees and supporting teams.

    He is the co-author of When Generations Collide and The M-Factor: How the Millennial Generation Is Rocking the Workplace. These books examine generational differences and their implications for organizational culture, management, and performance.

    David also co-authored Gen Z @ Work with his son, Jonah Stillman. Published by HarperCollins, the book explores seven key traits of Generation Z and their relevance to the workplace. Their collaboration brings perspectives from two generations into a shared conversation about how organizations can understand and work with emerging talent.

    His commentary has appeared across major broadcast and print platforms, including CNN, CNBC, the TODAY show, NPR, Fast Company, The New York Times, USA Today, and The Wall Street Journal. This experience has helped him make generational topics accessible to a broad audience.

    David’s background also includes award-winning creative communications work, with recognition including a CLIO Award and gold medals at the New York Film Festival. He brings that communication experience to the stage, translating complex workplace dynamics into clear, engaging discussions.

    For conferences, leadership meetings, and employee events, David offers a framework for examining generational expectations and their influence on everyday interactions. His presentations encourage audiences to ask better questions, communicate more deliberately, and find opportunities for collaboration across age groups.

    David Stillman helps organizations turn the generational conversation into a useful starting point for stronger relationships, more informed leadership, and a workplace where people can contribute across career stages.

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