"Same Team, Different Decades: Building Connection Across Generations"

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Today's teams routinely span three or four generations — and conventional stereotypes say that this creates problems. Older workers can't keep up with technology. Younger workers don't know how to communicate. The narrative is so familiar it feels like fact.

 

But it isn't. Research consistently shows that we overestimate generational deficits and underestimate the conditions that actually determine whether a team connects, collaborates, and performs. When a cross-generational team struggles, the instinct is to blame the age gap. The real culprit is almost always something more structural: people don't feel safe raising concerns, contributions go unrecognized, support flows in one direction, or the team lacks shared clarity on what they're actually trying to accomplish together.

 

This session introduces Team Vitals—Support, Recognition, Energy, Alignment, and Safety—as a practical framework for diagnosing what's really going on when multigenerational teams underperform. Rather than training people to "manage" generational differences, we focus on the relational infrastructure that makes any team work: Can people ask for help? Do they feel valued for what they specifically bring? Is it safe to disagree? Do interactions build energy or drain it? Is everyone pulling toward the same goals?

 

Through research insights and hands-on table exercises, participants will discover that the problems they've been attributing to generational mismatch are often vitals under strain — and that targeted, low-cost interventions (adjusting how feedback flows, how goals are made visible, how recognition happens) unlock performance far more effectively than any generational sensitivity training ever could.

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Participants will leave ready to:​

• Diagnose team challenges using the Team Vitals framework. Learn how to apply the Team Vitals framework (Support, Recognition, Energy, Alignment, and Safety) as a practical diagnostic tool, shifting conversations away from generational stereotypes and toward the underlying conditions impacting team performance.

• Challenge generational assumptions with research-backed insights. Explore evidence showing that many perceived generational conflicts are actually symptoms of broader team health challenges. Discover how strengthening team vitals can turn age diversity into an advantage rather than a point of friction.

• Apply practical strategies to strengthen multigenerational teams. Leave with two to three actionable ideas tailored to your own team context, focused on improving areas such as feedback, recognition, visibility, and collaboration to strengthen the team vital most under strain.

 

Speaker Bio:

Jen Lipsey is the Chief Growth Officer at Sunny Workplace and a longtime HR, commercial and operational leader who has spent more than 20 years helping companies scale people, performance, and culture together. 

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She’s led global teams across sales, client success, operations, and people strategy, with leadership experience spanning startups, SaaS, behavioral science, and enterprise organizations. At Sunny, Jen focuses on helping companies create workplaces where connection, leadership, and team performance actually reinforce each other instead of competing priorities. 

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What makes Jen’s perspective unique is her ability to connect business performance with human experience. She speaks candidly about leadership, burnout, manager effectiveness, employee engagement, and what it actually takes to build high-performing teams in today’s workplace. Her approach is practical, honest, and deeply grounded in the realities leaders and employees are facing right now. 

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Known for her candid and relatable style, Jen brings a real-world perspective to conversations about workplace culture, team dynamics, resilience, and the future of leadership. She’s passionate about helping organizations build workplaces people genuinely want to be part of, without losing sight of the business outcomes that matter.