Leading Across Generations: Harder Than It Looks, More Valuable Than You Think

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This Week’s Insight: The Challenge (and Gift) of Cross-Generational Leadership

Leading a team of talented humans is challenging. Leading a cross-generational team? That’s next-level leadership.

It’s not just about navigating different communication styles, expectations, and work ethics—it’s about learning to recognize and leverage the unique contributions each generation brings to the table.

When I stepped into my first major leadership role, I inherited a newly reorganized team that spanned three generations. Some had been my peers. Others had barely entered the workforce. A few had already seen multiple leadership transitions and weren’t exactly excited about another one. I learned fast: managing people from different generations isn’t just about adjusting your language—it’s about adjusting your mindset.

Here’s what I’ve learned:

• Generational differences are real—but not absolute. Stereotypes won’t serve you. Curiosity and empathy will.

• Shared purpose bridges age gaps. A unifying goal gives everyone a reason to show up and contribute, no matter their birth year.

• The best teams aren’t built on sameness—they thrive on contrast. From Boomers to Gen Z, each perspective adds depth. Your job as the leader is to integrate those differences into forward momentum.

In Feed Your Team, I talk about feeding your team not just with meals, but with clarity, purpose, and connection. When it comes to cross-generational leadership, that means nourishing relationships by listening deeply and honoring different life experiences.

This week, I challenge you to have a one-on-one with a team member who is at least a generation apart from you. Ask them about their values at work. Ask them what energizes them. And most importantly—ask what they need from you to succeed.

^{Taken from “Feed Your Team: A Leadership Playbook for Building Trust, Belonging, and High-Performing Teams.” due out later this year.}

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The Speakers Collaborative: What's Next for Our Storytellers

While we’re on a summer break from live cohorts, The Speakers Collaborative is still buzzing behind the scenes. Our mission — to elevate bold voices and powerful personal narratives — continues to grow.

Veteran Scholarship Fund Launched
We’re proud to announce TS Collaborative, Inc., a nonprofit dedicated to providing full scholarships for U.S. veterans to share their stories on stage and in studio. These voices are vital. Their journeys of resilience, recovery, and reinvention don’t just inspire — they change lives.

2026 Site Selection Is Underway
Our 2026 cohort schedule is taking shape. We’re planning events in:

• Houston (Q1)

• Chicago (Q2)

• Los Angeles (Q3)

• Raleigh (Q4)

We’re Always Looking for Speakers
Whether you’ve been itching to step onto a stage or want to sharpen your storytelling and media presence, our coaching cohorts and recording sessions give you the tools, support, and platform to shine.

Want to nominate someone (or yourself)?
Hit reply and let’s talk.