What if the secret to unlocking true leadership isn’t about knowing all the answers, but about learning to ask the right questions—especially across generations?

In this eye-opening episode of the “Gen Mess with Tess,” host Tess Brigham sits down with powerhouse executive coach Kristi Royse, founder of KLR Consulting, to uncover the real challenges—and unexpected opportunities—leaders face in today’s rapidly shifting workplace. You might be surprised to learn that the biggest workplace problem isn’t generational conflict, but something much sneakier: ignorance and a reluctance to adapt.

Tess and Kristi pull back the curtain on why leadership has changed so drastically since Kristi’s early Boston Market days—from command-and-control to flexible, empathic management. Together, they slice through stereotypes about “lazy” young workers and stubborn older bosses, revealing why every generation falls into the trap of judging the next—and how that holds companies back from monumental growth and innovation.

Key highlights from this episode include:

• The shocking stat that in just a few years, most Americans will have a boss younger than themselves—and what that means for workplace dynamics.
• Kristi’s candid stories about turning tech engineers into inspiring people leaders (plus, just how important real coaching—not checkbox training—can be).
• Why understanding and embracing generational differences will make your team 49% more innovative (yes, there’s research to prove it).
• The myth of “work-life balance” for Gen Z and Millennials, and how blending personal and professional lives is reshaping workplace expectations.

Whether you’re a CEO, manager, or early-career professional, this episode will challenge your assumptions and equip you with practical tips to create a healthier, more connected, and future-ready workplace. Get ready to make sense of the generational “mess”... and maybe even learn to thrive in it.

Timestamped Episode Overview:

00:01 – Tess introduces Kristi Royse and her extensive leadership background

01:13 – Kristi shares her origin story: from Boston Market COO to leadership consultant

02:25 – Night-and-day differences in leadership then and now

03:34 – The complex realities of leading five generations at once

06:01 – Tess and Kristi discuss fear, assumptions, and resistance to change among leaders

08:25 – Generational stereotypes: Why every young cohort gets accused of being “lazy”

09:48 – Coaching leaders to communicate and collaborate across generational divides

11:02 – The pitfalls of promoting technical stars to management without support

12:54 – Case study: Transforming engineers at Strava into people leaders

14:09 – Gen Z and the new meaning of work-life blend

15:26 – Building trust: How real conversations and vulnerability build stronger teams

18:00 – Younger vs. older generations: What key assumptions are holding us back?

20:17 – How to invest in employees—even if you fear they might leave

22:03 – Simple, actionable ways managers can support every direct report

23:27 – Overcoming resistance: Why the “it’s too much work” excuse falls flat

26:28 – Kristi on the greatest workplace struggle: ignorance and culture clashes

29:30 – Coaching, courage, and patience: The real keys to personal and company growth

40:02 – Doing meaningful work: When passion and purpose trump the paycheck

43:52 – Kristi’s positive spin: The generational “mess” is actually the best opportunity of our time

47:49 – Where to find Kristi’s work & resources for leaders ready to do better

Listen in and discover how you can turn generational tension into your organization’s biggest asset!

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