Episode Overview

Podcast: At Work with The Ready
Episode: 37 – “Leadership Across Generations with Raven Solomon”
Air Date: November 17, 2025
Host: Rodney Evans
Guest: Raven Solomon (CEO, Future Ready Institute; Author; Speaker)

In this insightful episode, Rodney Evans sits down with cross-generational leadership expert Raven Solomon to discuss how inclusion, evolving generational dynamics, and rapid technological change are shaping the future of work. The conversation delves into what older generations need to unlearn, how Gen Z and Gen Alpha are changing expectations around work and leadership, the importance of authentic and actionable inclusion, and the real-life impact technology and AI will have on organizations and individuals.

Key Discussion Points & Insights

1. Unspoken Truths About Leadership Professions (01:00–04:05)

• Check-in Round: Both Rodney and Raven share “what they can’t say on stage,” offering a window into their real experiences as leaders and facilitators.
  • Raven: Speakers can feel audience energy and engagement, and are impacted by it—a reciprocal relationship rarely acknowledged.
    • “I can see you. I can tell whether you're engaged or not...I feed off the energy of the room.” (01:44, Raven)
  • Rodney: Change is imperative, but most in power will not do what’s necessary because of ego and resistance to discomfort.
    • “So many people who have worked themselves into positions of power have such a calcified ego...they're just not gonna.” (02:49, Rodney)

2. Generational Divides: What Needs to Be Unlearned (04:05–09:00)

• Reference Point: Older generations (Gen X, Boomers, elder Millennials) must relinquish the belief that their “way is the right way” and recognize the distinct stressors and lived realities for younger generations.
  • “We have to unlearn this idea that our way is superior, that because it worked for us, it should work for them. That's just not the case.” (05:13, Raven)
  • Example: Constant digital connectivity has made bullying and mental health challenges omnipresent for Gen Z.

3. Parental and Societal Anxiety in the Internet Age (07:17–09:03)

• Rodney shares: The amplification of shame and surveillance via social media impacts parents and teens alike—“the whole community gets involved” now regarding mistakes or missteps.
• “When we were in high school… the worst thing that happened was on Monday, somebody's like, narc mom called her and got mad. But...the community didn't get involved...Now you're, like, watching it real.” (08:21, Rodney)
• Insight: Empathy is the foundation for spanning generational divides.
  • “Empathy...is not about necessarily understanding the experience...but rather the emotions that underpin that experience.” (09:18, Raven, citing Brené Brown)

4. Generational Disillusionment with Work & Shifting Values (10:16–15:27)

• Younger generations are skeptical of work’s promises—financial, emotional, relational—largely due to witnessing parental disappointment post-2008 recession.
  • “Gen Z has watched their parents be let down economically, emotionally, mentally, by the workplace.” (11:47, Raven)
• Millennials’ and Gen Z’s skepticism: They see alternatives outside traditional “good corporate jobs” (influencer, gig economy, entrepreneurship).
  • “They're kind of pushing back…They’ve seen the failure and they're like, I don't want that for myself.” (14:36, Raven)

5. Redefining Ambition and the Rise of Lifestyle Design (15:27–20:10)

• Individual contributor roles: Choosing not to pursue leadership is increasingly common; work-life boundaries are re-prioritized.
  • “A lot of my peers are getting pushback for not being ambitious enough…But how do you blame them when they see you have zero work life integration.” (15:36, Raven)
• Midlife revelations: Even veteran entrepreneurs are turning toward “lifestyle businesses” and away from endless scaling.
  • “Everybody's sort of going, like, for what reason would I double down now?...Let’s design a life that is not just about maximization.” (17:15, Rodney)

6. Inclusion: From Concept to Strategic Imperative (20:24–29:15)

• Defining Inclusion: Difference isn’t just about visible diversity, but any “presence of difference.” Inclusion means welcoming, valuing, and leveraging those differences strategically.
  • “Diversity is...the presence of difference. Full stop… Inclusion [means] making sure that difference is welcomed, valued, appreciated, respected, leveraged…” (21:18, Raven)
• Pragmatic Case: Corporate success hinges on authentically reflecting and serving an increasingly diverse and value-driven marketplace.
  • “If you don't have the kind of organization that mirrors the population in the market, you are shit out of luck.” (25:09, Rodney)

7. Measuring and Genuine Commitment to Inclusion (30:10–38:03)

• Authenticity is Key: Younger generations are adept at discerning performative vs real inclusion (the “Conway’s Law” principle).
  • “They’ve developed this skill of deciphering between what is real and what is fake…do you think that they're not going to be able to tell when your diversity...promises are real...?” (31:08, Raven)
• Trade-offs: Inclusion requires sacrificing short-term ease for long-term productivity; outcomes are hard to measure; “belonging” is especially nebulous.
  • “It's not always the easiest thing to measure...we want this fluffier term...but it's a lot harder to measure. And that is only going to set us back.” (34:22, Raven)
• Leadership Challenge: Inclusion demands personal discomfort, learning, and unlearning deeply ingrained behaviors.
  • “So much of this work is personal…can you unlearn what you think you know and can you relearn again?” (39:19, Raven quoting Alvin Toffler)

8. The Skills of Future-Ready Leaders (41:35–48:15)

• Top future-ready, human-centered skills:
  • Empathy
  • Humility
  • Adaptability and agility
  • Cultural intelligence (ability to adapt and relate across difference)
  • Relatability
  • Complex, multi-layered problem-solving
  • Transparency and vulnerability
• “All of those things that we once kind of turn our head to when it comes to leadership, I think are the most important now.” (47:43, Raven)

9. AI as a Generational Tsunami (48:15–54:23)

• AI’s impact will define new generational norms, just as the internet did; for Gen Alpha, AI will be “like a friend,” providing companionship and advice.
  • “AI...is going to be one of those generationally defining things…AI to them is going to be more like a friend, like a trusted peer.” (48:47, Raven)
• Rodney’s analogy: AI is a tsunami—looks small now, but immense power is approaching, bound to reshape everything.
  • “AI right now is sort of like a tsunami...as it moves toward land, it gets bigger and faster and then it completely reshapes where it makes contact.” (50:21, Rodney)
• Urgency for future-ready skills: As AI automates knowledge tasks, only deeply human capabilities stand out.

10. Closing & Resources

• Raven shares where to find her work and webinars:
  • https://ravensolomon.com
  • LinkedIn: Raven Solomon
  • “Future Ready Fridays” monthly webinar
  • Upcoming course: “Generations Unlocked”

Notable Quotes & Memorable Moments

• On Audience Engagement:
  “I can see you…give me what you think I deserve in return.” (01:44, Raven Solomon)

• On the Legacy of Work:
  “Work extended a promise it has not fulfilled… Most of us were sold a line of about what work was going to do for us…” (10:16, Rodney Evans)

• On Inclusion as Strategy:
  “I don't think you can talk about the future of work without talking about inclusion. If you are, you are not talking about the future of work.” (21:03, Raven Solomon)

• On the Authenticity of DEI:
  “Gone are the days where you can just tell your team who you are. They want to see who you are. Right. And that is what they're going to follow.” (31:20, Raven Solomon)

• On Unlearning and Relearning:
  “The illiterate of the 21st century will not be those who cannot read or write, but it will be those who cannot learn, unlearn and relearn again.” (39:19, Raven Solomon quoting Alvin Toffler)

• On AI’s Implications:
  “There will be work that can be done with AI that is now being done by a human being…How do you start thinking about developing those future ready skills that are not replaceable by AI because AI can't heal?” (53:23, Raven Solomon)

Timestamps for Key Segments

• 01:00 – 04:05: Unspoken truths from stage about leadership and change
• 04:05 – 09:00: Generational divides and the need for unlearning
• 09:03 – 11:30: Empathy as a critical generational skill
• 11:30 – 15:27: Why younger generations are rejecting the old work promises
• 15:27 – 20:10: The shift to lifestyle design and redefining success
• 20:24 – 29:15: Inclusion defined pragmatically; demographic shifts and business imperatives
• 29:15 – 38:03: Authenticity, trade-offs, and real challenges in inclusion work
• 38:03 – 41:35: Personal discomfort, learning/unlearning, and leadership
• 41:35 – 48:15: The future-ready skills leaders need
• 48:15 – 54:23: AI as the defining feature of new generations; urgency for human skills

Conclusion

This episode is a rich, engaging exploration of generational change, the necessity for authentic inclusion, and the shifting ground of work amid technological disruption. Raven Solomon offers actionable insights for leaders seeking to future-proof their organizations and themselves—centered on humility, empathy, and the willingness to evolve. Rodney Evans grounds the conversation with candid stories and pointed questions, ensuring the episode remains accessible, practical, and highly relevant to anyone interested in navigating the future of work.