What if the generational "mess" at work isn't just about age—it's about culture, communication, and what no one ever tells you on your first day?

In this revealing episode of Gen Mess with Tess, host Tess Brigham sits down with Tracy Ward, award-winning HR executive and corporate culture strategist, to unpack the real dynamics that shape our workplaces. Together, they dive deep into Tracy's unique journey from aspiring bioengineer to HR leader, and share eye-opening insights on why so many new employees feel lost—not because they're unprepared, but because companies forget to teach the "unwritten rules" that create true belonging at work.

Key Highlights:

• The hidden pitfalls of workplace culture that trip up new hires—and how to fix them before burnout sets in.
• Generational patterns at work: How Gen Z's desire for purpose, Gen X's "work first" mentality, and evolving attitudes toward boundaries and self-care are changing the way leaders need to engage and retain talent.
• Actionable ways to make your onboarding process more intentional, including assigning buddies, demystifying strange company jargon, and leveraging peer support.
• The critical importance of communication around employee benefits, and why reminding your team about available resources is an act of genuine care.
• Why relationships at work—not just salary or perks—are the #1 reason people stick around (or leave).
• Balancing business goals with creating sustainable, people-first workplaces—and the business case for happiness and trust.

Ready to clean up the gen mess at your own workplace? Tune in and discover practical strategies to create a place where every generation—and every individual—can thrive.

Resources: Find Tracy Ward and learn more about Forward Talent Strategies at www.forwardtalentstrategies.com, or connect with her on LinkedIn. And don’t forget: the path to a healthier, more vibrant work culture starts with one intentional conversation—maybe yours!

00:00 "Passion for HR Leadership Journey"

06:05 Onboarding: Organizational Responsibility Debate

08:53 Generational Shifts in Workplace Values

10:25 Empowered Employee Communication

15:45 Enhancing Employee Benefits Communication

18:45 Promoting Resources Through Accessibility

22:50 Workplace Bonds and Purpose

24:51 "Impact of Employee Turnover"

27:13 Leadership Change and Influence Struggles

33:03 Importance of Third-Party Trust

34:34 Balancing People and Profits

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What if your company’s employee benefits plan could be the secret weapon that keeps your top talent loyal—and even attracts new superstars through the door?

In this enlightening episode of Gen Mess with Tess, host Tess Brigham sits down with powerhouse employee benefits strategist, Sirena Dimas, to pull back the curtain on what really makes benefits matter in today’s rapidly changing workplace.

Key Highlights:

• Why company benefits aren’t just an expense—they’re an underused asset that could drive business growth and retention (and how to shift your mindset).
• Sirena’s unique journey from young mom to industry leader, and the “listening” skill that launched her success.
• The generational evolution of benefits: what companies (and employees!) wanted 20 years ago versus today, including a powerful look at the rise of mental health support and financial wellness benefits.
• Candid stories on multigenerational workplaces and families—like what happens when a Gen X, an elder Millennial, Gen Z, and Alphas all live together (hint: mediation skills come in VERY handy!).
• Practical tips for boosting benefit engagement—open enrollment meetings, digital resources, FAQs, and why communication must match each generation’s style.

Whether you lead a business, manage a team, or just want to understand how work culture is evolving across generations, this episode is packed with the wisdom (and real-world stories) you need to start fixing the Gen Mess—one conversation at a time.

Loved this episode?

• Share it with a manager or HR pro who wants to rethink their benefits strategy!
• Try a new way of communicating with your colleagues this week—see what clarity and connection you can create.
• Stay tuned and subscribe for more insights on navigating generational dynamics at work and at home.

Remember: Your benefits package and your people are your company’s greatest assets. Make sure everyone knows how to use them!

00:00 "Gen Mess Podcast with Tess"

03:27 Insurance: A Personal Journey

07:25 Consumer Mindset: Expense to Asset

11:19 Employee Financial Literacy Gaps

13:47 Navigating Employee Health Benefits

19:54 Children Witness Work Stress

22:39 Graduating in the '90s vs. '00s

25:28 Supportive Client Relationships

29:05 Hands-On Learning Beats Tech

31:20 Printer and Battery Misunderstandings

34:18 Parenting Approaches Across Generations

37:18 "First Speaker Buys the Product"

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What if your “common sense” approach at work is actually causing a generational divide you don’t even see?

In this thought-provoking episode of Gen Mess with Tess, host Tess Brigham sits down with leadership coach and author Rachel Burr for a refreshingly honest and practical look at why generational misunderstandings are so rampant in the workplace—and how leaders (and employees!) can finally start cleaning up the “gen mess.”

Key Highlights:

• The Circuitous Path to Great Leadership: Rachel shares her real, non-linear journey from clinical psychology into executive coaching—and how detours are often where true growth happens.
• The Emperor’s New Clothes in the C-Suite: Discover why senior leaders often stop hearing the truth from their people, and why intentional listening is the most overlooked tool for powerful leadership.
• Inside-Out Leadership: We explore what it means to show up as an authentic leader (regardless of personality type), and why “cookie-cutter” solutions always fall short.
• Generational Blind Spots: Dive into the biggest misunderstandings between Boomers, Gen X, Millennials, and Gen Z. You’ll learn how “common sense” is built on common experience—and why neither side is right or wrong.
• What Gen Z Really Wants (and Needs): Rachel shares what young professionals are seeking from their leaders—context, purpose, and the why behind what they do—and how these are human essentials, not generational demands.
• The Hard Truth About Transformation: Rachel’s new book, Butterfly Goo, challenges the Instagram myth that growth is glamorous. Real transformation is messy, uncomfortable, and never happens overnight.

Want to go deeper? Check out Rachel’s book, Butterfly Goo: The Down and Dirty Truth of Transformation, for raw, real stories and practical strategies for authentic growth.

Curious to break your own generational cycle at work? Start by sharing this episode with your team, and open up a real dialogue. Because cleaning up the gen mess starts with one honest conversation at a time.

00:00 "Humorous Memoir on Nonlinear Journeys"

06:18 Leadership Disconnection Challenges

08:40 Promotion Challenges Within a Team

11:35 Core Values and Leadership Identity

15:50 "Leaders Seeking Context and Purpose"

18:02 "Generational Experiences and Challenges"

23:00 Generational Perspectives on Change

24:38 Internalize Less, Respect More

28:36 The Challenge of Common Knowledge

32:14 Rethinking Success: Sink or Swim

34:33 "Emotional Intelligence and Management"

38:09 Shaming: Ineffective Leadership Strategy?

42:12 Bridging Generational Understanding

46:51 "Choose Your Own Transformation Adventure"

50:07 "Comfort Zones Limit Growth"

51:11 "Conscious Choice and Growth"

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What if fear isn't your enemy, but actually your greatest secret weapon?

In this powerful episode of Gen Mess with Tess, host Tess Brigham sits down with the dynamic Jacqueline Wales—TEDx speaker, author, coach, and all-around powerhouse—to unpack how fear runs (and often, ruins) our lives, across every generation. Jacqueline, whose inspiring journey includes overcoming childhood trauma, financial devastation, and a life rebuilt from scratch, reveals why “being fearless” is a myth—and why courage is really about making your next bold move in the face of fear, not its absence.

Key Highlights:

• Fear Exposed: Hear why Jacqueline calls fear a “strategic advantage”—and how to use it as fuel for your own growth.
• The Science of Fear: Gain crucial insight into the biology and stories your mind fabricates, including how fear operates on a subconscious and cellular level, and why most of our fears are based on imagined threats.
• Generational Mess: Explore why Gen Z is more risk-averse and anxious than previous generations, and what boomers get wrong (and right) about the next wave of leaders.
• Deceitful Thinking: Discover how “deceitful thinking” tricks us into believing self-doubt, procrastination, and perfectionism are facts—not just stories we’ve internalized over time.
• Real-Life Tools: From simply saying “thank you” to a compliment, to breaking through resistance and perfectionism, get actionable steps to flip the fear narrative in your daily life.

Ready to clean up your gen mess by turning fear into your fiercest ally? Listen in, challenge your old beliefs, and take bold steps toward the life you want. And don’t forget—stay curious, stay courageous, and stop letting fear run the show.

Connect with Jacqueline Wales:

• Website
• LinkedIn (search Jacqueline Wales)
• Email for the free 30-Day Fear Busting Challenge: jacqueline@jacquelinewales.com

Let us know how you’re using these lessons—share your breakthroughs and questions with us, and keep the conversation going. Until next time, own your power and don’t let the gen mess mess with you!

00:00 "Gen Mess Podcast: Fear as Advantage"

05:32 Confronting Fear and Self-Limitation

06:50 Struggles with Self-Worth

13:20 "Deceitful Thinking Explored"

16:28 "Growing Up in Unsettled Times"

17:57 "Personal Growth and Social Impact"

22:49 Fostering Understanding and Curiosity

26:41 "Embrace Self-Worth Over Validation"

27:51 Healing Emotions at Cellular Level

30:49 Reclaim Your Personal Power

34:38 "Horror Curiosity and Women's Voice"

37:16 Generational Workplace Expectations Clash

40:42 "30-Day Fear-Busting Challenge"

Hosted on Acast. See acast.com/privacy for more information.

What if your career achievements are actually the least memorable thing about you at work?

In this captivating episode of "Gen Mess with Tess," host Tess Brigham sits down with John Garrett, a former Big Four CPA turned stand-up comedian and award-winning keynote speaker, to dig deep into the messy world of generational workplace dynamics—and why bringing your whole self to work is your biggest asset.

Episode Highlights:

• The Surprising Power of Your “And”: John reveals how your outside interests—not just your job title—define who you are at work and are what people actually remember years later.
• From CPA to Comedian: Hear how John’s journey from cubicles to comedy clubs (and back again as a corporate culture guru) taught him lessons every leader should know about authenticity, connection, and communication.
• Authenticity vs. Professionalism: Why embracing your passions and quirks doesn’t mean sacrificing professionalism—and how leaders can balance both for a thriving workplace.
• Generational Differences, Demystified: Tess and John dive into whether Gen Z, Millennials, and Boomers really want such different things—or if we’re all just seeking belonging in our own way.
• Actionable Connection: The show unpacks research, real stories, and simple strategies to build rapport across generational divides and foster a workplace where people want to stick around.
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Continue the Conversation: Want practical tools, leadership trainings, or just a dose of fun inspiration? Check out John Garrett’s book and resources at whatsyourand.com and tune in for more real-talk every week here on "Gen Mess with Tess."

Remember: The Gen Mess gets cleaned up one authentic conversation at a time. So what’s your “And”—and how will you share it this week?

00:00 First Comedy Paycheck Surprise

04:46 Midwest Comedy Opportunities

07:26 "Comedy and Identity Merge"

10:07 Technical Skills Aren't Enough Anymore

16:10 "The Power of Speaking Out Loud"

17:29 Conversational Language and Comedy Confidence

21:28 Ego and Miscommunication Issues

23:40 Reevaluating Work-Life Balance

27:48 Redefining Success Across Generations

30:09 "Balancing Work and Personal Identity"

32:55 COVID's Impact on Mutual Understanding

38:39 "Workplace that Values Whole Self"

41:19 "Embracing Imperfection in the Workplace"

44:17 Intentional Time Between Work Hours

48:26 Vetting by Conversation

49:25 "Pug Passionate Conversations Thrive"

Hosted on Acast. See acast.com/privacy for more information.

What if the real reason your team is struggling isn’t just about generational clashes—but about whether your employees feel seen, heard, and valued at work?

On this eye-opening episode of Gen Mess with Tess, host Tess Brigham sits down with Dr. Ryan Warner, award-winning consulting psychologist, military leader, and Fortune 500 organizational strategist. Together, they dig beneath the surface of generational dynamics to reveal the hidden causes of workplace stress and conflict—and show you what truly builds inclusive, high-performing teams.

Key Highlights:

• Dr. Warner’s riveting journey from college athlete to military psychologist, and how his passion for health and wellness led to a global consulting career.
• Behind-the-scenes in the military: the surprising generational dynamics and why communication, not just hierarchy, drives team success.
• The truth about DEI (Diversity, Equity, Inclusion) in 2024: Why performative checkbox initiatives fail and how truly embedding inclusion into daily practice can transform organizations—regardless of what the headlines say.
• How real inclusion boosts productivity, mental well-being, and innovation—plus why addressing bias and building psychological safety are essential.
• Actionable advice for leaders who feel overwhelmed: Where to start, how to create more inclusive systems without piling on more work, and why even small changes (like feedback loops and cross-generational mentoring) can make a massive impact.

Connect with the Show: Visit TessBrigham.com or find Dr. Ryan Warner at rcwarnerconsulting.com to learn more about their work and upcoming opportunities.

Don’t let generational misunderstanding or outdated workplace practices hold your team back. Dive into this episode for real strategies—and start cleaning up your “gen mess” today!

00:00 Passion for Health and Education

05:06 Military Leadership and Entrepreneurial Journey

07:56 "Internship Insights and Career Paths"

10:35 "DEI Changes Spark Reflection"

14:24 "Addressing Workplace Generational Challenges"

19:13 Generational Bias in Organizations

23:26 Inclusion's Impact on Workplace Productivity

25:35 Balancing Work Culture and Leadership

27:50 "Mindful Leadership & Inclusion"

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What if everything you think you know about addiction and recovery is wrong? In this eye-opening episode of Gen Mess with Tess, host Tess Brigham sits down with Shirley Wantland, cofounder and principal of Recovery Consultants LLC, to dismantle the conventional wisdom around substance abuse, mental health, and healing. Shirley argues that no one is born an addict—and that true recovery comes from healing the inside, not just modifying behaviors on the outside.

Key Highlights:

• Inside-Out Healing: Shirley reveals why the traditional "outside-in" approach to recovery often fails—and how focusing on internal healing leads to lasting change.
• Generational Shifts: Delve into how Baby Boomers, Gen X, Millennials, and Gen Z view substance use, achievement, and even parenting differently. Shirley exposes the intense pressures younger generations face and how this is reshaping addiction trends.
• Social Media & Isolation: Discover the surprising role social media plays in driving both addiction and disconnection among young people, and the social skills crisis it’s fueling.
• Cannabis Culture Unpacked: Hear why today's parents need to be extra vigilant about cannabis use—even if their kids “seem fine”—and the long-term consequences of chronic use.
• Generational Challenges at Work: Shirley shares personal insights on managing multi-generational teams—why simple things like phone vs. text can be a minefield, and how leaders can foster inclusive, resilient workplaces.
• Radical Compassion: Why seeing the pain behind anger—and focusing on understanding, not just fixing—can transform how we support loved ones struggling with addiction.

Follow-Up with Shirley Wantland: Ready to dive deeper or need support? Visit recovery-consultants.com to book a free consultation, or connect on Instagram, Facebook, and LinkedIn for more insights.

Don’t let the ‘gen mess’ mess with you—listen, reflect, and join us as we turn understanding into action, one conversation at a time.

00:00 "Exploring Generational Dynamics and Recovery"

05:32 Holistic Addiction Recovery Approaches

08:32 Generational Parenting Shifts

11:05 Social Media's Impact on Self-Image

14:47 In-Person Mentorship Benefits

17:49 Overprotective Parenting and Weed Concerns

22:06 Cannabis-Induced Psychosis Concerns

23:47 "Embrace Risk in Love and Life"

29:29 Evolving Language and Inclusivity

33:04 "Employee Needs Beyond Money"

34:42 "Value Beyond Money"

38:41 "Understanding Addiction Beyond Disease"

41:12 "Understanding Anger's True Source"

43:48 "Generational Identity Revelations"

Hosted on Acast. See acast.com/privacy for more information.

Is Empathy the Missing Link in Bridging Generational Divides?

In this captivating episode of "The Gen Mess with Tess," we dive deep into the world of generational dynamics with Katherine Manning, an authority on leading with empathy when it matters the most. Ever wondered how understanding and transparency can shift the way generations interact in both personal and professional spheres?

Prepare to be enlightened as Tess and Katherine explore the crucial role of empathy in tackling generational challenges.

We’ll walk you through Katherine's inspiring journey from a hotline counselor at a domestic violence clinic to a pivotal advisor on high-profile cases like the Madoff scandal and the Boston Marathon bombing. Discover the universal truths she uncovered about our shared needs during times of trauma, and learn how these apply to everyday workplace struggles.

Key Highlights:

• Katherine shares her insights on the vital need for information and consistency during periods of upheaval, emphasizing the importance of communication in the workplace.
• The discussion delves into the generational perception gap on transparency, with Tess uncovering the reasons why Gen Z craves it more than ever.
• Real-life stories and anecdotes illustrate the power of curiosity as a gateway to empathy, offering practical approaches to fostering a culture where empathy thrives across all generations.

Join us as we clean up the Gen Mess, one conversation at a time. Stay curious, and let's transform the way generations connect and thrive together. Don't miss this enlightening discussion on building an empathetic workplace!

00:00 Legal Career Highlights and Insights

03:56 Craving Information During Turmoil

07:55 Transparency and Accountability Issues

12:50 "Trust Building in Firehouse"

13:50 Band Stage Requirements as Safety Checks

17:09 Evolving Work-Life Balance Perspectives

23:09 "Tackling Workplace Generation Gaps"

24:54 Empathy Hindered by Survival Instincts

28:47 Trauma as a Catalyst for Growth

30:27 "Empathy's Ripple in Workplace Culture"

36:01 Clarity and Consistency in Communication

37:51 "Effective Support Communication Strategies"

40:01 Empathy in Multigenerational Workforce

44:15 "Leadership Tips via Text"

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