Workplace Weirdness™

Henna Pryor, keynote speaker with two TEDx talks and author of Good Awkward and the upcoming The Signal Gap (out November 10), joins host Maya Kadar Kovalsky to unpack why awkwardness at work is so hard to shake. 

Henna shares how growing up as the firstborn child of immigrant parents shaped her interest in fitting in, and explains the signal gap: the distance between the message you intend to send and the one a skeptical, “verify-first” audience actually receives. Together they react to a viral clip of a CEO who says he fired his HR department, with Henna arguing that the signal he meant to send (running lean) is not the one people are hearing. 

The conversation also covers how Henna made two career pivots by keeping one foot on the ground, why she dislikes the phrase "pick your brain," and how to ask for five minutes of someone's time. Henna answers a Reddit post from someone who wants acquaintances but not work friends, with tips on small talk.  Tune in to hear the most awkward elevator story that makes the workplace weird and learn how owning that awkwardness turned it into a connection. Stay Weird! 

Chapters:

00:00 – Intro: Why Workplace Awkwardness Is So Hard to Shake

04:15 – The Signal Gap: Intent vs. Impact in Leadership

11:30 – Viral CEO Reaction: When Internal Messaging Goes Wrong

18:45 – How to Make a Career Pivot Without Risking Stability

25:10 – Stop Saying "Pick Your Brain": Better Networking Scripts

31:20 – Small Talk for Introverts: Conversational Threading & Boundaries

38:50 – That Utah Elevator Story: Leaning into the Awkwardness

Resources and Links:

***Free for our listeners- the first chapter of Henna’s new book, The Signal Gap: https://www.thesignalgap.com/weirdness

The Official Workplace Weirdness Amazon Store: https://www.amazon.com/shop/workplaceweirdnesspodcast 

Henna Pryor:

· Website: https://pryoritygroup.com/

· Instagram: https://www.instagram.com/hennapryor/?hl=en

· LinkedIn: https://www.linkedin.com/in/hennapryor

Maya Kadar Kovalsky

· LinkedIn: https://www.linkedin.com/in/mayakadar/

Workplace Weirdness™

· Email: [email protected]

· Website: workplace-weirdness.com

· Instagram: @workplaceweirdpod

· Tiktok: @workplaceweirdpod

· Substack: https://workplaceweirdness.substack.com/

Join our YouTube community for exclusive content and more! https://www.youtube.com/@WorkplaceWeirdPod/community 

Disclaimer: The content of this podcast is intended for entertainment purposes only and should not be construed as professional, legal, or workplace-specific advice. Listeners are encouraged to seek guidance from qualified professionals for their individual situations.  

Return-to-office is making people lonelier, AI is changing the rules of leadership, and most companies are still getting the human part of work wrong. Maya Kadar Kovalsky and workplace strategist Erica Keswin break down what actually makes workplaces feel connected, productive, and worth showing up for.

Maya and Erica unpack why five days a week in the office is usually unnecessary, why some offices drain energy while others create real momentum and why intentional in-person days matter more than attendance for attendance’s sake.

Erica Keswin is a bestselling author and internationally recognized speaker focused on human-centered leadership, employee engagement, and the future of work. She is the author of Bring Your Human to Work, Rituals Roadmap, and The Retention Revolution, and her LinkedIn Learning courses on human leadership have been watched by more than 120,000 people.

Chapters:

00:00 — Why being in the office doesn’t guarantee connection

03:41 — Why “we’re like family here” can backfire

05:42 — Finding the office-day sweet spot

08:10 — Apprenticeship and why early-career employees value the office

09:23 — The research behind the Spaghetti Project

11:09 — The “magic question” for building workplace rituals

12:57 — Turning a daily habit into a meaningful ritual

15:05 — What leaders misunderstand about employee needs

17:25 — Staying human in the age of AI

19:24 — Why thank yous and feedback should stay personal 

Resources and Links:

The Official Workplace Weirdness Amazon Store: https://www.amazon.com/shop/workplaceweirdnesspodcast 

Erica Keswin:

· Website :https://ericakeswin.com/

· Instagram: https://www.instagram.com/ericakeswin/

· LinkedIn: https://www.linkedin.com/in/ericakeswin

Maya Kadar Kovalsky

· LinkedIn: https://www.linkedin.com/in/mayakadar/

Workplace Weirdness™

· Email: [email protected]

· Website: workplace-weirdness.com

· Instagram: @workplaceweirdpod

· Tiktok: @workplaceweirdpod

· Substack: https://workplaceweirdness.substack.com/

Disclaimer: The content of this podcast is intended for entertainment purposes only and should not be construed as professional, legal, or workplace-specific advice. Listeners are encouraged to seek guidance from qualified professionals for their individual situations.  

Welcome to Workplace Weirdness Season 3! 

Maya Kadar Kovalsky kicks off the season with a special guest, VAN JONES, a political commentator, social entrepreneur, CNN host, Emmy Award-winning producer, bestselling author, and founder of Dream Machine Innovation Lab and Rapport.  

Join a fascinating conversation about working across radically different environments, from the rules of working in the White House to Silicon Valley to the future of AI in the workplace. Van and Maya explore why psychological strength matters more than psychological safety and why the best managers need better tools to navigate a diverse, distributed, and divided workforce.

If you manage people, lead teams, or just want to understand how humans actually work together, this episode is packed with practical insight and motivation.

Chapters:

00:00 - Disagreeing agreeably

04:28 - Workplace slogans: Keep It, Kill It, or Fix It 

09:47 - Can we be apolitical at work?

14:41 - Psychological safety versus psychological strength

18:18 - The three D workplace: diverse, distributed, divided

19:55 - Why Rapport exists and what problem it solves

25:47 - Why managers need help interpreting people data

28:59 - Technology can bring out the worst in people

29:39 - Culture shock across different work environments

35:10 - The weirdness of living and speaking on live TV

39:20 - High-amplitude careers come with real lows

44:43 - Final thoughts on Rapport and a free consultation offer

Resources and Links:

The Official Workplace Weirdness Amazon Store: https://www.amazon.com/shop/workplaceweirdnesspodcast 

Rapport

· Website: www.rapport.co 

Offer to our listeners: A 30-minute leadership and talent development strategy audit.

Receive a complimentary, private 30-minute Leadership & Talent Development Strategy Session to uncover opportunities and sharpen your talent strategy.

Email [email protected] and mention "Workplace Weirdness Podcast”.

Van Jones

· Rapport Website: www.rapport.co

· Website: https://www.vanjones.net/

· Instagram: @vanjones68

· YouTube: @vanjones68

· Tiktok: @vanjones68

· Substack:https://vanjones.substack.com/

Maya Kadar Kovalsky

· LinkedIn: https://www.linkedin.com/in/mayakadar/

Workplace Weirdness™

· Email: [email protected]

· Website: workplace-weirdness.com

· Instagram: @workplaceweirdpod

· Tiktok: @workplaceweirdpod

· Substack: https://workplaceweirdness.substack.com/

Disclaimer: The content of this podcast is intended for entertainment purposes only and should not be construed as professional, legal, or workplace-specific advice. Listeners are encouraged to seek guidance from qualified professionals for their individual situations.  

Welcome to Workplace Weirdness: Work Drama, a new series where we break down the workplace chaos happening on screen, so hopefully you never have to experience it in real life.

In this special episode, we break down the hit Korean drama See You at Work Tomorrow, and explore the chaos, pressure, and quiet emotional survival of modern work life. 

Join Maya as she examines the tension between speed and quality, the burden placed on capable employees, and the dysfunction of a manager who rules through fear instead of leadership while enjoying a masterpiece of Korean television.

Whether you relate to Ji Yoon’s mission to leave on time, her quiet resistance to being overlooked, or that unexpected post-helicopter spark with Si-woo, this episode is packed with real takeaways for surviving the modern 9-to-5. Hit play to explore what it really costs to keep showing up, and how to protect your peace the moment you clock out. 

Don't forget to like, subscribe, and drop your thoughts in the comments: what’s the hardest boundary for you to set at work?

Chapters:

00:00 - Introduction & Korean Drama Setup

00:46 - The Premise of See You at Work Tomorrow 

01:34 - The Corporate Ladder & Team Dynamic 

03:00 - Gi-yoon’s Boundary: Leaving on Time 

04:15 - Fear-Based Leadership & High Expectations 

05:52 - Helicopter Crisis & Bonding with Si-woo 

07:12 - Burnout vs. Passion in Modern Work 

08:35 - Quiet Resistance & Self-Preservation 

09:48 - Final Reflections & Takeaways

Resources and Links:

Maya Kadar Kovalsky

· LinkedIn: https://www.linkedin.com/in/mayakadar/

Workplace Weirdness™

· Email: [email protected]

· Website: workplace-weirdness.com

· Instagram: @workplaceweirdpod

· Tiktok: @workplaceweirdpod

· Substack : https://workplaceweirdness.substack.com/

· Amazon Store: https://a.co/d/07aWiiPi

Disclaimer: The content of this podcast is intended for entertainment purposes only and should not be construed as professional, legal, or workplace-specific advice. Listeners are encouraged to seek guidance from qualified professionals for their individual situations.  

Work is weird - and these are the stories that prove it. From a possum trapped in the office to a naked neighbor derailing a meeting, Maya Kadar Kovalsky pulls the all-time weirdest, most cringe-inducing, and laugh-out-loud workplace moments from the last seasons and places them into The Workplace Weirdness™ Hall of Fame.

Join Maya and enjoy true workplace chaos, uncomfortable stories, and good laughs that make your worst day at the office feel completely normal. 

Because every 9-to-5 has a story to tell. Stay weird!

Chapters:

[00:12] Welcome to the Workplace Weirdness™ Hall of Fame

[01:05] An unwanted nighttime visitor in the office

[2:24] Free Tesla charging and breakfast

[2:53] Meeting Anthony Kiedis at the urinal

[4:16] A Bloody Mary gone wrong at 30,000 feet  

[5:08] The goodbye Heimlich

[6:07] The Bloody Interview

[7:51] Mysterious white powder…

[9:13] The drunk futurist 

[11:34] BBC conflict zone training gone weird

[13:48] The naked man on the rooftop

[15:10] Maya’s final thoughts 

Resources and Links:

Maya Kadar Kovalsky

· LinkedIn: https://www.linkedin.com/in/mayakadar/

Karen Bochert

· LinkedIn: https://www.linkedin.com/in/karenborchert

Menaka Chang

· Website: https://www.gofractional.com/member/menaka-chang

Neil Sharma

· Website: https://www.solarkal.com/

Ann Rhoades

· LinkedIn: https://www.linkedin.com/in/annrhoades

Nicole Ramirez

· LinkedIn: https://www.linkedin.com/in/nicolerayeramirez

· Website: https://nrdigitalconsulting.com/

William Tincup

· LinkedIn: https://www.linkedin.com/in/tincup

Dethra Giles

· LinkedIn: https://www.linkedin.com/in/dethragiles

· Website: https://www.dethragiles.org/

Kane Calamari

· LinkedIn https://www.linkedin.com/in/kane-calamari-53268014

Lucy Adams

· LinkedIn: https://uk.linkedin.com/in/lucy-adams-1058b5252

Paul McDowall

· LinkedIn: https://www.linkedin.com/in/paul-mcdowall-00b0b11

Workplace Weirdness™

· Email: [email protected]

· Website: workplace-weirdness.com

· Instagram: @workplaceweirdpod

· Tiktok: @workplaceweirdpod

· Substack : https://workplaceweirdness.substack.com/

· Amazon Store: https://a.co/d/07aWiiPi

Disclaimer: The content of this podcast is intended for entertainment purposes only and should not be construed as professional, legal, or workplace-specific advice. Listeners are encouraged to seek guidance from qualified professionals for their individual situations.  

In this episode of our Workplace Weirdness™ summer series, “Out of Office,” Maya Kadar Kovalsky discusses parental leave: the double standards parents face, the pressure to appear “serious” at work while caring for a family, and why parental leave parity matters for both moms and dads. 

Our notable guests discuss how parental leave intersects with identity, ambition, caregiving, and workplace culture, using candid stories to show how maternal and paternal leave policies and leadership behavior can either support families or quietly penalize them. 

The episode is a reminder that employees should never have to choose between starting a family and succeeding in their career.

Chapters:

[00:12] Why parental leave is really about identity, power, and workplace culture

[00:42]  Leave policies only matter if people feel safe using them

[1:07] The double standard: men praised for caregiving, women penalized for it

[2:02]  A pregnancy “stretch assignment” turns into a public demotion

[3:56] U.S. Parental leave system depends heavily on company policy

[4:23] Leadership behavior sets the tone for whether parental leave is acceptable

[4:50] Why parity in leave matters for both mothers and fathers

[6:14] The pressure on dads to return early

[6:41] How to request leave without apologizing for it

[7:09] Setting boundaries early so family time is non-negotiable

[7:38] Parenting and professional ambition should not be treated as opposites

Resources and Links:

Maya Kadar Kovalsky

· LinkedIn: https://www.linkedin.com/in/mayakadar/

Randi Braun

· LinkedIn:https://www.linkedin.com/in/randi-braun-312a5423

· Website: https://www.somethingmajorcoaching.com/about-randi

Peter Vincent

· Website: https://www.vincentcs.com/

Nicole Ramirez

· LinkedIn: https://www.linkedin.com/in/nicolerayeramirez

· Website: https://nrdigitalconsulting.com/

Workplace Weirdness™

· Email: [email protected]·

Website: workplace-weirdness.com

· Instagram: @workplaceweirdpod

· Tiktok: @workplaceweirdpod

· Substack : https://workplaceweirdness.substack.com/

Disclaimer: The content of this podcast is intended for entertainment purposes only and should not be construed as professional, legal, or workplace-specific advice. Listeners are encouraged to seek guidance from qualified professionals for their individual situations.

We sometimes feel that certain meetings could have been an email; yet in most cases we don’t have a choice. In this episode of our Workplace Weirdness™ summer series, “Out of Office,” Maya Kadar Kovalsky unpacks why poorly planned meetings can drain morale, hamper innovation, and signal a lack of respect for your team's time. 

Our expert guests share eye-opening insights, such as how unresolved conflicts in meetings cost billions annually and how practical frameworks for empathy and inclusivity across time zones can enhance team inclusion. 

Discover best practices that can redesign meetings from arbitrary routines into intentional, engaging experiences and transform meetings into powerful catalysts for collaboration and culture-building

 Ready to make meetings better? Tune in now!

Chapters:

[00:12] The problems with unproductive gatherings  

[00:40] The bigger picture: making meetings better, more creative, and more human

[1:09] Conflict in meetings: unresolved issues costing billions annually

[1:37] Why your meetings reflect your organizational culture

[2:05] Designing purposeful meetings with clear goals and pre-work

[2:34] The impact of post-COVID work culture on meeting frequency and quality

[3:04] How to get better at meeting facilitation: tools, goals, and human-centered design

[3:32] Emotional experience: making meetings feel valuable and engaging

[4:01] The power of personality and humor in meetings for building trust

[5:24] Managing time zone differences with empathy and transparency

[5:54] Practical approaches to inclusive meetings: acknowledging time zones and involving participants

[6:24] Strategies for making remote participants feel involved and valued

[6:51] Why meetings shape company culture and how to improve them

[7:20] Tips for creating engagement and making meetings worthwhile

[7:49] Takeaways: your meetings are an extension of your organizational culture

Resources and Links:

Maya Kadar Kovalsky

· LinkedIn: https://www.linkedin.com/in/mayakadar/

Dethra Giles

· LinkedIn: https://www.linkedin.com/in/dethragiles

· Website: https://www.dethragiles.org/

Hannah Dubin

· LinkedIn: https://www.linkedin.com/in/hannah-feldberg-dubin

· Website: https://www.thegroupforward.com/

David Homan

· Website: https://orchestratedconnecting.com/

Nicole Ramirez

· LinkedIn: https://www.linkedin.com/in/nicolerayeramirez

· Website: https://nrdigitalconsulting.com/

Billy Somoa Saleebey

· LinkedIn: https://www.linkedin.com/in/billysamoa

· Website: https://podify.com/

Workplace Weirdness™

· Email: [email protected]

· Website: workplace-weirdness.com

· Instagram: @workplaceweirdpod

· Tiktok: @workplaceweirdpod

Disclaimer: The content of this podcast is intended for entertainment purposes only and should not be construed as professional, legal, or workplace-specific advice. Listeners are encouraged to seek guidance from qualified professionals for their individual situations.

In this episode of our Workplace Weirdness™ summer series, “Out of

In this special summer-edition episode of Workplace Weirdness™, Maya Kadar Kovalsky sits down with Alan Philips, founder and CEO of The Marketing Department, to unpack the strange, powerful forces behind brand obsession, company culture, and how to create an influential movement. 

Alan shares his eccentric stories working with industry leaders and celebrities, from Mr. Beast to DJ Khalid at Reef Technology to the Golden Days of WeWork with Adam Neumann. 

Maya and Alan talk about building consumer brands, offering candid lessons on ego, authenticity, and the difference between momentum and real value. From the “architecture of a movement” to the rise and fall of ambitious startups, this conversation explores what makes people believe in a brand and what happens when that belief outruns execution. Alan also opens up about his current ventures, including Sunshine Coffee and What's Good Miami, and why building something meaningful in a specific place can be the foundation for lasting success.

Episode Chapters:

00:43 Inside WeWork's Rise and Fall

06:49 Trusting Yourself When Everyone Else Disagrees

11:17 Rapid Fire: Social media content creation is gold

13:18 Building What's Good Miami & Local Media

17:21 Reef Technologies, MrBeast Burger & DJ Khaled

23:23 Why Ghost Kitchens Didn't Last

25:14 Lessons on Branding, Leadership & Entrepreneurship

Resources and Links:

Alan Philips

· Sunshine Coffee: https://sunshinecoffee.com/

· What’s Good Miami: https://www.whatsgood.miami/

Workplace Weirdness™

· Email: [email protected]

· Website: workplace-weirdness.com

· Instagram: @workplaceweirdpod

· SubStack: https://substack.com/@workplaceweirdnesspodcast 

· TIkTok: https://www.tiktok.com/@workplaceweirdpod

Maya Kadar Kovalsky

· LinkedIn: https://www.linkedin.com/in/mayakadar/

Workplace Weirdness™

· Email: [email protected]

· Website: workplace-weirdness.com

· Instagram: @workplaceweirdpod

Disclaimer: The content of this podcast is intended for entertainment purposes only and should not be construed as professional, legal, or workplace-specific advice. Listeners are encouraged to seek guidance from qualified professionals for their individual situations.

In this episode of our Workplace Weirdness™ summer series, “Out of Office,” Maya Kadar Kovalsky shares her own bad boss story and revisits conversations with guests who have survived bosses of every variety, from the yellers, screamers, and office tyrants who throw things, to the masters of the backhanded compliment whose manipulation is far quieter, but no less damaging. 

The episode is a must-watch for anyone who has ever experienced emotionally unpredictable managers, toxic work environments, and the psychological toll of bad leadership. 

Chapters:

[00:12] Introductions with host, Maya Kadar Kovalsky  

[01:04] Toxic Leadership with Mita Mallick

[4:04] Toxic Male Bosses with Randi Braun

[6:29] Backhanded Compliments with Chester Elton

[7:55] Prototypical Bad Bass with Maya Kadar Kovalsky

[9:17] Fear Based work Culture Gary Ridge

[10:37} Reflections and Conclusion

Resources and Links:

Maya Kadar Kovalsky

· LinkedIn: https://www.linkedin.com/in/mayakadar/

Workplace Weirdness™

· Email: [email protected]·

Website: workplace-weirdness.com

· Instagram: @workplaceweirdpod

· Tiktok: @workplaceweirdpod

Disclaimer: The content of this podcast is intended for entertainment purposes only and should not be construed as professional, legal, or workplace-specific advice. Listeners are encouraged to seek guidance from qualified professionals for their individual situations.