Humor In The C-Suite

What does leadership look like when your boardroom is a remote jungle and your team is scattered across time zones navigating geopolitical complexity? For Lisa Pagotto, founder of Crooked Compass, it looks like authenticity, resilience, and a finely tuned sense of humor. In this episode of Humor in the C Suite, Kate Davis sits down with Lisa to explore how the principles that make Crooked Compass extraordinary — cultural respect, genuine connection, and bold decision-making — translate directly into a leadership philosophy that any leader in any industry can learn from.

Key Topics Covered

Lisa and Kate explore how humor functions as a genuine leadership tool in high-stakes, high-complexity environments — not as performance, but as a way of managing expectations, building trust, and keeping teams grounded when the terrain is genuinely unpredictable. They dig into the cultural intelligence required to know when humor works and when it doesn't — how some cultures welcome levity while others require a more measured approach, and why reading that distinction correctly is a core leadership skill. Lisa talks about how sharing mistakes and failures with humor makes her more relatable to both her team and her clients, and why that vulnerability is actually one of her greatest strengths as a leader. They also cover what Crooked Compass by Air taught Lisa about pivoting under pressure, how she leads a remote team with authenticity and openness, and why she believes the future belongs to those who dare to do things differently.

"Sharing failures or mistakes or errors and turning them into humor just makes it more relatable." — Lisa Pagotto

About Crooked Compass

Crooked Compass is a multi-award-winning experiential travel company specializing in immersive journeys to remote and lesser-known destinations across the globe. Every experience is designed to prioritize cultural integrity, authentic connection, and meaningful exploration — free from the constraints of mass tourism. Visit https://www.crooked-compass.com

Connect with Lisa Pagotto 🌐 Crooked Compass Website 📼 Youtube

Additional Links & Resources:

• Interested in being a guest on Humor in the C-Suite? Reach out to book a call with Kate!
• Learn more about me and my work at katedavis.ca

Thank you for tuning in to this episode of Humor in the C-Suite! If you enjoyed this episode, be sure to follow the podcast, share it with your friends, and leave a rating or review. Your support helps the podcast continue to grow. 

Hosted by Kate Davis
Edited by Chris @ Wider View Studios

What if one joke — sent on a Friday morning — could remind someone they matter? What if three words from a stage could stop someone from ending their life? Greg Kettner has seen both happen. In this episode of Humor in the C Suite, Kate Davis sits down with her old comedy circuit friend turned keynote speaker to explore the unexpected intersection of humor and mental health — and why the leaders who get this right are the ones their teams never forget.

Greg's Advice for Leaders

Start small and start safe. If you're nervous about using humor with your team, test it at home first — with your partner, your kids, your friends. Look to late night TV for clean material that's already been vetted. Send a funny Friday email. Share a meme. You don't have to be a comedian to show you have a sense of humor. And when it comes to mental health specifically: ask the question twice. "How are you doing?" gets you the polite answer. "How are you really doing? I've got time" — that's where the real conversation starts. That's where trust is built. That's where leaders earn the loyalty that no bonus structure can buy.

Additional Links & Resources:

• Interested in being a guest on Humor in the C-Suite? Reach out to book a call with Kate!
• Learn more about me and my work at katedavis.ca

Thank you for tuning in to this episode of Humor in the C-Suite! If you enjoyed this episode, be sure to follow the podcast, share it with your friends, and leave a rating or review. Your support helps the podcast continue to grow. 

Hosted by Kate Davis
Edited by Chris @ Wider View Studios

Episode Summary

What happens when the person who's been protecting everyone else forgets to protect herself? For Isabelle Tremblay, the answer was burnout so complete she couldn't draft a simple email. In this episode of Humor in the C Suite, Kate Davis sits down with Isabelle to trace the arc from 24 years of high-pressure global brand leadership to a full reinvention — and the role humor, empathy, and heart played in every part of that journey. This is a conversation about what it really costs to lead inside hustle culture, and what becomes possible when you decide to lead differently.

Key Topics Covered

Isabelle and Kate explore how humor was a cornerstone of Isabelle's leadership style long before burnout entered the picture — including the Two Truths and a Lie meeting exercise that consistently turned into genuine laughter and connection. They dig into how hustle culture systematically squeezes humor and humanity out of leadership, and what Isabelle wishes she'd done differently to protect not just her team but herself. Isabelle speaks candidly about how burnout eroded her ability to laugh — and how consciously rebuilding a humor-filled environment was part of her healing. They also cover why Isabelle believes humor is a genuine leadership superpower, how it moves leadership from transactional to human, and why authenticity and levity together create what she calls a love story in business. Kate brings in the broader cultural shift happening in leadership — more heart, less hustle — and why that's exactly what the next generation of employees is asking for.

"A leader's job is really to serve their team — so all of it, the authenticity, the humor, the transparency, will become a beautiful love story in business." 

Isabelle's Advice for Leaders

Keep humor authentic to who you are and always be respectful — never punch down, never make it about a person. The Two Truths and a Lie exercise is a simple, low-stakes way to bring playfulness into any team setting without pressure. Set boundaries not just for your team but for yourself — protecting only others while neglecting yourself is a fast track to burnout. And if the environment is truly toxic and damaging your health, give yourself permission to leave. Life is too short, and you have unlimited potential — at any age.

Connect with Isabelle Tremblay 🌐 Eyenovating  💼 LinkedIn

Additional Links & Resources:

• Interested in being a guest on Humor in the C-Suite? Reach out to book a call with Kate!
• Learn more about me and my work at katedavis.ca

Thank you for tuning in to this episode of Humor in the C-Suite! If you enjoyed this episode, be sure to follow the podcast, share it with your friends, and leave a rating or review. Your support helps the podcast continue to grow. 

Hosted by Kate Davis
Edited by Chris @ Wider View Studios

What happens in the silence when nobody laughs? That question sits at the heart of this conversation between Kate Davis and Scott Burgmeyer, founder and CEO of the Become More Group. Scott has spent over three decades moving through manufacturing, technology, HR, and consulting — and in all of it, he's learned that humor isn't decoration. It's infrastructure. Used well, it builds trust, opens people up, and makes it possible to have conversations that actually matter. Used carelessly, it collapses the very relationships it was meant to strengthen. This episode is about knowing the difference.

Key Topics Covered

Scott and Kate cover how humor functions as a pressure valve in high-stress environments and why that matters more than most leaders realize. They explore the five levels of trust and why humor only becomes truly available at levels three and four — when people feel safe enough to risk a little vulnerability. Scott speaks candidly about the loneliness that comes with being a CEO or business owner, the weight of decisions that affect people's livelihoods, and why humor can be one of the only tools that cuts through that isolation. Kate brings up dark humor in high-stakes professions — nurses, military, firefighters — and Scott digs into why it works, why it's powerful, and why it can never be targeted at a person. They also talk about how humor shifts depending on group size, how to use it to soften an uncomfortable message without losing credibility, and the critical difference between laughing at someone versus laughing about something.

Standout Quotes

"It's lonely as hell at the top. You're making decisions that impact the lives of everyone in the company — their families, their livelihoods. And who do you have to talk to?" — Scott Burgmeyer

"Your delivery is not allowing people to hear your message." — Scott Burgmeyer

"It's like going to the symphony and living in those moments of silence." — Kate Davis

"Take your work seriously. You don't have to take yourself too seriously." — Kate Davis

Scott's Advice for Leaders

Build a relationship first. Humor without trust is a gamble you'll often lose. Scott breaks trust down into five levels — and meaningful humor, the kind that actually opens people up, doesn't really become available until you're in levels three and four. Start small, test the waters, and pay close attention to how people respond. Know your audience — not because some people don't deserve humor, but because humor lands differently for everyone, and what works for one person can alienate another. And when it comes to dark humor specifically, it can be a genuine survival tool in high-pressure environments, but the moment it becomes targeted, it stops being humor and starts being harm.

Additional Links & Resources:

• Interested in being a guest on Humor in the C-Suite? Reach out to book a call with Kate!
• Learn more about me and my work at katedavis.ca

Thank you for tuning in to this episode of Humor in the C-Suite! If you enjoyed this episode, be sure to follow the podcast, share it with your friends, and leave a rating or review. Your support helps the podcast continue to grow. 

Hosted by Kate Davis
Edited by Chris @ Wider View Studios

What does summer camp have to do with building a high-performing workplace? According to Matt Kaufman — everything. In this episode of Humor in the C Suite, Kate Davis sits down with Matt to explore how the conditions that make camp transformational — safety, humor, vulnerability, and shared challenge — map directly onto what the best workplace cultures are built on. From managing 500 employees to raising a two-year-old at home, Matt brings a warm, scientifically grounded perspective on why joy isn't a distraction from great work — it's the engine of it.

Key Topics Covered

Matt and Kate cover a lot of ground in this conversation, touching on how humor functions as a neurological tool for reducing stress and building energy, why vulnerability is the foundation of trust — and how humor creates the conditions for it, the "X Words" morning meeting tradition that gets leadership teams laughing before the day even starts, the "Fun Professional" core value that Matt's team uses to hold the balance between culture and accountability, what teams that lack psychological safety look like from the outside, why former campers-turned-counselors always lean too far toward fun (and what to do about it), and the parallel between a runner's high and the endorphin-fueled energy of a great camp summer.

Standout Quotes

"I think people often think you have to look like you're not enjoying work. But the best employees I've ever worked with are having a good time when they're doing their jobs." — Matt Kaufman

"When you tell a joke, it's extremely vulnerable. And a first step towards building trust is to create vulnerability." — Matt Kaufman

"People have to feel safe before they can thrive." — Matt Kaufman

"Kids laugh 300 times a day. Adults laugh about 15. When do we lose that?" — Kate Davis

Matt's Advice for Leaders

Start small. When you're new to a team, use humor gently and build from there. As trust deepens, so does your ability to push the edges. Know your audience — humor that works in a tour for prospective parents won't land the same way in a hard conversation. And when humor misfires? Admit it fast, apologize genuinely, and move on. Nobody's perfect, and pretending otherwise only makes it worse.

The Books

The Summer Camp MBA — Ideal for anyone leading, hiring, or developing teenagers and young adults. Draws directly from camp management and culture.

The Campfire Effect — A broader exploration of what makes camp so transformational, and how those same principles apply to families, schools, and workplaces. This is the book for leaders, parents, and educators who want to build environments where people become the best version of themselves.

Both available on Amazon. Links above.

Additional Links & Resources:

• Interested in being a guest on Humor in the C-Suite? Reach out to book a call with Kate!
• Learn more about me and my work at katedavis.ca

Thank you for tuning in to this episode of Humor in the C-Suite! If you enjoyed this episode, be sure to follow the podcast, share it with your friends, and leave a rating or review. Your support helps the podcast continue to grow. 

Hosted by Kate Davis
Edited by Chris @ Wider View Studios

In this inspiring episode of "Humor in the C Suite," Kate Davis welcomes Bruce Mayhew, corporate trainer and author of the newly released book "The Path of an Inspired Leader." Bruce shares his journey from 11 years at Scotiabank (where he helped launch debit cards) to becoming a sought-after leadership trainer specializing in authentic communication and team building.

The conversation explores how Bruce uses humor strategically in leadership—not as performance, but as a tool for building genuine relationships that enable difficult conversations. His famous "Grease Wednesdays" story demonstrates how simple, authentic fun can dissolve departmental tensions and create lasting team bonds. Bruce emphasizes the importance of authenticity over forced humor, sharing practical strategies for leaders who want to incorporate levity while remaining true to their natural style.

Key Takeaways:

• Authenticity trumps performance when incorporating humor into leadership
• Building relationships through humor creates trust necessary for difficult conversations
• Simple team-building activities (like "Grease Wednesdays") can transform workplace culture
• Email humor should be used extremely cautiously due to misinterpretation risks
• Cultural sensitivity is crucial when adapting humor across diverse teams
• Leaders often fear humor after being "burned," but authentic fun is always accessible

Notable Quotes:

• "Humor helps us humanize each other. It allows us to understand each other, to see each other more than just a job or a coworker."
• "Be really careful that you're never laughing at somebody... but allow yourself to laugh, allow yourself to have fun."
• "Humor helps prime the pump beforehand so that when you have to have the difficult conversation, you can be serious."
• "Be authentic... don't be something you're not."
• "Find authenticity is really important... I still tried to be who I was."

Resources:

• Book: "The Path of an Inspired Leader: Authenticity, Courage, and Impact" - Available February 16, 2026. Available on: Amazon, Indigo, Barnes & Noble
• Bruce Mayhew Consulting
• Bruce's Instagram
• Connect with Bruce on LinkedIn

This episode offers practical wisdom for leaders seeking to build authentic relationships while maintaining professional effectiveness. Bruce's approach proves that humor in leadership isn't about being funny—it's about being human.

Additional Links & Resources:

• Interested in being a guest on Humor in the C-Suite? Reach out to book a call with Kate!
• Learn more about me and my work at katedavis.ca

Thank you for tuning in to this episode of Humor in the C-Suite! If you enjoyed this episode, be sure to follow the podcast, share it with your friends, and leave a rating or review. Your support helps the podcast continue to grow. 

Hosted by Kate Davis
Edited by Chris @ Wider View Studios

In this episode of "Humor in the C Suite," host Kate Davis takes a retrospective look at the year 2025 to extract key lessons about humor's role in leadership. Kate reflects on recurring questions from listeners concerning the effectiveness of humor in building strong workplace cultures and its impact on trust, collaboration, and productivity. With over 50 episodes behind her, Kate is poised to usher in 2026 with a strong emphasis on humor's role in creating synergy between labor, creativity, and human connection in corporate settings.

Key Takeaways:

• Humor Builds Trust: Humor is a fast-track to trust, enhancing collaboration and diminishing hierarchical barriers within the workplace
• Navigating Stress with Humor: By diffusing stress and challenges, humor acts as emotional oxygen that allows for constructive problem-solving without escalating tension
• Humanizing Leadership: Self-aware humor helps leaders connect with their teams, allowing employees to perceive them as approachable and relatable
• Creativity and Innovation: Playfulness fostered by humor encourages divergent thinking, creativity, and exploration of novel ideas
• Importance of Boundaries and Sensitivity: Understanding and respecting boundaries enhances humor's effectiveness, ensuring it is inclusive and respectful to all cultures and contexts

"Humor really is the fastest shortcut to trust. You can have a mission statement on your wall, but one shared laugh in a meeting does more for culture."

Additional Links & Resources:

• Interested in being a guest on Humor in the C-Suite? Reach out to book a call with Kate!
• Learn more about me and my work at katedavis.ca

Thank you for tuning in to this episode of Humor in the C-Suite! If you enjoyed this episode, be sure to follow the podcast, share it with your friends, and leave a rating or review. Your support helps the podcast continue to grow. 

Hosted by Kate Davis
Edited by Chris @ Wider View Studios

Host Kate Davis sits down with Bill G. Williams, affectionately known as Electric Bill, to explore the powerful role humor can play in transforming corporate culture. The conversation delves into Bill's personal journey, highlighting his struggles with perfectionism and self-acceptance rooted in his early experiences. Through humor, Bill has learned to embrace love over fear and build more profound connections within teams. His anecdotes and thoughtful insights illustrate how humor can be a catalyst for shaking teams out of complacency, fostering creativity, and enhancing collaboration.

Key Takeaways:

• Humor can shatter static routines and encourage a more engaged and creative work environment.
• Self-deprecating humor aids in self-acceptance and strengthens interpersonal connections.
• Humor fosters a safe, inclusive workplace culture that encourages team bonding and innovation.
• Effective use of humor in the workplace requires knowing and respecting colleagues' boundaries.
• Even in times of challenge, maintaining a humorous outlook can provide clarity and opportunity.

"I'm here to shock you out of your static daily routine." – Bill Williams

Resources:

• Website 
• Bill's Book: Electric Life

Additional Links & Resources:

• Interested in being a guest on Humor in the C-Suite? Reach out to book a call with Kate!
• Learn more about me and my work at katedavis.ca

Thank you for tuning in to this episode of Humor in the C-Suite! If you enjoyed this episode, be sure to follow the podcast, share it with your friends, and leave a rating or review. Your support helps the podcast continue to grow. 

Hosted by Kate Davis
Edited by Chris @ Wider View Studios

In this episode of Humor in the C Suite, host Kate Davis converses with Frank Brown, a respected business executive with a rich history in international markets. Frank shares humorous anecdotes and insightful lessons from his 43-year career that began with a chance job as a sales rep and culminated in his role as President of Wall Canada. His journey is filled with unexpected turns, wise advice, and a steadfast belief in the power of humor to enhance business culture.

Key Takeaways:

• Humor can be a powerful tool in fostering employee engagement, team collaboration, and relationship building within a corporate setting.
• Authenticity in leadership, coupled with genuine respect for employees, breeds a work culture where humor thrives and success follows.
• Transformational career growth can emerge from unexpected and challenging scenarios, emphasizing the importance of adaptability.
• Business isn't just about strategic acumen; it's also about connecting with people on a human level and making work enjoyable.
• The modern workplace is increasingly valuing individuality and authenticity, also reflected in the evolving cultural dynamics within organizations.

Notable Quotes:

"It took me a while to discover that humor was kind of a secret sauce or a key ingredient to success."

Resources:

• Book: How the Hell did I Become the Boss? 

Additional Links & Resources:

• Interested in being a guest on Humor in the C-Suite? Reach out to book a call with Kate!
• Learn more about me and my work at katedavis.ca

Thank you for tuning in to this episode of Humor in the C-Suite! If you enjoyed this episode, be sure to follow the podcast, share it with your friends, and leave a rating or review. Your support helps the podcast continue to grow. 

Hosted by Kate Davis
Edited by Chris @ Wider View Studios

In this engaging episode of Humor in the C Suite, Kate Davis interviews Steve Carey, a media industry veteran known for his unique blend of humor and expertise in launching media startups. With over two decades of experience, Steve shares his journey from starting as a coffee-fetching runner to becoming a successful producer and business owner, adding humorous anecdotes and insights along the way. Now living in Surrey, UK, Carey continues to contribute to the world of media with his witty and insightful writings, including his latest book exploring the lighter side of LinkedIn.

Key Takeaways:

• Humor is an indispensable leadership tool; it helps to relieve stress and build stronger team dynamics, particularly during challenging startup phases.
• Cultural differences can affect humor perception, with British humor often being dry and ironic, whereas American humor is more direct and expressive.
• LinkedIn provides ample material for humor, and Steve's book catalogs these experiences in a funny yet revealing manner, shedding light on the quirks of professional networking.
• Steve emphasizes the importance of self-deprecation in leadership, advocating for an approach that is careful not to alienate or undermine but instead unites and uplifts team members.
• Despite cultural differences, humor remains a universal language that can bridge gaps and foster a positive company culture.

"LinkedIn's like an uncle that you love but keeps doing questionable things."

Resources:

• Steve Carey's Book: "The New Dictionary of LinkedIn"
• Steve Carey's LinkedIn Profile

Additional Links & Resources:

• Interested in being a guest on Humor in the C-Suite? Reach out to book a call with Kate!
• Learn more about me and my work at katedavis.ca

Thank you for tuning in to this episode of Humor in the C-Suite! If you enjoyed this episode, be sure to follow the podcast, share it with your friends, and leave a rating or review. Your support helps the podcast continue to grow. 

Hosted by Kate Davis
Edited by Chris @ Wider View Studios