Talks on Vulnerable Leadership, Storytelling and Human Connection
Real Stories. Warm Laughs. Unforgettable Lessons
If your next event needs more than buzzwords and bullet points, you’re in the right place.
Jason Reid is a vulnerable leadership keynote speaker and award-winning storyteller, as well as a former journalist, news manager, and comedy writer, helping organizations lead and communicate with real humanity — not corporate jargon.
Drawing from decades of experience crafting stories for both the screen and the stage, as well as his career as a senior manager and inclusion advocate, Jason shows leaders and teams how to inspire action, build trust, and create lasting impact through the power of story.
If you’re planning a leadership conference, corporate event, or executive retreat, Jason’s story-driven keynote presentations will leave your audience energized, equipped, and ready to lead with heart.
This Might Get Awkward: Real Stories of Vulnerable Human Leadership That Worked
In a world obsessed with AI and perfection, what if your real leadership superpower… was being unapologetically human?
In this fast-paced, funny, and story-driven keynote, award-winning news manager, master storyteller, and former comedy writer Jason Reid flips the leadership playbook on its head. Forget polished perfection—Jason shows how vulnerability, honesty, and a little bit of awkwardness can unlock connection, trust, and serious results. Drawing from behind-the-scenes moments leading award-winning newsrooms and inclusion projects, Jason shares raw, hilarious, and powerful stories of real leadership including:
- How revealing his chronic illness doubled his team’s productivity.
- How a “ridiculous” idea turned into an award-winning news series that elevated an entire organization.
- How a simple conversation about a broken screw solved an intractable HR problem.
With the timing of a stand-up comic and the wisdom of an executive, Jason delivers a keynote packed with real talk, insight, and even bigger takeaways.
This keynote is packed with honest, often hilarious stories that cut through corporate jargon and get to the heart of what leadership really is: human connection.
In this keynote, Jason shares stories about:
- Why vulnerability is your leadership advantage.
- How awkward honesty builds unstoppable teams.
- Why the best ideas are hiding where you least expect them.
“Jason takes a deeper dive into the human side of things that greatly complements our work coaching leaders”.
Ethiopia Gultneh, Redfin
Jason’s casual and humourous style makes this perfect for a lunch, dinner or closing keynote.
The Art of Storytelling for Leaders
Build Trust. Inspire Change. Lead with Heart.
What separates a good leader from a great one? It’s not just strategy or skill—it’s the ability to tell the right story at the right moment. In this powerful keynote, award-winning journalist and leadership expert Jason Reid explores how authentic storytelling can transform workplace culture, build deep trust, and drive lasting performance.
Drawing from his own experience leading high-stakes newsrooms while managing invisible disabilities, Jason shows how vulnerable leadership isn’t a liability—it’s a superpower. Audiences will laugh, reflect, and leave inspired to lead more openly, communicate more clearly, and connect more deeply with their teams.
Key Takeaways:
- How storytelling unlocks trust, clarity, and engagement
- The hidden power of vulnerability in leadership
- A simple framework for crafting impactful leadership stories
- When and where to use stories to inspire your team
“Jason masterfully balances emotional depth with strategic communication.“
Greg Williams, The Master Negotiator
Caught In the Act: How A Little Drama Can Turn Moments into Momentum
If you want to inspire people to act, don’t just tell them a fact — show them a moment that moves them.
In this engaging and humorous keynote, award-winning storyteller Jason Reid breathes new life into one of Hamlet’s most famous scenes: the “play within a play” designed to catch a guilty king. With wit, insight, and a delightfully modern sensibility, Jason explores how this clever theatrical moment proves a timeless truth — the most powerful communication doesn’t just tell a story… it builds a scene that reveals deeper truths.
Using Shakespeare’s famously awkward moment as a launchpad, Jason shows how great leaders, salespeople, and visionaries don’t just inform — they create emotional experiences that spark action and leave lasting impact.
This funny, fast-paced keynote dives into the real magic behind influence: crafting moments people can feel, remember, and act upon.
Perfect for a lunch, dinner, or closing keynote, this talk blends humor, drama, and practical insights to inspire your team to communicate with more emotion, clarity, and unforgettable power.
Book this talk — and show your audience the moment where better leadership, storytelling, and communication begin.
“Hilarious, Educational and Fun!”
Ron Desmarais
Invisible Differences: Navigating the Last Mile to Belonging (Dynamic Theatrical Keynote)
What if the final barrier to true workplace belonging wasn’t visible at all?
Leadership experts Jason Reid and Kristin Light tap into their showbiz backgrounds to bring their signature mix of comedy, storytelling, and real-world insight to this unforgettable keynote experience.
Invisible Differences explores the unseen challenges employees face—like chronic illness, mental health, and neurodivergence—and how organizations can create cultures where people feel safe, supported, and genuinely valued.
Through a series of sharp, theatrical scenes, Jason and Kristin tackle:
- The hiring process and who’s left out
- How leadership culture shapes who rises
- The role of communication in building (or breaking) trust
It’s funny. It’s moving. And it gets people talking—in all the best ways.
Why it works:
Jason and Kristin don’t just talk about workplace challenges—they’ve lived them. Drawing on personal experience and decades of leadership, they show how being real at work isn’t a liability—it’s a strength. Their chemistry, candor, and deep expertise make this keynote a standout choice for any organization ready to go deeper in its conversations about difference, trust, and belonging.
“It resonated on a deep level. This eye-opening keynote has made me really reflecton my leadership style.” L. Crawford, Canadian Council ofMinisters of the Environment
“Incredible performance! Skits were an awesome way to handle sensitive subjects quickly and effectively. Great job!”
K. McKinley
CALA.ca
More Interested in Storytelling Workshops? Find out how Jason can help you tell better stories here.
Learn more about Jason’s leadership and storytelling journey here.