Leadership Keynotes

Lead The Moments Others Avoid

Jason Reid is a leadership keynote speaker, former Head of Content at The Weather Network, and is known for the concept of Awkward Leadership—a practical, memorable approach to building trust, communication and team performance in modern workplaces.

Drawing on his experience leading a national newsroom while navigating a chronic illness, Jason shares real stories of vulnerable, “awkward” leadership that led to measurable results.

Blending leadership insight, humour, and award-winning storytelling, Jason delivers keynotes that are grounded, relatable, and immediately useful for leaders navigating real-world challenges.

JUMP TO A TALK:

• Awkward Leadership
• Leading through Chaos and Change
• The Leadership Power of Storytelling
• Theatrical Keynote on Belonging

Jason Reid’s signature keynote on Awkward Leadership, trust, and team performance.

Most leaders try to avoid awkward moments at work. Jason Reid believes those moments are often where the best leadership begins.

In this engaging and unexpectedly funny keynote, Jason introduces Awkward Leadership—a practical approach to management that embraces uncomfortable conversations, honest storytelling, and moments of vulnerability.

Drawing from his experience leading a national television newsroom, Jason shares the moment that changed his team. At a national staff meeting, he spoke openly about his own invisible disability.

Instead of losing credibility, he gained something far more valuable: trust.

Soon, team members began sharing challenges of their own. Communication improved. Collaboration deepened.

Within a year, productivity doubled—and the department began winning major national and international journalism awards for the first time in its history.

Through humor, real-world leadership stories, and practical insight, Jason shows audiences how the moments leaders instinctively avoid are often the ones that build trust, strengthen culture, and unlock the full potential of a team.

Navigate difficult conversations, build trust quickly, and lead with more clarity and confidence.

What audiences will learn:

• Why vulnerability can strengthen leadership credibility
• How honest conversations build stronger, more resilient teams
• Why the moments leaders avoid are often the ones that build trust
• How to navigate uncomfortable conversations without losing authority
• Practical ways to lead with openness, courage, and humanity

Ideal for:
Leadership conferences, management teams, HR professionals, and professional or industry associations. Also great for new or emerging leaders and supervisors.

Format:
Works well as an opening keynote, lunch keynote, or closing keynote.

“Jason takes a deeper dive into the human side of things that greatly complements our work coaching leaders”.

Ethiopia Gultneh, Redfin

Jason Reid’s keynote on influence, communication, and leadership during uncertainty.

When change creates a leadership vacuum, communication is what fills it.

In this fast-paced and thought-provoking keynote, Jason Reid explains why moments of disruption are often the best opportunities to lead, particularly for people who know how to communicate with clarity, empathy, and vision.

Through stories from his career—navigating disruption in a national newsroom and even fronting a corporate rock band—Jason shows that leadership doesn’t come from titles. It comes from action, inclusion, and influence.

With vulnerability and wit, he explores what it means to lead without authority, inspire people through change, and build trust when the path forward isn’t clear.

Bring clarity to uncertainty, steady your team, and become the leader people turn to.

What Audiences will learn:

• Why communication is often the missing piece in change leadership
• How vulnerability builds trust and strengthens team performance
• The three traits leaders need most during uncertainty
• How change creates leadership vacuums—and how to step into them
• Practical ways to lead even when you don’t have the title

Ideal for:
Leadership conferences, emerging leader programs, professional associations, and organizations navigating rapid change.

Format:
Ideal for opening keynotes, leadership summits, and conference general sessions.

“He has a wonderful gift for storytelling and truly engaging his audience. Jason’s message was a powerful reminder to lead with heart and purpose.“

Jen Nepoose, CACE

Jason Reid’s keynote on communication, influence, and the leadership power of authentic storytelling.

Leaders don’t struggle with ideas—they struggle to communicate them in a way that actually lands.

Jason focuses on how leaders can cut through noise and say what actually matters, using storytelling to make complex ideas clear, relatable, and hard to ignore.

Make your message clear, memorable, and something people actually act on.

What Audiences Will Learn:

• How storytelling builds trust, clarity, and engagement inside teams
• Why vulnerability and authentic communication strengthen leadership credibility
• The storytelling principles great leaders use to make ideas memorable
• How stories help leaders inspire action and navigate change
• How great leaders use stories to connect people to purpose
  

Ideal for:
Leadership conferences, communication leaders, and organizations focused on culture and engagement.

Format:
Ideal for opening keynotes, leadership conferences, and communication-focused events.

“Jason masterfully balances emotional depth with strategic communication.“

Greg Williams, The Master Negotiator

What if the final barrier to belonging wasn’t visible at all—but lived in the leadership challenges we don’t talk about, or sometimes don’t even see?

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.

“It resonated on a deep level. This eye-opening keynote has made me really reflect on my leadership style.” Laura Crawford, Canadian Council of Ministers of the Environment

“Incredible performance! Skits were an awesome way to handle sensitive subjects quickly and effectively. Great job!”
K. McKinley
CALA.ca