Leadership Keynotes
Keynotes for Leaders Navigating Difficult Human Moments
The moments leaders avoid are often the ones that build the most trust. And when trust improves, performance follows.
Lead the Moments Others Avoid
Jason Reid is a leadership keynote speaker, former Head of Content at The Weather Network, and creator of Awkward Leadership™—a practical framework for navigating the difficult human moments that shape trust, communication and team performance.
Through real leadership stories, humour and decades of communication experience, Jason helps leaders recognize what happens when people avoid, dismiss or assume—and decide when to move toward the moments that matter.
His signature keynote, This Might Get Awkward, brings these ideas to life in a memorable, story-driven presentation for people who lead humans under pressure.
Explore the presentations
- Signature keynote: This Might Get Awkward
- Leading Through Chaos and Change
- The Leadership Power of Storytelling
- Workshops & Leadership Development
Trusted by organizations including Bell, TD, the U.S. FDA, Coinbase and professional associations.
This Might Get Awkward
Leading the Moments Others Avoid
Signature keynote | Awkward Leadership™
Some of the moments that most affect a team are easy to overlook: the difficult conversation postponed, a concern brushed aside, an assumption no one questions, or the uncertainty a leader tries to manage alone.
These are not always failures of skill. Often, they are ordinary human responses to discomfort. Jason calls this the Hiding Instinct: when things get awkward, we protect ourselves by avoiding, dismissing and assuming.
In This Might Get Awkward, Jason uses humour, memorable stories and real leadership experience to help audiences recognize these patterns and think differently about what leadership requires in difficult moments. It is not about chasing discomfort or having every uncomfortable conversation. It is about understanding when silence, hesitation or a quick assumption is quietly shaping trust and performance.
Jason shares how a vulnerable decision while leading a national television newsroom changed the way his team communicated. When people began speaking more openly about the barriers they faced, problems surfaced sooner and trust grew. Within a year, department productivity doubled, and the team won national and international journalism awards for the first time in its history.
The keynote gives leaders a practical way to notice the moments others avoid—and exercise the judgment to respond well.
What audiences take away:
- How the Hiding Instinct appears in everyday leadership.
- How avoidance can let tension and problems quietly grow.
- Why dismissing concerns too quickly can stop people from speaking up.
- How untested assumptions can limit decisions and possibilities.
- How to judge when to intervene, ask a better question or give people room to work things through.
- Why trust and accountability work better together.
Ideal for: Leadership conferences, management teams, HR audiences, professional associations and organizations navigating change or uncertainty.
Format: Opening, featured or closing keynote.
“Jason takes a deeper dive into the human side of things that greatly complements our work coaching leaders.”
Ethiopia Gultneh, Redfin
Other Leadership Keynotes
Additional presentations for events with a particular focus on change, influence or communication.
Leading Through Chaos and Change
How to Lead Even if You Don’t Have the Title
A keynote on influence, communication and leadership during uncertainty.
When change creates a leadership vacuum, communication is what fills it. Jason explores why moments of disruption create opportunities to lead, including for people who do not have formal authority.
Drawing on disruption in a national newsroom and his experience fronting a corporate rock band, Jason shows how clarity, empathy, initiative and communication can help people influence what happens next.
What audiences will learn:
- Why communication is often the missing piece in change leadership.
- How trust supports people during uncertainty.
- 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: Opening keynote, leadership summit or conference general session.
“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
The Leadership Power of Storytelling
Say What Matters. Make It Stick.
A keynote on communication, influence and storytelling.
Leaders don’t struggle with ideas—they struggle to communicate them in a way that actually lands. Jason draws on his career in broadcast storytelling to explore how leaders can cut through noise and make complex ideas clear, relatable and memorable.
What audiences will learn:
- How storytelling supports trust, clarity and engagement inside teams.
- Why authentic communication strengthens leadership credibility.
- Storytelling principles that make ideas memorable.
- How stories help leaders inspire action and navigate change.
- How to connect people to purpose through a clear message.
Ideal for: Leadership and communication conferences, and organizations focused on culture and engagement.
Format: Keynote or conference general session.
“Jason masterfully balances emotional depth with strategic communication.”
Greg Williams, The Master Negotiator
Beyond the Keynote: Workshops & Leadership Development
Awkward Leadership™ can also be explored through interactive sessions that give leadership teams time to apply the ideas to their own situations. These are available as stand-alone engagements or as practical follow-ups to a keynote.
The Rescue Loop: Why Even Good Leaders End Up Taking Over
You delegate responsibility to capable people, give them room to work, and focus on your own priorities. But small problems can drift until they become urgent, and suddenly taking over feels like the only option. Then the cycle repeats.
Using a memorable ship-and-iceberg analogy, this interactive workshop explores how to spot drift earlier, create visibility without micromanaging, address problems without automatically taking ownership, and debrief constructively when intervention really is necessary.
Best suited to: People managers, senior teams, leadership retreats and conference breakout sessions.
Format: Interactive breakout or customized organizational workshop.
Companion article: Why Do Even Good Leaders End Up Taking Over? The Rescue Loop.
Emerging Leader Development
Build judgment, trust and influence before the title catches up.
Practical development for new and emerging leaders learning how to navigate the human side of leadership. Jason helps participants ask better questions, understand organizational context, build trust through difficult moments, and create evidence that they’re ready for greater responsibility.
Format: Interactive workshop or multi-session development program, tailored to the organization and experience level of the group.
Why Organizations Book Jason
- A distinctive, memorable idea: Awkward Leadership™ gives audiences a new way to think about trust and performance.
- Leadership experience: Real stories from a high-pressure national newsroom.
- Engaging delivery: Humour, communication experience and practical ideas without a training-lecture feel.
- Strong audience fit: Leadership, HR, professional associations and teams navigating change.
- Planner confidence: A collaborative, low-maintenance approach to events.
- Stage and screen experience: Confident virtual and in-person delivery backed by a broadcast career.
Looking specifically for storytelling training? Explore Jason’s storytelling workshops.
Planning a Leadership Event?
If you’re looking for a keynote on trust, communication and the moments leaders tend to avoid, let’s explore whether Jason’s work is a fit for your audience.