About Jason Reid:

Meet Jason Reid

The Awkward Leader

Jason Reid is a leadership keynote speaker who developed the concept of Awkward Leadership—the idea that uncomfortable human moments that leaders want to avoid are often the ones that build the most trust. And high-trust teams lead to great performance.

As Head of Content at The Weather Network, one of North America’s most trusted broadcast brands, Jason led diverse teams through rapid change and high-pressure environments — doubling productivity, sparking innovation, and helping his team win national and international journalism awards for the first time in the network’s history. 

Under his leadership, The Weather Network became a respected news and information brand. Jason’s clear communication and people-first leadership also led to successful leadership roles on multi-million-dollar media projects.

His leadership philosophy is simple but powerful:

Lead the Moments That Others Avoid.

Drawing on his own experience managing teams while navigating invisible disabilities, he shows organizations how authenticity, trust, and a willingness to embrace uncomfortable conversations can unlock engagement, collaboration, and unexpected performance inside teams.

Jason’s background in journalism, screenwriting, and comedy adds a strong storytelling layer to his work on awkward leadership.

His talks leave audiences laughing, reflecting, and ready to embrace the awkward.

Behind the scenes, Jason is also a speaker and storytelling mentor who helps leaders and subject matter experts communicate in a powerful way.

Jason is the author of Embracing Invisible Disabilities in the Workplace. The book explores how leaders can succeed in those awkward conversations that support neurodivergent and chronically ill employees, and build stronger teams.

The Awkward Leadership Moment that Changed Everything

The story below shows how Jason’s Awkward Leadership approach transformed the culture and performance of a national newsroom: When Jason took over as Head of Content at a national television network, the newsroom was struggling. Productivity was declining and morale was low.
At his first national staff meeting, Jason made a decision many leaders would avoid: he shared his invisible disability.
What happened next surprised him.
One by one, team members began sharing their own invisible challenges — from mental health struggles to neurodivergence and chronic illness.
That moment of honesty transformed the culture of the entire department.
Within a year, productivity had doubled, and the newsroom won national and international journalism awards for the first time in the network’s history.

The feedback we received on Jason was entirely and overwhelmingly positive. Our people loved the balance of anecdotes and concrete actions that they can immediately take away and use.

Melanie Bodi, Ontario Teacher’s Pension Plan

The event we did with you was such a success, our entire company is now putting more emphasis on how to address these types of people issues in the workplace. It’s being tied into our values and goals moving forward.”

Rebecca Mole, Tek Resources Ltd.

More than 80 percent of our members gave Jason’s keynote the highest rating possible.

Ryan Strang, Executive Director, Canadian Association of Communicators in Education

Jason has a lot of testimonials. This PDF includes six pages subdivided by industry. Simply click here.