The moments leaders avoid are the ones that build trust.

Jason Reid is a keynote speaker known for Awkward Leadership, an approach that focuses on the moments leaders instinctively avoid—and how those moments shape trust, communication, and performance.

Why Awkward Leadership Builds High-Trust Teams

The difference between an average team and a great one is discretionary effort. It’s the extra energy, creativity, and commitment people give when they feel trusted and supported.

Leaders don’t command this effort. They earn it through trust. And trust is often built in the moments that feel uncomfortable.

1. Trust begins with saying what other’s wont.

People don’t respond to corporate jargon and slide decks. They respond to clarity, honesty, and emotional truth. That’s why great leadership communication goes beyond sharing information. It creates connection – and that builds trust.

Storytelling helps leaders create that connection, especially when the message is difficult or uncomfortable to deliver.

2. Trust unlocks ideas and initiative.

When people feel trusted, they speak up sooner, share ideas more freely, and collaborate more effectively.

That shift often starts when leaders are willing to ask honest questions, admit uncertainty, or address issues directly—moments many would otherwise avoid.

3. Trust creates future leaders.

When you lead with empathy, clarity, and trust, you set a standard others want to follow. You create space for people to step up, take initiative, and lead in ways that drive real results.

This is the leadership principle behind Jason Reid’s keynote on Awkward Leadership.

Jason Reid is a leadership keynote speaker serving organizations across Canada and the United States.

The Awkward Leadership Moment That Changed Everything

Jason took over a busy newsroom where productivity had been declining for months. Then he made a leadership decision most managers avoid: he talked about his own challenges. What happened next surprised him. Half his team opened up about their own issues and together they removed the barriers holding them back. Within one year, productivity doubled. It wasn’t pressure that changed the team. It was trust.

“I could listen to Jason for hours.”

Charmainne King, Brand Manager
Kellanova

Jason has been trusted by leading organizations and agencies across the globe.

What Audiences Learn:

After Jason Reid’s keynotes, audiences walk away with practical ideas they can use immediately:

• How to build trust faster—especially in the moments that feel uncomfortable
• How to handle the leadership conversations most managers avoid
• How to communicate in ways that create real connection and influence
• How to unlock discretionary effort and initiative inside teams
• How to lead more effectively through change and uncertainty

Looking for Jason’s programs on invisible disability and neurodiversity in the workplace? Go here.

Why Organizations Book Jason Reid

• A clear, memorable leadership idea: the moments leaders avoid are often the ones that matter most
• Real stories from leading a national newsroom—not theory
• A balance of insight, humor, and practical application
• Content that resonates across different roles, industries, and experience levels
• A collaborative, low-maintenance approach—no drama, no surprises
• Strong virtual and in-person delivery backed by broadcast experience

Looking for a keynote that will challenge how your leaders think—and give them something they can actually use?