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Jason Reid

Leadership Keynote Speaker | The Awkward Leader™

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Category Archives: Uncategorized

Jason Reid sharing Olympic leadership story about difficult conversations

The Olympic Leadership Mistake: An Awkward Conversation I Avoided

A leadership story from the Olympics about a small budget, a much larger partner, and the awkward conversation I should have had earlier.

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Jason Reid shares an awkward workplace story about a Facebook friend request and when leaders should stay out of employee conflict.

When Should Managers Avoid Stepping In

The closed office door suggested a serious conversation was coming. But was it a problem I should be addressing?

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Leadership speaker Jason Reid explains how vulnerability can improve workplace trust and team performance.

Can vulnerable leadership actually improve team performance?

Can vulnerable leadership actually improve team performance?
In my case, it helped me double my team’s output in less than a year.

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Jason Reid shares a funny workplace story about nearly knocking out his CEO during a team-building exercise and what leaders can learn from forced connection.

Why TeamBuilding Activities Sometimes Backfire

I once came dangerously close to knocking out my CEO during a team-building exercise. Funny in hindsight, but it raised a bigger leadership question: can trust actually be forced?

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Jason Reid shares a leadership lesson on why managers should avoid hiring people who think exactly like them.

Leadership Mistake: Hiring People Like Yourself

When I first became a manager, I wanted to hire people who thought just like me. Then my boss explained why that was one of the worst hiring instincts a leader can have.

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Jason Reid in The Awkward Leader video thumbnail about building workplace trust.

Dumpster Diving For Trust

I once climbed into a dumpster for an employee after making a management mistake. Oddly enough, that awkward moment ended up building far more trust than I expected.

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Jason Reid discusses how AI is changing job applications and hiring

Why Job Applications Feel Generic in the Age of AI

A lot of HR managers are getting upset about the AI-generated slop they’re receiving from job candidates.

But who’s really to blame? Stay tuned.

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Jason with the words: AI vs HR: Candidate Personality Tests

HR and AI – Candidate Personality Tests

Recently I talked to a sales person from a firm that offered AI personality tests to prospective job candidates so that organizations could filter the right people to hire. What do I think of that?

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How do you define great work?

What Does Great Work Look Like?

Are you a leader who wants consitently great work from your employees?
You may want to ask yourself a simple question first: What does great work actually look like?

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The Awkward Leader: It's not about you.

“It’s Not About You”: A Leadership Lesson from an Awkward Mistake

What do you do when you mess up in front of your team or a candidate?

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Jason Reid | Leadership Keynote Speaker on Awkward Leadership™
Building trust, communication, and performance in the moments leaders often avoid.
Keynotes on leadership, difficult conversations, team trust, workplace culture, and navigating change.
Based in Toronto. Speaking across Canada, the U.S., and internationally.

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or email Jason (at) jasonreid.ca

You can also find Jason here

  • Invisible Disability Speaker – chronicillnesskeynotespeaker.com
  • Reid & Light – Neurodiversity and Belonging
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