The Awkward Leader Video Series

“The moments leaders avoid are often the ones that build the most trust.
And when trust improves, performance follows.”

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  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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  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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  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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  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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  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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  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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  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.
• 
  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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  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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  What is Awkward Leadership? [sticky]
  People often ask me, what I mean when use the phrase “awkward leadership” If you’ve wondered that yourself – this is for you.

For our full archive you can visit our

Jason Reid is a former manager, journalist and sought after leadership keynote speaker . For more information on Jason’s availability or to request a new topic in his Awkward Leader Series, you can use the button below.

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