By Jason Reid –Vulnerable Leadership, Storytelling and Human Connection
Recently, I did something that made me cringe: I sent the wrong video link in a batch of important conference submissions.
Yes, the guy who makes a living teaching strategic storytelling and leadership forgot his own setup. (Cue the facepalm.)
But instead of pretending I’d done the right thing all along, I did what I always encourage leaders to do—I leaned into the awkwardness. I owned the mistake, sent a follow-up email with the correct link, and smiled through the mild embarrassment.
It felt a little uncomfortable.
It also felt completely on-brand.
After all, the keynote I was submitting is literally called:
This Might Get Awkward: Real Stories of Vulnerable Human Leadership (That Worked)
Why Awkwardness Is a Leadership Superpower
Over the past decade, I’ve spoken around the world about invisible disability inclusion, team dynamics, and human leadership. Along the way, I noticed a recurring theme in all my most powerful leadership stories:
- They started with an awkward or difficult human moment.
- They required me to be vulnerable in that moment.
- And they led to some of the most impactful leadership lessons of my career.
Take it from someone who once burned out in a toxic newsroom and later doubled productivity by being honest about his chronic illness—awkward honesty works. It builds trust, creates connection, and makes you real.
The Problem With Polished Leaders
I’ve worked with many leaders who were determined to come across as perfect. But here’s the irony: their pursuit of perfection often made them seem cold, arrogant, and ultimately untrustworthy.
Because let’s face it—if your team believes you’re more concerned with saving face than doing what’s fair or addressing tough issues, there’s only so far they’ll go for you.
We don’t follow flawless leaders.
We follow human ones.
Vulnerability Isn’t Weakness—It’s Leverage
In my keynote, This Might Get Awkward, I share real-life stories from my time leading national newsrooms, managing inclusion projects, and navigating invisible disabilities in leadership roles. Stories like:
- How revealing my illness doubled team productivity
- How a “ridiculous” idea turned into an award-winning news series
- How a 10-cent screw solved a complex HR issue everyone had overcomplicated
The stories are raw, real, and a little awkward. And that’s the point.
Want to See the Video I Meant to Send?
If you’re curious to see the actual highlight reel I forgot to attach (yes, this blog post is part confessional), here it is:
And if you’re a conference organizer, HR leader, or event planner looking for a keynote that blends laugh-out-loud stories with strategic insight—one that gets real about what it takes to build trust, drive performance, and lead with authenticity—let’s talk.
Final Thought
We all make mistakes. We all have awkward moments. But when we stop hiding from them and start using them, that’s when leadership becomes transformational.
Because awkward leadership isn’t just relatable—it’s powerful.