Top 3 Takeaways from “Be Awkward”

Henna Pryor joined me to share highlights and wisdom from her new book Good Awkward: How to embrace the embarrassing, celebrate the cringe and become the bravest you. Over the course of this jam-packed hour we explored why awkwardness is having a moment, what we can do to embrace our awkwardness and why being awkward can actually make things, well, less awkward. 

Here are my personal takeaways from this lively conversation with Henna. Watch the full recording here.

  • Our Social Muscles are Atrophying… And That’s Not a Good Thing: With the rise in technology and the convenience it brings, we’ve started to lose our ability to connect smoothly socially. Small social interactions like ordering dinner, hailing a cab or knocking on a front door have been easily replaced by online bookings and text messages. Add to the mix a global pandemic, and the last three years have seriously challenged our casual social interaction muscle, making very minor situations feel weirdly awkward. Getting intentional about creating small connections – say hi to the cashier at the grocery store instead of opting for self-checkout, chatting with the person beside you at the bus stop, holding the elevator for someone – are all ways that we can polish up our connection skills. And, as leaders, we can get intentional about finding ways to bring our team members together to increase personal connection. 
  • Awkwardness Is an Inside Out Job: What makes you feel awkward might be different from what makes me feel awkward. Taking some time to reflect on what fears or beliefs may be playing into our self-talk about what we perceive as awkward situations helps us to recalibrate. Henna shared a powerful tip: when an awkward situation happens, instead of falling into the trap of “contamination” thinking, shift to “redemptive” thinking instead. For example, if you tend to struggle with putting out your ideas and blurted out an idea in meeting that fell flat (awkward!), praise yourself for taking the risk of throwing out the idea vs. beating yourself up for not having the idea land. 
  • Get Intentional About Being Awkward: We’re currently living in a world that is highly curated and where individuals are afraid to speak up for fear of being on the wrong side of a thought or argument. As organizations grapple with the need to become more agile, innovative and collaborative, leaders are going to need to get intentional about making awkwardness less awkward. Henna shared a quick technique to try: take 10 minutes at the start of a meeting to share really bad ideas. This cultivates the awkward muscle and normalizes the idea that there probably isn’t a “right” answer, so take a risk by throwing out the wrong ones. I once worked with colleagues who used to share their worst client experience of the week every Friday over drinks. It built camaraderie, accelerated learning and allowed members to normalize missteps vs. get stuck in negative thought patterns. 

This was another of these rich conversations that could have gone on for hours. Grab a copy of Henna’s book and learn more about how you can embrace your awkward to get more out of your career and life. 

And, thank you to all who expressed interest in our #Impact215 campaign in support of Indspire. Learn how you can get involved and help us continue our quest to fund 215 student bursaries for Indigenous youth. 

We’ll see you again on November 23, when I’ll be joined by Stephen ‘Shed’ Shedletsky who will be talking about his new book Speak-Up Culture. It’s going to be great and I look forward to sharing in the conversation with you! 



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