Dare to Lead – Leadership Questions

Screenshot 2019-07-06 at 1.52.07 PM

The second book in our the Leadership Book Club (2019) was Dare to Lead by Brene Brown. As we were finishing the book, Brene’s Netflix special – ‘the Call to Courage’ came out, which is a must see if you don’t have time to read the book!

As promised, here are some questions to spark conversation – feel free to use with your own book club group, and/or engage in the discussion below in the comments section:

  1. Have you ever struggled or avoided tough conversations, including giving or receiving honest productive feedback? When? Why?
  2. Do you have an example in your career of a time when a leader spent time proactively addressing fears/feelings? Did it make you feel differently about your employment and career? Alternatively – do you have an example of the opposite?
  3. Share some examples of leaders actions that created trust, and/or destroyed it in your experience? What makes you feel connected to your team and/or leaders?
  4. How can/would you, as a leader, encourage and facilitate room to take smart risks and share bold ideas in your own team? What would be some of the roadblocks & how could you mitigate these?
  5. Have you experienced shame in your career? Or have you witnessed shaming activities of others? How can you be a leader of integrity and address this in your workplace?
  6. Have you ever avoided conversations (such as those on diversity) because you fear you will say something wrong? Do you believe we should choose hard conversations over comfort in all situations?
  7. Does your current organization integrate their values into behaviors that can be taught, measured and evaluated? If not, how could they?
  8. Who are the people in your life, whose opinions really matter? What’s one commitment you can make to strengthen these connections?
  9. How would you define vulnerability? How does it show up in your life?
  10. Which forms of ‘Armoured Leadership’ are you most prone to? (pg. 76)
  11. What are your two main core values? (pg.189) What actions support these at work?
  12. Does your workplace struggle with gossip? What actions can you take to resolve this?
  13. What boundaries have you set in your career (what is ok; what isn’t)?
  14. Which masking emotions do you usually lean on (withdrawal, pleasing, anger)? Are there specific actions you have noticed that trigger these responses from you?
  15. Do you think there are ever leadership scenarios where vulnerability is not the right tactic?


<<Next up: Never split the difference by Chris Voss. I hope you join us!>>

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Herding Tigers – Leadership Questions


The first book in the Leadership Book Club (2019) is Herding Tigers: Be the Leader that Creative People Need by Todd Henry.  If you haven’t already picked up a copy and devoured the contents, you need to pronto! This book is one that will stay on my shelves for reference.

As promised, here are some questions – feel free to use with your own book club group, and/or engage in discussion below in the comments section: Continue reading

Leadership Book Club (2019)


A couple months ago, while curled up leisurely reading in front of a roaring fire, with my bestie at Nordik Spa (here in Ottawa) – an unexpected conversation launched with two other spa-goers inquiring about the books we were reading.

There was laughter. There was insight. It was awesome.

I left feeling more connected, uplifted, and motivated – longing to keep that sort of energy going, I posted on social media about wanting to start a Leadership Book Club.

Continue reading