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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13 thoughts on “Dare to Lead – Leadership Questions

  1. I just finished listening to the audio version and I have a book club discussion with my work colleagues later today. Thanks for the the questions so i have an idea for some topics of discussion!

    I particularly like #3 Share some examples of leaders actions that created trust; brought me back to when a new mgr approached me and asked abt myself and what I want to aspire to, made me feel seen for once. After listening to Brene i made that conncection that it was in that moment that she earned a marble 🙂

    Liked by 1 person

    1. You’ll have to let me know how the discussion goes! So glad to have helped. Your story about you manager helping you feel seen really resonated with me – easy but meaningful 15 minutes can change everything. Sharing that was a marble moment for me as well 😉

      Liked by 1 person

      1. Hey Laura, just an update that sadly i didnt get the chance afterall to join onto the book club conference call because the queue were super busy (i work in a call center)
        But thank you again for the mini book club reflection 😉

        Liked by 1 person

  2. Really great questions, thanks for sharing. As there as several definitions of leadership it is interesting to focus on some actions linked to the manifestation of leadership in organization, it makes it concrete. On leadership I also like the book « True North » from Bill George which is interesting to develop an authentic leadership.

    Liked by 1 person

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