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Book Group Discussion Questions

1. Share an example of someone you know personally who you consider to be a great leader. (For example: a parent, grandparent, teacher, coach, boss, co-worker or colleague.) 


What is it about that person’s leadership you admire?

2. Thinking over Shackleton's story, which moments of great leadership particularly stand out to you?



3. Shackleton led by example, According to his crew, he never asked anyone to do something that he wasn’t willing to do himself.


Share an example of someone you have seen lead by example.



4. Shackleton communicated effectively with his team. At every crisis, he called everyone together so they would hear about the situation directly from him.


What impact can brief, straightforward messages from a leader have?


What is the result when such communication during a crisis is lacking?



5. Forty years after the Endurance expedition, a crew member recalled the Boss was “very friendly and easy to talk to.” Everyone had a personal connection with Shackleton.


What is the importance of such a direct connection?


How would you open, or limit, the lines of personal communication with your team?



6. Shackleton worked hard to keep up morale. A tent mate recalled, “He realized fully the enormous and almost instantaneous effect of food on the morale and took all kinds of trouble to vary the ration or try some new way of cooking things, to issue a little tidbit to commemorate something, a birthday for example, or some other anniversary.”


What gestures do you think are most appreciated in building morale and camaraderie in a team?



7. A crew member said of Shackleton, “He didn't care if he went without a shirt on his own back so long as the men he was leading had sufficient clothing.” When Hurley lost his gloves on the boat journey to Elephant Island, Shackleton tore off his own gloves and insisted Hurley take them.


Have you experienced a leader like that?


What might be the equivalent of that action in our world?



8. In Shackleton’s account of the Endurance expedition, he wrote, “A man must shape himself to a new mark directly the old one goes to ground.”


How might this apply in business or personal goals today?



9. Shackleton said, “I have often marveled at the thin line which separates success from failure.”


What lessons can we learn from failure?



10. Through tremendous difficulties, Shackleton maintained a positive attitude.


How do you think this affected his crew's chance of survival?


What strategies can you use to maintain a positive attitude in your life?



11. Shackleton often used psychology on his crew members to ease their stress, such as putting the most nervous among them in charge of supplies or convincing his exhausted crew members that they had slept much longer than they had.


What strategies do you use to keep mentally fit under stress and to help those around you?



12. Shackleton was a master of leadership in crisis. During the worldwide pandemic, what were the examples of leadership you most admired and why?

13. Have you ever wanted to write a book? The process of writing Shackleton's Way began with a 36-page outline that served as a map for the project.



14. Brainstorm with your group strategies to:


  • Lead by example

  • Communicate effectively

  • Keep up morale

  • Maintain a positive attitude

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