Strategy: Resilient Leadership

30 September 2020 

This installment of our webinar series on strategy asked and answered key questions: From which internal resources do strategists draw when they repeatedly face failure? How does one keep their heads level in the face of insurmountable odds? How do leaders see things through? 


In this webinar, our CEO Jamie Dobson looked closely at resilience, tackling the following concepts.

  • Hardships. At age 26, Theodore Roosevelt, then a fast-rising political star, lost his mother and his wife on the same day. These events caused him to abandon long-term plans and instead adopt a fantastically adaptive mindset. In this webinar, we will look closely at this mindset.


  • Autodidactism. Abraham Lincoln loved learning—yet had a poor formal education. He  became a ferocious autodidact, which let him ‘learn on the fly’, fixing problems in real time. This journey, plus early setbacks, turned him into a giant capable of seeing through the most daunting tasks. 


  • Experimentation. Franklin Delano Roosevelt took office in 1933, the depth of the Great Depression. A willingness of the new leader to take risks and "fail fast" helped the nation begin to recover, and can inspire us to use what we know to build experiments to figure out what we don’t know. 


There is a relationship between hardships, autodidactism, and experimentation, which is captured in resilient leaders. In this webinar, we study how leaders are not born but made, then transformed through study, reflection, and experimentation—the three core capabilities of the resilient strategist.


  • Reflective self-accountability, a technique that can facilitate tremendous personal growth. 
  • Design of experiments.
  • Leadership selection and identifying resilient leaders.

Who should watch? 

  • Executives who may have had uncertainty thrust upon them and now need to build a path into the future.
  • Team leads who are developing their own resilience as their responsibilities expand.
  • Managers who may have hoped they could leave the soft, ‘icky’ stuff behind but are slowly realising they cannot


Meet the Speaker:


Jamie Dobson, co-founder and CEO of Container Solutions, a professional services company that specialises in Cloud Native transformation. With clients like Shell, Adidas, and other large enterprises, CS helps organisations navigate not only technology solutions but also adapt their internal culture and set business strategy. Jamie is the co-author of the new book Cloud Native Transformation: Practical Patterns for Innovation, published by O’Reilly. A veteran software engineer, he specialises in leadership and organisational strategy, and is a frequent presenter at conferences.