9 - Inside out or Outside In - Sukhinder Sing Cassidy on her book – Choosing Possibility – How to master risk and thrive

Sukhinder speaks about the myth of the hero’s journey that often goes along with several successful people. She also goes onto say that we think we make a few clean choices which drive our outcomes but it is a lot of the micro-choices that determine the shape of our journey. She speaks about some of the small choices and micro-risks that shape our destiny.

Sukhinder speaks about the fact that we often make decisions once we have sized up all the risks and rewards. She says that “take risk and iterate” approach beats “plan and implement” as a strategy. She says that people feel that risk taking begins when we make a choice. She goes on to say that taking risks will ensure that we end up with the right kinds of choices.

Sukhinder speaks about how she has built her self-awareness along the way. She goes on to say that she spends time figuring out “who she is” because what she wants often evolves along the way. She also speaks about the criticality of negotiating and having conversations with people around us to solve for the future that we want to go after.

Sukhinder speaks about her decade long journey with David Lesser and speaks about the different ways in which he added value to her. She speaks about the benefit of cumulative context that David had that helped him work with Sukhinder to reconcile various pieces over time and across her distinct identities.

Sukhinder speaks about her experiences working with Bill Campbell. She speaks about how he got her to be proud of her team and how he got she and her team to be proud of the “dirt underneath their fingernails” given what they were building at Google. She speaks about his unique brand of coaching which combined tough love with cheerleading.

Sukhinder speaks about her transition from Google to Accel as a CEO in residence post which she moved in as a CEO at Polyvore. She speaks about some of the challenges in establishing a healthy dynamic with the Founder and the Board and the criticality of values fit in addition to complementary of skills and capabilities.

Sukhinder speaks how one could possibly discern some of the elements around values fit while considering an opportunity at the very top. She speaks about how some of these could be unearthed in a conversation and how we could reference some of these from the ecosystem the leader operates in.

Sukhinder speaks about the notion of White spaces in an organization. These are the activities that are often at the interfaces of different functions and are often not captured in role descriptions. She says that very often people might be “green” in their respective roles but the project might be at a “red” in terms of status. She speaks about demonstrating and looking out for that behaviour as a leader wherever you are in the organization.

Sukhinder speaks about the scene from the movie where Nemo’s father catches the East Australian Current to get to Sydney quickly to rescue his son. She speaks about how we can look for some of the tailwinds that can turbocharge our career and how we can marry that with our understanding of ourselves as we think about our career.

Sukhinder speaks about how we should think about going Broad initially to explore different pathways and then once we know our sweet spot, we should think about going deep in a certain space. Eventually, she speaks about how we should consider going broad to leverage the distinctive capabilities we have built-in a certain area and apply it in different contexts. She also speaks about how women sometimes prioritize specialization overgeneralization and how that can sometimes come in the way of CEO / GM roles that require breadth.