From CIA to CEO: Leadership Lessons with Rupal Patel

Rupal Patel is a former CIA analyst turned international speaker and corporate consultant. She is the author of the international best-seller, “From CIA to CEO: Unconventional Life Lessons For Thinking Bigger, Leading Better, and Being Bolder.” Rupal has also been named one of the "Most Influential Women of 2023” by Startups Magazine.  Rupal shared her journey of embracing her unique identity as a daughter of Indian immigrants and her passion for soccer. She emphasized the importance of "owning your weird," which has helped her overcome feelings of being an outsider.  Rupal shared lessons from her time at the CIA, highlighting an unconventional leader who valued collaboration over hierarchy. This approach built loyalty and trust, demonstrating that leadership isn't about fitting traditional molds.  She discussed the limitations of data in decision-making, acknowledging that while the fear of failure is universal, everyone has a responsibility to engage proactively in leadership, regardless of their role.  Addressing the fear of failure, Rupal noted that larger organizations often become risk-averse, despite fewer real consequences compared to intelligence work. She believes leadership is everyone's responsibility, urging individuals to take ownership regardless of their role. Rupal reflected on a personal failure where she was overlooked for a briefing opportunity, learning the importance of self-advocacy. She also stressed the need for diversity and expanding our sense of community while acknowledging how different experiences, like gender, shape leadership.     Key Takeaways [02:06] Rupal Patel shared a personal detail about herself: she is a massive soccer fan, having played since the age of five and now follows the sport closely. She often incorporates soccer-related anecdotes and metaphors into her work, reflecting her passion for the game. [05:05] Rupal discussed the concept of "owning your weird," emphasizing its significance in her life as a daughter of Indian immigrants. She explained that she often felt like an outsider due to imposed labels and societal expectations, but through reflection, she learned to question those beliefs and embrace her unique identity. [11:01] Rupal illustrated unconventional leadership through an example of a chief of station she worked under at the CIA, who was collaborative and prioritized the best person for each job over hierarchy. This approach fostered deep loyalty among team members, showcasing that effective leadership doesn't conform to traditional stereotypes. [13:22] She highlighted the chief's ability to manage relationships effectively, demonstrating confident humility in interactions with congressional delegations and local officials. Rupal noted that she fluidly adapted her leadership style, leading from the front or behind as needed, which enhanced her effectiveness across various contexts. [15:11] Rupal shares  the mentality we need to have to operate better in ambiguity. She emphasized that no data set is perfect for predicting future outcomes, explaining that data only helps analyze past events. She stressed the need for leaders to accept the limitations of data and focus on identifying gaps in information to make informed decisions. [19:48] Rupal acknowledged that the fear of failure is universal in both the CIA and the private sector. She noted that the larger an organization becomes, the more rigid and risk-averse it tends to be, despite the fact that mistakes in business often carry less serious consequences than in intelligence work. [24:22] Rupal asserted that leadership is everyone's responsibility, regardless of one's role in an organization. She encouraged individuals in support functions to take ownership of problems and outcomes, asserting that proactive engagement is essential to contribute meaningfully to the organization's success. [28:29] Jim asked Rupal to share a meaningful failure that shaped her leadership. Rupal described being overlooked for a briefing opportunity despite her contributions, highlighting the importance of advocating for herself. [33:26] Rupal noted that the person who delivered the briefing lacked self-awareness and was focused on the opportunity, reflecting how such individuals often thrive in organizations by surrounding themselves with those who reinforce their shortcomings. [35:58] In response to Jim's question about diverse groups working together, Rupal urged listeners to expand their views of community and seek commonalities beyond superficial differences while acknowledging that experiences can vary significantly based on factors like gender. [41:22] Rupal emphasized that parents can pursue their ambitions without sacrificing themselves. She shared her experience of accepting a TED talk on her daughter's 6th birthday, highlighting the importance of showing kids that they can still follow their dreams and be individuals even while parenting. [47:12] And remember,  "Don't worry about not fitting in. The things that make people think you're weird are what make you unique, and therefore your greatest strength." — Bridget Jort Sorensen   Quotable Quotes “Every individual has a unique set of skills, a unique combination of strengths and blind spots that in many ways need to be worked with as opposed to ignored or made to feel like they have no place in that context.” “It’s about accepting who you are not feeling like you constantly have to work on yourself and fix things about yourself.” “We have this strange human need to box people in... every single one of those labels comes with its own level of expectation and baggage.” "Fundamentally, it comes back to this acceptance of the reality that there is no such thing as a perfect data set."  "Leadership is everyone's responsibility." "We all need to expand what we think our tribe looks like, because it is... very superficial." "You can make whatever it is that you are trying to build or do or achieve something that works for you and not have to sacrifice parts of yourself."   This is the book mentioned in this episode Resources Mentioned The Leadership Podcast | Sponsored by | Rafti Advisors. LLC | Self-Reliant Leadership. LLC | Rupal Patel LinkedIn | Rupal Patel Instagram | Rupal Patel X | Rupal Patel Website |