Lessons from Rupal Patel’s CIA Career to Entrepreneurship

Bookpleasures.com welcomes Rupal Patel, author of “From CIA to CEO: Unconventional Life Lessons for Thinking Bigger, Leading Better, and Being Bolder” to our online interview series, where we dive into the fascinating lives and careers of extraordinary individuals.

 

Rupal splits her time between New York and London, and is an author, executive consultant, CEO, and renowned speaker. 

Born and raised in New York, Rupal’s career journey is nothing short of remarkable. 

Inspired by her parents’ dedication to collective progress, she accepted an invitation to join the CIA as an analyst, a role that saw her advising Four-Star Generals and receiving accolades for her superior support to the President of the United States.

Her high-octane career has taken her from military briefing rooms in jungles and war zones to corporate boardrooms and international stages. 

After leaving the CIA, she earned her MBA from London Business School and went on to establish her first award-winning business over a decade ago. 

Recognized as a “Power Woman” by Harper’s Bazaar Magazine and a “super strategist” by her clients, Rupal is a sought-after international speaker and corporate consultant who has delivered leadership and talent development programs for Fortune 500 companies and even the White House.

Her newly released book, “From CIA to CEO: Unconventional Life Lessons for Thinking Bigger, Leading Better, and Being Bolder,” offers a unique blend of memoir and practical guidance, serving as a comprehensive manual for leaders, entrepreneurs, and anyone looking to chart their own path. 

Today, we look forward to exploring Rupal’s incredible journey, the insights from her diverse experiences, and her vision for the future. Welcome, Rupal!

Norm: Good day Rupal and thanks for taking part in our interview.

Can you describe the transition from working as a CIA analyst to becoming a serial entrepreneur? What were the biggest challenges and surprises?

 

Rupal: The hardest part of that transition was having to define myself for myself. Up to that point, I had always been affiliated with prestigious organizations, from the schools I attended to the CIA. 

But when I left the Agency, and started my own businesses, suddenly I was a “nobody” building a “no-name” business from scratch that I had no idea if it would succeed or not. Learning how to separate my sense of self-worth from my job title/work affiliation was really hard. 

It took me years to do the work of self-definition, but it was so worth doing because it is a life skill that I think so many of us need to master, and doing that work has given me confidence that does not rely on external validation.

The other major challenge, was battling persistent loneliness. I am a very outgoing person and I went from being in vibrant, intellectually engaging, social contexts at work and through my studies, to suddenly working for myself, by myself, at home in the middle of nowhere. 

The loneliness was deep. And I had to re-learn how to be by myself most of the time. It took a lot of effort, and many years, to see myself through the loneliness and isolation. 

But it was another gift in disguise, because learning how to be alone and NOT feel lonely is a skill that I know I will need throughout my life and career. 

Norm: What specific skills or techniques from your CIA training have you found most valuable in the business world?

Rupal: Relying on “all-source intel” is one of the best skills I brought from the CIA to the business world. At the CIA, we would look at all of the information about a certain topic or area of the world: the Top Secret information as well as the publicly available information, and everything in between. 

And by drawing on all sources, we were able to create more robust assessments about any given issue. 

The same “all source-ness” is also incredibly valuable in business, in two ways. First, organizations can learn a great deal from other sectors or industries, or even other parts of their own organization, instead of operating in silos and looking at their world very narrowly. And second, businesses can also draw on the “all-source intel” within each individual in their organization. 

So, even if someone is hired to perform a legal function, they might also have talents that are valuable in sales, or marketing, or strategy. By thinking laterally – being “all source” – about the resources they draw on internally and externally, organizations can become much more agile and innovative. 

I do a lot of work with large multi-nationals on becoming “all-source” because doing so helps them future-proof their organizations (being agile and innovative) and it helps them retain high-caliber employees who want to use the full spectrum of their talents and grow within the same organization, instead of being pigeon-holed into doing once thing for their whole careers.

Norm: From CIA to CEO” is described as both a memoir and a trade craft toolkit. Can you elaborate on what readers can expect from the book?

Rupal: I share all of the insights, lessons, and tools I picked up in my career and life that have helped me succeed and achieve things I never thought possible.

And some of those insights are from my time at the CIA, some are from my experiences building two businesses from scratch, some are from my experiences as a parent, as a woman, as a daughter of immigrants, as a life-long learner and everything in between. In my previous answer, I talked about drawing on “all source intel” and that’s exactly what I do in the book: 

I draw on all of the “intel” I’ve gathered over the course of my life and distill all of the key lessons, takeaways, and adaptable tools I learned or developed along the way that have enabled me to succeed and burst through barriers. 

What readers get is a very interactive book, full of tangible frameworks and exercises that will help them answer some of the biggest questions about how to lead a life on their own terms and in a way that is true to who they are. 

At its core, From CIA to CEO is about the reader, finding, discovering, and honoring their inner powerhouse, and letting who that is come out to shine in every way possible. 

It is, as the subtitle promises, a book that arms readers with “unconventional life lessons for thinking bigger, leading better, and being bolder,” not just in theory, but in practice.

Norm: Can you share a story from your time in the CIA that had a profound impact on your views on leadership?

Rupal: When I was deployed to a war zone, my Chief of Station was one of the most ego-less people I have ever met. He treated all of us as equals. 

He shared resources and glory and credit and access to exciting projects instead of hoarding them. And he always made himself the least important person in the room. 

He was so secure in who he was that he didn’t need to be in your face or lord his authority over you. 

He empowered everyone to do their best, got out of their way if needed, wasn’t afraid to learn from others, and operated as a “first among equals.” 

His leadership style earned him the loyalty of everyone around him, and made us want to do our best for him. 

And what that taught me is: 1) leadership can look like anything; you don’t have to act a specific way or take on certain qualities (aggressiveness, assertiveness, charisma, etc) to be an effective leader; 2) being a good leader doesn’t mean that you pretend to have all the answers; it’s essential to know what you are the expert at, and what those around you are experts at; 3) instead of being “all-knowing”, good leaders are “all-growing” and don’t let their egos drive their decisions. He was one of three “greats” that I worked with at the Agency, and they all taught me similar things in their own unique ways.

Norm: Identity Driven Leadership and Personal Energy Mapping are intriguing concepts mentioned in your book. Can you explain how they work and how leaders can apply them?

Rupal: Fundamentally, both are tools for better self-analysis and self-understanding so you can lead authentically as you are instead of following a paradigm or model that is external. 

So, Identity Driven Leadership is not about superficial identity or “identity politics”, it’s about doing the work to crystallize what your values are and how they show up (or not) in your life and how you lead; about gaining clarity on your unique strengths and leveraging them as much as possible in your day-to-day; and about understanding what you need to be and perform at your best, and then doing what you can to create those conditions as frequently as possible. 

Personal Energy Mapping is just one element of this work. And charting your PEM is about paying attention to the natural fluctuations in your mental and physical energy and the kinds of tasks you gravitate towards at certain times of the day, week, month, season, or year. So, for example, it’s not just about being a “morning person” or “night owl”, but about understanding when you find strategic tasks easier to deal with, when are you most creative, when are you best able to handle details, etc. 

And then charting the patterns and rhythms so you can work within them as often as possible and remove some of the friction in your life.

NONE of this is about wholesale overhauls to your life or dictating “my way or the highway” to those around you. 

It’s about understanding how you operate and who you are at the deepest level so you can leverage that knowledge to be a better leader and person.

Norm: How do you think your experiences as a woman in the CIA have influenced your leadership style and business strategies?

Rupal: Being a woman has made me much more attuned to the subtleties of the environments I operate in, from the energy in the room, to the subtext of conversations, to the shifting dynamics between people. 

And while these situational awareness and emotional intelligence skills were fine-tuned at the CIA, as someone who has always navigated between and among many different contexts where I often didn’t “fit” – and as someone who is an introvert at my core – I have always paid attention when others were making noise and learned how to operate in shifting contexts. 

How I lead, how I drive my business, and how I advise other organizations is grounded in these analytical and emotional intelligence skills, and in the strategic situational awareness I have developed by paying attention.

 I see what others don’t see, bring a critical eye to established “best practice”, and work to understand the fundamentals so I can identify better ways of achieving certain outcomes. 

Some of this skill set was developed because of my experiences as a woman, but many of them are just how I am wired; the CIA helped hone the skills that were already there. 

Norm: What motivated you to move from such a high-stakes government role to the world of entrepreneurship?

Rupal: I like operating in high-performance environments because I have a need to push myself and stretch myself so I can discover what I am made of. 

There was no big reason to leave the CIA, and there was nothing specific calling me, I just wanted to test myself in a different way. 

At the CIA, I had done a lot of the exciting meaningful work I had wanted to do, and learned skills I never thought I could learn, so I wanted to push myself and test myself in a different way and see if I could succeed in another high-performance context. Entrepreneurship seemed like the ultimate test of my mettle, so that’s why it appealed to me, and that’s why I went down that path.

I also like being my own boss and getting to decide what direction my businesses and I go in. I like being able to drive my success in the ways that I want to drive it and explore the world of work and giving back in ways that mean something to me and in ways that I craft and control. 

Norm: How do you handle the high-pressure situations in business compared to those in the CIA? Are there similarities in your approach?

Rupal: In every area of life and in every career, there are infinite elements that you can’t control and a tight group of elements that you can control. 

So in any high-pressure situation, I don’t get distracted by noise, or atmospherics, or what everyone else is doing or worried about. 

Instead, I zero in on the things I can do something about and then focus all of my energies on doing something about them. 

This was the same approach I had at the CIA and it is the approach I bring to everything I face now: control the controllable and don’t worry about the rest.

Norm: In your book, you emphasize thinking bigger, leading better, and being bolder. Can you provide an example of a situation where you applied these principles successfully?

Rupal: Thinking bigger: I never thought I would be a best-selling author, but always dreamed of being one. 

So I focused on what I can control and started moving in that direction: always writing, asking for help, asking for advice from people who were qualified to give it, and then doing the work, and persisting. 

I believe anything is possible, but you have to create the right internal and external context to make it so. So whenever I am thinking bigger – setting bold ambitions for myself – I create the context around me that will support that ambition: I curate my inputs carefully (something I talk about a lot in the book), I get smart on the topic, and then the rest is doing, experimenting, learning, and persisting.

Leading better: I believe that at home and at work the people at the “top” have a duty to lead by example, so my duty to everyone I interact with is to be the best example I can be. 

For me, this means paying attention to what I am saying with my words AND my deeds, and to course-correcting whenever needed. It’s also about being honest when I don’t know how to do something or fix something and about having tough conversations when necessary. 

Leading better is a constant practice that takes equally constant vigilance, so I make sure I have good people around me who are willing to have honest conversations with me and not just tell me what I want to hear or to give me empty praise.

Being bolder: For me, this last part is about testing and pushing myself. It’s about asking “why not me?” whenever I have that voice inside me telling me I can’t do something. 

In leaving the safety of my CIA career and charting a totally unknown path, I did something bolder than I thought possible, and I did it by starting with that question. And then doing the work to figure out the answers along the way.

Norm: You’ve advised Four-Star Generals and earned War Zone Service Medals. How do these experiences shape your current work and message to entrepreneurs and leaders?

Rupal: Two big lessons I bring from my past experiences are: 1) Everyone is equal. It doesn’t matter if you are an entrepreneur, or an investor, or an analyst, or a Four-Star General. 

Everyone is equal and everyone has something of value to bring to the table. So focus on what value YOU are bringing instead of getting intimidated by how “impressive” everyone else around you is. Investors need business to invest in; generals need advisors. 

Everyone plays a role, so don’t diminish yours. 

And 2) It is essential to communicate effectively with the person in front of you and not stick to a script. 

If you want to engage or influence or have impact, you have to do the work to understand your audience, know what’s important to them, and speak their language. 

You are the least important person in any conversation (and yes, I appreciate this somewhat contradicts what I just said in #1, but it’s a superficial contradiction; both #1 and #2 are equally true), so it’s not just about what you have to say and how right you are. 

It’s about interpreting what you say so it will be received by the person in front of you based on how THEY operate and think. 

I had to do this translation/interpretation all the time at the CIA because the same analysis shared with the President had to be shared differently than how I would share it with a Special Forces commander; they have different needs, wants, requirements, and languages to some extent. 

And this is a skill that we all need to master in life and in business: speak the language of the person in front of you. Understand what’s important to them. And then adapt your delivery – not the message – accordingly.

Norm: Can you share any upcoming projects or initiatives you are excited about that align with the themes of your book?

Rupal: Yes! I’m working on my next book which looks at leadership from a perspective that’s never been looked at before and which has been hiding in plain sight. 

I can’t divulge details just yet, but it builds on the concept of “All-Source Intel” and is going to shake up the way we look at “work-life balance”, gender equality at work, and the future of work.

Norm: Where can we find out more about you and “From CIA to CEO: Unconventional Life Lessons for Thinking Bigger, Leading Better, and Being Bolder?”

Rupal: You can visit the Book’s Website and follow me on Instagram @rupalypatel

Norm: As we conclude our interview, what advice would you give to someone who wants to pivot their career in a significant way, similar to your transition from the CIA to entrepreneurship?

Rupal: It may take longer than you expect so don’t wait! Talk to people who have made similar transitions, start researching areas you think you might want to build businesses in, and get all the practical considerations (how are you going to pay the rent, feed yourself, etc) out of the way before you leap. 

Also, your next move doesn’t have to be your last move. So, just because you want to be an entrepreneur or move to a different industry, doesn’t mean you have to quit your job today. 

You can stay in work, start banking a savings pot that will fund your early days as a founder, or start working part-time, then slowly migrate into the world you want to enter: you can start a side-hustle, work for another start-up, do part-time work at a different company (as long as it doesn’t conflict with your other job!), and just test the waters. 

There’s too much pressure to make big, drastic changes but success at anything takes time, and it takes its own time. So don’t force it, and just keep moving in the direction you want to go in. It doesn’t have to happen all at once right away.

Norm: Thanks once again and good luck with all of your future endeavors.