Q&A With Andrea Cillara Rossi, Cross Cultural Journey+Coaching!


Andrea Cillara Rossi helps C-level executives define and prioritize their digital transformation priorities while balancing this corporate role with one-on-one executive coaching. Previously, as a core member of the Digital Practice at Boston Consulting Group, he was actively involved in Agile Transformations. As part of his consulting experience, he has worked with organizations in financial services, industrial goods, telecommunications and public sector both in Europe and Asia. Andrea has a strong background in operations, finance, and corporate strategy and is truly a cross cultural expert. He speaks four languages fluently and has lived in five countries across Europe and Asia. Andrea is an accomplished freelance coach who challenges and supports ambitious executives across a range of industries and geographies.

Andrea, you’ve had incredible work experiences across sectors and geographic regions! Tell us about your experiences and how they set you on a path to professional coaching...

I think I would start back when I was a child, I was lucky to have wonderful parents and a good childhood. Even though we did not have that much growing up, my father always believed in letting me try things, to discover new passions. I had access to many experiences, starting with sports, tennis and futbol/soccer, but I wasn’t passionate, I stood around with my hands in my pockets! Then at five years old, my parents brought home an Amiga 500 computer and I went mad with it! I loved it and I would not leave my room...Back then, Italy in the late 80s/early 90s, it was like the U.S. minus 5 or 6 years...but I began to learn how to code first by learning how to create a game, to make it work. Fast forward a few years and I learned to code at age 12. I was interested in all things electronics and computer science and then I began to explore hardware, opening up PCs and building board cards. At that time I developed a strong passion for telecommunications because I felt I knew everything about coding and telecomm was expanding/booming at the time. This brought me to my first sector and path to coaching. I left Italy in 2005 for an exchange program in Finland. It was an amazing experience and this set me on a path discovering new places and cultures. After the program, I knew I had to find another way to travel again. I went to Paris next and began working as an engineer in the energy sector. These life events--along with the 2008 financial crisis--brought me into a corporate model that was very ‘old style’. Even though, at just 23, I had a leadership track role where I represented the company in international conferences, I had what people would call a job for life, one that people spend their whole lives in, I became restless… I knew that I wanted to change the world...

Tell me more about your time at INSEAD for your MBA, what was that experience like?

From there I began to think about doing an MBA and had shortlisted INSEAD and Stanford. I chose INSEAD because it was an accelerated MBA program and a perfect match with my values of diversity, inclusion, and geographic distribution (students, faculty, campuses). These are all strong parts of the curriculum, you meet people from all over the world and explore different perspectives in team exercises and case studies from various industries. My time at INSEAD was life changing for many reasons, but one thing did surprise me, my organizational behavior course that introduced me to the science of Leadership. Going into my MBA, I thought the classes were going to be all about ‘hard skills’, finance, marketing, etc. In my first organizational behavior class I found I could not define leadership! The non-quantitative side of things opened up a new world for me. Also at INSEAD, I was first introduced to coaching. By exploring reflective listening exercises and learning more about all of the aspects that go into being an effective leader, all the skills that matter to leadership, I was hooked.

A year after INSEAD, and after a bad break-up that left me feeling lost for some months, I found myself in a high-functioning, dark place. At work, I was an ambitious young professional on the executive track, selected for a high profile talent management program, but on the inside, I was dealing with anger, frustration, and disappointment. As part of the program, we were also given a coach and for the first time in a while, I was super excited as I heard that coaching was of tremendous value and I grabbed at the opportunity to get coached and learn more about it. Coaching really opened up my mind, particularly around what is in my zone of control and how that influences your mindset. I had the opportunity to explore conversations about life purpose and fulfillment, and for someone who grew up in a religious family but who isn’t religious, I finally had a different framework to answer these core questions, to approach this meaning in another way. We also explored joy, and if you aren’t exercising your passion, you aren’t experiencing joy... It made me understand that I experience joy from being with, and being in service of other people, and this allowed me to say yes to opening up to relationships more.

What made you want to coach?

The first thing that comes to mind is a brilliant educational experience my father gave me… When I was six or seven years old, his advice to offer kindness, to offer understanding, to another child who stole from me, transformed my encounter with that other child. It was a powerful lesson, one that I still remember each day. Building on this, I became a coach because someone helped me along the way-- in my path, in my career, in my life--and it is my way of giving back. I get tremendous joy from helping others and being of service.

What different types of coaching roles have you held? What did you learn from each?

  • Agile Transformation Coach (South Korea and Singapore)
    • I had the opportunity to bring Agile coaching to South Korea and Singapore for Boston Consulting Group (BCG). I learned the value of coaching in the Agile way in improving communication and building authenticity in work relationships. I also learned to adapt agile concepts to the culture in SE Asia by empowering both individual contributors and leaders.
  • New Hire Orientation Program (Germany and Bangkok).
    • As part of BCG’s new hire orientation program, employees would run through project simulations meant to replicate real-world client interactions. Conflict came up often with groups of Type A, ambitious/driven, strong personalities. I would observe team dynamics and then meet with new hires one-on-one and in group sessions. This gave them the opportunity to learn about themselves and foster improved emotional intelligence to serve them as they progressed in their career.
  • Freelance Coach Working with Individuals
    • Since 2019, I’ve been coaching individuals on leadership topics. While the starting point of my clients is typically managing difficult work relationships or addressing their struggle to reach career goals, my coaching aims at helping clients reflect on their whole life and values. I’ve learned that, often, clients experience a huge transformation when looking at their initial topics from very different perspectives, and sometimes they even realize that their initial goals are not actual anymore. Such shifts are truly life changing, and I feel lucky to be able to be part of such transformative processes.

What would you say are essential skills for professional coaches?

  • Honesty and vulnerability, you need to role model these values for your client. This is the basic starting point from the coach and both need to be there for the coaching relationship to work.
  • You are a mirror for your client. Design your alliance so that this is understood by your client and encourage them to bring their highest level of honesty. Without having a mirror to really ‘see’ our reality, we cannot solve any issue. That mirror is coaching!
  • Self management is critical for the coach. Manage your timing, the structure of the session, the coaching logistics, and take charge for your client when appropriate, so they know you know where they are going...and they will feel confident to speak up and go with the flow.

What do you love most about coaching?

Seeing a client discovering a new way of doing things, of figuring out a solution to achieve something meaningful...seeing my clients take a different path and reach a new level, the transformation!