Blazing the Leadership Path A candid conversation with Deloitte Tax LLP partner Jorge Caballero

One of Jorge Caballero’s mantras is “Never, never, never give up.” And it shows. He has overcome considerable challenges with steadfast determination and a keen focus on his goals. From making $1.50 a day at age 12 to now wearing many leadership hats—such as Deloitte Tax LLP Northeast deputy managing partner for U.S. India Tax, Deloitte Tax LLP Diversity leader, and lead client service partner on numerous clients—Jorge has come a long way.

In celebration of Hispanic Heritage Month, we selected Jorge for an up-close conversation. "Jorge is not only a prominent leader and mentor to many within Tax, but also a major role model for Hispanics within Deloitte,” said Paul Estrada, Hispanic/Latino(a) Employee Network & Allies BRG (HNet) national leader, Deloitte Tax LLP.

Our interview focuses on Caballero’s path to leadership and the obstacles he’s overcome…and how he’s excited and energized by the challenges that lie ahead.

First, tell us a little bit about your background and where you grew up.

I was born in Cuba and immigrated to Danbury, CT, with my parents and sister when I was 10. This happened after my father’s dairy farm was appropriated by the (then) new Castro regime. We were blessed to be welcomed in America with open arms. Sadly, one month into my new life as an American, my father passed away. He was the only one in our family who spoke English at the time. It was a tough time for us all and I had to take on new responsibilities to help support my family. My first job was at age 12 where I did gardening and other chores for $1.50 per day.

Eventually, my mother moved us to New Jersey. It’s there I went to college, earning an accounting degree from Rutgers University. To put myself through school, I scheduled all my classes in the morning so that I was done by 1:30pm. From there, I would head directly to a now defunct discount department store where I worked fulltime as a salesperson until closing and on the weekends.

With all the years that I’ve worked so far, I like to say that I’m well past retirement age [laughing].

After graduation, what did your career path look like?

I began my career with another of the then Big 8 accounting firms in New Jersey. I stayed there for four-and-a-half years and then left to go to industry, where I accepted a position as assistant vice president of Tax at a Fortune 500 financial services company. After three-and-a-half years, I decided to return to public accounting and joined Deloitte as a manager in our Morristown office. Six months later I was promoted to senior manager and then two years later I was admitted to the partnership.

Currently, I serve as the national Diversity leader for Deloitte Tax LLP and am a deputy managing partner in the Northeast region leading US India Tax. I also serve as a member of the Deloitte Tax Board of Directors, the Northeast Region Tax Management Committee, and the Tax Executive Group. Previously, I served for seven years as Office Tax Managing Partner (OTMP) for New Jersey. Recently, I was appointed by Governor Christie to serve on the New Jersey State Board of Accountancy and I also serve on the Boards of The College of New Jersey and United Way of Essex and West Hudson.

How would you describe your leadership style?

I consider myself an inclusive leader who highly values the diverse perspectives of my team. But in order to have leadership, you need to have followership and build consensus. A vision is important, but you also need to be able to articulate that vision with others and take them on your shared journey. There are always going to be some people who don’t understand the need for change or the goals behind it — and that’s okay. If you are on the right path and they start to see that the change is good for both them and the business, they will eventually come around.

Were there any turning points in your career that helped position you for more advanced roles?

Yes, my very first assignment as an auditor at the previous firm was very tough but it gave me immeasurable on-the-job experience and helped build character. I was assigned to the largest client of the office at the time and they were going through a very difficult time. The new CEO’s first major decision was to lay off 800 people at corporate headquarters. It became very difficult to navigate the environment and do our job as auditors.

Many of our contacts were laid off and those who were left were clearly worried about their future. The time period to complete our audit was significantly compressed after we were told to stay away for a month after the cuts were made. We worked 67 14+ hour days consecutively. Despite never seeing the sun for 67 days and working for a difficult senior, I learned a tremendous amount about audit work and, more importantly, about myself. I am grateful for that experience.

What was it you learned about yourself?

After that assignment I learned to persevere and, as Winston Churchill once said, to “Never, never, never give up” – despite what others may say. You see, after that very long engagement ended, I received my first review. It was dreadful, and my senior told me, “Your future at this firm is contingent at best.” I couldn’t believe it after all the hard work I had put in, and here I was on the verge of being fired. A couple of days after receiving that feedback, the partner on the engagement called me into his office. My first thought was, “This is it. He’s going to tell me to get lost…you’re out of here.” But instead, he told me that he read my review and disagreed with it. He further encouraged me and said he saw how hard I worked and that I understood the business. So my job was not only saved, I also felt validated.

From that point forward, I have always been determined to achieve my goals despite what obstacles lay ahead. I also learned how important it is as a leader to be inclusive. During that difficult assignment with my previous firm, the environment was very cliquish and it was difficult to assimilate. The senior who reviewed me perhaps didn’t like me because I had not joined his clique. One thing I always say to our younger professionals is that they should not only do good work, but also work hard at developing strong relationships and truly becoming a part of the team. On the other hand, to our leaders, I say, make sure you connect with everyone on your team and get to know them as individuals.

On that note, what advice do you have for Latino(a)/Hispanic professionals for being successful?

I would give this advice to anyone: Find your passion, focus on it and excel at it. Doing those three things can help get you recognized and positioned for the right assignments.

You have to love what you do. I’ve been doing this for over 30 years and I still feel the same passion for it each and every day.

You have to excel at what you do. In this business we sell what we know—our technical expertise. There is no substitute for excelling at what you do.

At Deloitte, we offer an immense number of opportunities to do enriching work and demonstrate your leadership. So continue to develop and learn as a professional—and always make sure that passion is the primary element in everything you do.

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