Interview with Kelly Cunningham, Managing Director of IT Operations at United Airlines

1. Where did you grow up? Do you think that it has any impact on your life’s work?

I was born in Houston and lived there until I was 5. At that time my family moved to Richmond, Virginia where I lived until I was 11 and we returned to Houston. I do not believe living in either place had an impact on my decision to pursue a career in IT.

2. Where did you go to school? Why there?

I went to college at the University of Houston. It offered the curriculum I was interested in, and the tuition was reasonable.

3. What did you do after your first degree (if second degree, where was that done, what did you do after that?) How did you get into your first major area?

I began doing paid internships at Texaco in my junior year of college. The pay was good, and it was terrific experience. My second internship happened to be, among other things, desktop support for the President of Texaco, USA, Glenn Tilton who later became the CEO of United Airlines. Mr. Tilton would later become the architect of the merger between United and my employer, Continental Airlines. This relationship didn’t play a role in my new position at United but certainly shows every relationship can come to have significant importance later in one’s career.

Immediately after graduating, Texaco hired me full-time into a position that was 1 part Service Desk support, 1 part technical course development, and 1 part training delivery.

4. Have you had any particularly significant mentors in your career?

I’ve had one significant mentor in my career. Bob Edwards, the current CIO of United Airlines, hired me away from IBM about 12 years ago when he was a junior VP at Continental. We’ve enjoyed a great and long relationship.

5. How has your career evolved?

I never eagerly sought a promotion. The first time I decided I had an interest in leading a team was after working for someone that was brought in from outside. That person had real challenges leading the team and I knew I could do better. When that leader was removed, I asked to be given a trial as the new leader. I was promoted and have had many promotions since then. That has been a pattern. Good work gets noticed, ambition has never played a role.

6. Looking back, what do you feel is your biggest contribution?

My biggest contribution has been recognizing and elevating the talent of others. Early on, I realized that recognizing talent was essential to building the right teams and getting the best outcomes. This has occurred with both employees and suppliers. When I worked for IBM as an outsourcing provider, we were treated as “less than,” even though we wanted the best for our customer. When I left IBM and joined Continental, there was a large outsourcing relationship with EDS. Continental’s demeanor toward EDS at that time was to treat them as servants, in many cases. I had a large team of EDS folks that provided services for me, and I knew from my experience at IBM that they probably were really invested. Beyond that, they were the team I had to deliver the service I needed. I treated them as such, and our performance changed the culture regarding supplier attitudes. For internal employees, I’ve always worked hard to ensure I had a succession plan. It’s never been about me, it’s been about the team’s performance.

7. What do the next 10 years hold for you?

I wouldn’t pretend to know. I’m happy doing what I’m doing, but I’m capable of managing new challenges. I have a team of about 450 people and a $100MM budget; far more than I ever imagined. I have peers that manage business-aligned application portfolios and that is interesting to me.

8. How has your view of leadership evolved over the years?

It’s all about the people. Get them to want to do a good job for you. That is infinitely more powerful than coercing them.