How a “deep geek” rose to leadership during the tech revolution

By Rahul Sampat

From an internship at NASA to running engineering at Reddit to developing business intelligence (BI) software first at Microsoft and now as chief product officer at Looker, Nick Caldwell, MBA 15, has been a leader in the tech revolution.

How did it all begin?

It started with my dad who was a bit of a geek himself. He got me hooked on computers when he brought home a Tandy 1000 from work one day. I’ve got a picture of me sitting on his lap at age 4, wearing a Thundercats T-shirt, typing something into the MS-DOS command line. Later on, at about the age of 10, he got me a book called Learn to Program C++ in Ten Easy Lessons. I started coding games and writing software shortly after that.

How influential was that NASA internship?

It was life changing and it opened the door for a ton of opportunities. I learned how to code professionally—real code that was going to get launched into space. And I gained a network of people who were influential in my getting into MIT. On the flip side, after dealing with the bureaucracy, I decided that I didn’t ever want to work for the government again—at least not as a software engineer.

You were at Microsoft for 15 years. What was the transition like, moving from an individual contributor to a manager at Microsoft?

I became a manager pretty early, after about three or four years. Part of that came from the fact that I don’t like being told what to do. I also realized early on that I got satisfaction in mentoring people and helping them achieve their goals. Caring more about people than tech is the best indicator that you should think about a management career.

What made you finally decide you needed an MBA?

I’ve always had an entrepreneurial streak even though I spent most of my career at a giant company. At Microsoft I worked on new technologies like machine learning and natural language processing long before they were commonplace. I also founded many product efforts, including Power BI [Business Intelligence].

At some point I knew I needed to get closer to where the real action was happening. Being in one place for 15 years meant I felt sort of stuck. I needed a forcing function to get me going to the next place I wanted to be. I saw the MBA as a way to force myself out of a very comfortable position and give myself the confidence to grow.

What convinced you Berkeley was the place for you?

I looked at a lot of places and Berkeley was the right fit. I wanted to learn specifically about entrepreneurship and technology and at Berkeley you’re going to be surrounded by people in that scene. As a practical matter, I needed to be able to do this while maintaining a full-time job at Microsoft. And Berkeley has a great evening and weekend program.

What was your favorite course?

I have to list two. The first is Improvisational Leadership -- a class that teaches a mixture of improvisation techniques with leadership training. For example, the instructor might give you a pretend scenario and you act it out or work with a partner to quickly improvise. It sounds hokey but the tools helped me overcome my natural introversion, gave me more confidence, and helped me be more authentic. I took these skills back to work and immediately put them to use.

The other was Fundamentals of Design Thinking. It was basically a hands-on lab that offered a systematic framework for how to empathize with customers to understand their core needs, experiment with solutions, and test feedback. It’s simply the best class I’ve ever taken on product design, and honestly the only one I’ve taken that’s worth remembering.

What influence do you think Berkeley has had on your career?

My MBA got me out of my comfort zone and on the entrepreneurial track I always wanted to be on. It also up-leveled my management skills to a higher plane. Berkeley also gave me the confidence that I could learn quickly and take on any new managerial role.

I hear a lot about “new thinking” when it comes to the Berkeley MBA program. What does that mean to you?

Two things. First, there’s been a shift that Berkeley has been at the forefront of: the integration of data science with business and management. Nowadays data play an important role in any critical business role. Many of my Berkeley courses were oriented toward preparing for this shift.

Second is the emphasis on networks. Modern businesses don’t function in isolation. We had multiple classes on network effects, not just with people but open innovation, how businesses are a network of ideas and how you need to tap into and then contribute to those networks.

What’s your leadership style and how has it evolved?

I think when I first started my management career, I thought it was my goal to hire people who thought and acted like me. Nowadays I see things much differently. A great leader tries to bring the best possible team to the field. So I’m much more focused on building organizations by finding great people and inspiring them.

A big part of that is looking for people who are fearless, don’t put boundaries on themselves, and can act independently. That freedom has to be balanced with accountability and the belief that the team comes first.

If I can find those people and give them an inspiring vision and clear execution path, great things will happen.

What more do you think you need to learn?

A wise woman once said, ‘The man who knows something knows that he knows nothing at all.’ Whether you call it growth mindset, or Student Always, or whatever -- it’s my belief that we can never stop learning.

Leadership is an unlimited space to explore and something I love studying. I’m excited to be learning more about conscious leadership and self-care, tools that are essential to leading the latest generation of workers.

Learn more about the Evening & Weekend MBA program

Posted on September 12, 2019
Themes: Technology
Rahul Sampat
Rahul was Director of Admissions for the Berkeley MBA Programs for Working Professionals from 2015-2019. He hopes these blog posts provide you with useful insights into the Berkeley MBA experience and questions you may have about the MBA in general.