Going Against the Flow: Kimber Lockhart, VP of Engineering at One Medical Group

Kimber Lockhart is VP of Engineering at One Medical Group -- a rapidly growing model of primary care that integrates innovative design with leading technology to deliver higher quality service while lowering the total cost of care. Previously, Kimber co-founded Increo, a web-based service that allows users to share and review documents in a secure space. Increo was acquired by Box in 2009, and she hired and scaled the web application engineering team over the next four years, ultimately responsible for building most user-facing features on Box. Kimber speaks frequently on technology, heath care, and engineering careers in San Francisco Bay Area and beyond. She holds a B.S. in Computer Science from Stanford University.

Kimber Lockhart

Q: What does entrepreneurship mean to you, and what underlying characteristics do you see in successful entrepreneurs?

KL: To me, entrepreneurship is taking responsibility to enact the change you see in the world. It's about creating value from your ideas -- about creating something that didn't exist before.

In college, I taught a class on entrepreneurship. In our first session, I had everyone take a personality quiz "Are you an entrepreneur?" My students dutifully filled out the forms, which promised a quick answer to their entrepreneurial potential. As soon as all the forms were handed in, my co-instructor and I promptly tore them in half, and, for good measure, shredded the pieces. All our students could be entrepreneurs. It turns out, we were on to something.

Great entrepreneurs, like great leaders, aren't all made from the same mold. Some exude tenacity and persistence, others execute on many different ideas at once, some are quiet and reflective, others are loud and ego-driven. Some thrive working on their own, others rely on their co-founders for support.

The good news here is that there's not a special formula for being an entrepreneur. It's less about who you are and more about what you choose to do. I find that empowering.

Q: What are you most proud of in your professional career? If you could do something over in your life, what would it be?

KL: I'm most proud of the fantastic teams I've built and the opportunity I've had to help people develop their careers. Our job is a huge part of our lives, and the opportunity to make someone's work experience more rewarding inspires me to do the very best I can as a leader.

While it's easy to think of experiences I'd prefer not to repeat, it's hard to come up with something I would change -- it's the tough experiences that inspire growth.

In fact, almost every time I've made a decision I regret, it's because I chose the less scary option. In college, I avoided the challenging machine learning class. As a software engineer, I didn't submit my code to an intimidating open source project. As a leader, I didn't have that tough conversation right away. As a free agent, I didn't move out of a comfortable situation quickly enough. Now, when I consider new decisions, I try to treat fear as a signal to consider the scary option just a little bit more.

Q: Tell us about an instance where you had to go against the flow to realize your goal?

KL: I think one of the most unexpectedly difficult parts of my career so far has been leaving the team I built at Box. While it was time for me to move on, I had great relationships with many people on my team, and I felt responsibility to ensure they were set up to thrive when I moved on. Actually making the jump took stepping outside my comfort zone, but it's been really fun to maintain many of those relationships after departing.

Q: What advice would you give to young college graduates interested in Product Management?

KL: "I'm studying computer science in college, but I really like working with people, and want to have strategic input on what I'm working on. I'm thinking about becoming a product manager..."

Please reconsider.

Now, I'm not down on product management. I work with many talented PMs, and their value is self-evident. From my observations, though, most college students that choose product management are selecting it for the wrong reasons. Perhaps they have heard that it's a fast track to taking control by becoming a "mini-CEO". Or, maybe, they hear software engineers just sit in isolation and implement the nitty-gritty details of what a product manager designs. Some want to be on the fast-track and consider the recommended 1-2 years of software engineering experience before moving to PM a waste of time.

I'm shocked how pervasive these myths are. And to be fair, in some companies they aren't myths. Excellent technology companies, however, are looking for PMs with functional expertise of some kind. Those PMs engage with software engineers as equals, focusing on how each role can contribute to the efficient development of excellent products. While you might have a CS degree, you don't have industry functional expertise in software engineering yet. That's the job of your first couple of years of building software full-time. I believe, by becoming a PM immediately after college, you generalize yourself out of future effectiveness.

Q: LinkedIn style - If you were to give advice to your 22 old self, what would it be?

KL: My 22-year-old self probably listened to advice from others a little too much. It's important to seek advice from others, but it's critical you understand the point of view that's inspiring those ideas before taking them at face value. Akin to flipping a coin to note which outcome you were wishing for more, it's important to consider how you'd feel if the advice as true, false, or even true to a much greater extent.

Follow Kimber Lockhart at @kimber_lockhart, and check out the other interviews in Going Against the Flow series at http://www.huffingtonpost.com/charu-sharma/ or thestartupsutra.com.