Adam: Thanks again for taking the time to share your advice. First things first, though, I am sure readers would love to learn more about you. How did you get here?
Keith: After business school at USC, I worked at American Airlines, in the revenue management and finance groups. Then I did the opposite of most and went from industry to consultant, working for the Boston Consulting Group. One of my BCG projects was to help start what became the online travel agency Orbitz. That was the start of my “travel expertise” and in 2004 I helped found KAYAK. In my 14 years there, I served in many roles, the last of which was President.
Adam: What failures, setbacks or challenges have been most instrumental to your growth?
Keith: When I decided I wanted to work for the Boston Consulting Group, I had to go through about 14 interviews in two different offices. I didn’t meet the usual mold, since I was coming from industry and not directly from business school. This showed me the power of persistence, and how important that is once you find something you really want to do.
Adam: In your experience, what are the defining qualities of an effective leader? How can leaders and aspiring leaders take their leadership skills to the next level?
Keith: Leaders need to understand what’s going on in their organization. I’ve incorporated a practice of meeting with employees a level below my direct reports. This way, I can get a more accurate pulse on what’s going on in the company and work to make improvements.
Effective leaders are also decisive. They do not get caught up in analysis paralysis or consensus-based decision making, though they understand when they need more information or advice to make well informed decisions.
Adam: What are your three best tips applicable to an audience of entrepreneurs, executives and civic leaders?
Keith: 1. Make decisions quickly, you can almost always fix a bad decision (and don’t be afraid to admit you made a bad decision!).
2. Just because one of your team members does things differently than you, doesn’t mean they’re wrong. Let them work the way that is best for them.
3. It’s OK to say “I don’t know” and then go figure it out.
Adam: What is the best piece of advice you ever received?
Keith: The only bad decision you can really make is to make no decision at all.
Adam: How do you pay it forward?
Keith: For me, a big part of paying it forward it to understand that the biggest part of creating and running a great company is to make sure the employees benefit from it. There needs to be a great work environment and every employee needs to own part of the company. Going public and selling KAYAK to Priceline changed people’s lives and I would like to do that again here at The Zebra.
Adam: What are your hobbies and how have they shaped you?
Keith: Cooking: it’s a great creative outlet and you can fix just about any mistake you make.
Fitness: I am not a triathlete or anything, but I try to workout everyday to maintain my focus and stay active.
Traveling: I have lived abroad twice and and living in and visiting so many different cultures really gave me a perspective that most people want the same things in life: to be happy safe and with people they love.
Adam: Is there anything else you would like to share?
Keith: When I give the advice “It’s OK to say ‘I don’t know’ and then go figure it out,” that’s advice I heed on a daily basis too. I joined as The Zebra CEO less than a year ago, and this role is my first time working in the insurance industry. In fact, prior to The Zebra, I didn’t have much experience with the industry at all, except as a consumer. At a staggering $200B, the industry is enormous, not to mention complex and highly regulated. I feel like I’m constantly asking questions and getting advice from the experts who know the industry very well. Despite being the CEO, I feel like I am learning as much as I’m teaching.