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Tips From The Top: One On One With Keith Krach, Chairman & Former CEO of DocuSign and Former Chairman of Angie’s List

I spoke to Keith Krach, Chairman and former CEO of DocuSign, founder and former Chairman and CEO of Ariba, and former Chairman of Angie’s List, about his best advice

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. What is something about you that would surprise people?
Keith: I was fired from my first job that wasn’t at my dad’s factory. I had been working at my dad’s machine shop for years, and I was so eager just to get outside. So I got a summer job as a tennis supervisor at the local club. My girlfriend kept coming by to see me, and I wasn’t paying attention to my work. The athletic director, who was a friend of my mom’s, got so frustrated, he finally asked her what he should do with me. She told him to “Fire the hell out of him!” He did. I was so scared to tell her. When I finally got the courage to do it, she said, “I knew that. I told him to fire ya.” She said, “Thomas Edison got fired from his first job, and it was the best thing that ever happened to him.” She also reminded me that what really matters is what you do when you think no one is looking. I learned a good lesson.
Adam: How did you get here? What failures, setbacks or challenges have been most instrumental to your growth?
Keith: I started working in my dad’s machine shop when I was 12. There were five of us at first, but business got slow and then it was just my dad and me. I didn’t realize at the time what a priceless experience that was. It built a real bond between us we wouldn’t have had otherwise. It taught me that in business you’ve got to expect trouble. When you’re on the top of the world, take a look over your shoulder, because here comes a freight train. It also taught me to keep an even keel. Don’t get too high on the highs, don’t get too low on the lows. When things are bad, just hang in there – they’ll improve. You can’t give up.
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: Range is an under-appreciated quality. If you ask me, “Which is better—an autocratic leader, or a consensus builder?” I would say, “Both!” It depends on the situation. Knowing when to apply different leadership styles takes good judgment. The way to build that wisdom and take that skill to the next level is just by jumping into water over your head—going into harm’s way. You’ve got to set big audacious goals that will expose you to the challenges that will build your judgment over time.
Adam: What are your three best tips applicable to entrepreneurs, executives and civic leaders?
Keith: First, never compromise your values. There are a million opportunities in life to give in to temptation. But if you stick with your values, keep your integrity, others will see that you’re a person they can rely on. And that pays off big time. Second, build trusted relationships. Everything in business and life is built on relationships, and relationships are built on trust. I’ve found one of the best ways to quickly build trust is by being vulnerable and open about who you really are. Finally, I’ve always found that being willing to make fun of yourself is priceless. My dad taught me this—one of the best ways to diffuse a difficult situation is to “mock yourself out,” in his words.
Adam: What is the single best piece of advice you have ever received?
Keith: Daniel Burnham, the architect who designed the 1893 Columbian Exposition in Chicago said, “Make no small plans; they have no magic to stir men’s blood.” That’s great advice.
Adam: What is one thing everyone should be doing to pay it forward?
Keith: I’ve been so privileged to have had great mentors, and to have been shaped by some really great institutions in my life—Purdue University, Sigma Chi fraternity, so many others… I believe fervently in mentoring and giving back to the things that provided you opportunity and made a difference in your life. Some people are afraid to give—they worry about being used up. But I find that giving increases your capacity.
Adam: What are your hobbies and how have they shaped you?
Keith: I’m a people collector. I love to study human nature, bring people together, build great teams, and challenge people to do things they hadn’t imagined they could do before. Here in Silicon Valley there are so many “tech leaders” who are focused on tech. For me, tech is fun, but it’s always about people.
Adam: Is there anything else you would like to share?
Keith: I believe we need visionary, transformational leaders now more than ever. Cultures, societies, governments are undergoing tremendous upheaval right now. New technologies are ushering in a lot of this change. We need leaders with strong values to help make sure that as society is transformed, it’s transformed in positive ways. We need to make sure that precious things like liberty, democracy, security and equality aren’t lost in the changes that are sweeping the world.
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