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Pragmatic coaching for mindful leaders
Chad Dickerson

I believe “strong back, open heart” leadership is the key to building great companies. The strong back is represented by fiscal discipline, strong process, and accountability. The soft, open-hearted front are values, purpose, connectedness, and compassion. Organizations and people are at their best when they manifest both in equal balance.

— Chad Dickerson

When I decided to become a coach a few years ago now, I did it out of a sense of service. During my time as CEO of Etsy, I was fortunate enough to work with one of the best coaches (and people) in the world, Jerry Colonna. I remembered the many hours I spent with Jerry discussing my triumphs and tragedies, whether business or personal, and how much it meant to me to have someone in my corner through it all.

As a leader, you have to manage a variety of stakeholders. As a CEO, it’s your board, investors, executive team, and your community -- among others. As a CTO, it’s your CEO, your executive peers, a team of inspired but opinionated engineers. Each requires strategic thinking and careful execution for you to achieve your and your team or company’s goals. I know because I’ve been a CTO and a CEO and done every aspect of the work in all stages of growth, from building great engineering teams as a CTO to taking a company public on the NASDAQ as CEO.

The coaching relationship is a uniquely safe place. You can say anything in our sessions and I will listen and empathize (I’ve very likely been there myself). You can test ideas, role play difficult situations, express frustration, speak freely about your worries, and strategize on the most challenging topics. I’ll push and challenge you if I think you need pushing and challenging. My interest as a coach is helping you achieve success, personally and professionally, which will help you build a great company -- and a great life.

Learn more

About me

More about my background, where I come from, my career as a CEO and CTO, and (most importantly) how I might be of service to you.

Coaching approach

Read on for more of what we might talk about if we work together, from purely pragmatic organizational challenges to the matters of the heart commonly faced by high-achieving leaders.

Leadership resources

In 25+ years as a leader, I’ve been continually collecting the most helpful resources on critical leadership topics, and I’m publishing them here (a work-in-progress, stay tuned).