Pragmatic coaching for
mindful leaders

Chad Dickerson, executive coach and former CEO of Etsy

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.

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.

Strong Back, Open Heart

In my coaching practice, I try to focus on the "strong back" and "open heart" in equal measure to help leaders grow themselves and their businesses.

Strong Back

The "strong back" represents the "operating system" of a business. Below are just a few of the areas that I work with clients on along with the kinds of questions we discuss in our sessions:

  • Culture. What kind of culture do I want? How do I set it, measure it, and continually shape it as my company grows?
  • Executive team and org structure. How do I build the most effective management team and overall structure for my company?
  • Strategy. How will my company navigate our competitive landscape to achieve our objectives?
  • Setting goals and objectives. How do I set corporate goals at the board level and translate them throughout the company?
  • Recruiting, hiring, and interviewing. How do I find and keep the best talent while shaping culture?
  • Feedback and performance management. How do I deliver effective feedback and hold my team accountable?

Open Heart

The "open heart" is the stance that feeds the inner life of a leader that ultimately binds an organization together powerfully in a common cause, bringing out the best in the people around the leader:

  • Purpose. How do I articulate the larger purpose of my company and align it with my own purpose?
  • Values. What is most important to me and how might that manifest in the company I am building?
  • Communication. How do I communicate clearly, compassionately, and authentically?
  • Connectedness. How do I inspire and motivate people from all backgrounds and keep them feeling connected as my company scales?
  • Accepting and processing feedback. How do I model accepting, processing, and integrating feedback as a leader?
  • Work/life integration. How do I honor and succeed at my other important roles in life while delivering high performance at work?

Let's talk

If you're interested in learning more, please get in touch.