Andy Crissinger: The Art of Asking Better Questions

This week, I talk with Andy Crissinger, a world-class coach and master facilitator who has guided leaders at some of the world’s most renowned startups and companies. Andy’s journey to coaching is remarkable, weaving through ministry, startup leadership, and eventually finding his calling as a coach. In the first half of our conversation, we explore his personal story, which is deeply relatable and filled with lessons about growth and resilience. In the second half, we dive into a coaching curriculum built around five transformative books, offering practical insights for personal and professional development. These resources can help you grow into the leader, partner, and parent you aspire to be. I loved this conversation with Andy about finding purpose, building trust, and achieving meaningful growth, and I think you will too. Let’s get to it!

In this episode:

(00:00) - Intro
(00:05) - Who is Leonard?
(03:25) - What music represents for Andy
(07:28) - Family, integrity, and sense-making
(14:15) - Andy's transition to ministry
(17:09) - What Andy learned about community through ministry
(23:13) - Coaching vs teaching
(30:20) - The journey through infertility
(39:16) - How impact and joy of fatherhood
(43:15) - Transitioning to coaching
(48:00) - Founding Worksong
(01:00:23) - Humble Inquiry by Edgar Schein
(01:13:11) - Inherited Family Trauma
(01:19:42) - Andy's beautiful future
(01:22:18) - Who And is becoming
(01:24:19) - Trees by Howard Nemerov

Key Takeaways

Embrace Your Subconscious in Creativity: Andy’s songwriting and poetry offer unique ways to tap into intuition and the subconscious. By exploring impressionistic lyrics and reflective storytelling, artists can uncover connections and truths that are not immediately apparent in other forms of expression.
Fostering Community Requires Intentional Facilitation: Building trust and vulnerability in groups involves creating a “container” that encourages inquiry over answers. Leaders can foster deeper connection and authenticity by resisting the urge to provide solutions and instead enabling individuals to explore their own paths.
Sensemaking as a Tool for Growth: Reflecting on life experiences can empower individuals to take ownership of their personal narratives. This process of sensemaking helps connect the dots between formative events and their impact on personal and professional choices, enabling more conscious decision-making.
Parenthood as a Crucible for Growth: Andy shares the lessons fatherhood has taught him about patience, humility, and embracing imperfection. Parenthood challenges you to navigate your child’s limitations while striving to support their individuality and growth.
Redefining Coaching as Empowerment: True coaching emphasizes the client’s inherent resourcefulness, avoiding a top-down dynamic. Effective coaching affirms individuals’ capabilities to solve their own problems, distinguishing it from teaching or directive advice-giving.

Quotes

“[Songwriting] is a way to express emotion, but it feels like it's more than just emotion. There's a way to express and reflect the nature of reality, the aspects that are more mysterious, oblique, the connections that are less obvious. My lyrics tend to be more impressionistic. I like that. I love language and I love putting words together. And then, only later, maybe seeing some of the connections that my subconscious was making.” ~ Andy Crissinger

“There are some ways that you can create conditions that are safe for people to show up and be vulnerable and to trust that they can be a little bit more of themselves. I found that when I encouraged small group leaders to turn to inquiry more than answers…you could actually create much more vibrant communities because people felt safer to be real and be themselves.” ~ Andy Crissinger

“I was really attracted to a form of helping that did not require one person to be above the other. It just gave this different way of helping. It was very much affirming of the giftedness, the brilliance, the resilience that was alive in that person that you were helping.” ~ Andy Crissinger

“Fatherhood reminds me on a regular basis how much more I have to learn and grow in that kind of others-orientation. I cannot be perfect for each of them all the time. And I’m certainly not. So that has been a humbling and, I think, forming part of the experience.” ~ Andy Crissinger

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