Powerful Questions

Image by  Tumisu  from  Pixabay

Image by Tumisu from Pixabay

Coaching is about helping clients find their own answers to the dilemmas they face.  Asking—rather than telling—is central to helping people listen to their “inner teachers” and find their own answers. That’s why one of the first skills you learn in coach’s training is that of asking powerful questions. A powerful question is one that invites the client look at the situation in a new way and discover new possibilities and fresh insights. As one of my coaching books put it, “Asking a powerful question is like sending the client not to a specific destination but in a direction filled with possible discoveries and mysteries.”[i]

You don’t have to be a trained coach to ask powerful questions, and you can even ask them of yourself. No matter who asks it, a powerful question draws you up short. It may render you silent for a few seconds. The most common initial response I get to a powerful question is “That’s a very good question.” When I ask the right powerful question, I can almost see the wheels start turning in the mind of someone who was feeling stuck.

In the time I’ve been coaching, I’ve begun to develop a little treasure chest of powerful questions. Most of them are pretty simple, but they challenge the client to reflect deeply. For example: What do you know for sure about what you want in this situation? What is your biggest self-limiting behavior? What is it possible for you to do to make this situation better for you? If you could have a do-over in this situation, what would you do?

I’ve learned a new powerful question from one of my coaching mentors, a man I’ve never met. His name is Jerry Colonna. He’s an editor turned venture capitalist turned executive coach. Some people call him the “CEO Whisperer.” I discovered Colonna about four years ago while researching the field of coaching. I began listening to his “Reboot” podcast, live coaching sessions with entrepreneurs. Colonna is a compassionate listener who helps his guests confront big life questions with humor, introspection, and honesty, and I have learned a lot from listening to him coach.

In one of the early podcasts I listened to, Jerry asked a podcast guest this question: in what ways are you complicit in creating the conditions you say you don’t want?

Whoa! I thought. That sounds a lot like Jerry is blaming this person for his own problems. But as I listened, I realized the question wasn’t about placing blame but about finding insight. The question made the guest cry. (Jerry is famous for making his podcast guests cry.) The question also led to a turning point in the conversation as the guest identified the ways he had helped create the situation that was driving him crazy.

As I listened to other episodes, I heard Jerry pose this question again and again, and it never failed to help the person receiving the question to see his or her situation in a clearer light. It helped them be more honest with themselves. Now it’s a question I’m trying out with clients. And with myself.

For example, I’ve written before about my tendency to focus too much on “doing”—on checking off a long to-do list instead of taking the time to just “be” in the world. When I decided to leave my academic career to be my own boss, I promised myself that I’d  take on fewer commitments and better match those commitments to my highest priorities. Still, every few months, I find my calendar too full because I’ve again taken on too much. At first, I feel sorry for myself. Some voice in my head says that the world demands too much of me (poor me). Then I realize that I am largely responsible for the situation.

Lately, when I realize that I’ve “done it again,” I hear Jerry Colonna’s voice in my head. In his new book Reboot: Leadership and the Art of Growing Up, Colonna said, “We must take the radical step of inquiring into our selves, seeking to see ourselves with clarity, grace, compassion, and a fierce commitment to cut through our own bullshit. We open ourselves up to the ways we’ve been complicit in creating the conditions we say we don’t want.”

 Honest introspection about why I become too busy can be painful, and the reasons that I make this mistake can vary. Sometimes, all the projects I’m working on are so interesting that I didn’t want to say “no” to any of them. Sometimes I agree to something because it feeds my ego. After all, it’s flattering when someone you respect asks you to take on a project because it signals that they respect your work. But a whole lot of the time, it all comes back to my lifelong need to feel valued and to feel like I belong—to measure my worth in the length of my list of accomplishments. As Colonna points out, admitting that to myself—compassionately—is the first step to changing the conditions I don’t want. And it’s a step I have to take again and again.

How about you? What are the conditions in your life you say you don’t want, and how are you complicit in creating those very conditions? Why do you do that, and how can you work to create different choices?

[i] Henry Kimsey-House, et al, Co-Active Coaching: Changing Business, Transforming Lives, 3rd edition, 2011, p. 70.