CEOs: If you don't ask, you'll never know

As a member of Vistage’s faculty, I travel around the world training fellow leaders on how to be a great executive coach. I cover a variety of topics including how to show up powerfully as a chair, what a strong peer group is, and how to build and facilitate one. However, the element that makes the most impact is the focus on creating real connections through impactful conversations. At the heart of a good conversation is listening and the art of asking a good, powerful question. It’s one of the critical skills of a great leader. If you are not able to explore in your question asking – it will be very hard to uncover what really motivates and drives your people and with that add significant value.

Cultural differences helped me hone my own inquiry skills. Having grown up in Europe, I didn’t always understand certain words or phrases people say in the U.S. I automatically had to ask questions, and challenge “known” assumptions. Fast forward to now, my curiosity and habit of asking a lot of questions, assists me greatly to help leaders generate self-awareness.

Let me share a (quite typical) example from early on in my career as a Vistage Chair. One of my members brought a topic to the group related to a not up-to-par leadership team member. After a few inquiries about the underperformer, we switched and geared the questions to the member. What is your relation like with her? Where are your fingerprints on this behavior? What relationship from your past does this one remind you of? Tell us more. How is that relationship now? How is that impacting you?

After several rounds we uncovered a pattern stemming from the member’s relationship with a family member. Not quite where we started and only uncovered because of deep insightful questions! 

At the end of the meeting the member was sitting at the edge of his chair, looking at the ground, shaking his head. I walked up and said, “What’s going on?” He let out a big sigh, “Niels, I realized this Vistage thing would be beneficial for my business, but I never ever thought it was going to have such an impact on me personally and we’re only one meeting in.” That is why we do what we do. We all work on improving each other’s lives, and that won’t happen with simple yes or no questions.

Whether you’re in the boardroom, interrogation room or out to brunch, here are some best practices to ask better questions:

You have to open yourself up first.

If you’re not comfortable exploring and talking about your own feelings, it’s going to be hard to ask others to do it. It takes courage to show vulnerability and you showing it first will make it so much easier for your conversation partner.

Don’t shy away from the tough questions.

The scary thing is you don’t know how much you’re missing by avoiding touchy subjects. By not asking, you only get surface-level conversation, blind spots, and status quo.

Dig deep, through questions, to uncover the problem behind the problem.

What we’re really doing is peeling the onion. When one of my Vistage members brings a topic to the group, the goal is to ask questions around what drives the actions of the person, their beliefs, and how it’s impacting that member’s life, family, and business.

LISTEN to the issue rather than trying to fix everything.

Leaders are often looked to for all the answers, but when you’re the one asking questions, it’s not your turn to talk. Stop yourself. The person answering questions will be more open if you’re tuned in.

All Vistage Chairs are trained to ask the kinds of questions that lead to clarity and a level of awareness CEOs and business owners can’t necessarily get anywhere else. Contact me if you’d like to learn more about Vistage. If you don’t ask, you’ll never know.

About the author: I’ve led Vistage groups since 2012 and coached over 80 CEOs and business leaders in Santa Barbara, CA and North Carolina. I’m a member of Vistage's Training Faculty and teach Chairs all over the world how to be great coaches, facilitators, and mentors. I can be reached: [email protected].