The Art of Asking Questions: A Design Thinking Workshop

At our OpenIDEO Los Angeles March event, we did a Skills Deep Dive into the empathy and definition stages of design thinking. We focused on interview techniques and “how might we” statements. We had a great turnout — mostly because we welcomed members from NELAUX. They came energized and ready to jump into the night’s activities, and that’s how ideators and ideas spilled out of our host’s conference room to set up shop in four other rooms about the office. Our fearless leader led everyone through a full docket of activities, and everyone had a great time. I heard from many newbies that they planned to be back.

However at the event, everyone left with questions about questions. How do you ask them? What do you ask? How do you know to ask the right one? So for the April event, I decided to keep digging deeper into this very necessary problem-solving skill. And it’s also something I’ve been trying to figure out how to teach for awhile: the art of asking dynamic and substantial questions!

This is an important topic to me because I’ve come to consciously accept this as my superpower. It’s a skill I continually sharpen and has played a role in all my personal and professional successes. From teaching ESL in Japan, to interviewing subjects for freelance articles, to conceptualizing and developing books to building out entire product strategies, questions constantly buoy me toward positive achievement.