The Art of Asking Questions: A Design Thinking Workshop

Sarah Dzida
May 21, 2017 · 9 min read

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.

So when our OpenIDEO April event rolled around, I planned out several activities for our members to practice this essential skill. By the way in each activity, there was the question-asker (Q) and the question-answerer (A).

Activity 1: Open-ended vs Close-ended Questions

There’s really only 2 ways to answer this question.

Close-ended questions are just … closed. They stop dialogue dead. They are demanding. They are stifling. As an example to the group, I turned to a member who I knew very well.

“How was your day?” I asked.

“Good,” she responded.

Conversation over.

Open-ended questions create the opposite scenario. They invite and indicate to the person you are talking to that you want to know more substantial things about them. They create a more friendly atmosphere, which is especially useful if you’re interviewing someone for professional purposes (user for UX, author for editing, personality for an article, etc.) And they give you a chance to practice your active listening skills. Open-ended questions imply that you want to hear what the other person has to say; that means they can talk and talk. This is key to the success of an interview!

So for this activity, I guided the group through a practice exercise. Q is only allowed to ask questions of A, but they must be open-ended. This means:

  1. The question must elicit MORE THAN a 1-sentence response. Therefore, questions like “What do you do?” don’t work. This is because the answer is generally a simple, close-ended sentence like “I’m a UX designer.”
  2. The question must follow the natural progression of the conversation. Therefore there can’t be any non-sequiturs.
  3. And most important, there shouldn’t be any awkward pauses.

One of the most interesting discussions that came out of this activity was around introductory questions. We found that many of our new-person questions are rote—like “how are you,” “what’s your job” and “what are you doing this weekend.” And to break that formula, the group had to think really hard about what would be a great open-ended question to use instead of our routine patterns of dialogue. Then halfway through the exercise, one member finally thought up a question she wanted to try.

“Are you learning anything new?” she asked me.

“Yes,” I answered, “I’m learning how to run.” This elicited a laugh, and I explained how I came to start running after years of not. Without needing to invite anyone else, other groups members naturally joined into the conversation. They contributed jokes, anecdotes and advice. We wandered down that thread for awhile before I laughed. “Look at what your question accomplished!”

Another interesting observation that came about was how the designated Q tended to stick to one subject, and that was generally work. It was because it was safe: “What are you working on right now?” “Why does that inspire you?” “What are you hoping to accomplish with that?” And etc. And the Q person, under the pressure of needing ask open-ended questions, had a difficult time thinking about expansive answers.

Eventually, I needed to create another rule: #4 No work related open-ended questions! That’s because those are also close-ended in a way. They kept the Q-person focused on just one silo of information, and the silo eventually ran out because as humans we generally have a full dimension of stuff happening outside of our careers. And that rule is actually what led to our “what are you learning” breakthrough!

Activity 2: Big vs. Small Questions

Imagine if this was the first question someone asked you in a job interview.

Big questions require deep and well-thought answers. Examples of big questions that go horribly wrong are: “What do you want to do with your life?” “What do you like to do for fun?” “What are you thinking/feeling?”

If you ask these questions too early on in a conversation, you will get the same results as if you asked a close-ended question. The A person won’t know how to respond because you haven’t primed them for that deeper, richer and more sincere answer that is buried somewhere in their head. They just aren’t prepared for it; it scares them into silence. It makes them unnecessarily anxious about saying the right thing. And they just don’t have any context as to why you need that answer or why you care. Too often, a poorly placed big question can stop a conversation cold.

Usually when you conduct an interview, it’s the answers to big questions that we actually want. In order to prepare our interview subject well for that answer, we need to use a combination of smaller questions (“What are you doing with your life now?” “What’s a fun thing you did recently?” “When was the last time you felt happy?”) and follow-up questions and responses to get them there. Using the combination helps you move the dialogue from superficial to more intimate AND tacitly prepares the person for that whammy of a question. When you ask it, they are unconsciously ready for it AND willing to explore it with you.

So to practice big questions, I first asked the group to write out examples of them on notecards. We then folded them up and put them in a bowl. The challenge this time was that the Q person would draw a question from the bowl. The A person wouldn’t know what the question was. However, the Q person had 5 minutes to use small questions and follow-up questions and responses to lead the A-person to the deeper question and answer.

Here are the interesting insights that came out of that activity:

  1. People began to notice that they didn’t even need to explicitly say the big question at the end of the five minutes. Because the entire 5-minute conversation would slowly draw out the answer in its entirety. They didn’t need to be so on the nose.
  2. One member realized that it wasn’t just important to ask good questions BUT to also be an active responder. Listening intently and making follow-up responses like “oh,” “is that so” or “tell me more” were just as crucial to the evolution of the conversation.

Activity 3: The Sound of Silence

Remember question askers: Interviews aren’t about you!

When I lived in Japan, I learned the value of silence. This is because culturally, the Japanese are OK with up to 12 seconds of silence between a question and an answer. Us Americans? We can only tolerate 3 seconds. Therefore, one of the biggest re-trainings of my life was learning to stand next to a student and count to 12 in my head before trying to fill the void with sound.

That’s why for the final activity, we focused on silence. I’ve found this to be an essential tactic in interviewing. Too often, question askers get uncomfortable with silence and jump in to fill the void. This stymies the A person and makes them forget their train of thought or discard the idea of giving you what could be important information. Silence is so important that one of my cardinal rules for interviewing is that the interviewer should do as little speaking as possible. When you do this, you actually empower the interviewee. It helps them trust in how much you personally care and are engaged in their answers. It also switches the Q person’s perspective on the purpose of the question. Rather than worrying about what makes a right or wrong question, the Q person focuses asking questions only when necessary AND giving their interviewee time to think about their response in order to encourage the flow of information on the A person’s side. I mean sometimes you do need to speak, but usually, a simple verbal or non-verbal indication will be enough to keep your interviewee going.

For this activity, we returned to the big question bowl. Only this time the Q person only had 3 questions to get to the big answer. AND the A person had the option of intentionally waiting 12 seconds or more to answer the question OR actually needing that time to figure out their response. The challenge for the Q person was not to break into that silence.

This was the most interesting activity of the night. The Q person drew the big question of “What is the afterlife?” So to start off the conversation, she asked something along the lines of, “Do you think there is something of us when we die?”

However, she didn’t know that her A person had recently experienced the death of loved one, and her A person’s entire attitude changed from teasing to serious. The entire room waited; I counted out 24 seconds of silence while the Q person fidgeted. Then the A person responded with her very true and intimate experience. She later explained that she felt she owed it to her loved one to answer the question honestly.

It was fascinating to watch the face of the Q person, however. She suddenly realized that she was wading into deep and vulnerable territory. That this wasn’t just an exercise anymore, but an important and very human moment between her and this person. The whole conversation slowed down. You could see her thinking very critically about how to approach the second question sensitively because it really mattered now.

Later, we talked about this as a group — how these are the reasons why we ask questions. It’s not just to fill time and space. It’s not just to get quotes for interviews or data for product testing. Questions are supposed to lead us into meaningful interactions with people. Because that’s how we build trust and honest relationships with each other. That’s how we really learn about what matters.

By the way, this will probably be the first in a series in which I discuss how to craft powerful questions. I’d like to thank everyone who came to the April event with an open mind and brave spirit! I learned a lot from the event, and I hope you did too!

Update 10–20–2017: Here’s part 2 of my series—“The Question Asker-er: Tactics on How to Use Questions to Get What You Want/Need.”

Update 11–8–2017: Here’s part 3: “The Tricky Business of Close vs Open-Ended Questions Especially in Interviews.”

Update 11–26–2017: Here’s part “The Parallels of Asking Questions and Learning Ruby on Rails.”

More Resources

Sarah Dzida

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UX & Content Strategist + Poet

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