The 3 Types of Questions and Why I Ask So Many

I love asking people questions. If you know me, you'll notice I do it much more than most people. I'm convinced it makes life more interesting. Let me convince you why.

I was in an Uber the other day. The driver was a somber man with short, wiry grey hair. I asked him where he was from. He said Rio de Janeiro. I told him I was just there for carnival! He said cool. I asked him how long he's been here. He said 2 years. I asked him why he moved. He said his daughter lives here. I was stuck with short answers. My intermediate Portuguese was running out of questions. Then I asked him what he misses most about Brazil.

His face changed. He started using his hands as he described that what he missed most was the people — in Brazil people are happy, they have tougher circumstances but they're in it together, here everyone is sad, especially Portuguese women and young people, they don't see a future. He used to have barbecues with his friends all the time and here his neighbor will barely say hello to him.

Why did this question have such a different response than the others? It's because it was a different type of question. I think there are three types of conversation questions: recall, reflection, and deep reflection.

Recall questions

Most questions that come up in casual conversation are recall questions. You know the information being asked and you verbalize it for the other person. For example, "How old are you?" or "What's your favorite food?" or "What do you do for work?" They're useful for getting a baseline understanding of the other person and they get the conversation going.

Reflection questions

The second type of question requires some reflection; either nobody has asked you before, or the answer changes. "How was your day" is the baby version because it requires a bit of reflection, "Hm, how was my day?"

Asking, "Why?" is often a reflection question, although asking it flat-out can come across as judgemental. A trick a user researcher taught me is to instead ask, "What lead you to that?" It's the same question, but less judgey and asks for more of a story. I also like the question "What surprised you about that?" because it simultaneously asks about expectations and reality.

Deep reflection questions

The third type of question is also the rarest: questions where the person answering it learns something new, often about themselves. Therapists and coaches are well-versed in asking these questions. They can unblock people. They're powerful. David Brooks talks about how we all grow up asking these questions:

Kids are phenomenal at asking big, direct questions. I have a friend named Niobe Way who was one day teaching a class of eighth grade boys how to conduct interviews. She made herself their first interview subject and told them they could ask her anything. Here’s how it went:

Student A: Are you married?
Niobe Way: No.
Student B: Are you divorced?
Way: Yes.
Student C: Do you still love him?
Way: [Deep gasp of breath]
Student D: Does he know that you still love him? Does he know?
Way: [Tears in her eyes]
Student E: Do your children know?

As adults, we get more inhibited with our questions, if we even ask them at all. I’ve learned we’re generally too cautious. People are dying to tell you their stories. Very often, no one has ever asked about them.

I used to be nervous when I asked big questions. Will people think I'm nosy? Will they tell me it's personal and change the subject? I started asking anyway, and so far I've been surprised by how much people light up. People want to talk about real shit. They don't want to talk about the weather.

In All About Love, bell hooks says love is:

The will to extend one's self for the purpose of nurturing one's own or another's spiritual growth.

Deep reflection questions nurture the spiritual growth of others. They show other people that we care about them and see them. Plus, you wouldn't believe some of the crazy stories people will tell you. All you have to do is ask.