9 Questions to Stop Asking and What to Replace Them With

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Read time: 5 minutes

Today at a glance:

• Topic: Children ask 40K questions, and most are better than yours

• Tactic: Avoiding bad questions and shifting towards the right ones

• Quote on Asking Questions

• Devin's Finds: 📰, 🎙, 🎞

• Commitments: 🤝

Over the last five years, I've been lucky to spend a lot of my time around my cousins' young children. Right now, all five are ages two through five. One thing that becomes clear after spending just a few minutes with them is that they are endless question-asking machines.

• In the morning: "where did the moon go?"

• On the subway: "where are the turtles?" (referring to those of the teenage mutant ninja variety)

• In the car: "why don't I get to drive?"

Some of them make no sense at all…

I did my best to think back to when I was at that age. I couldn't remember any specific questions I asked but I certainly remember never feeling shy to ask them anytime and anywhere.

It turns out, the average kid asks over 40,000 questions between the ages of two and five.

But at some point in adolescence, that comfort with asking questions fades. Asking questions becomes a strangely vulnerable activity. Almost as if we're always admitting to not knowing something.

That becomes a bigger pill to swallow when society tells us

• Don't show emotions

• Don't get too personal

• Only show the best part of yourself

Because if we do show who we really are or the knowledge we lack, others might not like us.

We then either avoid questions that don't show how well-informed we are, or we stick to the safe and boring ones like "what do you do?" or "what's up?"

In the worst case, we don't ask any questions at all.

How can we break free of these bad questions and refocus on the right ones?

Avoiding the Worst Kinds of Questions

The worst kinds of questions come from trying to take perspective through questions. There are a few common ways these play out.

1. Questions Not Involving a Surrender of Power

These are questions that imply "I'm about to judge you" such as:

• What do you do?

• Where did you go to college?

• What neighborhood do you live in?

2. Closed Ended Questions

These are questions where the asker is imposing a limit on how you can answer the question—often to yes / no or good / bad scenarios. They include:

• Do you like your job?

• Were you and [person] close?

• Are you excited about the [event]?

The answers to questions like this are almost always more complicated than yes or no. So we should avoid boxing people into only those two responses and allow people to answer in their own words and from their own perspective.

3. Vague Questions

These are the questions that are impossible to answer. They are often our default questions because they check the box of "asking a question" while avoiding the asker needing to be vulnerable. They include:

• "What's up?"

• "How's it going"

• "What do you like to do?"

In reality, by asking these questions, we communicate that we don't care much about the answer.

Shifting Towards the Right Kinds of Questions

Good question askers adopt a posture of humility. After all, they are basically admitting they don't know and want to learn (which isn't a bad thing!).

They ask humble, open-minded, and open-ended questions that encourage the other person to take control and take the conversation wherever they want it to go. They often begin with:

• How did you…

• What's it like…

• Tell me about…

• In what ways…

Here are a few situations to ask these kinds of questions.

1. Good Introductory Questions

If you want to prompt someone to dive into their background and family history, try some good introductory questions:

• Where did you grow up? This gets them talking about their hometown.

• That's a lovely name. How did your parents choose it? This opens up the conversation to their childhood and background.

These are good questions for mutual exploration

2. Bigger Questions

When you play it safe and stick to small questions, you can expect a perfectly pleasant (and potentially unmemorable) conversation. But for a truly memorable conversation, you should move to bigger ones—of course, make sure it's appropriate given the relationship you have with them.

These are the types of questions that stop people in their tracks and really make them reflect on their lives. David Brooks has a great list of these questions:

• "What crossroads are you at?" At any moment, most of us are in the middle of some transition. The question helps people focus on theirs.

• "What would you do if you weren't afraid?" Most people know that fear plays some role in their life but they haven't clearly defined how fear is holding them back.

• "If you died tonight, what would you regret not doing?"

• "If we meet a year from now, what will we be celebrating"

• "If the next five years is a chapter in your life, what is that chapter about?"

• "Can you be yourself where you are and still fit in?"

3. Positive Questions

People often think that because a question is big, it will lead to painful conversations. But if you ask these framed towards the positive sides of life, you'll be able to compensate for that.

I found another great list of these by David Brooks:

• Tell me about a time you adapted to change?

• What's working really well in your life?

• What are you most self-confident about?

• Which of your five senses is strongest?

• Have you ever been solitary without feeling lonely?

• What has become clearer to you as you have aged?

Remember, you don't have to come out of the gate with "if you died tonight, what would you regret not doing." Instead ease in with open ended questions and let the conversation take its course. The most important part is not boxing the other person into a limited set of answers…because people love to hear themselves speak!

In fact, a 2012 study by Harvard neuroscientists found that people often took more pleasure from sharing information about themselves than from receiving money.

Quote on Asking Questions

These people don't just spill their own mysteries, so work on becoming a good question asker so you can unravel them.

Devin's Finds:

📰 How I used gratitude and relationships to focus on the present (3 minute read): I wrote a blog post about my gratitude story for my company, Gratitude Plus—maybe you relate. As children, we live in the moment, but as we grow we become obsessed with chasing distant goals, often at the expense of our well-being. This story is how I used relationships and gratitude to help with depression and refocus on the present.

🎙 Carole Robbins on progressive disclosure and the 15% rule (3 minute clip from Lenny’s Podcast on Spotify or YouTube): Deepening relationships doesn’t happen at the snap of a finger. It takes many little steps in the right direction. This clip (starting at 21:36 in the podcast) has Carole Robbins explaining her technique of progressive disclosure and the 15% rule when it comes to deepening relationships. Basically, by stepping 15% outside of your comfort zone with the questions you ask, you settle into a new, slightly larger, comfort zone. As you repeat this, you deepen the bonds you have.

🎞 A one minute video of 5 questions you can ask yourself or others for deeper self-reflection ⬇

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Best of luck building,

Devin