One of the more awkward phases of small talk (and ​making the transition to deeper conversations​) can be the one where you realize you want to keep the conversation going, but can’t think of good questions to ask.

It’s a moment that can feel a bit like grasping at straws for many of us.

We don’t want to ask “boring questions” that kill ​the vibe​. We also don’t want to talk about ourselves the whole time. And ​silence, being the great revelator that it is​, would only highlight our internal struggle.

If you’ve followed my work for quite a while now, you know what my advice would be:

Just tell the other person what you’re feeling. Tell them that you want to continue the conversation and find yourself struggling to come up with a good question. Possibly ask them if they ever have that too.

This is the way.

That said, I don’t just want to leave you with that today. Asking great questions is still a learnable skill.

Counterintuitive Advice for Asking Better Questions

When people don’t know which questions to ask, the common advice would be something like “become more interested in the other person”.

There’s truth to that. But I’d also argue that if you are not interested yet, you might simply not want to be in a conversation with them.

And more importantly: When we try to become more interested in someone, we tend to do so by putting more of our focus on them. Which makes logical sense, but it’s not where your curiosity is felt.

Funnily enough, asking great questions starts with keeping part of your focus on yourself.

Being fully aware of what’s happening inside you while you are with the other person.

Feeling exactly which curiosities they awaken in you.

What do you naturally wonder about them?

Follow that aliveness and speak it out loud.

There is no end to this.

There’s a universe inside each person, and it keeps expanding.

How deeply can you get to know and appreciate it?

Tune into this sense of wonder about them.

If that doesn’t lead to questions you wanna ask, ask yourself: “What are some things I don’t know about this person?”

Then ask that.

When you’ve known someone for years, sometimes it may seem like there’s nothing left to discover.

But we can always get to know more of each other. Because in each new moment we have a new experience that impacts us. (Including the “nothing left to talk about” experience. It’s a profoundly impactful experience. We can only wonder how the other person is experiencing it.)

In a way, the more you know a person, the more connective the remaining curiosities can be.

Because at some point, the pool of informational knowledge is exhausted.

Now all that’s left is to ask about what’s really here. What’s on their mind? How does it feel for them to share this moment with you?

This will naturally ​take the conversation to a deeper level​, should they want to answer it.

Finding Fun Follow-up Questions

A conversation, of course, doesn’t merely exist to satisfy your own curiosity.

It’s just that your curiosity is where your aliveness is, so the questions it asks can light a spark in the interaction.

Once you’ve asked some questions sparked by your own curiosity, look for glimmers of aliveness in the answerer:

A spark in their eyes, a warm flush on the face paired with a smile, skin that seems to tingle and come alive. Those are the conversational threads to explore further.

Great follow-up questions are found on the intersection of what makes them come alive to answer, and what leaves you longing to know more.

This is how you keep fanning the flames of connection.

But how do you know which questions to avoid? Same thing:

When you ask someone a question, and in response their replies get shorter, their body language closes, their skin loses color or they generally look turned off, then it’s a good idea not to continue in this direction.

…of course, the same advice I gave you at the start applies here: When in doubt, you can always reveal and ask:

“How are you enjoying these questions? I’m eager to get to know you and worried that one went a bit too deep. “

(Side note: A fun way to attune to each other’s desired level of depth is to just agree to spend some time asking questions back and forth. By the type of questions they’re comfortable asking you, you’ll often get a sense where they are at with you—and it keeps the conversation balanced too.)

How Open-Ended Should My Questions Be?

The scope and specificity of a question can influence how enjoyable it is to answer (or to get an answer to).

This map’s a good starting point when learning:

In case you’re wondering why I recommend minimizing broad scope + high specificity questions or label them as effortful, think of it this way:

If someone asks you for your favorite movie, that’s an easy answer if you have one. But if you don’t, it prompts the listener to either evaluate every movie they’ve enjoyed and rank them or give you an answer that’s possibly false.

If you have no problem with such questions, the answer seems obvious. You reply: “I don’t have a favorite one, but one I enjoyed a lot is ____”

But not everyone will do this. Some people do get stuck on it.

Yes, there are exceptions to this rule. E.g. experienced coaches ask amazing broad scope + high specificity questions. But that’s because they are already great conversationalists.

If asking good questions is a skill you’re still working on, it’s useful blanket advice to focus on the upper-left and bottom-right quadrants. You can use the lower-left for small talk, and save the top-right for when the answer really matters to you or could meaningfully improve the interaction.

The Context Changes the Meaning

What makes a question “good” is also determined by context:

If at a party, you ask a lawyer your law-related question, it can seem like you’re trying to get free service.

If you ask your employee an intimate question, there’s a power dynamic that can make it feel invasive.

Some contexts create potential consequences for answering certain questions, making it best to avoid them entirely.

For example, if you work in a political or toxic environment where personal info can be leveraged against you, you might not want to ask about anything too personal.

(If you haven’t experienced this, you might be surprised how real this gets. I once witnessed 2 influencers struggling with small talk because answering any question about how their life was going could mean giving the other person prime access to gossipping about it on their channels.)

Similarly, asking questions about situations about people not present in the room that you both have a separate relationship to isn’t always the best idea.

If you commonly run into situations where people seem to find your questions either uninteresting or overwhelming, one of the reasons could be that they don’t match the current depth of the conversation. If that applies to you, ​here’s an article about different levels of conversational depth​, so you can calibrate.

Exploring Tension, Edges and Juiciness

If you’ve dropped into deep connection with each other, and are well attuned to the other person, a new category of great questions appears:

Those that explore tension, ​vulnerability​ and potential dissonance.

Leaning into these edges together can make for some of the most connective and alive conversations. But uncalibrated, they can do the opposite.

Because that’s exactly it: By exploring the places that could potentially break it, the strength of your connection is highlighted.

The “right” question asked at the “wrong” time can feel creepy, invasive or accusatory.

The “wrong” question asked at the “right” time can make a room full of people comfortable with each other as they make eye contact and recognize in each other a kind of laughter that only occurs at that rare sweet spot when shame and self-acceptance become one somehow.

My favorite questions walk the edge of uncertainty. They draw us into the present. They feel exhilarating to answer because we don’t even know what our answer will be until the words leave our lips. But we know they’ll be true.

By asking the kind of questions you “shouldn’t” (or don’t want to) ask, at a time and place that’s exactly right for both of you, you discover that you can do this. That you are able to be adventures together. And there’s enough mutual care to risk some bruises in exchange for something better.

I wouldn’t get mathematical about this, but if you’re going to ask spicy or vulnerable questions, aim to match that level of vulnerability with your own disclosure. Preferably even going first. Otherwise it can feel exploitative or unsafe.

When in doubt, you can always ask for ​feedback​:

“How did that question land for you?”

“Did that question feel good for you?”

(I sometimes literally ask “How spicy would you like your questions right now?”)

Understanding Where Your Question Is Leading

While this is a little more advanced, and probably not the first thing to focus on when improving your questions, one thing that’s rarely taught about questions is that they essentially shape the other person’s thinking by launching a search query.

Remember how I gave the example of how “what’s your favorite movie?” is a search query for movies in your brain?

Now imagine the following:

You see someone’s facial expression and you ask them “What’s wrong?” or “Why are you upset?”

These questions are search queries for wrongness and reasons to be upset. They inquire for that even if you misinterpreted the expression. If the other person is in a receptive state, your question may have now created a sense of wrongness, or given them something to be upset with.

A more neutral question would be: “How are you feeling?” or even “I’m noticing the expression of your face and wondering what it means?”

Similarly, some questions can be an accidental setup for something undesirable.

Here’s an example of such a question I have asked about 100 times:

“Wow that’s delicious! Did you make that?”

This is a bad setup, because if they didn’t make it, I just highlighted that. Which can lower​ the vibe​ for some people.

“Wow, that’s delicious! Where did you buy it??” has way better odds. Just look at these possible answers:

• “Buy it? I MADE it! Thanks for the compliment.”
• “My favorite store. Let me tell you all about this great find!”
• “It was given to me by someone else, they’re such a great cook.”

It’s essentially the same question but it only leads to uplifting places where the other one often doesn’t.

(Side note: this applies to all the questions you ask yourself too. It’s good to become aware of the mental places you are leading yourself to. In general you can take all my writing about interpersonal relationships and apply to the relationship with yourself, or with life, or money, or anything else. And vice versa.)

The Interaction Between Speaker and Listener

I’ve written before about how I believe ​honesty is a two-way street​.

The same applies here. If you want to ask questions that people enjoy answering, a huge factor is that the person who answers them knows you will:

• Give their answer your attention
• Won’t judge or get reactive about something you just asked them
• Be okay with any disagreement between both of your perspectives

Sometimes the reason questions aren’t met with excitement isn’t about the subject but the presence of the listener.

My favorite questions allow the “answerer” to feel more of themselves through the “questioner’s” inquiry and presence.

And they allow the “questioner” to feel more of themselves by letting the “answerer’s” answer land in their body and light up parts of themselves they didn’t even know existed.

It’s always a dance of give and take. And as long as there’s mutual commitment to connection, there’s always more to explore.

So if you genuinely feel blocked on asking a good question, why not ask the other person to help you?

Here are some questions you can keep in your back pocket for situations like that:

• “If I really wanted to know you, what would I have to ask you about?”
• “What’s a question you wish you were asked more often?”
• “What can you talk about all day?”
• “Did you get asked any really good questions lately?”
• “What are some questions you love asking strangers?”
• “What are you often curious about in other people?”

And if you want them a little more spicy:

• “How is this conversation feeling for you?”
• “What’s happening in this conversation that we’re not talking about?”
• “How could we make this conversation more wonderful?”
• “What do you secretly hope I won’t ask you?”
• “Why do I think I struggle so much with finding questions to ask you?”

Asking great questions is a skill worth learning.

A great question can light up a room.

A great question can turn strangers into people who already know they’ll become friends (or lovers) later.

The right question at the right time can even pop a bubble of illusion we’ve been living in for years.

I hope what I shared can serve all of that for you.

And in the meantime, feel free to practice by asking me anything.