Note: We know this piece is a little longer than usual, so feel free to jump to the 'Wrap-up and Takeaways' section at the end. However, we believe you'll find it to be an enjoyable read.
There was a time, not so long ago, when curiosity felt like an impossible skill for me.
I would sit in a conversation, racking my brain for anything I could say. The only options were to talk about myself - which felt awkward unless they’d asked - say a non sequitur, or come up with a question.
But I felt so frozen that no questions came to mind. What was off limits to ask? What would they want to talk about? What if I wasn’t really interested? They say that only boring people get bored in conversation. What if I was, secretly, really boring, and that’s why I couldn’t find my curiosity?
Eventually I did what I do with all problems:
play a bunch of Authentic Relating Games to practice the skill,
research the heck out of it, and
start teaching others how to do it.
Gradually, slowly, I learned how to start conversations. Then I learned how to deepen them. Teaching myself this skill from scratch as an adult came with a large benefit: I can help others learn it, too.
In this article, I'm going to break down the subtle skill of asking great questions by identifying some questioner archetypes. Maybe you’ll recognize yourself in a few of them! We’ll discuss small talk, non-sequiturs, scientific curiosity, spaceholding, and more. By the end, you’ll have many ideas of how to make even the most prosaic conversation a meaningful experience.
The 5 Types of Question-Askers
By studying human interactions, I've identified 5 kinds of questioning, which I call the Seeker, the Socialite, the Scientist, the Spaceholder, and the Non-Sequitourist.
Each type is practice-based, not personality-based. In other words, you may use any of these styles of questioning at any time. Most of us gravitate towards one during a conversation - but conversation after conversation, your style will change, as will other people's. So, as you’re reading these, ask yourself:
Where do I use this type of questioning?
Where or with whom could I use it more?
How do I relate to people in my life who use this questioning style?
How could I relate more kindly and effectively with them?
As we go through, we’ll explore when each style of questioning is useful, and how to relate with someone who is using it. As a result, you’ll greatly expand your range of options in conversation.
Style 1: The Seeker
Here’s one version of a Seeker conversation:
“Where are you from?”
“I’m from Austin, Texas.”
“Don’t you have trouble with the politics?”
“I mean, they’re not my favorite, but I live there more for the people.”
“Yeah, but what do you think about the governor?”
And another version, perhaps encountered on a street corner:
“Where are you from?”
“Austin, Texas.”
“Have you heard of Jesus Christ?”
The Seeker is the Questioner with an agenda. And before we judge this type, let’s be honest: we have all been the Seeker at one time or another. In fact, it’s hard to get through a conversation without Seeking at least once.
Someone mentions a problem they’re having? We start asking pointed questions, seeking for where we can help.
Someone talks about job openings at their company? We start exploring what potentials there might be for us or our friends.
Someone begins talking about their day? We prompt them with something DEEP, to make the conversation more interesting to ourselves.
Seeking happens when the conversation becomes goal-directed, usually with the dominant direction set by one member.
When to take the Seeker approach
Seeking can be useful when the goal is clear, and both parties buy in. We might co-explore a topic or theory, as in science, with the goal of finding truth together. We might mutually try to solve an issue, as in coaching, with the goal of improving one person’s life. The most important thing, when Seeking, is to be honest with yourself (and ideally the other person) about what your goal is.
If you’re asking questions to convince the other person of how their view is wrong, admit that to yourself so that you can moderate your intensity. If you’re asking questions as a form of flirtation, at some point, you should probably communicate your interest in a date or it will start to feel sleazy.
Seeking is also useful when you’re in a boring conversation and/or one in which you’re minimally invested. In those situations, I often entertain myself by pursuing an agenda. There is little to lose, so I feel okay trying for a gain.
The agenda I personally tend to pursue is understanding a person’s field or topic and getting interesting information out of them. But sometimes, I’ll try out new communication techniques on them, or mine them for contacts or advice.
Relating with a Seeker
If you find yourself talking to a Seeker and you want to change the style of conversation, stop, drop the topic, and roll for insight.
“Hey, I’m noticing you seem to have a point you are driving towards. What do you expect out of this conversation?”
Or just, “What do you want from me here?”
This works best if you can append the “what do you want from me?” with some options. Especially when upset, people are not good at brainstorming. Let’s say you’re in a Seeking conversation with your partner who is overwrought because some undefined need of theirs isn’t being met. You might say: “What would you like from me? Questions? Reassurance? A specific commitment?”
If you enjoy a more directed style like Seeking, try to navigate towards a topic you want to discuss. For me, the speed and intensity that often comes with these conversations can be really fun.
If you are being a Seeker
First, notice that you have an agenda. It can be hard to see when we’ve switched into a Seeking role. Start noticing the subtle signs. For myself, my vision gets more focused in; I stop noticing peripherals. My questions come faster. I use shorter sentences. The other person starts to look confused or suspicious, leans back, uses more “ums” at the beginning of their sentences.
When you notice these signs - whatever they are for you - take a deep breath. Relax your shoulders. Ask yourself what’s at stake if you drop your agenda. What’s at stake if you continue pursuing it? Make a choice of which direction you’d prefer to go. (There often won't be a definite right answer here.)
Bonus points: if you’re comfortable doing so, reveal your agenda to your conversational partner(s), and ask directly if they can meet it. Sounds weird, but it often works great: if they say yes, you can pursue your agenda with consent! To return to our first example:
“I know I’m asking lots of questions about your political opinions. The Texas governer’s policies are really worrisome to me, so I like sharing my view and hearing others’. Are you interested in talking politics right now?”
Style 2: The Scientist
“So, what do you do with your time?”
“I like to publish nerdy psychological articles on my Substack.”
“Why psychology?”
“Research is fun! I like learning new things that are supported by -”
“Where do you do your research?”
“ScienceDirect has been super useful, since they publish excerpts of actual studies and academic books. Sometimes I find sources through Perplexity.ai too.”
“Oh, you use Perplexity? What are your thoughts on AI?”
The Scientist is a slightly different version of the Seeker. They look for learning in every conversation. Their questions tend to follow a topical thread until it is exhausted, or until a more interesting one pops up.
Personally, I am a Scientist in almost every situation. I ask questions to learn about people, and about the world through them. I compare them to the model in my mind and ask questions about the discrepancies (“what has you, in particular, so interested in psychology?”). I pay attention to what I don’t know and try to fill in the gaps in my understanding. I can take over an entire conversation with my curiosity about one person.
When to take the Scientist approach
Scientist questioning can be useful to deepen a 1:1 conversation or learn about a topic that interests you. There are upsides and downsides to this type of questioning.
Upside: people like having questions asked of them, and the Scientist hyper-focus can be enjoyable. Also, Scientists are possibly the most likely of any type to ask questions you haven’t heard before, because they seek interesting angles.
Downside: in a group, Scientist curiosity can take over with its single-minded attention. The Scientist will focus on one person or topic and may not leave space for others to interject. Be cautious of using the Scientist at length in a group, especially one where you are not the highest-status individual. (If you are high status, whoever has your attention will love it, and the others will defer.)
Relating with a Scientist
If you’re open to their questions, you can use them to learn more about yourself or about the gaps in your own understanding. The Scientist can be a great co-explorer of your internal authenticity.
If you’re getting annoyed at the barrage, just offer a re-direct. “I don’t really want to talk about my job right now. I’ve been more focused on my relationships lately.” Chances are, the Scientist will focus on the new topic, and you’ll get to talk about something you care about!
If you are being a Scientist
First, notice when you’ve become hyper-focused and the other person (or people) are feeling disengaged. If you’ve been the only one asking questions for a couple minutes, take a pause. Leave some silence for the other person(s) to ask a question or take the conversation in a new direction.
Second, as a Scientist, it can be hard to find curiosity when it’s for the other person’s benefit (for instance, if they proffer a topic that interests them but not you). Learn to use the Socialite or Spaceholder approaches (discussed below) a little more. It can be a loving act to ask others about the things they want to say.
Style 3: The Spaceholder
To wit:
“How have you been lately?”
“Oh, pretty well.”
“You sound a little down. What’s been going on?”
“Well…things have been a little tough at my job.”
“Tell me more. I’m happy to listen.”
The Spaceholder is the most other-focused of the questioning types. Whereas the Seeker, the Scientist, the Non-Sequitouist focus on their own agendas, and the Socialite on social cohesion, the Spaceholder has their attention focused on you. They track your subtle changes and follow whatever seems most alive.
Spaceholders can be off putting to people who enjoy privacy, or have secrets to protect. But in general, their attention can be so loving that they attract and even get overwhelmed by those who crave it.
When to take the Spaceholder approach
If you want to make friends - as long as it’s genuine. The Spaceholder is seductive, but it is also hard to fake. You have to find your care and curiosity. If you can, however, you will charm almost anyone you want to engage, whether it be for pleasure or for profit. You may find yourself having to choose between those who want to be your friend!
The Spaceholder can also be a relaxing way to forget yourself for a while. If you’re prone to anxiety or depression, try Spaceholding for a friend. Offering caring, focused attention is the best way to get outside your own head and spread some love. As one of my favorite quotes says:
“Anyone who says money can’t buy happiness, hasn’t given enough away.”
- Alex Hormozi
Relating with a Spaceholder
Enjoy it! Let yourself be held in this person’s curiosity, for as long as you feel comfortable or they want to give it.
If you can’t enjoy it, direct their gift towards someone else who you think will. And make sure to ask the Spaceholder some questions too. They usually ask more than they get in return.
If you are being a Spaceholder
Choose friends who can both give and receive curiosity, or who you at least enjoy having your attention on. Avoid those with constant drama or need - they will make you feel useful, but drain you in the process.
If you ever find yourself feeling down or self-conscious, take stock of how many small, positive impacts you have on those around you. How many friends have you listened to this week? How many tiny conversations have others walked away from smiling or slightly transformed?
Last, know that it’s okay to be self-directed sometimes. You can show up publicly even if you don’t have much to give. Even if you Socialize, Seek, or talk about yourself for a while, you will likely still be wanted.
Style 4: The Socialite
You’re out for coffee with a lovely community leader/Italian man/southern belle/mother of a friend. When you sit down, they begin the exchange:
“So good to see you! How was the drive over here?”
“It was good. Minimal traffic.”
“I’m glad. 1-35 can be rough at this time of day. How is your family?”
“They’re doing well. Jerry started a coaching practice.”
“Oh, I hear that can be a hard field to break into. How’s he liking it?”
Almost every conversation starts with the Socialite approach. It’s like the opening handshake: it should not be painfully intense (“How’s your trauma today?”) or, unless you have a lot of context with the person, entirely absent.
The Socialite touches lightly on the details of one’s life. They find out about your family, job, and feelings about the weather. They are often warm and engaging, and ask followup questions, but rarely so many on one topic that emotions begin to flow.
Even when seeking more intimacy, it is hard to “get deep” with someone until you’ve established trust and safety through the Socialite approach.
Recently, I was in a meeting with a prospective new collaborator. I was asking Socialite questions, getting to know her work and life, and we were having a great time.
Suddenly, the third member of the meeting, who hadn’t said anything yet, chimed in with a Seeking question about the purpose of the meeting. The collaborator shut down and expressed a lack of trust. We almost lost the contract. Things only recovered when the other member opened up about his motivations and started asking softer questions.
When to take the Socialite approach
Socializing can help put others at ease. As the questions rarely follow too deep into a single line, lest the other person get uncomfortable, it’s also a good option to return to if you’ve accidentally touched a nerve. For instance:
“How’s your father doing?”
“Honestly…not so well.” [begins shifting in chair]
“Ah. How about your mom? I know she was excited about her new business venture.
“Oh, she’s great…”
Using Socialite questioning is also useful for gathering information. I have a friend who makes spreadsheets of what he learns about people’s lives - their childrens’ names, their employer, city, etc - to reference before talking with them again. These become the base of future questions, which has the other person feel cared about through the catch-up.
Relating with a Socialite
If you’re enjoying the interaction, simply answer their questions.
If you want to get deeper, pause after each question and really consider your responses. Make eye contact and give them a thoughtful answer. This may bring them into more presence with you.
If you are being a Socialite
Stop and ask yourself what you’re really curious about. It’s easy to re-use the same question set every time and get bored with it. Often, when I’m in this mode, I start asking a question. Then I pause myself - “No, that’s not what I’m actually curious about. I’d love to know…” and then ask something more interesting to us both.
You can even come prepared with opening questions such as these. My current favorites are “What’s something you’ve been learning lately?” and “What are you passionate about?”
Style 5: The Non-Sequitourist
Envision the following conversation…
“Where are you from?”
“Austin, Texas. I’ve been there for about 4 years…”
“Have you ever been to Bermuda?”
“What? No, I haven’t, I -”
“What’s your favorite color?”
Conversation with a Non-Sequitourist is like getting taken on an unexpected and often uninvited trip through someone’s mental landscape. We may get stared down and peppered with a scattershot of questions, or the asker may do everything they can to avoid eye contact and seem to pull their questions from outer space. Either way, the focus of conversation is clearly on the interests of the asker, not the answerer.
This is, I believe, a classic type of interaction for autists. But it’s common for socially anxious folks too (who may struggle to know what to ask and so just ask the first thing they can think of), or those who have just never learned how to follow a thread of conversation.
When to take a Non-Sequitourist Approach
Non-Sequitourist questioning is useful when trying to catch someone off-guard. There are situations when being confusing is an asset, such as when a person is approaching you with anger or mal-intent. Asking non-sequiturs can make you hard to predict, and thus break whatever frame an antagonist is approaching you with.
Non-sequitur questioning can also be valuable when you have a short period of time to get a lot of disconnected information, as in an interview.
Relating with a Non-Sequitourist
If you want to change the interaction, one technique you can use is to pause them.
“Hey, I’m appreciating your questions, but I’m getting a little overwhelmed. Can we take a breath for a second? Ok - what would you REALLY like to know about me?”
You can also ignore some of their questions and turn the conversation around.
“Have you been to Bermuda?”
“Have YOU been to Bermuda?”
This may result in confusion, but it creates a pattern interrupt. You can then move the conversation in a direction you want.
If you are a Non-Sequitourist
If you want to change your interaction style, practice putting your attention on the other person. Really listen to their responses. Ask follow-up questions. You can still ask what you’re curious about - just ask at least one follow-up question for each curiosity. Remember to allow some silence into the conversation as well, so the other person can ask about you.
Wrap-up and takeaways
Let’s contrast the different styles of conversation. Say a friend is complaining to you about their medical problems. To respond from with each style, you might say:
The Seeker - Focuses on the goal of improvement: “Would you like help? Have you tried seeing a doctor?”
The Scientist - Focuses on understanding: “What symptoms are you experiencing?”
The Spaceholder - Focuses on what might make the other feel seen/held: “How are you feeling? What’s been the impact on your life?”
The Socialite - Focuses on lightening the conversation: “Have you gotten out much since this started? What have you been doing that you liked?”
The Non-Sequitourist - Focuses on their interests: “How’s your dog?”
To wrap it up, here is a table with the different questioner styles we've discussed, and the most important information about each one. You can refer to this anytime you need a new conversational option.
The takeaway here isn’t to pick one questioner style and commit to it like a bad tattoo. The real goal is to recognize these styles in conversation, learn how to navigate them and switch things up when needed. If you can do that, you’ll have an easier time deepening connections. You’ll become someone people actually enjoy talking to (imagine that!), and make all your interactions more engaging and meaningful.