7 Unusual Question Types That Help You Appear More Charismatic
Ask questions like you're writing a viral Medium article
7 Unusual Question Types That Help You Appear More Charismatic
When asked If I lean more introverted or extroverted, I’ll often answer with a famous line from Kendrick Lamar’s DNA:
“I’m a shine like I’m supposed to, antisocial, extrovert.”
It means I enjoy meeting new people, but I find just as much stimulation at home, reading a 600-page biography about Benjamin Franklin.
The antisocial part of me used to stress about charisma. For example, I would worry about asking too many questions during conversations. “Charismatic people tell stories,” I’d think to myself. “They don’t ask questions.”
I learned in my twenties that the opposite is true.
Charisma doesn’t care how many questions you ask, only that you ask thoughtful questions.
“The paradoxical secret of charisma is that it’s not about trumpeting your good qualities but making the other person feel good about himself. Real charisma makes the other person feel important; when they finish an interaction with you, they feel better about themselves than they did before.”
Brett and Kate McKay, The Art of Manliness
Charisma is egoless. It’s the art of giving space for someone else to speak their full opinions, ideas, and feelings. In that regard, charisma has nothing to do with you, it’s about how the other person feels.
So what’s the best way to give someone space to voice themselves? Ask a question. But not just any question.
Here are 7 unusual question types I picked up in my twenties (along with a few examples from popular shows) that will help you appear more charismatic.
1.) The highlight/lowlight question
Is there anything worse than returning to the office after vacation and getting, “Did you have fun?” or “how was it?”
Despite everyone asking the same question, these basic yes/no questions are more burdensome than empathetic because it places all the pressure on you to steer the conversation somewhere.
But where?!
Make the conversation easy by asking a highlight/lowlight question whenever you’re curious about someone’s vacation, event, meeting, or new situation. “What was the best part of your trip? What was the worst part about your trip?”
Watch Sean Evans interview celebrities on Hot Ones. He’s the king of highlight/lowlight questions. (Skip to 8:20).
Notice how a lowlight question prompted Olivia to open up about a unique story from her stay in the English countryside. Most importantly, she obviously had fun telling the story.
Highlight/ lowlight questions work because they create a platform for people to express their full range of emotions about a topic.
In every way short of saying the words, it shows you care about what they think.
2.) The viral medium article question
We know a boring question when we hear it.
If we’re on a date, it’s: “Where are you from?”
If we’re being interviewed, it’s: “Do you enjoy working here?”
It’s polite but not charismatic.
Howard Stern didn’t build a radio empire by asking celebrities the same questions they’d get on a late-night talk show. He peels the onion by asking surprising questions that cut deeper.
Take his interview with Metallica (one of my favorite bands). He doesn’t ask James Hetfield how he wrote “Nothing Else Matters.” That would’ve received a cookie-cutter response. Instead, Stern asks, “What if I said this song was about Lars.” For context, Lars Ulrich is the band’s drummer who has a notoriously estranged relationship with James. (Skip to 1:25)
The unexpected question stirred a lot of emotions, and at one point, Lars says, “I think I’m going to cry.”
Think of it this way.
Charismatic questions are like viral Medium articles. The best-performing articles take an old subject and offer a surprising twist, better research, or unfamiliar points.
Charismatic people do the same thing with questions.
That’s memorable. That is charisma.
3.) The Jerry Seinfeld question for talking to anyone
First impressions are difficult, even if you’re naturally charismatic.
Most people hate networking and dread first dates for that reason. How do you know what to ask if you don’t know anything about them?
The always charismatic Jerry Seinfeld has a strategy for awkward first encounters.
“Here’s my trick for talking to people.” He declared on an episode of Comedians in Cars Getting Coffee. “Numbers! Ask them a question to which the answer is a number.”
“How long have you lived here?” “What time did you start your day?” “When is the baby due?” Careful with that last one.
Getting a numbered response isn’t the point. The point is, you’re asking a question that will have an interesting answer from which you can propel the conversation forward. It’s also taking pressure off the other person because it should be an easy answer.
Next time you’re stuck talking to a stranger, ask a numerical question. That should break the ice.
4.) The perfect first date question for your back pocket
If you’re on a date or talking to someone you’re kind of into, ask this one question at some point during the conversation.
“What’s your go-to karaoke song?”
It opens the door to so many avenues like which bar they like to hang out at, their favorite kind of music, or a crazy story about the last time they performed.
I know it’s simple, but this question guarantee’s a fun conversation for at least the next 30 minutes.
5.) The preamble + open-ended question
You want to shoot for open-ended questions, but it’s better if you can lead up to the question with context.
Back to the hot wing king Sean Evans. I didn’t have to dig for an example because all his questions come with a prepackaged preamble. Watch a few minutes of his interview with Billie Eilish.
Here’s the lesson: Don’t jump straight into a question. Tell a personal backstory, a fact or statistic describing why the question is important, or the reason you want to ask that specific question.
It’s charismatic because it allows you to drop some knowledge while keeping the spotlight on the other person. It also gives them time to prepare a unique answer.
6.) The perfect follow up question
According to Harvard research, the best way to appear charismatic is to master the art of follow-up questions.
“When people are instructed to ask more questions, they are perceived as higher in responsiveness, an interpersonal construct that captures listening, understanding, validation, and care.” — Harvard research
A dorky way of saying questions makes you cool.
So what’s the perfect follow-up question? It’s pretty simple: why?
Joe Rogan created a $300 million podcast by asking why? While most reporters ask, “tell me about your experience on that project.” Joe will challenge his guest and ask why they choose it.
Why questions are the perfect follow-up because it gets people thinking and uncovers what they truly value.
Q: Why did you go there for vacation?
A: My roots are in Ireland.
With that answer, you can ask a question about their Irish roots. Now you’re on a topic that’s valuable to them.
7.) The most annoying thing that happened today
I don’t have celebrity examples or empirical data for this type of question.
I started to use it on first dates and with my friends. I don’t mean to puff my chest, but I’m on to something. It’s the most effective question in this article, and I’m shocked I haven’t read about it elsewhere.
A lot of people ask, “what’s the best thing that happened today?” It’s a brilliant question and gets people thinking about all the positive things in their life. My mother used to ask me it every day after school. I reverse-engineer the question and ask, “what was the most annoying thing that happened to you today?”
I’m not sure why it works so well, but I have a theory.
The question gets people to open up, but instead of reflecting positively on their day, it provides a platform to vent grievances — a rare opportunity for most people.
Hey, we all need to vent sometimes.
Summary
Write down these 7 questions in your journal and apply them on your next date, interview, or Bumble connection:
Highlights/lowlights
The viral Medium post question
The Seinfeld technique for talking to anyone
The perfect first date question — Karaoke!
The preamble + open-ended question
Follow up with why
The most annoying thing that happened today question
It takes effort to find out what makes people tick. In my experience, it’s rare to find people who make an effort. Most people ramble about their accomplishments because they want to make themselves feel better or cover up their imposter syndrome.
That’s not confidence or charisma. That is insecurity.
Always remember, interesting people are confident enough not to be the center of attention.