What Are The Top 5 Questions That Can Make Anyone Sound Very Interesting And Smart?

1) Damian Birkel 

Perhaps the most important things to sounding interesting & smart are

a) Your sincerity and your genuineness.

b) Continuous eye contact is crucial.

c) Fight the urge to “pan” the room; looking everywhere for the next person to talk to.

d) By far, the magic is in the listening. Most people do not know how to listen. It is hard work to look a person in the eye and just hear what they have to say, and not jump ahead in your mind and think about how you were going to respond.

e) You want to ask igniter questions. These are the type of non-threatening questions that allow a person to talk about other things that are important to them, and don’t involve anything controversial like politics or religion.

Ignitor Questions include:

(These questions are situation and can be adjusted as needed. If in a social or networking event, generously reach out, smile, shake hands ; especially to those who are visibly uncomfortable.)

– What do you do for a living?

– What about them Yankee’s? (insert your favorite team here)

– How did you meet your spouse or significant other?

– Have you always lived here?

– Where are you from?

– What is your favorite restaurant?

– Have you seen (name of a popular movie)?

– Where do you like to go on vacation?

– What’s on your Bucket List?

– Where do you go to unwind?

Questions like these “ignite” a conversation, and genuinely make you sincerely interesting & smart. I have found these questions helped across thousands of conversations across 28 years of pro-bono service at Professionals In Transition, Support Group, Inc.

2) Luka Arežina

I think that answering the question isn’t as nearly easy as it might seem- mostly because questions that make you smart vary from the occasion. 

I would say that the general tip to look smart in a conversation is to observe the person you’re talking with, listen carefully, and ask questions that resonate with their experience while giving them a subtle compliment. That way, you’ll be able to bond on a more intimate level and create relationships that will last.

3) Alex Magnin

Overall, the most interesting questions are the ones that help me learn – either about the other person, the world, or myself. These are questions I like to use in interviews, with close friends, at cocktail parties, on first dates, with my family, etc. Each one helps me learn something, which is the way to *become* interesting and smart, rather than just seeming it.

A) This question is a two-parter, mostly for someone you are just getting to know. First, ask “What do you do?” This is a normal question, almost boring and uninteresting. But then, whatever they say, simply respond with, “That sounds hard,” and let them go. 

One of every human being’s most salient experiences is their day to day challenges and difficulties, so they are likely to expound at length about them. And for you, you get to learn the real story behind their profession, hobby, or daily occupation – making you sound smarter and be smarter.

B) What is the goal? – this is the single smartest, most important question a person can ask in a work setting. So often, organizations do things for reasons that do not line up with their ultimate goal. They get distracted, or do things for social reasons, or pursue sub-goals that conflict with the ultimate goal. Continually ensuring the goal is kept in mind in any endeavor is one of the smartest things you can do.

C) If you were stranded on a desert island, what are the things you would have to have?. This question is about learning about people, and what they value. Knowing someone else’s values is the best way to ensure long-term, joyous, fruitful relationships. By not limiting the question to a set number of things (e.g. the 3 things), you also learn about their mindset – are they simple, stoic, or abundant?

D) Tell me about something you know a lot about that I probably don’t? This question taps into the fact that all human beings have multitudinous interests, and every single human knows a lot more about some particular subject than you do. In my case, this is woodworking, and I would get great joy educating you about all the finer points of the hobby, broadening your world.

E) What do you think about X?. This question makes you seem smart and be smart because of how important it is to take in multiple perspectives. When you ask this question, about current events or politics or scientific issues or emotional matters or family, make sure to listen. You will surely leave smarter.

4) Andrew Taylor 

Here are a few questions that I have been asked that have struck a chord with me as being quite insightful.

A) Rather than asking ‘what do you do for a living?,’ someone once asked me ‘How do you spend your days’. It is essentially the same question but isn’t as drab or boring as the former. It also gives people a chance to talk more about what they love, rather than what they do.

B) If you don’t mind sharing, what was the last photo you took on your phone about? This one was great fun and a real conversation stimulator. Asking this question makes people feel like you are genuinely interested in their lives (so don’t ask strangers I suppose), and lets people get their phones out, which most people jump to immediately. There is always energy and excitement that follows this question.

C) Do you have a favorite word? This kind of catches people out, but lets you catch a glimpse into their lives as well. Sets them off thinking, which is what questions are all about. I often prompt with my favorite word – petrichor. Sometimes this rags into ‘least favorite words’, but best to keep positive as it’s too easy to get negative, isn’t it?

D) What did you plan for that never happened? This is a great business question, which I often speak with to my clients. Often we forget about the good things in our relationships or business ventures and focus just on the bad. By reminding ourselves that we spent energy fearful of something that never happened, we are more appreciative of everything good that is happening in our lives.

E) Another business-minded question, as I’m not sure what you’re after would be ‘Where do you find the best source of information for ?’ Open-ended questions allow for long answers and this one is content-driven. We can compare sources – essentially both interesting and smart.

5) Paul Flanagan

Here are my top 5 questions that can make one sound very interesting and smart:

A) What business are you in and how long have you been involved in that business? (Most people ask this question or another form of it the first time they meet someone. When you ask this question it means that you are focused on financial matters. Asking it also implies that you are interested in increasing your financial and social status.

B) What is your family history? (Asking this question has the word history in it. History is a school subject. It takes intelligence to know and be concerned about historical matters.)

C) How long have you been married? (Marriage heightens your social status. This makes you a smarter person because someone else was willing to marry you.)

D) How many kids do you have and how old are they? ( this question implies that you place high importance on family and that having a family gives you higher social status)

E) Where does your family vacation? ( this question suggests that you and yourself take vacations. Hence implying that you are smart and therefore have a good-paying job that enables you to afford a vacation annually.)

6) Paige Arnof-Fenn

Here are the best questions to ask in my experience:

A) What is your story?

B) What do you do for fun?

C) What keeps you up at night?

These are all great to ask because it allows them to talk about themselves and you learn what makes them tick. You sound interested in them so they will find you interesting and smart for asking such great questions. 

They come away from the conversation feeling like you took the time to get to know them, and now when you follow up it can be substantive with details you learned in the conversation reinforcing how smart you are.

7) Simon Nowak

A) Be like Winston Churchill.* Do you know Churchill’s strategy to win one’s trust and interest? No, there was no trick. He was just genuinely interested in other people’s lives or occupations. So to be considered as an intelligent and trustworthy person, always ask about the others and let them talk.

B) But why?* I must admit it’s one of my favorite ones. Asking why not only allows you to get a deep insight into any topic but also leaves your interlocutor engaged in the conversation. However, for your own sake, try not to overuse this question.

C) How can I do this? *This question shows you in a really good light! You appear to be a goal-oriented and decisive person, who wants to learn more?

D) What will happen if…? * This is one of the best questions to endorse your interlocutor to reevaluate some of the plans or opinions. It also may be a good conversation starter.

E) When are you going to do this? *A good call to action, right? I know dozens of people who are day-dreamers or have numerous unaccomplished plans for the future. The problem is that apart from dreaming, they are afraid to act. So to support your old or new friends (and to force them a bit from time to time), just feel free to ask this question.

8) Nancy Baker

Here are the Top 5 questions that make sound interesting and smart:

A) Can we have a more detailed conversation after lunch?

When people raise questions that you cannot answer or do not have the materials to support, use this sentence. It will buy you some time to prepare your response. Others will think that the content is too important or too long to be discussed over a meeting.

B) Where’s the evolution?

No matter what you’re doing, something came before it and something will come after. Probe how similar projects fared in the past and anticipate how parallel efforts could play out. Inquire about the pivotal moments in comparable plans.  This kind of questioning shows that you can link big trends to specific actions and that you’re looking for patterns of success. It also signals that you’re interested in building the future, not just reacting to it.

C) How can I be of greater help on that?

By asking this question, it shows that you think independently and are willing to carry more responsibilities. You are outstanding at your assigned duty and are capable of accomplishing more. Moreover, this reveals your leadership skills.

D) What were you doing exactly one week ago?

You might provide the person with good fodder for a story, or you might prompt them to pivot quickly. For example, my literal answer to this question right now would be: Packing to go away for Christmas. But that could easily lead to a description of where we went, and what we did, and that would be far more interesting.

E) What are the details of this plan?

When someone puts out a plan that seems too good to be true, ask them this question. It shows whether the plan is merely conceptual or if the presenter has prepared details to substantiate it and show its feasibility. It is a good question to keep the conversation going and get everyone involved.

In sum, asking questions is the key to understanding and gaining the knowledge you need to advance.

9) Jeremy Harrison

As a seasoned manager for several companies, I have learned how to sound intelligent in board meetings and interdepartmental meetings. It’s quite easy if the session is only within your team, you’ve probably established your superiority and wouldn’t need to do more. But when it comes to other kinds of meetings, here are questions I ask to sound intelligent.

A) What don’t we know? Knowing the unknown is something that only leaders do. Preparing yourself is the key to overcome all obstacles. After carefully taking notes, it’s now time to think about those that haven’t been discussed. Opening the discussion for this shows that you’re intelligent enough to accept your weakness.

B) Have we talked to anyone about this? As the saying goes, two heads are better than one. An intelligent person always prepares for everything. Getting a second or third opinion doesn’t diminish your intelligence but instead enforces it. Only a smart person can accept that he can’t do it alone and will need all the help he can get.

C) Will it scale? This is the age-old question that’s difficult to answer. The goal of all businesses is to raise profit. The problem here is how. The timing on when to ask this question should also be perfect. Consider asking this question when everything has been discussed. This will show everybody that even though the presentation was excellent, you’re always looking at the big picture. You’re so intelligent that nothing can distract you from the objective.

10) Miguel Cairo

These are my top 5 questions that can make anyone sound smart and interesting:

A) What do you do? This is a very simple question that people appreciate because everybody likes talking about themselves and feel that others are interested in them.

B) What is your opinion of success? This question is loaded as everyone has a different answer for it. But what comes out is the foundation for continued conversation.

C) Do you have kids? This one just builds rapport and shows genuine care. Even bad parents like to talk about their kids so this question will certainly put you in an interesting category.

D) Do you listen to Impact Theory? Most people will say no, but ask what it is. It’s a YouTube channel ran by Tom Bilyeu in which he interviews the great minds of society to help others achieve their dreams… If they don’t know about the channel they’ll be curious and think you’re smarter than you might be.

E) Any sports question: If you notice the person likes sports just ask them something about it even if you have nothing back to say. The key to being interesting is more about getting people to talk and for you to listen intently, not the other way around.

11) Shelly Bortololotto SCMP

Here are the top 5 questions I use in daily life, at conferences, in

meetings, workshops, etc.

A) How did you feel? This question has been a life-changer for me since I started using it. However, it takes a bit of practice to get it right.

When it works: When there is a bit of a rapport, and the opportunity is there for the speaker to go a bit in-depth. For example, when having lunch or sharing a coffee or going for a walk. 

Another situation would be when in the middle of a story, and a big experience(s) that recently happened is revealed. And so, a follow-up question would be “how did you feel?” using the same intonation and excitement/empathy that the speaker used, which would serve as a smart invite to the speaker to go further with the story. 

Asking people to tell you more about themselves is a sure-fire way to get them to appreciate you.

When it doesn’t work: At the grocery checkout. This is because a bland, happy answer is expected and there is no social space provided for a longer conversation. It can be disheartening to have to give the same good thanks response to everyone.

B) Do you like your reason? This can make people stop and think. What is your reason for writing this article? Do you like it?

It can help people identify if they are coming from a place of commitment and dedication, or a place of scarcity. This question also has to be presented very carefully and empathetically. It works well in one on one conversations, but can shift or derail the conversation. 

Best used when people are in a loop, and you would like to get them to shift the conversation and start looking at it from a more third-person perspective. If used poorly, it can make you look mean and a bit confronting. Use with caution.

C) What result do you want? I have been using this myself lately. It helps people get clear about what they want. The minute they start focusing on what they want, rather than what they don’t want their feelings and action can start to shift. 

Hence, if you ask this question and get a negative response, then go ahead and help the person rephrase it positively. Once they are clear on what they want, it’s easier to come up with the actions that they would need to take to get there.

D) Is there anything else you wanted to ask? This is what I use at end of personal, one on one phone conferences, especially sales calls. It helps the other person feel like you have answered and heard all their concerns and listened to them. 

Hearing a long pause at the end of the line is a sure sign there is one more thing that is concerning to them. It’s the equivalent of the most important part of the conversation, the after meeting talk that reveals a nugget of gold.

E) Ask the question that everyone is thinking, but is too afraid to ask.

This works best in conferences and meetings, especially if there is a question period in the end. It helps to wrap the meeting up. It can be used to either support the speaker/leader or discredit them. However, you do have to have actively listened to the presentation and picked out the flaws, gaps and things they didn’t explain well.

I do this always, and frequently have people come up to me later and say thank you for asking that. Do it correctly a few times in one session or for days and people will come to see you as a leader. 

This question works well for naturally introverted people who can summon up the courage to ask the questions. It presents you as an extrovert. It also provides a fantastic ice breaker later for people to interact with you in the session breaks.

12) Tim Bigknee

These, for me, are the top 5 questions that can make anyone sound interesting and smart:

A) When’s the next Space X shuttle launch? This shows that you follow modern space travel and that you’re interested in science, technology, and Astronomy.

B) What do you think the implications of Artificial Intelligence (AI) will be? Asking this question shows that you look deeper into technology and the social implications of modern technology. AI is highly theoretical at the moment so it’s an excellent way to stir interesting and intelligent conversation.

C) What do you think the outreaching effects of the coronavirus will have on cultural and societal norms? Coronavirus is a hot topic, but most people are only talking about toilet paper. Asking what other effects the coronavirus will have shows depth to your intelligence and depth in your *knowledge of sociology. 

D) Why don’t people go back to using handkerchieves and paper bags? This shows that you care about the environment and also that you have class and sophistication. You want to be practical but also don’t want to produce more waste. You give practical advice and answers to difficult world issues in the form of a nonchalant question.