Getting to know someone, whether it’s for business, friendship or a relationship, means knowing how to ask the right kind of questions in the right way.
Making a connection is key to relationship building, whether it’s a healthy work partnership, friendship or even fostering a productive work environment in team situations.
In business, for example, building relationships and connections is a must, whether that be with suppliers, partners, employees or the customer; it is central to success.
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Breaking the Ice Can Be Nerve Wracking
At times, if you’re new to a group or situation- say you just moved, want to make a new friend, want to get to know someone better, or just got hired to a new position- it may seem impossible, or at the very least nerve wracking to ease the tension.
The answer to how to break the ice is simple, and obvious: conversation.
The motive of most conversations is getting to know someone better, whether it’s breaking the ice with small talk during a public interaction or gaining someone’s trust to close a business deal.
The key to having a productive conversation is not only listening, but also asking and responding to questions that allow you to understand the person you are talking to.
You can begin to build bonds and gain comfortability with the questions I’ll give you in this article. I’m dividing the questions into categories to make it more simple, and to also give you a scale on the types of questions you can ask.
Each category will increase in “level” of how personal and in-depth you want to get with the person you’re talking to. The categories go from surface-level to super personal.
To deepen any relationship, even just trying to get closer with a good friend, it is very important to understand their likes and dislikes.
For instance, if I plan on being candid around a group of associates about a view I have politically, I would be remiss to go on a political tirade knowing someone there held opposing views. It would be in bad taste.
Politics are a no-go.
Always be aware of your situation and the thoughts and feelings of those around you.
Conversation is the catalyst to lowering walls and inevitably bringing things to a more casual level. Reading this it may sound blatantly obvious, but in real life situations it’s more difficult than it seems. People tend to overthink and get nervous, and when someone is nervous it becomes very difficult for them to gauge the conversation.
Getting lost in your own head is exactly what good conversation will prevent. The goal is to relax and give yourself the headspace to think and listen critically, and let the conversation happen naturally.
These questions I’ve compiled are broken down into three different categories.
The first set, I would label as “starter” questions or “safe” questions. These are casual questions that won’t raise any eyebrows and will pretty much ease your way into the conversation. They are very surface level and will come off as harmless.
If I just met you I’m not necessarily interested in your divorce, or how your life is ending. That would be off putting.
Oddly enough if I talked to that same person for an hour progressing to deeper conversation, and then they brought it up, it would seem much more normal and I’d have empathy for them.
No one wants to look unhinged, so if you just met someone. Take it easy. You don’t know their likes or dislikes, so tread softly.
- What do you do for a living?
- Do you enjoy your job?
- How often do you work?
- Do you enjoy going out a lot?
- What do you like to shop for?
- Favorite character from a movie or show?
- Do you have any hobbies?
- Favorite way to de-stress?
- Any siblings?
- Favorite genre of music?
- Favorite movie?
- Favorite movie genre?
- What do you think about social media?
- Any funny family members?
- What did you major in?
- Where did you go to school?
- Favorite class?
- What do you cook best? Signature meal?
- What’s your longest Netflix binge?
- Were your parents strict?
- The most boring thing in the world to you?
- What’s the most exciting thing?
- What would you have to get paid a million dollars to do?
- What’s your favorite tv show?
- Do you smoke cigarettes?
- Are you a night owl or an early bird?
- Do you have any allergies?
- Favorite color?
- Do you play video games?
- Do you like to play board games?
- Card games?
- Do you have any pets?
- How often do you drink coffee?
- What’s the longest car drive you’ve ever been on?
- Have you ever been somewhere exotic?
- Have you ever done anything “extreme” like parachuting or bungee jumping?
- What’s your favorite animal?
- Do you know any jokes?
- What’s your favorite motorsport?
- Train or fly?
- Favorite foreign culture?
- Favorite sport?
- Least favorite sport?
- Do you enjoy documentaries?
The second group of questions up the level just slightly. These are questions that dig a little deeper than “did you have any siblings growing up”. These aren’t meant to scare anybody off, but just remember to be objective and see how you’d respond to the question before you ask it. Also, I think it’s clear you don’t want to make anyone feel like they are being questioned.
- What century would you choose to live in and why?
- Who is your favorite historical character?
- If you could meet anybody from the past who would it be?
- What historical event do you think has changed the world?
- If you could go back in time and stop something what would that be?
- What do you think the most important invention is to humanity?
- Would you be able to live without a cell phone or computer?
- What kind of inventions do you think we will have in one hundred years?
- What’s your favorite piece of tech?
- What the most useless invention of all time to you?
- Do you think technology is benefiting us or hurting us?
- Are we really living in the age of information?
- If we had no electricity what would you do?
- What do you like to do in your free time?
- Is there anything you are particularly good at?
- What would you do if you could transform a hobby into a high paying job?
- What’s your favorite song out right now?
- What’s your favorite song of all time?
- Who is your favorite band?
- Who would you say is the best musician of all time?
- Do you listen to classical music or like any composers?
- What is the best album of all time to you?
- What was your favorite restaurant growing up as a kid?
- Did you ever have a special restaurant you would go to for your birthday?
- Is there any restaurant you would never go to?
- Worst dining experience?
- What’s your favorite quick stop place to go to?
- What your favorite “hole in the wall” spot to eat at?
- What’s your favorite comfort meal?
- What your favorite type of cuisine?
- If you could only eat one thing for the rest of your life what would it be?
- What’s one type of food you couldn’t get paid to eat?
- What the craziest thing you’ve ever eaten?
- Have you ever gotten food poisoning?
- What’s your favorite meal to cook for yourself?
- Who is your favorite actor and actress?
- What is the greatest role of all time?
- What is the best acting performance you have ever seen?
- Do you like any cult movies?
- How many movies have you gone to see on opening day?
- If you could move anywhere in the world where would that be?
- What’s the craziest vacation you’ve ever been on?
- What’s the most exotic place you’ve ever been?
- How many times have you left the country?
- What’s one place you need to see before you die?
- Is there somewhere you will never go back to?
- What’s your idea of the worst vacation ever?
- Who is your favorite sports team?
- Did you ever play on any sports teams in school?
- Is there any sport you’d say you’re good at?
- Have you ever been to a game?
- Have you ever won or lost money betting on a game?
- Do you prefer living in the city or in the country?
- What part of town do you live in now?
- Do you like your neighborhood?
- What was it like growing up in where you did?
- Is there anything interesting about where you grew up?
- What part of town would you live in if you had the choice?
- Where’s your dream home?
- What kind of shows do you like watching?
- Have you ever binge watched an entire series before?
- What’s your favorite tv show on the air right now?
- What’s your favorite show of all time?
- What character do you most relate to on television?
- Is there any tv show you’d recommend me watching?
- What’s the worst tv show of all time to you?
- Are you obsessed with any type of social media?
- Do you agree with the collection and selling of information perpetrated by facebook?
- Is there any type of social media you find stupid?
- What’s the dumbest thing someone can do on social media?
- How important is your web personality and profile compared to the real you?
- Do you think social media has been helpful or damaging to society?
- What is the most trouble you ever got into at school?
- What kind of school did you go to?
- Were you required to wear uniforms?
- Were you a good student or a bad student?
- What’s the worst grade you ever received?
- What group would you say you were in during high school?
- If you had to teach any subject what would it be?
- What’s your favorite model of car?
- Who is your favorite car manufacturer?
- If you could drive any car what would that be?
- What the ugliest car to you?
- What’s do you think about self-driving cars?
- How many people who own expensive cars are do you think are actually wealthy?
- If you could drive anywhere where would that be?
- How fast would you go if you were driving on the autobahn?
- Who was your best friend growing up?
- What do some of your friends do for work?
- Do you have any friends who have ever gotten into major trouble?
- What’s an important quality you look for in a friend?
- Are you highly social or do you like to keep to yourself?
- Do you have a lot of loose friends or a few close friends?
- Who is your best friend now?
- How did you guys get to know each other?
- Have you ever won any awards?
- What’s the most important thing you have accomplished in your life?
- Is there anything you are proud of?
- Is there anything you are currently working on to accomplish?
- Have you ever gone on a pub crawl?
- How many times have you been to a club?
- What kind of people do you think go to clubs?
- What’s the most embarrassing thing that’s ever happened to you on a night out?
- Have you ever been in the vip?
- What’s the worst place to go out to in your mind?
The final set of questions I would list as personal. This is if you want to get to know someone on a deeper level, maybe they’re an associate who is becoming a close friend, maybe you just want to be better friends with one of your old pals, or maybe you’re about to head off into a major venture with someone and you’re keen to find out their “real” side.
These questions are personal, and may be intrusive to some, so make sure the walls are down for both of you and that you are each sufficiently comfortable. Being comfortable when asking is essential as well.
Again, remember! You are not trying to reenact the Spanish inquisition!
- How many times have you felt so hopeless you wanted to give up on life?
- Have you ever had any serious trouble with the law?
- Have you or anyone you’ve known struggled with an addiction to substance?
- What’s your biggest fear in life?
- What’s your biggest regret?
- What’s the most important thing that happened to you in your childhood?
- Have you ever hated someone or something?
- Do you think one day technology will be so advanced we may live forever?
- Do you think humans will ever know the real reason behind existence?
- Do you think being conscious is a blessing or a curse?
- Do you believe in extraterrestrial life?
- What do you think finding life other than ours in the universe will do to change our society?
- In the future could you ever see an Orwellian universe controlled under a new world order being played out?
- Do you think one day the earth will reach its maximum population causing the destruction of humanity?
- Would you ever feel justified in killing someone?
- Have you ever felt so passionately about something you would die for it?
- Have you ever almost died before?
- Have you ever had a close family member, or a friend pass away?
- How long do you think you’ll be remembered after your death?
- Do you believe in life after death?
- Do you believe good people will be ultimately rewarded for their charity and sacrifices?
- Do you believe in any sort of god?
- Are you religious?
- In what ways do you measure the value of your life?
- Do you think that some life has more value than others?
- What is your final goal in life?
- What do you think the point of life is?
- Do you take anything for granted?
- If you created a miracle cure would you sell it and become a billionaire or give to people for free?
- Do you believe that true evil exists?
- Do you believe in fate or destiny?
- Do you find life to be fair?
- How important do you think our lives are in comparison to entire known universe?
- If you had one day left to live what would you do?
- Are you afraid of a possible forthcoming apocalypse or world war three happening in your lifetime?
- Do you think it’s possible we are living in a virtual world like the one Elon Musk believes?
- Have you ever felt totally alone?
- What’s the saddest moment of your life?
- Why are some people perfect for each other, and why are some people so toxic for each other?
- Would you take care of your parents when you get older or would you send them to an old folks’ home?
- Is poverty something that is innate within society or can it be solved?
- What is the purpose of pain?
- What is the most unnerving thing to you going on in the world today?
- Have you ever been depressed?
After getting the answers to some of these questions you’ll have a much clearer picture of who you’re talking to and should have some good conversation.
The point of asking questions is to let them act as a catalyst. It’s only a starting point. You want the conversation to evolve and flow freely. A surface level question can easily transform into a meaningful dialogue, and that’s exactly what you want.
Just remember to stay cool. Making the other person get defensive or feel like they are being questioned in a negative way is not the way to strengthen bonds. In fact, it does the opposite.
Being a great listener is imperative. People are only comfortable opening up when they feel the other person is genuinely listening to them and giving them cohesive answers that show they understood exactly what was said.
Want to find out what’s holding you back? Click here to take our quick (and shockingly accurate) “What’s Blocking You From Success” Quiz right now and find out exactly what stands in the way between you and success…