Before I begin, I’m going to cut right to the chase. If you want to learn how to connect with people and improve any of your relationships, you need to ask good questions.
Before you sigh and think about ditching this article, you should think twice. This is the real deal. This is that one skill that, if you develop, will 10X your life.
In this article, I provide stories, examples, and research that show you why the questions you ask are so important and how you can improve yours. You can literally change your life with the advice given below.
But this is a long read. So sit back and get ready to learn something you won’t find anywhere else.
Although I don’t recommend it, if you want to get straight to the “how to” part, go down to the section How to Ask Good Questions that Help You Connect with People. I put the only other photo in this article there to make it easy to find.
For those of you who want to fully understand a skill that works miracles, read on.
Why I Learned How to Connect with People
Years ago, I moved by myself to a new city where I had zero friends.
Since I wanted to make some friends, I went to a social mixer for young professionals. But, in the moments preceding the event, I kept imagining how the scenario would unfold.
I’d walk in, look around the venue, and nervously think to myself, Who do I talk to? What do I even say?
Then, one of two things would happen. I’d be too scared to try talking to people and would leave feeling embarrassed, insecure, and angry with myself for being such a coward.
Or, I’d somehow start a conversation, ask a few questions, and feel the ice-cold expression from the other person that seems to say, why are you even talking to me?
Well, the worst of both worlds came true. I started talking to a young, pretty brunette and quickly realized she did not care to have this conversation. Maybe you know the feeling: no smile, short one-word answers, and the look of annoyance.
So I left feeling both annoyed with myself and inadequate as a human.
This may seem like a sad story, but it’s not. Instead of basking in self-hatred, I made an oath to myself: I would vastly improve my social skills and enjoy life the way I desperately wanted to – with people who love being around me.
And I did exactly that.
That one oath put me on a path to learning, researching, and practicing social skills in a way I never expected. And this journey led to a breakthrough that I now want to share with you.
Learning how to ask good questions dramatically improves your ability to connect with people.
You may be wondering how questions can be so important since social skills are dynamic and complex and require a multitude of abilities.
That’s a valid concern that I’ll answer very shortly.
You’ll soon see that this one skill will help you start meaningful conversations with anyone, quickly get to know people, and, most importantly, enable you to turn acquaintances into best friends.
Why Questions are So Important for Connecting with People
If you want to build a strong, meaningful relationship with someone, there are two critical things you must do:
- You must get to know each other.
- You need to uncover similarities.
Sure, there are other aspects to meeting people and building friendships that are important, like making good first impressions, being attractive, building trust, and earning their respect, but people don’t see nearly as much improvement by working on those as they do by improving their ability to get to know people and uncover similarities. And when you ask good questions, you increase attraction, trust, respect anyway.
So, let’s go through these two necessities:
1. Get to Know Each Other
Think about any of your good relationships. I’m willing to bet that there is a direct correlation with how well you know someone and how strong your relationship is.
This doesn’t mean your relationship is great though. Any relationship can turn sour. But it’s much less likely that you know an acquaintance’s deepest secrets or that you are best friends with someone you barely know.
Why is this? Because you can sympathize and empathize with them. They are no longer a stranger, but someone you know personally.
And the better you know them, the better you understand their dreams, fears, goals, and problems. You stop using stereotypes to judge them and you start understanding their unique story.
Mother Teresa once said, “If I look at the mass, I will never act. If I look at the individual, I will.”
This is exactly why this applies.
For example, you may care about helping poor people improve their unfortunate circumstances, but you’ll care more about the person whose unique life story you know. When you hear how they got there and what they’ve gone through, all while looking them in the eyes, it’s nearly impossible to not deeply care.
And when people open up to you, they trust you more. Their mind subconsciously thinks, I must trust this person if I’m willing to open up to them, especially since they truly care to hear what I’m saying.
That’s one reason why asking good questions is such an important skill. It’s the best way to get people to share stories that express their feelings, values, beliefs, and interests.
And that helps you get to know them better while discovering similarities between the two of you, bringing us to our next point.
2. Uncover Similarities
People become friends with people who are like them.
As The University of Kansas points out, “not only do ‘birds of a feather flock together’ but…‘birds of a feather find each other before flocking.’” They found this after reviewing one of the largest studies on friendship formation, which proves that friendships are highly driven by pre-existing similarities.
This isn’t necessarily shocking news, but it does confirm the importance of finding similarities with people that we want to befriend.
Use this to your advantage. If you want to learn how to connect with people, now you know what it takes. You need to find some common ground.
And the good news? Similarities are not hard and set in stone.
Similarities are based on perceptions. For example, I may quickly like someone because he has a “positive outlook” similar to mine. But that’s just my perception. It’s very possible I formed that opinion from one statement he made.
Here’s another example: Let’s say I tell a story about a trip to Panama. The other person may believe we have a lot in common because we both like to travel, even though that could be the only time I’ve ever left the country.
I’m not encouraging you to lie, mislead, or exaggerate. I’m purely demonstrating that similarities affect your connection with another person due to beliefs, not reality.
By asking good questions, you’ll discover the other person’s beliefs, attitudes, values, and interests. You can then express that you share the same passion for the ones that apply, and connect on your commonalities.
This is where most people fail. They struggle to get this information from people, so they aren’t able to build connections.
I’ll discuss this in more detail so you can avoid the pitfalls.
Why People Struggle to Form Strong Connections with Others
It’s not that people don’t know how to ask questions or that they never do it. But people do make two very critical mistakes when asking questions.
1. They Ask Poor Questions
Good questions encourage good answers, which get people to open up. When people open up, you learn more about them and get to know them on a personal level.
Remember, this is exactly what you need to build strong connections. You need to get to know people and you need to find similarities. Getting them to open up is the best way to do this.
Good answers involve stories full of emotion and deep-seated beliefs. They’re personal. They’re important to the other person.
Poor questions elicit facts and one-word answers.
Although you need facts to get to know people and form similarities, they aren’t enough. You may know that someone works as a freelance writer, but it’s much more important to know how they got into it and why it’s important to them (or why they hate it so much).
Here’s how a common conversation might go:
Jeff: What do you do?
Peter: I’m a freelance writer.
Jeff: Do you like it?
Peter: Yeah, it’s cool.
Jeff: Right on. So what do you like to do in your free time?
Jeff is only getting facts and short answers from Peter. The conversation is quickly turning stale because he’s not getting any emotions, beliefs, or stories from him.
And that’s because his questions aren’t asking for them.
If you ask poor questions, you’ll get short responses that thwart the conversation and diminish your ability to connect with people.
But this isn’t the only error people make.
2. They Ask Good Questions at the Wrong Time
Timing matters in conversation because people are expecting different things during different stages.
Here are the main stages of a conversation:
- Why are we talking to each other?
- Let’s fill the awkward silence.
- Let’s get to know each other.
- Let’s enjoy each other’s company.
We’ll go through these stages in more depth shortly, but for now, just understand that they just refer to the way a person subconsciously thinks about the conversations you’re having.
For example, let’s say you see another shopper at the grocery store. If you start talking to them, you’ll be in the “why are we talking to each other?” phase because you’re both strangers and they aren’t expecting to talk to you.
So when you’re in this phase, you need to have a good reason for talking to the person.
If you’re at the deli counter and ask the shopper next to you if they know whether the honey ham is good or not, it makes sense. They’ll think, “Okay, he’s talking to me because he’s trying to determine what to get and thinks I might be able to help.” You have a valid reason.
But if you ask them what the scariest situation they’ve ever experienced is, they’ll wonder why the hell you’re asking them this question. It doesn’t make sense because of the stage of the relationship and conversation.
Now, if you ask this same question to a friend, you could get a great story that tells you more about your friend. That’s because you two are in the let’s enjoy each other’s company phase.
And this is where people screw up all the time. They ask let’s get to know each other questions when they’re really in the why are we talking to each other? phase. Or they’ll ask, let’s fill the awkward silence questions when they’re in the let’s enjoy each other’s company phase.
Unfortunately, the other people trying to teach you social skills and relationship tips don’t understand this nuance of timing. It’s actually one of my biggest pet peeves.
For example, type “conversation starters” into Google and click any of the top results. You’ll get lists of questions to use as conversation starters. Here are a few that I see right now:
- If you were in a circus, which character would you be?
- What is the worst advice you have given?
- Working on anything exciting lately?
Do you see the problem here? These can be great questions when asked at the right time, but they are terrible for starting conversations.
Once you start asking good questions at the right time, you’ll notice that it’s much easier to quickly connect with people. Now let’s get to the good stuff so you can learn how to ask these great questions.
How to Ask Good Questions that Help You Connect with Anyone
Below are five easy steps to help you improve your ability to ask good questions at the right time, so you can get to know people, find similarities, and build strong connections with anyone you want.
1. Know Where You Are in the Conversation
As we just discussed, if you want to learn how to connect with people, it’s vital that you know where you are in the conversation because asking a good question at the wrong time will not help you build a strong connection.
So that’s the first step. Here are some examples to help you understand the different stages as well as some tips on the types of questions to ask in each one:
Stage 1: Why are we talking to each other?
You know you’re in this stage when the other person would genuinely wonder why you are talking to them. Like when you’re at the grocery store and start talking to another customer in the aisle. Or when you walk up to a coworker you’ve never spoken to and ask them a question.
Contextual questions – questions about something relevant to the person, environment, or situation – are the best questions for these situations. Ask your coworker something work-related that they specifically would have an answer to. Ask the grocery customer if they know which salsas are good when you’re in the salsa aisle. Or give them a sincere compliment and ask them about the shirt they’re wearing.
Stage 2: Let’s fill the awkward silence.
This usually occurs when you’re both waiting for something in the same place. Maybe the coffee pot is filling up while you and another coworker are waiting to fill your mugs. Or you could be waiting with a stranger in an elevator, in a line, or sitting next to them at a park bench.
This isn’t much different from the first scenario, but people are more willing to talk to fill an awkward silence. Therefore, they aren’t wondering why you are talking to them when you strike a conversation.
Contextual questions are still your best option, but they can be a little more personal. You can ask if they are enjoying the weather, how their day is going, if they’ve tried the coffee here, etc.
Stage 3: Let’s get to know each other.
Once you make it to this stage, you really start to build connections with people. You’re both in a position where you are expecting to talk to each other and get to know each other better.
The context of any social situation plays a big role here: If you’re at a party or social gathering, people are expecting to meet and talk to others. When you’re out in public, people are just trying to get on with their day. But it also matters where you are in the relationship and conversation.
You could be at a party when you start a conversation, introduce yourself, tell them why you’re there, and continue the conversation. Or, since it’s a slow day at the coffee shop you frequent, you walk up to the barista and ask how he’s been. In both scenarios, you’re both expecting personal questions from the other person.
Good questions at this stage help you get to know each other. FORD questions (Family, Occupation, Recreation, Dreams) are great for getting the person to tell you about what’s important to them, like:
- How long have you been working here?
- How long have you lived in this city?
- Is your family originally from here?
Stage 4: Let’s enjoy each other’s company.
Once you’ve gotten to know someone and you both seem to like each other, you enter this final stage. This is where best friends are created.
You’ll continue getting to know each other but on a much deeper level. You start learning very personal things about them – their pains, fears, hopes, and dreams. You learn what makes them tick and how they became who they are, including the deep pain they’ve experienced and some of their most personal secrets.
Questions of this nature widely vary, but could include:
- What’s the scariest situation you’ve ever been in?
- How did you know that you wanted to call off your marriage?
- How did it feel to leave your secure job to start an unproven business?
Regardless of which stage you’re in, your goal is to get to stage 4 if you want to build a lasting relationship. Once you have a reason to talk to someone, you want to get to know them and find similarities. Then, hopefully, you both like each other enough to make it here.
It will take a while with some people (multiple conversations spanning days or even months), and it can happen in just minutes with others. Just keep getting to know them, finding similarities, and having a good time.
Once you know when to ask your questions, it’s time to ask good ones.
2. Ask Good Questions that Incite Stories and Emotions
This article is focused on helping you build strong connections with people, and that happens primarily in the last two stages – once you’re both getting to know each other and enjoy each other’s company.
That’s where we’re going to focus. I already have an article that will help you start conversations with strangers if you need it.
So, how do you ask good questions that help you get to know people and find similarities?
Use the FEW Steps Process
- Fact – Get a fact about the person
- Emotion – Ask about an emotion related to the fact.
- Why – Figure out why or how they felt or feel that emotion
It’s okay to ask questions that elicit one-word answers if you plan to follow up with deeper questions. A lot of one-word answers will give you important facts, like what a person does for work, how many siblings they have, and where they like to travel. That information is very useful.
But you also need to dig deeper to find out whether these things are important to them and how they feel about them.
Here’s an example of this technique in use:
John: So what do you do for work? (This is where John is trying to get a fact about Chris.)
Chris: I’m a graphic designer.
John: Oh, cool. Do you enjoy your job? (Here he’s asking about an emotion related to this fact.)
Chris: Yeah, man. I really enjoy it.
John: That’s awesome, dude. What is it about your job that makes you like it so much? (Now John is trying to figure out why Chris feels this way about his job.)
Chris: Well, I’m a freelancer, so I get to choose which clients I work with, which projects to take on, my workload, etc. That type of freedom amazing. Also, I rent out my workspace from a design company that I’ve built a great relationship with. And I sometimes do work for them, if I choose. So I get the nice social aspect of working in a company, but the freedom of working on my own. Plus, I love the work I do. I would be creating and designing in my free time anyway, so I’m killing two birds with one stone by doing it for a living too.
As you can see, the conversation only opens up once John asks Chris why he feels the way he does about his job. By asking a good question, John extracted some of Chris’ personal values and beliefs.
In addition to using the FEW Steps Process, you can ask questions that explicitly ask for stories or elaborations. This works well because you can decide whether you want them to be fun and interesting or serious and emotional. Here are a few examples:
- If you had more money than you could ever spend, what would your life look like? What would you do during a typical day?
- What’s the scariest (you can replace scariest with any adjective, like most nerve-racking, wildest, insane, happiest, strangest, you get the picture) moment you’ve ever experienced?
- What’s your favorite traveling story?
- What’s a unique experience you had while growing up that most people don’t know about you and helped shaped who you are today? (Love this one BTW)
- What’s one of your favorite stories from your childhood?
As you can see, you’re asking personal questions that get them to really open up to you. Some of these are more personal than others, so make sure they are comfortable and you’re in the right situation before asking them.
As a general rule of thumb, start with the fact-based questions that are less secretive and slowly move into the deeper, more personal ones.
3. Have Good Questions in Your Back Pocket
One of the best ways to ensure that you ask good questions is to memorize a few or keep a small list on hand (in your phone or even on a note in your pocket).
There are thousands of good questions you can easily find on the internet by searching for “good questions,” “deep questions,” or something similar, so I’m not going to provide you a list.
You just need to find a few that you like. I recommend finding three for getting to know someone and three for digging deeper.
Here’s what your list could look like for getting to know people:
- If you could only do one activity that you enjoy for the next 5 years – it could be physical, mental, social, it doesn’t matter – what would it be and why?
- Do you have any siblings? (Then follow up with) What was your favorite part about growing up [insert scenario – as a single child, with two older brothers, etc.]?
- What is one thing you truly want to accomplish in the next few years? Why is it so important to you?
And here’s what your list could look like for deepening your relationship:
- What is the worst relationship you’ve ever been in and what did you learn from it?
- Who do you consider your best friend and how do you think that came to be?
- How do you want people to remember you when you die? How come that’s important to you?
As you can tell, these are similar to the FEW Steps Process. They don’t always specify the emotion, but they get a fact and then they ask the person to embellish the answer with their beliefs, thoughts, values, or a personal story.
When you start, focus on using just one question. The more you ask it, the better you’ll get at asking it and the easier it will be to remember.
Once you have one down, add another. Then you’ll always have some backup questions to help you build strong connections with people.
But you can’t rely solely on prepared questions.
4. Be Curious
It’s great to have questions in your back pocket, but you won’t have that many and you can’t always rely on them. Often, it’s best to flow with the conversation and use your genuine curiosity.
When someone mentions their brother in passing, get curious. Is he your only brother? How many siblings do you have?
Curiosity is the best way to learn more about any subject, especially people. You won’t get to know people or find similarities if you really don’t care to know more about them.
I’m not going to elaborate here because it’s pretty self-explanatory, but I’ll give you a couple tips for using curiosity to your advantage:
- Listen intently. When you hear everything the other person is saying, you’ll notice all aspects of the conversation. It’s from these words that you’ll find something to inquire about.
- Develop your curiosity. Understand that you can learn interesting things from anyone as long as you ask the right questions.
If you find it difficult to do this with strangers, don’t worry.
5. Practice with People You Know
One of the main reasons this is hard for people to learn and integrate is that they don’t have enough opportunities to practice.
If you want to get better at shooting a basketball, you just need a ball and a hoop. Then, you shoot over and over.
But with social skills, you don’t always have another person to converse with. And even in you find strangers, you don’t start in the let’s enjoy each other’s company phase.
That’s why I recommend practicing these questions with people you know. I can always ask my wife about her dreams and past childhood events. And it doesn’t just help me practice, it helps me build a stronger relationship with her too.
You can ask coworkers questions that help you get to know them better. You can ask friends questions that help you deepen your relationship.
Think about which people you can ask these questions too, then practice using your prepared questions and being genuinely curious. It won’t always work out as planned, which is perfect. Think about what you could have done differently, adjust, and keep practicing.
Asking good questions, like any other social skill, takes time and practice to improve. But the rewards are worth it.
Watch Your Life Improve Right Before Your Eyes
The benefits you’ll encounter from improving the questions you ask can be dramatic.
You can improve your marriage.
You can turn acquaintances into best friends.
You can quickly turn strangers into friends.
And it’s not just your social life that can improve. These interpersonal skills can help you professionally at work, in your business, and at conferences. They can help your relationships with sports coaches and teammates.
It can literally help you in any part of your life that involves other people.
And if it all seems like too much to remember, here’s a simple breakdown for you:
- Understand the different stages of conversation.
- Ask questions that incite stories, emotions, values, or beliefs.
- Choose a few questions to keep in your back pocket – or even better, just choose one to start.
- Be genuinely curious when talking to people.
- Practice with people you know.
That’s it. You now know how to connect with people in a much better way.
Improve your questions. Change your life.
It’s that simple.