In any conversation, the questions you ask matter.

I recently presented at a board training in New Jersey.

The night before the training, I attended an event where I had the opportunity to meet a lot of new people.

With the exception of only one person, everyone’s first question to me was, “How are you?”

Given the world we live in, that’s a loaded question. And probably one of the most controversial questions you could ask someone.

It’s right up there with questions like, “Are you married?” or “Do you have any children?”

Be sincere in your questions.

To create a connection with someone, it’s important to be genuine in the questions you ask and only ask questions you want to know the answers to.

For example, when you ask someone how they’re doing, are you honestly interested in knowing how they are actually doing? If not—don’t ask the question.

If you’re not even interested in knowing the answer, it’s definitely the wrong question for you to be asking.

Still, as a society, we’ve been conditioned that when we meet someone, we immediately ask the question, “How are you?”

And because this is often our go-to question when meeting someone, we all have the same go-to answer, “I’m fine, thank you.”

But what does fine actually mean? It means Freaked out, Insecure, Neurotic, and Emotional.

We all have real challenges we’re dealing with at any given time. Yet we all answer the question with that one simple word, “Fine.”

I, on the other hand, tend to answer that question more truthfully.

When someone asks me how I’m doing, I’ll either say, “I’m doing great!” because I actually am doing great. Or I will say, “I’ve had a really bad day. Let me tell you about it.”

Sadly, when I answer with that second answer, I get the sense that the person asking feels as if they’ve jumped in for far more than what they wanted.

If you want to connect with people, ask better questions.

I love how Dale Carnegie created a system we can use in our efforts to ask better questions.

In his system, known as the Conversation Stack, each question builds upon the previous question.

It begins with simply introducing yourself—the most important thing you can do at an event.

Why? Because you’re not going to be the only one there who is uncomfortable.

I read a statistic that said 93% of people say that they are shy when they attend an event. The joke is that 63% of statistics are made up. But I honestly believe that this statistic is true. Being outside of your comfort zone is uncomfortable for just about everyone.

When you’re at an event, there are going to be a lot of people feeling pretty uncomfortable. So when you see someone just standing there, say hi. Introduce yourself and ask them their name.

Once you say your name and ask them theirs, the next question just builds on that. Tell them where you’re from, and then ask them where they are from.

You can ask this question several different ways, “Where do you live?” “How long have you been here?” “Where are you from?”

When asking questions, there has to be some give and take. You offer something about your life, then ask them something about theirs.

Before you know it, a connection will be made.

The right questions can help you learn a person’s story.

I love learning another person’s story.

And asking the right questions allows you to learn more about the person you are talking to without them feeling uncomfortable.

As one question builds upon the next, you’ll start to see commonalities and connections that you didn’t even know were there.

Here are some great questions you can ask to learn a person’s story:

“What was it about this event that brought you here?”

“What are your hobbies?”

“What are you passionate about?”

Open-ended questions are the best kind of questions to ask—questions that have to be answered with more than just a yes or a no.

Be sensitive with the questions you ask.

When it comes to family, avoid asking the often uncomfortable questions, “Do you have kids?” or “Are you married?”

It could even get a little touchy if you were to ask, “Do you have any siblings?” You can’t determine by looking at someone what the status of their life actually is, so try to be sensitive to that.

You can do this by keeping things a little more vague and just focusing on generalities.

You could ask questions like, “Where is your family from?” or “Where does your family live now?”

This leaves the conversation open for the other person to give you as much or as little information as they want to.

We never truly know what someone else is going through, so when questions get too personal, it may cause people to want to abruptly end the conversation.

To avoid causing others discomfort or creating an awkward silence, ask questions about the really fun aspects of a person’s life.

Some of these questions could be:

“What do you like to do for fun?”

“Do you like to travel?”

“Where have you been recently?”

These kinds of questions help a person open up and talk about their life, allowing you to really get to know their story.

There are so many different questions you can ask to learn someone’s story. And just like building blocks, each question stacks upon the other.

There’s a beginning and an end to every conversation.

Good conversations almost always begin with a good question.

And at the end of those good conversations, it’s a good idea to get into the habit of thanking the person for their time.

Not only does this help the person feel seen, heard, and valued, but it’s just a nice way to end any conversation.

Kindness can go a long way in disarming people and helping them feel at ease.

In the end, the right questions and genuine conversation, combined with your kindness and expression of gratitude for them, will leave the other person a little bit more at ease than when you found them.

This is how we can change the world—one person and one conversation at a time.

Asking good questions is a strategy you can use in any situation.

Whether you’re at an event, an airport, a party, or spending time with friends, learning how to ask good questions can help you become more at ease in any situation. And it will help those around you feel more at ease, too.

This is a strategy that you can use in any aspect of your life.

It’s important to remember that most of us are struggling when we go out—especially since Covid. We’re all still just trying to put ourselves back out there again.

Let’s help one another by getting great conversations started instead of just standing on the outskirts and watching others from a distance. Practice asking good questions and learn the stories of the people around you.

I always say that I’m an extroverted introvert. If I had a choice at the end of the day, I would probably be sitting on my couch watching a movie and drinking a glass of wine.

But you don’t get to meet people when you live your life that way. The extroverted part of me happens because I choose to go out—even when it’s uncomfortable. This is why I force myself to get outside of my comfort zone and ask questions.

I truly believe you can learn something from every person that you meet. That’s why it’s important for me to get out there and learn people’s stories. And the best and most natural way to do that is to ask good questions.

So if you are an introvert like me, but you want to make a change, learn to ask good questions.

For me, this one strategy has made all the difference.

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