Last week, I went over how to hold a conversation. This week, I want to explore my favorite questions to ask when talking with others.

Conversation and Questions


Questions help us understand others

Conversations are built on asking compelling questions that provoke engaging answers. When we fail to ask good questions, our speaking partner may become bored or listless. By asking great questions, you’ll show how exciting and confident you are as well as ensure everyone is engaged.

A good question accomplishes three things: 1) gives us insight to as well as an understanding of our speaking partner, 2) helps our partner think critically and reflectively about their own lives, 3) allows us to gain any wisdom we can from the answer our partner gives.

The following is a list of my favorite questions to ask during a conversation. I offer questions for when you first meet someone and questions for when you’ve known someone for a few weeks.

First Conversation

good questions

Good questions help us think

  • What do you like to do for fun?
  • Where did you get that piece of clothing/jewelry/accessory?
  • What’s one place you’ve always wanted to travel?
  • Who has impressed you most with what they’ve accomplished?
  • What’s the best piece of advice you’ve ever been given?

When meeting someone for the first time, we want to avoid delving too deep into their history and beliefs. Primarily, people are protective of their beliefs and histories and if we try too hard to discover what they are “hiding” then we can appear aggressive and nosy. Additionally, when we first meet people, we may not have a lot of time to really explore these larger topics which can create the feeling of being rushed.

However, when we start by asking expansive yet surface level questions, we can better understand someone without delving too deep. When we delve too deep, we may bring up uncomfortable realities about a person’s history or their own individual failings. We always want to avoid this when first meeting someone.

A question such as “what do you do for fun?” will not be attached to a painful memory or require much backstory to understand. No matter the answer, when we learn what people do in their spare time, we gain an understanding of what they love, find joy in, and wish to pursue.

Lastly, all the questions above require personal answers from our partner which shows we value their opinion and are curious about them. Additionally, these questions aren’t about consumption but experience, personality, and passion. We’re asking people what they care about, what matters to them, and what they wish to do.

By asking questions like these when we meet people, we signal our curiosity and desire to learn more about whoever we’re speaking to.

Getting to Know Each Other

list favorite questions

Keep a list of your favorite questions

After a while, the surface-level questions will be ineffective when getting to know someone. In order to develop meaningful relationships, we have to explore the histories and failings of other people. Our failings, mistakes, and personal pains make us who we are, and in order to succeed in the world, we push those things aside. However, pushing these faults to the side means we present a more positive version of ourselves that isn’t the whole package.

I’m not criticizing this. It would be difficult to get through the day if I had to tell everyone about the abuses I suffered as a child. However, I cannot claim to be close to my wife if I did not tell her of the traumas that happened to me in the past. Otherwise, she’ll only have this perfect, shallow version of myself with no realization of my flaws or pain.

Therefore, these questions are excellent for talking to an individual that you’ve had a few conversations with. By knowing someone for a reasonable amount of time, it becomes easier to ease into more profound, personal questions that may explore an individual’s background or personally held beliefs.

questions forward

The best questions move relationships forward

  • What’s the last great book you read?
  • What do you wish you knew more about?
  • What are some small things that make your day better?
  • What was something you’ve done that made you feel extreme happiness?
  • Knowing what you know now, what advice would you give your 18-year-old self?
  • If you weren’t working here, where would you like to work?
  • What do you give a damn about?

Additionally, these questions are great for getting to know people but also helping them think critically about their own lives. Questions such as “if you weren’t working here, where would you like to work?” assist our conversational partner in reflecting on their own lives and hopefully making better decisions. Helping people positively reflect on their path in life is a valuable skill to have.

We never want to cut corners when getting to know other people. Ask these questions to help develop a deeper appreciation for the person you’re talking to.

Questions to Avoid

avoid negative questions

Avoid negative questions

  • What’s a bad habit that you have?
  • What takes up too much of your time?
  • What are you interested in that most people haven’t heard of?

We always want to dodge having people critically think about their lives negatively. Our goal is to a positive influence, and when we question the competency of our partner (“what takes up too much of your time?” sounds like “why can’t you better utilize your time?”), then they’ll want to talk to us less and less.

Always be curious. Never be aggressive or seek an adverse outcome with others. If you ever steer into politics, for example, discuss topics with an open mind and try to understand their position while sporadically, yet firmly, stating your own opinions. Don’t fear politics or religion. A sound mind, a firm understanding of your own beliefs, and patience for the inherit tenseness of the conversation will make it easier to deal with these topics if they do come up.

Additionally, we should always avoid making people think about the opinions of others. We want to ensure our conversational partner realizes that we’re focused on them, not what the rest of the world has to say (e.g., “what are you interested in that most people haven’t heard of?”).

Lastly, when it comes to questions, quality trumps quantity. Don’t just barrage people with questions – make comments, express opinions, then ask for more info. Never make it an interrogation, make it a conversation.

I know it’s easier said then done, but try practicing asking these questions with others and see if questions like these don’t help in improving the quality of your conversations.


  1. How often do you talk to people? Would you like to converse with people more or less? Why? (I know I used this question last week, but I think it’s worthwhile to explore again).
  2. What question is your favorite (in general)? Why is it your favorite question?
  3. What’s the best question you can remember being asked? Why do you think it was the best?

Please remember that it’s important to do the actionables. You’re not on this earth to simply read but to do. To become an individual, you must act more than you consume.

*Image credit to Unsplash.