how to have a deep conversation | Conversation tips | How to have a better conversations with people

have you ever found yourself talking to someone and the conversation just dies? Then you get that awkward silence going on because you are both trying to think of things to say. I think it is safe to say that at some point we have all been there!

I remember in school being taught that when you are talking with someone you look them in the eye, nod your head to show you are listening. That worked once upon a time ago but now most of our conversations are done through the phone. Which is making more awkward situations when talking with someone face to face.

The skills of being able to talk with people are fading. You may be struggling with talking to random people, your spouse, children, family, and even friends.

Now a little disclaimer. I did not come up with these 10 ways I heard them from Celeste Headlee from Ted Talk and it was so phenomenal that I had to share it with you! ( I will put the link to the full video at the end of this post)


1. Don’t Multitask 

This doesn’t just mean to set down your phone or your tablets. It’s about being present in the moment. Being present in the conversation and not be thinking of what you got to get at the grocery store or what you need to do tomorrow. Don’t be half in the conversation. If you want to get out of a conversation get out of the conversation.

– I have found myself sometimes when my husband is talking to me and I have completely zoned out because I was looking at something else, reading something or watching a video on Facebook. He will ask me a question like do you agree, or what do you think and I have nothing to say because I wasn’t listening.

We might have all had an experience like this. So It is important to be present in the conservation and be here and now.

2. Don’t Pontificate 

Pontificate means to express one’s opinions in a pompous and dogmatic way. Conversations are not fun when you are both arguing over who is right based of opinions.

“You need to enter every conversation assuming that you have something to learn.”

“True listening requires a setting aside of ones self” – M Scott Peck 

Everyone is an expert in something…

3. Use Open-Ended Questions 

Start your questions with who, what, where, when, why or how.

If you asked someone were they terrified that word they are going to respond to is terrified. They will answer either yes they were or not they were not. Go even deeper into asking them what was it like.

– Asking open-ended questions is a great way to keep the conversation going. And you are most likely going to get a more interesting response when you ask open-ended questions. Asking open-ended questions takes you below the surface of the conversation. You might even find that you have something in common with that person that you wouldn’t have known if you did ask open-ended questions.

When talking with your children, spouse, and even family members and you are asking open-ended questions, you are being engaged in the conversation you are showing to that person that you care.

4. Go With The Flow 

Thoughts will come into your mind and you need to let them go out of your mind.

– For me, this is something I defiantly need to work on. When I get a thought or an idea during a conversation I forget to listen to the person I am talking to because I am so set on remembering my question! When ideas, thoughts, stories come to your mind don’t hold on to them let them come in and let them go out.

5. If You Don’t Know…Say That You Don’t Know

Error on the side of caution. People on the radio especially MPR are much more aware that they are going on the record. So they are more careful to what they claim to be an expert in and what they claim to know for sure.

– I love that! Saying I don’t know does not mean that you are not smart or something you should be embarrassed saying. If you don’t know you don’t know. Simple as that.

6. Don’t Equate Your Experience With Theirs 

If they are talking about how they lost a family member. Don’t start talking about the time you lost a family member. If they are talking about the trouble they are having at work don’t tell them how much you hate your job. It’s not the same. ALL EXPERIENCES ARE INDIVIDUAL  

Remeber it is not about you. You do not need to take that moment to prove how amazing you are or how much you’ve suffered.


– Have you ever had a time where you were sharing a story and someone was saying that they can relate but you just know they simply can not understand your emotions, your pain or even your happiness? I love that she said that all experiences are individual and that conversations are not a promotional opportunity. That is so KEY!

7. Try Not To Repeat Yourself 

It is condescending and really boring. And we do it a lot. Especially in work conversations or in conversations with our kids because we have a point to make so we just keep rephrasing it over and over.

– Now, this is a hard one to do. You really just want to make sure someone is understanding what you are trying to say. I have been trying to be more aware of how I talk in conversations because I don’t want to keep saying the same thing over and over. And if you are again you are just showing that you are not invested in the conversation and that you simply don’t care.

8. Stay Out Of The Weeds 

People do not care about the years, the names, the dates all those details. What they care about is you. They care about what you are like, what you have in common. So forget the details.

9. Listen

This is the most important one! Listening is one of the most important skills you can develop. 

” No Man ever listened his way out of a job”- Calvin Coolidge 

Why don’t we listen to each other? Because we rather talk. When you are talking you are in control. You don’t have to listen to anything your not interested in. You’re the center of attention and we get distracted.

– Listening can be very tiring and hard because our attention spans are short. I totally understand why she said that listening is one of the most important skills we can learn. People love to talk but people always want to just be heard or listened to.

10. Be Brief 

Be interested in other people and always be prepared to be amazed.

” A good conversation is like a miniskirt; short enough to retain interest, but long enough to cover the subject” – Celeste Headlee’s sister

– Conversations do not have to belong. Sometimes the shortest conversations have the biggest impacts. I love that she says always be prepared to be amazed. People are amazing! everyone has something that is truly amazing about them.

If you would like to watch the full video click on the link below!:

10 Ways To Have A Better Conversation


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Kara is the founder of the Dollar Mommy Club and a full-momma and who loves every minute of it. Ever since she was a little girl (around two years old actually) she has wanted a baby of her own. She even asked her mom for “a crying and pooping baby doll” for Christmas when she was just 6 years old. Certain events took place to where Kara was diagnosed with Endometriosis, and doctors told her that having her own children might be impossible. She spent years trying to figure out her health by trying everything under the sun that you can think of. It wasn’t until a few years after she was married that both she and her husband figured it out, and they were blessed with their first baby girl! When Kara isn’t managing the Dollar Mommy Club and it’s wonderful members and contributors, she enjoys spending time with family, binge-watching The Office on Netflix, and creating art.


  1. I remember when i was in my grad school, we use to have special classes on personality development. That last point ; one should be a good listener..has always helped me a lot.

  2. Great tips and isn’t pontificate a fantastic word?! haha Sad to think that conversation is dying. I actually prefer to use the phone (text) but I am from an age before computers and mobiles and it is a shame that my kids are not going to have the same conversations I used to with my friends.

    • Yes! Pontificate is a great word and super fun to say haha! Yes, it is sad to see that children will have a hard time communicating because everything is done on the phones.

  3. I do focus on eye contact and listening. I think one of my faults though is to control my enthusiasm. There’s a time and a place for excitement or eagerness.

  4. This is all so important. Even though I was taught a lot of these in college for one of my classes, it’s great to have a reminder. I am bad about multi-tasking, I really am. I have been trying to get better at this. And your sister’s quote, awesome!!

  5. What great tips! My worst habit is multitasking. I find it hard sometimes to put down what I’m doing and just listen.

  6. Thanks for sharing those great tips. Having conversations with strangers was difficult for me and I am getting better. One thing, I am still working on is listening, even with my children I tend not to fully listen and answer even before they are done.


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