5 Ways To Improve Your Conversation Skills To Build Deeper Connections

We can all learn to become effective conversationalists

Aug 23, 2023

I couldn’t help overhearing them. It wasn’t what they were saying I found captivating; more how they were responding to each other. Or, rather — how they weren’t responding to each other.

The first lady described a horrific-sounding, fatal vehicle collision. Her granddaughter knew one of the deceased. This lady expressed her shock and disbelief. I could tell by her tone of voice how shaken she was.

When there was a pause, the second lady jumped in with a “that sounds like …” story. She gave an account of a vehicle collision involving someone close to her many years ago. I sensed this was her attempt at reaching out and showing support, but she missed the mark.

I squirmed in my seat. The first lady was seeking connection, empathy, and comfort. The second lady might have thought she was giving this by verbalizing a comparable story. But by doing so, she didn’t appear to listen. She changed the subject to herself. She didn’t ask any follow-up questions, and she didn’t engage with the initial story. There was no empathy.

When the first lady spoke again, she didn’t comment or react to the story the second lady relayed. Her words boomeranged back to her own vehicle collision.

These two ladies, whilst sat together, were worlds apart. They were talking at each other, not with each other. Whilst they were talking about collisions, their conversation was a collision! I wonder how they felt when they parted ways.

Did they feel energized or drained? Did they feel heard or frustrated?

Interested and Interesting

At the most basic level, a strong conversationalist is one who is both interested in what others are saying and interesting themselves; they add value to the conversation.

If only it were as simple as this.

There are many variables at play when it comes to our conversation skills. I am a talkative person. I find it easy to start a conversation with others and carry it through a natural progression.

But this doesn’t necessarily make me a good conversationalist.

Only with insight and hindsight have I learned to recognise my weaknesses. This has helped me improve and develop my conversational skills.

Over the past few years, I’ve found myself analysing my conversational skills.

Do I talk for an appropriate time, or do I hog the conversation?
Do I listen and ask relevant questions?
Do I show understanding and empathy?
Do I harness the power of silence? Or do I jump in to fill this?

And how do I react when conversations are not going as expected?

Please Stop Speaking Over Each Other

My idea of hell is a busy environment where no one is listening and everyone is talking over each other. In this atmosphere, my skin feels itchy. I shrink away. I do not compete; rather, I withdraw into my shell and switch off.

A wonderful friend shared a gem of a podcast with me. It’s hosted by Glennan Doyle and called “Real Talk: How we can begin using real conversation as a key to unlocking each other.”

It blew my mind!

It articulates my recent thoughts on conversations. It wraps them up in a beautiful and eloquent package allowing us as listeners to reflect on our own conversational skills. This podcast teaches us new skills and develops us as conversationalists.

Glennan hooks me in immediately with, “It strikes me that everybody is talking and nobody is listening to each other.” I listen to the podcast twice. Permeated by its learnings, I want to share the key takeaways.

5 Ways To Improve Your Conversations

The podcast discusses five key conversational habits we can improve on.

1) Interrupting

What’s a sure way to enrage someone and stifle a conversation? Interrupting!

When we interrupt someone, it feels like a violation to them. It’s almost as if the interrupter asserts themselves as having greater importance. Thus they are at liberty to interject and insert their own views over and above those of the person already speaking.

I am a recovering interrupter. From my perspective, it’s not that I think my input takes precedence over anyone else’s. In fact, quite the contrary. My excitement at being part of an energising conversation often makes me want to prove myself. To force a connection, to show myself as valid and worthy of being in such a conversation. So I try too hard.

Abby, Glennan’s wife, says something similar in the podcast. She talks about interrupting often coming from a desperate need to fit in and feel seen.

But here’s the thing. Very often, people who interrupt are so keen to have their say. Meaning they don’t follow the organic growth and flow of a conversation. This can stagnate a conversation by holding it back from its natural development.

Sometimes, we miss a gap in a conversation, and the topics morph and expand. We miss our opportunity to say our piece. Let’s learn to be ok with this. It’s better to go with the flow of the conversation rather than assaulting it with our interrupting.

There are exceptions to this, including neurodivergent people and some cultural differences. For instance, according to this piece, in France, interrupting someone and asking questions is a sign of interest.

2) Talk-time awareness

Those who were active in my life about a decade ago may laugh at me for having the gall to discuss talk time awareness. Back then, I didn’t have talk time awareness.

Conversations can become toxic when one person dominates without any self-awareness. This can lose others. They may be physically present but are vacuous inside, waiting for the talk-time hogger to stop. Talk-time hoggers may present with a sense of entitlement to talk-time. At best, they are assertive in a conversation. At worst, they are domineering.

Some people are naturally more talkative than others. But, we can learn to be sensitive to this and use our own conversational skills to draw others into a conversation. It does not mean we can cipher off the talk time of those who appear less talkative and use it ourselves!

Extroverts and introverts function very differently. We also all vary with the speed of our talking.

I am a fast talker. Previously I believed all silences in conversations required filling. Now, I recognize these are an opportunity to reflect and gather our thoughts before speaking. A five-second silence may seem like a lifetime to some. To others, this is enough time to collect their thoughts and feel able to enter into a conversation.

Think of your most recent conversations. They could be in a business or personal setting. Were you aware at the time of the amount of time you were talking for? On reflection, are you aware now?

Being mindful of our talk time, we can learn to slow ourselves down and use silence as a means to encourage others into the conversation.

3) Keeping confidences

Evolutionary psychologists suggest gossip has its roots in our survival. In a social setting, we shared information on who had food, who was ill, and who could help us.

Gossip is enticing and exciting—junk food for the brain. Sometimes we can’t resist. We often gossip to prove our worth, to obtain validation for knowing the “thing” first.

But, it goes without saying that anything said to us in confidence should stay there. Gossip isn’t always negative; most gossip is positive or neutral. Talking about anyone else, without them being present, is gossip.

Sharing secrets helps human cohesion. But, if these secrets are not yours to share, the reverse can happen. You may inadvertently lose the trust of the people in the conversation. In their mind, if you can break someone else's confidence, you can just as easily do it to them.

“Great minds discuss ideas, average minds discuss events, small minds discuss people” — Eleanor Roosevelt

There is also the danger of gossip being slanderous. I was blissfully unaware of a rumor circulating at work for several months. Apparently, I was sleeping with my boss! Everyone knew, except for me.

Be cautious with speaking about others if they are not present. Of course, there are many times when this is acceptable or even necessary. But, by keeping this in check, you will keep the trust of others.

4) Know when to make it about you and when not to

This is fascinating — on average, we spend 60% of our conversation talking about ourselves. And why? According to scientists, it feels good and fires up the same area of our brain as sex, drugs, and good food!

So, on the one hand, self-disclosure is a good thing. Sharing our vulnerabilities, fears, joys, hopes, and struggles is positive. It helps us cultivate bonds in our relationships.

However, on the other hand, if someone is confiding in us, this is not a time for our own self-disclosure. It can be a natural human reaction to search through our own experience bank and bring out a comparison to try and illustrate our understanding. All this does is make the other person feel invisible.

For instance, if someone is talking about their divorce or a recent bereavement. Our own personal experiences are almost irrelevant. Unless they are specifically asking us for advice, but even then, it is helpful to remember what works for one person may not work for another.

Our role is to listen, ask questions, and recognize no matter what our own lived experiences are, we can not know how this person feels.

The two ladies’ conversation at the start is an example of knowing when to make the conversation about you and when not to. The second lady tried to use her own experience to connect with the first lady. But instead, it created a division and made the conversation about the second lady.

We don’t need to come up with our own experience or story to meet someone on their level. Even if we have a wealth of knowledge, this is not a time to tap into it.

Showing up for others in their time of need and focusing on them in conversation will help them feel seen, listened to, and supported.

5) Ask better questions

The podcast ended with the final conversation tip; to ask better questions. My heart soared.

We are responsible for the conversations around us. If I want to know how a friend is, I don’t ask them how they are. I ask them alternatives, such as “What colour is your world?” or “What is today’s song?”

We are surrounded by incredible people. People are Aladdin’s caves; if only we knew how to tap into their treasure. Well, we can start by being creative with our questions.

Change “How was your day?” to “Did anything happen today that changed your energy?” This leads to deeper honesty and greater self-reflection. It creates wonderful cohesion through conversation.

I appreciate thinking of creative questions can be a challenge in itself. Several years ago, whilst drained from small talk, I stumbled upon a game called Vertellis Classic. It encourages deeper connections through greater conversations. Some of my favorite questions in it are “At what moment did you laugh the hardest?” and “What is one of your most exciting experiences?”

This Is Not an Exhaustive List

These five conversational tips are by no means an exhaustive list. However, they are a great place to improve our conversations and deepen our connections.

I would also like to add the importance of keeping an open mind in a conversation and not remaining rigid in our view. Fighting to be “right” in a conversation is not conducive to growth.

Asking inciteful questions, listening to the answers, and responding appropriately allows us to harness our strong conversational skills empathetically and intuitively. This deepens our relationships.

Remember, simple checks to improve your conversations:

No interrupting
Be aware of your talk time
Keep confidences
Know when to make it about you and when not to
Ask better questions

Now, go forth and have great conversations.

This piece was originally published on Medium for members only in 2021; due to its popularity, I’ve repurposed it to share with Abnormally Normal. I hope you enjoyed it.