top of page

The Art of Good Conversation

Brave of me to write a blog of this title.

I am not sure that I would be known for my ‘art of conversation’, but hey, that never stopped a poor teacher teaching!

In the day job recently, I have been running quite a few sessions around performance coaching. It’s a topic that I enjoy delivering because it is about helping people get from good to great.

Powerful coaching relies of the dual skills of asking good questions and listening effectively. The same duo paves the way for good conversation and great connection. I share below some of the content on this simple, but fascinating subject.


There are five broad categories of questions.

TED questions – Tell. Explain. Describe.

“Tell me how your day went?”

“Explain the movie to me?”

“Describe your dream job?”

These are wonderful questions for allowing the other person to take the front seat in the conversation. They say: ‘Tell me because I am all ears and I want to hear from you’.

Open questions

“I keep six honest serving-men.
They taught me all I knew.
Their names are What and Why and When
and How and Where and Who”.

These are the opening lines from Rudyard Kipling’s short poem on curiosity.

Open questions are questions that don’t allow for a yes/no answer and allow the conversation to expand and explore.

“What was the hardest part of that experience?”

“How did that make you feel?”

“Why was that so important to you?”

Probing questions

These ones get us in deeper and help the talker be more specific. Probing questions show that we are listening, really listening because we want to get to the detail and the heart of the matter.

“Sounds like you were just exhausted from it all. Was it that you were just tired, or that you didn’t get the support?”

“Your eyes light up when you talk about that job. What is it that made working there such fun?”

Hypothetical questions

If probing questions take us deeper into the conversation, hypothetical questions allow us to indulge in ‘what ifs’ and to imagine new or different scenarios.

“Let’s suppose you move jobs, what would that mean?”

“What if time was not an issue?”

“Assuming we could provide more support, what would you do first?”

Hypothetical questions are a lovely way to offer advice without becoming an advice monster, for guiding someone to possible solutions rather than telling them.

Clarifying questions.

Finally clarifying questions don’t always sound like questions.

“So, if I have heard you right, the thing that worries you most is…”

“Now we agreed that you will do this, and I will do that...”

“Sounds to me that on balance, it was everything that you wanted it to be…”

Clarifying questions also allow us to conclude a conversation and end on a relative high, irrespective of the content. They show the other person that we have:

- Listened to what they said.

- Understood what they said.

- Recognised the emotion they have experienced.


Of course, there is no point is asking great questions if we don’t listen attentively to the answers!

Just as there are different types of questions, so there are different levels of listening.

Generous listening. Here, we just let the other person talk. If they just want to rant or rave on about a good or bad experience, we just let them. Think, meeting up with long lost friend, a colleague back from holiday, a neighbour on their plans for the weekend.

Empathetic listening. At a deeper level than generous listening, we are listening to hear not only the details of the conversation, but also the emotions experienced.

Q: “How was the interview?”

A: “Fine. It was alright.”

If we only hear the words, we hear that the interview was great. Because it was ‘fine’ and nothing ‘went wrong’ because it was all ‘right’. However, the tonality and delivery might tell a different story. If we are listening empathically, we might hear that the interview was not great and certainly not everything was all ‘right’.

Listening for the ‘feelings’ experienced as well as the ‘facts’ of the situation, helps the talker to feel listened to and to feel ‘felt’.

Solution based listening. This is all about listening to solve a problem or find a solution. While on the face of it, it might seem like a good listening filter, it does depend on context. If I am a frustrated customer on a call to the IT help desk, I most likely want an agent with the solution-based filter. But if I am talking to my partner at the end of a long hard day a work, I mightn’t want a solution, I might just want an empathetic ear.

Critical listening. This is listening to find the fault in the argument. Not as harsh as it first appears. Critical listening is essential to successful debating and negotiation. It can be a great filter when coaching others to be even better by listening out for things to improve. But most effective when used with an empathetic filter as well.

All filters serve a purpose. It’s about;

(i) being aware of which filter you are using.

(ii) being adaptable to change if required.

It’s like a bag of golf clubs, the putter is no good to you on the tee box and the wood won’t help you on the putting green, but you need both in the bag.

Micro aggressions and Micro affirmations

This is a nice piece of content that I came across recently when preparing a session on coaching skills. Micro aggressions are tiny actions that we often don’t realise we are making, which show that we are not listening to the other person. E.g., shifting eye contact, quick check of the phone, over nodding. Micro affirmations are also tiny actions that show we are listening. E.g., good eye contact, gentle nodding, open body language. MIT researchers found that within a one-minute conversation everyone will send between 40 – 50 micro messages to the other person – that’s a lot of talking without saying a word!

And why does this matter?

We all want to be heard. Even in conflict, we want to be heard more than we want to be agreed with. I have a good friend who has an amazing ability to remember the smallest detail of a conversation, and the minutiae of life. We’re a gang of girls that get together every so often and there is a lot of talking. Of course, some of us, me included, talk more than others. This friend is a listener. In that listening she picks up on the details of everyone’s day and remembers it. Then several weeks later she asks you ‘about that thing’ that you briefly mentioned when you last got together. In that moment she has the incredible ability to make you feel listened to, heard and respected. It’s a wonderful feeling.

“If you can’t be the most interesting person in the room, be the most interested person in the room”

Wise words from my mother who still has wise words to share at 95.

Growing up as part of a large family, we had lots of visitors to the house. Before they arrived, Mum would always say:

“Make them feel special”.

This is so relevant to the workplace and careers today. I mention this in my blog on Career Trait Swapsies – how kindness matters more than charisma.


Sometimes when I show up to deliver a virtual training session, there is NO-ONE on camera.

I am reminded of the lyrics from Simon & Garfunkel’s epic song “The Sound of Silence” – “hello darkness, my old friend”.

That’s just how it feels – me there in a sea of visual silence – like I am doing all the talking and no one is listening. Fortunately, it doesn’t happen too often. People are much more comfortable with cameras on, and our new way of work is embracing the technology. Of course, there are times when there is a good reason for not having the camera on, not least ‘zoom fatigue’ which is a real thing in terms of the ‘constant on’ pressure on the brain. However, there are other great ways to engage, not least the humble but mighty chat box. At the start of the pandemic, I was involved in a programme to upskill refugees for a virtual working environment. One guy calling from Africa had very poor internet access. He had real challenges when it came to visual and audio connection. But each time he logged on he was straight into the CHAT box saying hello and explaining his situation. He continued to engage throughout the session by commenting into the CHAT box, ‘liking’ and reacting to the comments of his fellow participants and asking great questions. As a result, he was all the time engaging in the conversation, without opening his mouth.

In summary

There is reason we were born with two ears and just one mouth. Listening is at the heart of good conversation.

Listen for feeling as well as facts. Good questions help us do that.

Disclaimer: I need much more practise to the ‘practise what I preach, but it’s still good advice!

Thanks for reading.


Sign up for it here to receive my newsletter directly to your inbox. sign me up

And thanks to the following for the images:

43 views0 comments

Recent Posts

See All


bottom of page