How to master great conversation, even if you’re shy

Josh Smith
Josh Smith has interviewed hundreds of celebrities from Oprah to Victoria Beckham to Olympic weightlifters - Heathcliff O'Malley

We have conversations every day. From surface level chats to internal ones, to awkward ones to deep and meaningful ones. But when did you last have a really great chat?

In a digital age, these chats are becoming rare. We’re too time poor to invest in conversations with new people. When it comes to friends and family, we feel like we are fully updated about their lives from what they share on social media. When we talk on Zoom or via streams of text messages, we forget the etiquette of conversation and how to make it actually interesting. When it comes to good conversations, we’re out of practice, underconfident and our wellbeing and sense of community is nose diving as a result.

Studies have long proven that talking is a fundamental human need on par with sleeping and eating and further research has shown we have less friends than we did 30 years ago with close to half of Americans now reporting they have less than three friends. So, if we want to improve our – and our collective – wellbeing we need to invest in our communication skills.

I have been a celebrity interviewer for a decade now interviewing hundreds of celebrities from Oprah to Victoria Beckham to Olympic weightlifters. My entire living is based around making conversation interesting and sometimes I will be the first to admit it can be very tricky.

Josh with Victoria Beckham
Josh with Victoria Beckham

I haven’t always had the confidence to have a great chat. I grew up with a speech impediment. I couldn’t say my ‘ph’, ‘f’, and ‘th’ sounds and it made speaking stressful. It affected my ability to speak and my confidence to speak up because I stumbled over the words repeatedly. I remember a dinner lady laughing in my face because I couldn’t say “fish fingers”.

When I was five years old my parents, seeing how much it was affecting my life, organised for me to start going to a speech therapist. After months of exercises, my speech gradually started to improve. But when my voice didn’t drop as a teenager, I lost confidence in it all over again and in secondary school, I became a target for homophobic bullies.

I’d grown up in the Cambridgeshire Fens, a very remote place where I struggled to find ‘my people’. Not feeling comfortable within myself or accepted for who I was meant making friends felt even harder.

Josh as a young boy. He grew up with a speech impediment which deeply affected his confidence
Josh as a young boy. He grew up with a speech impediment which deeply affected his confidence

Things started to get easier for me when I came out as gay and went to sixth form in Cambridge which felt like a bustling cosmopolitan city in comparison to my hometown. It wasn’t easy, but putting myself out there repeatedly has shown me how impactful and important conversation is. It’s how we build community and understanding of others. It has also shown me that everyone has the ability to communicate effectively, no matter what social obstacles or nerves they might have.

Chatting has changed my life. It has increased my confidence immeasurably. I grew up a shy boy in the countryside but today, I have the confidence to interview anyone.

All of these conversations have taught me one thing: everyone in life is a teacher or a lesson to you. You just need to be willing to have the conversations.

Josh with Natalie Portman
Josh with Natalie Portman

It’s surprising to me that we don’t talk about talking more, how to do it well or how to use it to help ourselves and others, especially as The World Health Organisation have recently declared loneliness as a “global public health concern” and an even greater concern than obesity. The US surgeon general has even gone as far to say the mortality effects of social isolation are the equivalent to smoking 15 cigarettes a day. Starting to talk more is the way to reverse those health effects.

One thing I regularly hear from people is: “I can’t stand small talk.” That’s because it can be clunky, awkward and so difficult to get right. But it is the foreplay of conversation, it takes up a third of our speech and you can’t get anywhere in life without it.

One study from the University of Kansas showed that when we engage in simple chit-chat we feel better, build connections and create a sense of belonging. So whether you’re socially anxious or simply just nervous about having awkward conversations, here’s how to become a more empowered communicator by brushing up on your small talk.

When you have to go to a wedding and you don’t know anyone

If you are going to a wedding, whether alone or with a plus one, don’t fall into the habit of asking someone if they have a partner if they are on their own, or if you meet someone who is married or with their partner, if they are going to have a baby. Many people lazily ask personal questions as a way to connect to someone quickly but it can have the opposite effect. You never know what their feelings are about their relationship status or their fertility. You have no right to someone’s personal life and it will immediately create a barrier to connection.

So instead of getting personal straight away, I always find that asking open-ended questions like “What piece of advice do you think you should give a newly married couple?” or “What do you love most about the couple?” These questions are unintrusive, give people the space to answer as specifically as they choose and they might reveal something that really stays with you, making for a memorable and friendly, comfortable chat. In any situation open-ended questions enable people to reveal parts of themselves that they want to talk about and it’s a positive question which could lead to many conversation avenues.

In a job interview

Do your research on the people who are interviewing you. People love to feel important. Find out what they have worked on recently or parts of their career journey and ask them about it when they open it up to questions: “I know you worked at X before, how have you found working here?” or “What has been the most career-changing moment for you in this job?”

On a first date

We make first impressions of someone within seven seconds of meeting them so you need to be asking positive and upbeat questions that create an immediate spark. Small talk forms our first impressions of each other and this is especially true in a dating situation.

Don’t start talking about how busy you are. It’s a default mode many of us slip into and it practically says, “I don’t really have time for this,” and even suggests, “even if this date goes well it’s going to be impossible to see me”.

Make small vocabulary tweaks like using words like “exciting” and “best” in your questions. “What’s the most exciting thing that’s happened to you lately,” is a more enthusiastic version of, “what have you been up to lately?”

You can also ask relationship specific questions – you know why you are both here – so ask: “Before we go any further, do you know what you are looking for?” Not only is it more time efficient – if you are looking for different things, stop there – you will quickly start sharing your thoughts, feelings and past relationship stories in no time.

Meeting your partner’s family or friends

Use your partner as the topic of conversation. Ask their family or friends about them, for instance you are meeting their parent(s) for the first time ask, “What were they like as a  teenager?” or “What’s your fondest or funniest memory with them?” Not only do you get some great stories about your partner, it will get the person you are talking to open up about their lives and experiences, too leading to more free information you can ask questions about. Trust me it worked like a charm when I met my partner’s parents – it really shows you care.

When you are at a networking event

Avoid talking about the weather at all costs. It’s default, it’s dull and we are all bored to tears with how awful this summer has been. Use networking as an opportunity to ask something interesting that will get people’s attention, even out of the blue questions. “If you were given a billion pounds right now, what is the first thing you will do?” is an improvement on how grey the sky is today. Left field questions will make sure they remember you. Always ask how someone is before you ask what they do. And never ever look around them to see if there is someone ‘better’ nearby. I have experienced this so often – the entertainment industry is notorious for it – and there’s no quicker way to show how little you care about someone than this.

When you know your family or friend is having a difficult time  

One of the most effective questions is: “How are you, really?” We ask people how they are every single day but we rarely listen to the answer. We skip right to the next question, say what we need to say or we have already walked off as they respond. It’s a flippant question but it can have a huge impact so if you know someone is struggling with something right now, ask them, “How are you really?”

Adding that one word at the end shows you care, you are interested and ready to listen. I remember asking Chrissy Teigen this at the beginning of my interview with her and it immediately opened a very insightful conversation about her mental health. ‘Really’ enables others to open up without you asking specific questions about their predicament which could stop them from opening up all together.


Josh’s top tips on how to sharpen your (small) talking skills

  • Rule number one is to put your phone away: Even if it’s turned over on the table it suggests your phone is more important than the person in front of you.

  • Small talk is a social ritual so get better at it: Ask questions, give responses but if they just aren’t giving you anything in return move on. Take your chat elsewhere. Politics and offering your opinions isn’t small talk. Don’t dive in with the political; it will only get people’s backs up. See it as the starter and don’t linger on it too long or the conversation will grind to a halt. You want to get to the main course.

  • Never give one word answers: Give people something to work with. “Fine,” is never a great response to “How are you?” for example. You need to say, for instance, “I’m good, thank you for asking. I am going on holiday soon and I can’t wait.” That invites the other person to ask where you are going and allows a whole conversation about a destination and holidays to unfold.

  • Remember conversation is a two-way street: If you feel anxious, small talk questions will get the other person talking and, before you know it, you will be chatting in return. Listen out for little conversation tit-bits that could spark another question from you. Channel any curiosity you have into your initial chats and approach the conversation with genuine interest. Curiosity not only invites further chat, it sets the tone.

Josh Smith’s book, Great Chat: Seven Lessons for Better Conversations, Deeper Connections and Improved Wellbeing is out now.