List 3: 30 Ways To Have An Awesome Conversation

30 Lists of 30 to Celebrate my 30th Birthday

12 min readAug 3, 2021

The What & Why Behind This Project:

This year I turn 30. And my gosh, I have been thinking about it a lot. I don’t know if it’s the pandemic, or the fact that this milestone is loaded with many societal expectations, but my mind has inundated me with reflections and memories from the past, with questions arising about my life choices and lesson learnt, about my expectations of being a human and about my desires for the future. And this combined with pandemic reflections has meant there has been a lot on my mind….🤔

I started writing a series of questions and lists of all the elements I wanted to capture and articulate. There were a lot, unsurprisingly; 30 years is a long time really! So I gave up on the 1 list idea that I normally write (30 reflections/lessons turning 30) and decided to write 30 lists.

30 Lists of 30, for my 30th Birthday.

Who are these lists for, you might wonder? I started writing reflections many years ago to get to know myself better. And when I shared these raw and real accounts with friends I discovered that what I wrote about my individual journey, touched upon something universally human. Beyond the masks and labels we wear is a messy, beautifully complex life, with highs and lows. And more similar to others than we might think.

So I share them in the hope that you too might feel something — intrigue, joy, resonance or maybe even difference — as you reflect on what it means to be a human. I recognise that my experiences are my own, that some come from a place of privilege and that they may not all be relatable or interesting to you. I know I can’t please everyone, so take what you can…(and let me know what lands!).

So, Back to Lists…

The Why Behind List #3:

As a conversation addict on a mission to understand the formula for meaningful conversations, this list has been wanting to be written for a long time! I’m obsessed with understanding the somewhat mysterious dynamics involved in interactions, and how they can be influenced to create positive impact. I believe this is an absolute superpower to have because literally everything in our lives starts with a conversation: friendship, dating and romantic relationships, business relationships, sales, influencing and negotiating, creative thinking, teaching. And in a tech-oriented world, the magical moments are when we get to be human with another human in real time. ✨

List #3– 30 Ways To Have An Awesome Conversation 😆

Let go of the plan you have about where the conversation is going — the best conversations are an adventure and have no destination. Conversations are by their nature improvisational. If you create a plan by yourself you will lose out on the co-creative element which is what makes it fun.
But, do lead! Treat a conversation like a dance, with a leader and follower that can change in any given moment. When a conversation is falling flat, choose yourself as the leader (don’t wait to be chosen) and help your partner by injecting some new energy or direction.
Start the conversation with statements and not questions. Statements about yourself (e.g. ‘I am feeling very excited/ hungry/caffeine-deprived’), about the other person (e.g. ‘you look like you’re surprised’, ‘you’re drinking orange juice’, ‘you have cool sunglasses’), or the shared environment (e.g. ‘this event isn’t what I was expecting’, ‘wow this queue couldn’t go slower’, ‘there are plants hanging upside down’). Sounds unusual, I know, but it is super powerful for many reasons. First, it helps lower the bar for someone to join the conversation because they don’t need to say much to join — they can simply acknowledge your statement through a head nod, yes or share their experience of what is happening. Second, questions take time to answer, require investment and have more of an agenda which can put people who don’t know you (e.g. strangers) or don’t have the energy to respond off. Thirdly, statements invite someone to become curious about you or the thing you have noticed in the present moment and shared, which means that the conversation feels both novel (and not scripted) and energising.
Be present by noticing and talking about the present — what is alive for you and your partner now. Your thoughts, feelings, desires etc. We often share stories about who we are (past) or our desires for the futures. Both are stories that we’ve shared before and are not novel, and can feel quite scripted. The beauty of tuning into now is that every moment changes so you’ll always have something new to reveal.
Notice (and share) the impact someone else is having on you when they share something. You can say ‘hearing that I notice… I feel curious about X/ I have some tightness in my chest/ I am reminded of/ I’m really happy for you….’ This authentic relating tool is incredibly powerful as it gives us an insight into how someone else is receiving us in the given moment. It is also a great introduction to how to safely give honest feedback to each other that builds emotional intimacy.
Don’t hijack the conversation when you hear about an experience you can relate to. We often engage in level one listening, where we are looking for other’s dots that are like ours, and waiting to find common ground so we can insert our own stories. E.g. when someone talks about their favourite sport, somewhere they went on holiday or something they learnt recently. In hijacking the conversation we miss the opportunity to understand what it is like for the other person to have their experience, because we assume their experience is like ours.
Ask questions but don’t just ask for facts (who, what, where, how). Facts are known answers so are for the benefit of the asker and not the receiver and can be exhausting to answer. They also don’t tell you anything about who someone is — knowing where someone is from, what they do or what they did on holiday will only give you a surface level and perhaps stereotypical view of them. It’s okay to ask some factual questions to get context, but keep them to a minimum.
Listen and ask questions about someone’s experience. What does something mean for them? How does this connect with what else they have shared? What motivated them to do X (drivers)? What was it like for them to experience Y? What is important to them (values)? What beliefs do they have? What might they be feeling?
Go first. Remember that drinks party where no one knows each other and you wish that someone would come over and say hi? You can be that person.
Shut up for at least 5 seconds after your partner has spoken. Slowing down, pausing and being silent create the space and permission for thoughts to emerge. This is often the moment when deeper truths emerge and are shared.
Create authenticity and vulnerability by modelling it. If you go self-disclose first and show up as yourself you create the context (safety and expectation) for this kind of behaviour and others will reciprocate. This can be especially powerful at the start of a conversation with someone new because there is no pre-existent behavioural pattern. It also works like a charm in groups — the first person to answer a check-in question will have a huge influence on the rest of the group’s responses.
Help your conversation partner by answering small talk questions with multiple hooks so it’s easy for them to ask follow-up questions. E.g. ‘What do you do? — don’t give your job title, instead share the project you’re working on, maybe something you’re also learning or curious about or what else is keeping you busy. Share a lot of (different) hooks to get others curious but also leave them hanging by not sharing the full story.
You don’t have to answer the exact question you’ve been asked. You can help your partner out by breaking the script and answering a related question that might have more of an unusual spin on it. For instance, ‘what do you do?’ = ‘what I’m thinking about a lot these days/ what I want to do / what I’m learning about / what I love doing / what I don’t do’ . Don’t answer ‘How are you’ with ‘fine’ — I like to give a number out of 10, like 7.5, sometimes with context, sometimes without to create curiosity. Or you can say ‘I’m curious about …. ‘ ‘caffeine-deprived’, ‘Desperately in need of a mortgage’ (!). Be bold, take a risk and don’t make assumptions about how something will hand.
Break the script when you ask small talk questions. Help others get off auto-pilot by giving them slightly related by different questions to answer. This is especially useful when conversation is used in transactional circumstances like buying coffee, food, tickets. Instead of saying ‘‘Please can I have a white Americano?’ you say ask for ‘the best americano in the world’. Instead of asking colleagues ‘how was your weekend?’ you can ask ‘what was the most surprising thing that happened on the weekend?.
Small talk is actually the gateway into conversation, not the conversation itself. Used effectively it builds comfort, rapport and trust, helps people share many things about themselves so you can choose one and then go deeper down that avenue. The key to navigating it successfully is being genuinely curious about the questions you ask, seeking more, and not giving others scripted responses.
Put up on your curiosity hat… be both humble enough to know you don’t know something but confident enough to admit it. Curiosity is all about the follow-up questions. When someone shares something, imagine you know nothing about that experience and you want to understand their reality (even and especially when you think you do). Let go of what you think their experience is like, why you think they act like they do, what words mean to them. Start to wonder how what is shared might connect with everything else in their life (after all how you do anything is how you do everything). E.g. this statement ‘yesterday, I went running along the Thames’ brings up themes of: exercise, sports, weather, location, health, travel, London, speed, effort, growth, challenge, resilience, drive, clothing, meditation, strategy, competition, independence, thinking, freedom, relaxation, routine, structure. Plenty you can ask about.
When someone asks how you are, actually check in with yourself and share how you’re feeling, what you’re thinking about right now, what you’re doing or a short story from your day.
If you want to break a social norm or do something that is slightly unexpected or different to the expected behaviour, first name the rule you’re going to break first. It keeps the flow by taking others on the journey with you, invites agreement for the change of direction, and signals social intelligence (you’re aware of the rules but choosing to break them). E.g. ‘I know you’re not meant to talk to strangers but..’, ‘this is going to sound quite deep…’
Echoing or reflecting back 1–3 words that someone has shared is the most impactful way to create the safe space for going deep fast in a conversation. Essentially you’re doing 3 things: showing active listening, signalling interest for more information (tell me more) and also reflecting others words helps them think more deeply about what those words mean.
‘Yes, and’ is not just an acting improvisation technique. Build on others ideas by acknowledging their reality and adding to it. Notice when you’re negating them (yes, but…). E.g. (1) someone says ‘I love the smell of the roses in the garden.’. Yes, and = ‘Yes, the red ones particularly smell great and take me back to days. Yes, But = They don’t seem to smell much. (2) ‘I think it would be cool to organise a trip abroad.’ Yes, But = ‘Well we can’t travel right now due to COVID.’ Yes, And = ‘There is a place I’m dreaming about visiting, with an old cobble street and a view of the sea…’ Yes, and can also be a great way to play — and co-create a reality with someone.
Reflecting back what you’re hearing or how you’re making sense of what your partner has shared (in a mix of their and your words) allows your partner to feel seen and helps them re-shape and build on their thoughts. Conversations aren’t opportunities to exchange ideas or information but to reshape them.
Build empathy by labelling the feeling or thoughts your partner might be having. e.g. “It seems/ sounds/ looks / feels like might be feeling….’This gives them permission to fully feel that feeling, helps them feel understood and seen (a universal human need), and if the feelings are challenging, labelling helps them calm down as the electrical activity in amygdala decreases when you label an emotion. If the feelings are positive (e.g. ‘you sound very excited’) it reinforces the feeling.
When you’re not sure where to go next in a conversation ask ‘what does this moment need?’ not ‘what’s the right question or thing to say now?’.
Be the lighthouse. Recognise that your energy is infectious — if you’re smiling and delighted, it is hard for others not to smile back. Set the intention you want others to feel in yourself first.
If you feel some anxiety about approaching a stranger, imagine that that they are your best friend and you’re wishing them the best day in the world or ‘love and kindness’ (metta). Your inner energy will shift and your smile will be received as more genuine and real.
Everyone is interesting, but it’s not up to them to prove it, it's up to you to discover it in them. Remember that the person in front of you is as complex as you are.
Likewise, if you want to be interesting to talk to you have to first believe and treat yourself like you’re (sometimes) interesting. I say ‘sometimes’ because we aren’t always interesting 100% so cut yourself some slack! Most of the time, how we show up in a conversation and the kind of behaviours we follow is down to what we believe: about ourselves (I am interesting, boring, unattractive or not enough) or the other person (they are super interesting, high status, boring or not worth my time).
Conversations are opportunities to make people feel (which leads to memorability and likeability). You can make others feel by building tension and then releasing it. For instance, by making statements that set expectations and misdirect (e.g. ‘I know I shouldn’t say this/ This will be awkward but…..PAUSE…. You’re an awesome friend.’ or ‘Can I ask you a really difficult question…PAUSE… where are the toilets?’
Create circularity in conversations (return to some of the previous themes or points — like the re-exposition/ recapitulation in the sonata form in music) but don’t close every loop. Leave the conversation and your partner wanting more.
Everyone is constantly changing — we are not the same person as we were yesterday, so check in with your assumptions about who others are and what they might say.

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Still Curious?!

💬 Watch my TEDx talk: Talking to Strangers: Having a Meaningful Conversation

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List 3: 30 Ways To Have An Awesome Conversation

30 Lists of 30 to Celebrate my 30th Birthday

The What & Why Behind This Project:

So, Back to Lists…

List #3– 30 Ways To Have An Awesome Conversation 😆

Written by Georgie Nightingall