The Complete Handbook of Creating Charismatic Conversations

Develop dazzling conversation skills which will leave people feeling like they have had the BEST conversation of their lives.

Why are conversations important?

Some people consider conversations as a necessary evil.  They actively try to avoid them at all costs and when they do have to converse they are shallow and limited to “How was your weekend” or “Crazy weather right?”.

Try to think of a conversation as the vehicle which drives you to your destination. You want to have a meaningful connection with someone (The destination) but how do you get there? With conversations (The vehicle).

Conversations can help you with:

  • Building rapport with clients and colleagues
  • Become more memorable with high-status people
  • Increase your likeability with others
  • Helps build your network
  • Enhances your current relationship with your partner
  • Help you grow
  • Creates a connection with others
  • Makes you more attractive

Conversation Starters

Conversation Starters Guide

A conversation is like a jigsaw, the object is to fit the pieces together to create the perfect picture. Where do you start with a jigsaw? The corners and the edges! Because there are less of them and they are easier to identify and more manageable to fit together. They also frame the jigsaw.

A conversation starter is very similar, just start with what’s easiest and frame the conversation from there.

Here are a few methods that I use:

Use your environment –

If you’re at a dinner party, networking event, meeting, or gathering use your environment to spark a conversation, try these examples:

  • See a painting on the wall “That painting is so beautiful, what do you think?”
  • Hears a song “Oh this song reminds me of summertime, what songs are you listening to at the moment?”
  • Sees an exhibition “What do you think that stall is exhibition is about, should we check it out?”
  • Food arrives “This food looks so tasty, what did you get?”

Compliment, the question

Give the person a compliment and then follow up with a question.

Some examples below:

  • “You have really good style, do you work in fashion?”
  • You look really sporty, do you go to the gym?”
  • You are so funny, have you ever considered stand-up comedy?”
  • “I love the tunes you are playing, are you passionate about music?”
  • “Your lunch smells so good, did you make that yourself?”

Make an assumption –

When you meet someone just make an assumption about the person, it doesn’t really matter if the assumption is right or wrong, it is just an opening line to kick start the conversation, try some of these examples:

  • “You look like a lot of fun so I thought I would come say hey!”
  • “You look like a famous person, has anyone ever told you that?”
  • “You look like such a people person!”
  • “You look like you would be really good at sports”
  • “You look like you run this company!”

Hi, my name is …

It’s a classic opener to any conversation you do not need to overthink your conversation starters sometimes a simple hi my name is… is the best option and will automatically put the other persona t ease and you come over as friendly and approachable.

The aim of a conversation starter is not to go deep into philosophical questions, you are just looking to spark a conversation.

Small Talk

This is the bit everyone hates, some people even think it’s pointless! However, small talk an important transition phase. It bridges the gap and is the first step from conversation starters transgressing into meaningful conversations. If you went from:

“Hi my name is Seb, so what is the relationship with your mum like?”

It’s too much, too quickly. Small talk warms the person up and transitions us to the main event.

How to Make Small Talk

Here are a few strategies to tackle small talk and transition into more meaningful connections

  • Ask Open Questions

Questions which start with How, What, Why are great because they make the other person give a response with is more detailed that a yes or no response. Open questions can be like this:

“What made you move to this city?”

“Why did you pursue a career in XXX?”

“How do you find the night life here?”

“Why are you considering changing career?”

“What are the cosiest coffee shops you have found?”

“Why did you choose to study XXX?”

“Why did you decide to study at this university?”

How to get DEEPER in conversation

Deep Conversation Guide

At this stage, you have built up some rapport and you are beginning to complete the transition from small talk into more meaningful conversations.

I will drop some science on you:

Conversations have the power to change the brain by boosting the production of hormones and neurotransmitters that stimulate body systems and nerve pathways, changing our body’s chemistry, not just for a moment, but perhaps for a lifetime.

As we communicate, our brains trigger a neurochemical cocktail that makes us feel either good or bad, and we translate that inner experience into words, sentences, and stories. “Feel good” conversations trigger higher levels of dopamine, oxytocin, endorphins, and other biochemicals that give us a sense of well-being.

In other words, for a conversation to feel electric, we need to release these “feel good” chemicals in someone’s brain. We can do this by getting them to talk about themselves and open up about their passions.

Here are some key things you are looking to get them to open about:

  • Their love for a subject
  • Their passion for a subject
  • Their desire for a subject
  • Their dreams about a subject
  • Their fear about a subject
  • Their pleasure for a subject
  • Their pain about a subject.

Emotions are powerful so if you can get them to begin to open up and tap into the above emotions the ‘Feel Good’ chemicals will start to be released. It’s worth noting that some of these emotions may be uncomfortable so you should only start to tap into them once you have made the other person feel comfortable and ready to open up, how long that takes will vary from person to person.

Questions to get deeper

Here are some questions you can use to go deeper:

  • What do you do when you are not working?
  • How did you get involved in that hobby?
  • Can you tell me about a memorable experience or adventure you’ve had in your life?
  • What’s something you’ve learned recently that surprised you or changed your perspective?
  • Tell me about a book, movie, or song that deeply resonated with you and why?
  • Is there a particular goal or dream you’ve always had?
  • How do you handle stress or challenging situations?


Using storytelling in conversation is also a powerful way to captivate your audience and convey your ideas effectively.

Here are some tips for telling stories in conversations:

  • When incorporating storytelling, it is a good idea to begin by selecting a relatable and engaging anecdote that aligns with the conversation’s theme or topic.
  • Set the scene by providing context and introducing the characters involved.
  • As you unfold the narrative, focus on emotions, vivid descriptions, and relatable experiences to evoke a deeper connection with the other person.
  • Keep the story concise

A well-told story not only makes your message more memorable but also fosters a friendly and approachable atmosphere, making others more inclined to share their own experiences and ideas.

How to keep the conversation going

How to keep the conversation going

A key skill that you will have to develop will be keeping the conversations going. There will always be some people you meet that who no matter what you ask will give you nothing back.

There are a few strategies you can use, however. For example:

  • “This reminds me of” – Next time where you’re in a conversation and you don’t know what to say use the phrase “This reminds me off”. Use your environment and find a song, picture, or anything that can be tied to a story that you have. Use the phrase then go into your story.
  • “Can I get your opinion/advice” – Ask for their opinion or advice on a subject, it could be related to something they have specialist knowledge in, something that they have a background in or it can be a random subject and you are just curious about what they have to say on it.
  • “Can you explain more?” – If you have asked someone a question and they have given a short answer ask them to explain more. Most people do not realize that they have given a small answer so be asking them to explain you are allowing them to provide additional information on their answer.

Mind-Set for Conversations

Before you begin to have conversations with people you need to adopt an optimum mind-set so you can set yourself up for success. People I see on Tiktok and Instagram usually have the attitude “What’s in it for me?”, “Why should I care?” or “Conversations are boring” it shocks me every time I read these comments.

Here is the mind-set you will need to develop to have successful conversations:

  • Be the Broker – Start to see the relationships you have with people as investments, like the stock market. Rather than investing money, you are investing time and energy, with the aim for your investment (Relationship in this case) to pay you back dividends (This being a fulfilling life, a business opportunity, or a potential life partner). If you approach relationships this way you will find more people will want to come to your funeral, share a pint with you, and bail you out of jail if necessary.
  • Spread Ammunition – Don’t be the person who just gives 1-word answers, give more information than is needed. This will help you because rather than asking one question, then another, and another if you give more information the other person has plenty of information to pick up on. Spread ammunition by saying more!

Challenges with Conversations

Conversation challanges Guide

When navigating through the jungle of conversations inevitably there will be lots of challenges facing you.

Here are just a few that you may encounter:

  • People not wanting to talk to you
  • Imposter syndrome
  • Nervousness
  • Social Anxiety
  • Lack of confidence
  • Dominating Conversation

All of these are valid and really understandable, however, you have to think how many of these problems are inside our own mind, and actually, we have assumed how the interaction will go before we have even had it.

Conversation Tips

There are lots of areas that are not in this specific ULTIMATE guide however they do deserve an honourable mention:

  • Active Listening – Don’t just ask a question and zone out. LISTEN to what they are saying because they could just drop a golden nugget which can help you to get them to open up.
  • Be Genuine & Authentic – Think about your values and what mean means most to you. If you value honesty then act in an honest way, if you value timekeeping then act in that way.
  • Stay Curious – The magic happens when you are genuinely curious about the other person so stay curious by asking “WHY”. Why do they do what they do? Why do they love sports? Why do they love Thai food?
  • Use Humour – Humour is a great technique and when used correctly can be very effective when it comes to being charismatic in conversations.


In conclusion, developing dazzling conversation skills can be a game-changer, leaving people feeling like they’ve had the best conversation of their lives. Conversations are not just mundane interactions; they are the vehicle that leads us to meaningful connections and opportunities. By honing our conversation starters, mastering small talk, and delving deeper into discussions, we can create powerful connections with others. Storytelling adds an extra layer of charm, captivating our audience and making our messages more memorable. Maintaining the conversation flow may come with challenges, but adopting the right mind-set and spreading ammunition in the form of engaging responses can help us overcome them. Remember, conversations are the gateway to building rapport, expanding our networks, and experiencing richer connections in both our personal and professional lives. Embrace the power of conversations, and you’ll unlock a world of possibilities and enriching relationships.