Make a Comment

Most casual conversations begin low key. You sow a seed without putting undue pressure on yourself and then you're easy about what might happen next. If a conversation gets going, that's great; if it doesn't, no matter. One way to sow the seed is to make a casual comment – just a simple remark into the air, easy to respond to or not, that doesn't put the other person on the spot or put them under an obligation to speak. For example, “What a cold day!” – yes, there's nothing wrong with the weather as an initial subject for conversation! – or, “Busy today … for a Monday.”

Any simple casual comment is okay. A person standing by you can pick it up or not without embarrassment. If they don't, you've lost nothing. If they do, you've started the ball rolling. Use your eyes and ears to comment on things you notice, any simple off-the-cuff comment so long as it's not negative or intrusive.

Float in a Simple Question

Another way to start a conversation is to ask a simple question. Again, take it easy, no pressure – it might get a conversation going, it might not.

You might notice that these are “closed” questions – questions that can be answered monosyllabically with “yes” or “no” – and therefore are not guaranteed to get a conversation going. But in practice that is fine – being answerable with just yes or no, they are not intimidating, and serve the purpose of gently breaking the ice. You may get no reply or a brief “yes” or “no”, but more often, especially as there's no pressure to do so, you'll find that people tend to expand a little on the yes or no.

Compare “Have you come far?” with “Where do you come from?”, which sounds more direct and therefore more demanding – though it all depends how you ask it.

Try a Comment Followed by a Question

Putting these two methods together, a comment followed by a question works really well. The comment is just put out there without obligation, and if it is picked up, you can follow with a simple question. For example:

You follow with another comment and a question tagged on the end:

Introduce Yourself Positively

At a social or work event, a good way to break into a conversation can be to take a more formal approach. Smile at someone, extend your hand in greeting and introduce yourself clearly: “Hi, I'm John Smith – pleased to meet you!” Then immediately follow up with a comment or question as before. Your general demeanour will make all the difference – if you look and sound friendly the other person is more likely to respond in a friendly manner.

When you first open your mouth, don't worry about thinking of something clever to say. Your initial approach doesn't have to be original. In fact, the art of small talk – the first important tool in the conversationalist's toolbox – is to start with something simple and everyday – and relevant. Great friendships and valuable connections grow from little conversations!

Adding a Little Extra

In more elegant play you don't bat the ball right back to the same place it came from, but vary the pace by adding a bit extra each time after the answer.

And so a conversation slowly grows from safe and unassuming beginnings into something more interesting, and by the time it is going well, no one is really thinking any more in terms of comment, question or answer – it's just flowing.

Taking It Gently

The art of questioning is to move gently, transitioning smoothly from one thing to another. A question doesn't work well with someone you don't know if it is too sudden, intimate, specific or challenging. Here are a couple of examples of what not to do at the outset of a conversation:

Wait until you have a measure of the other person and have built up some trust before you introduce subjects that attract strong views – like sex, religion, politics and money – unless you like to live dangerously! It's best to build up to controversial subjects rather than launching straight in if you want the other person to feel at ease.

Be a bit careful of humour too. Mostly humour helps a conversation, but if you have a dry sense of humour or humour with an edge to it, it might take the other person a little while to tune in and cause awkward misunderstandings at the outset. Warm up to humour; get a feel of what the other person is like first.

Open Questions

After the initial exchange you'll get more from the other person if you ask questions that invite an explanation rather than a yes or no answer. For example, “How do you find living in Sydney?” rather than “Do you like living in Sydney?” Notice how questions that start with what and how invite fuller answers:

Questions are essential for conversations, but they're only half the story. A good conversation never feels like a question and answer session; it's less structured than that. Conversational partners take a turn in leading, and good listening keeps the conversation flowing. We look at listening a bit later.

Changing the Subject

It's a great feeling when a conversation starts to flow and gains its own momentum. Often when that happens, you will both happily move from theme to theme without even noticing how that is happening.

At times though, you may find that you want to move on from the current subject, or you might suddenly want to say or ask something that is unconnected. In that case, it's a good idea to pave the way for your new theme so that a sudden change of direction doesn't jolt your partner or confuse them with its “foreign” content. You can do this by adding an introductory sentence. For example:

By adding such a sentence the other person – though momentarily surprised by your shift to something new – has time to gather themselves by the time you actually say the core of what you are intending to say.

Dropping Conversational Clues – and Picking Them Up

People who are skilled at casual conversation often drop the odd comment into an exchange to offer the other person a gentle lead if they wish to take it, like a free gift:

The obvious response would be to answer the direct question:

But that whole year in New Zealand tossed casually into the sentence sounds interesting, so you might prefer to follow that up instead:

And a fascinating exchange might follow.

Sometimes a clue placed in a conversation can build a more intimate connection if you're prepared to pick it up. For example:

And suddenly you're on a different level of conversation from chatting about films you've seen.

Picking up clues takes curiosity and awareness. They often appear half-hidden in the waft and weave of something else, and it won't always feel appropriate to follow up on them. It doesn't interrupt the flow of conversation if you fail to pick them up, but if you do, you have the opportunity to develop the conversation into something different and potentially more interesting.

Picking up such personal clues is a risk. But, on the whole, someone drops the mention of something personal into a discussion only when they are prepared to talk about it; and if you go gently it may lead you to an interesting discussion and the chance to get to know the other person better.