How to Keep a Conversation Going

I've oft found myself in one-sided conversations, ready to falter as soon as I cease my struggles to maintain conversational flow. How can this be avoided? Just as well, I've found myself in conversations that flow seamlessly from topic to topic. How does that happen successfully?

Obviously both outcomes depend not just on my actions, but on my conversational partner. If we are out of alignment, out of practise, or simply too tired to converse well then we end up with stilted conversation.

Yet if we are in accord, and committed to the art of conversation? Then the back and forth flows like sweet honey – slow enough to savour the flavour, quick enough to keep things interesting.

There's a few things that comprise good conversation, but I see one major strategy that drives it:
Always leave an opening for your partner to engage with, either by inviting inspired comments or by asking questions.

This avoids the selfish trap of focusing on yourself too much. If you both abide by this strategy, then you both will have ample opportunity to range discussion over lots of interesting topics.

Asking questions is the main tool to create opportunities for your partner to speak. This is quite straightforward when you use open-ended questions, such as "Why do you like violet wands?"

Open-ended questions give control to the person answering them, and open up a world of possibilities to their reply.

The other tool is inviting inspired comments – also known as jumping-off points. These are stray comments embedded in your conversation that allow your counterpart to pick what's relevant to them to engage with. For instance, if you mention "I took up sword lessons as a break from my job last month," your conversational partner has three easy points they can follow up on: swords, taking a break, and work. If they are passionate about swords as well, they can easily slip into that topic – and if they would rather not talk about them, they have the out of talking about a mundane topic like work.

Sprinkling in tidbits like this allows your counterpart to become inspired by one of them to make a connection to their own life. For instance they could respond "I also practise the blade, what type of swords do you use?" or even "I know what you mean about using a hobby to take a break from work, I've been learning to knit to help me relax. How does sword fighting help you decompress?"

With this strategy in mind, there's a few tactics we can employ to smooth out wrinkles in the details.

One such tactic is narrow to open questioning. You start with a narrow question or several, which allows you to broach a broader open question. For instance you might start with a basic such as "Are you kinky?" followed by a specific "Oh, do you use violet wands?" then an open "Why do you like them?"

Another tactical decision is to balance your content length. You don't want to ramble on for too long, domineering the conversation. You also don't want to be too terse, leaving no room for inspirations and forcing your counterpart to do all the speaking. One guideline is to keep your conversational turn under twenty seconds, though this rule is harder to quantify in text mediums. Several sentences is reasonable, several paragraphs may be less so.

Novel tricks are also handy tactical tools to shake things up. Instead of answering small-talk and rote questions in the expected manner, you can instead say something unique to awaken your counterpart and get them engaged. Developing a repertoire of unique responses takes time and forethought, but it's well worth it.

For example, I always grew up watching my father navigate social situation with ease. If a service staff asked him if he needed anything else, he'd often reply with a goofy answer, such as "How about a statue of a baby's arm holding an apple?" It's clearly ridiculous of a request, and it usually gives pause to the staff as they laugh and ask follow-up questions to make sense of it.

It need not be so blatant, however. For instance instead of the call and response small-talk like "How are you?" followed be "I'm fine, how are you?" you can immediately delve into an inspirational point. "I'm fine, despite having just finished touring a waste treatment facility."

As with all things, conversation is a skill. It's worth it to develop your storytelling skills with practise. Stay concise, ensure you're sending a specific message, and be relevant to the listener.

You'll notice that these points are all in favour of not wasting the other person's time. Extraneous information, rambling on, or irrelevance are all unwelcome and can lead to boring your counterpart. Remember that first and foremost conversation is a group activity, and respect should be at the foremost of your mind.

Finally, there remains one last resort to dealing with broken conversational flow. What if you employ the above tools, but find your inspirations are consistently ignored and your counterpart never asks questions back?

Be willing to metaphorically pack up and move on to new conversations. Conversation is about your partner as much as it is about you, and if you find one who doesn't match your style then you may as well stop burning your precious time trying to make it work.

It's important to correctly attribute the reason for poor conversation: sometimes people are exhausted or distracted. In that case you should likely give them more chances to recover and converse. Yet if they are reliably poor conversationalists, you may provide only common courtesy to them.

Remember always that the goal is to create a shared fulfilling experience for the participants in a conversation, and you will not go astray. Your own enjoyment is just as important as your counterpart's, so try to find common ground that engages you both.