Somebody recently asked me this: I was walking to the train station with somebody who’s in my Toastmasters* class. It was a 15 minute walk, but I didn’t know how to start a conversation, so we just walked in silence for the whole way. How can I start a conversation with him next time?
Good question. Let’s dig in.
* Toastmasters is a club that helps you build your presenting skills
Open with a question
My favorite way to start a conversation in a situation like this is to ask an open question. These are usually why, how or what questions.
With the answer to that question, you can keep the conversation going.
It’s a bit like casting a net: the wider it is, the more you’ll catch.
Critical: don’t make it a question that can be answered with 1 word like “yes, no, good, alright etc.”
Here are the questions he could have asked:
What made you join Toastmasters?
This question is a natural result of you being at Toastmasters together. But you’re also asking a “why” question, disguised as a what, which means that you’re skipping the small talk. You can jump into what makes people tick, which at least for me makes conversation far more interesting.
How long have you been at Toastmasters?
This question will get you a number of weeks, month or even years. It’s a short answer, but it can be a lead-up to the question above. It also helps you gauge how advanced somebody is.
What was your favorite speech of tonight?
Excellent question to ask, because it opens the door to deep talk (as opposed to small talk). You might get a short answer like “I thought Jack’s speech was best”. Use that as info to then ask why he thought that that speech was best. What did he like about it?
Don’t make the mistake of asking bad questions that will very quickly kill the conversation. Bad questions to ask are:
- How are you doing with Toastmasters? – the answer can be “good”, and your conversation is dead in the water
- How did you like the speeches tonight? – Mediocre, because they can be answered with one or two words
- How are you doing? – This is such a standard question that we automatically pick the default “ok” answer
Despite the fact that these are indeed how questions they are still terrible. They don’t invite somebody to keep talking and they don’t get past the small talk level of conversation.
“But they’re not talking to me either!”
You might be thinking that you’re bothering somebody by asking a question like this. I don’t believe that that’s the case.
The other person might be just as socially awkward or as desperate about a conversation as you, but they don’t know how to start.
Recently I saw the movie Green Book (recommended by the way!) in which one of the main characters says:
That really stuck with me.
I think that there are far more lonely people who would really like to talk than you might think. The trick is to just get them going.
And since quite a few people don’t know how to initiate a conversation, it will be up to you to start. Consider it good practice 😉.
Speaking of practice
Based on the situation above, try to think up 3 questions that you could have asked the person.
Consider how the person might respond. Would they be short answers, or would you get more stuff to talk about?
Send your questions to firstname.lastname@example.org if you’d like my feedback on them!