How to break into a conversation (and what to do when you cannot)

Dear Danye,

Nice blog! Very informative and definitely helpful to me who is approaching graduation in a few months.

I read several articles of yours and wonder if you have talked about how to stand out in a conversation/info session where people are beyond talkative. I mean, I don’t think I’m a quiet person but I got frustrated at times when I couldn’t break into a conversation because they talk non-stop. Any tips to out-talk these people or be memorable in a good way (through talking etc)?

Thanks – K

I received the above message through Ask Danye a couple of days ago. Great great question, and probably quite a popular concern among many us young professionals and particularly women and internationals. So let me go through my thought process with you regarding this issue, and share some practical tips you can apply to your situation right away.

 

5 Practical Tips on BREAKING INTO A CONVERSATION

 

1. Understand your goals

It is important to understand, first of all, that you don’t always have to break into a conversation, especially if this very process gives you mental pressure. You should only focus on the situations when people are discussing important stuff (of course you need to decide what is important for you), and you should only even TRY to break into it when you actually have something important to say. 

What I meant is, if your coworkers are talking about football games non-stop but you have absolutely no interest in football and have next to zero knowledge about what’s going on, it does not make sense for you to try to cut in because you are probably going to look stupid, and I would try very hard NOT to let that happen. I understand that this kind of discussion would be a team bounding experience, but I’m sure football is not the ONLY topic your team would be talking about.

 

2. Listen and Observe

If you want to be a good speaker, you need to be a good listener first; if you want to be a good presenter, you need to observe how other people present first. It sounds like so basic and so simple but in real-life situations I am telling you this is very hard to do. Especially if it is a somewhat competitive environment (like a group interview or an intensive seminar) and it involves high profile people (like the head of the department or some world-renowned professor/business figure), you would probably spend most of the time rehearing what you would like to say next while other people are talking one after another and making great points surrounding the topic.

This phenomenon is especially popular among international students when people are subconsciously not as confident or competent with their language skills and would always want to practice before actually speaking. And that was what exactly happened to me in the beginning years at college when I sat through discussion seminars, and I think you would agree with me that a lot of international kids would go through the same; but chances are, after you finally finished rehearsing and are ready to speak up, they are moving on to the next topic! 

In reality, this is a BAD HABIT and the MORE you focus on rehearsing the LESS you hear about the important stuff being discussed right in front of your eyes. And if you don’t even know what was just being discussed how do you even position yourself when you try to break into the conversation? So listen first, and do whatever you can to make it happen.

 

3. Eye contact and Facial expressions

I ran into an old friend at a conference a while back and he looked kind of frustrated. I asked him why and he told me he didn’t know anyone else and he felt really awkward introducing himself to anyone he didn’t already know (sounds familiar?) And let me stress that this friend is a Wharton graduate, so this is not a problem unique to you. 

And then he asked me if I knew a lot of people there; and I said, well a few, not a lot, but getting to know more. And his eyes widened, “how do you do it?” 

And here’s what I said: you go around the room, come close to some group you might want to join, and stare at the main person who’s talking, and you smile and you should wear that facial expression as if you are really interested in what they are discussing (like nodding or something), and you keep doing that until he/she notices you, and then you smile bigger, lean forward, and follow up with a hand shake and start talking.  

My friend was amazed; he almost thought I was joking. But he is a good friend, so he tried it out accordingly. And at the end of the conference, he showed off the business cards he gathered and complimented me that it really worked! 

My description may sound quite awkward, I know. But trust me, this is how it’s done, again and again. Especially if it is a networking environment already, more often than not people ARE IN THE MOOD to meet more people so they will make sure their eyes meet up with yours, eventually.

 

4. Start with something in common

This is probably common sense, but so many people still don’t know how to introduce themselves in the first place; and more importantly, how to introduce themselves to different people, and how to keep it very concise but very memorable.  

So my suggestion is to go with something in common between you and the speaker, for example:

• Hey sorry I missed the beginning part of this but I heard you just mentioned Yale, I just graduated from Yale this summer and I work at XXX now.
• It was a great talk you just gave by the way, I really resonate with your point on XXX. I have been doing some research on similar topics and would love to know more about the industry.

And what if someone else is talking non-stop and everyone else in the group seems like too afraid to jump in? I know you want to be polite, you want to let other people speak first, and you want to WAIT YOUR TURN, but DON’T!

Because you can do better, and you can simply say to the other non-stop talking person:

• That’s an interesting point and I totally agree with you.

And then turn to the speaker and say:

• But I would like to suggest XXX is more important in my opinion because of XXX.

 

5. Ask one good question, just one

So I talked about rehearsing is not the best you can do when other people are talking, which means you need to do your homework BEFOREHAND. If you already did the research on the company, on the speaker, on the relevant information about the industry and what is being discussed, you should have already discovered the angle you can break into a conversation, and you should have already come up with one or two really good questions you can ask.

So if it is a networking or informational session, in most cases you don’t HAVE to be too outspoken to be memorable. You can simply introduce yourself (practice your 30-second elevator pitch) and ask ONE GOOD QUESTION (something that connects what you do and what you want with what he does and what he wants), and then politely ask for the person’s business card (remember to bring your own) and give other people the opportunity to talk to the speaker as well!

Again, go back to point 1 and 2 and you will realize you can learn so much more by listening to other people too. 

 

That being said, WHAT IF YOU JUST CAN’T

 

Finally, let’s be practical. The most meaningful realization about these networking and information events is that: DON’T EVEN EXPACT that other people will seriously “get to know you” through a group conversation. So to be honest, it doesn’t make too much sense to me if you even try to outtalk other people. If other people are throwing out amazing ideas and the topics are interesting, if it’s me, I would love to just stand by and listen.

But what is actually really important is that one way or another you LEAVE AN IMPRESSION so when you FOLLOW UP via email or LinkedIn he/she will vaguely remember that you guys did meet. If this is really someone you would like to connect with in a more profound fashion it would only make sense if you lock down an opportunity to meet ONE ON ONE. And again, a lot of people are more than willing to do that if you follow up in a timely manner and know how to position yourself, see my other article on networking here.

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I hope these tips and thoughts would give you some reassurance on what needs to be done and some comfort on the fact that there is nothing to freak out about. Let me know if you have any additional thoughts in the comments and good luck!