Part I: How to Have an Interesting Conversation (in a Group Setting)... told using a Rocket Launch metaphor (because they seem to be the same difficulty level)

Interesting conversations make life better. But they can be hard to find and have. They can be extremely challenging for us mentally and emotionally. Let's make them easier.

Let’s start with a situation where you find yourself at a party, mixer, happy hour, meet & greet, Thanksgiving dinner with the extended family, busy bar scene…you name it. Basically, it’s you and a bunch of other people, some you may know and others you don’t or maybe you don’t know a soul. What do you do?

Uh, Houston, we’re not ready for takeoff…can we come out and do this another day?

Rocket Launch.jpg

The one undeniable truth that NOBODY understands is that EVERY person in these social group settings wants someone else to come up to them and, without being creepy, spark up a really interesting conversation without an agenda. Everyone is hoping for this same outcome. Nobody wants to be the person standing by themselves all night. Nobody.

It’s important to BELIEVE this is the case and that NOBODY is comfortable in these settings (some people are just better at hiding their apprehension). If you can’t accept this, nothing else really matters in these situations.

REMEMBER: You are all in this same setting because you either want to be or you feel you have to be (social pressure, your boss told you to, or maybe you’re genuinely interested). In either case, everyone at the event is EXPECTED to talk to someone else; nobody in that room will find it odd if someone approaches them to chat. And remember that while talking to someone else is really nerve-wracking, it’s better than being the person who doesn’t talk to ANYONE else the whole night (that is the worst case scenario).

What’s the Holy Grail at this kind of event? Easy: someone super interesting approaches you, time flies, you share some really interesting story about your life, and hear a story or two from the other person that you can’t wait to tell your friends because it’s so interesting. That’s it. And it’s not hard to do…it’s just hard to get the nerve to take the first step.

"If we have no other choice, then let’s start the countdown…10, 9, 8…"

What’s next? Take the first step: look around the room and pick anyone who isn’t already talking to someone else. We are looking for others who might feel a bit uncomfortable because they are hoping someone will come to them. We’re also initially avoiding the more technically-challenging jump into a conversation that’s already underway between others (we’ll address that separately in another post).

So, walk up to anyone standing solo to start your conversation. Notice I said ANYONE. We aren’t talking about the person who’s about your same age or income level or gender or race; we’re talking about anyone. Even the bar tender will work (they can be the best starting point imaginable in fact).

Pilot to Commander: “That’s your advice? Don’t crash?” Commander to Pilot: “Yes.”

Focus: learn something new & be honest.

Focus: learn something new & be honest.

As you’re walking towards you soon to be conversation partner, I wanted to share some advice @CelesteHeadlee gave that nails this next part on the head (see her interview on the The Art of Charm podcast): your single goal as you begin your conversation should be to learn something new from that other person. That’s it! You’ll notice this applies to a person you know already (co-worker, cousin you haven’t seen in two years, neighbor, celebrity, etc.) AND it applies to complete strangers. There’s no thinking involved here, just try to learn something new from that other person. It will force you to actually listen and all the other things people tell us about how to have a good conversation that get in the way will become meaningless. Which is good.

It's important we pause here to debunk some of these common ERRORS we’re all told throughout our lives (particularly when we get advice from others or a magazine) about what to do when we talk to someone else.  You’ll notice that the goal of learning something new from this other person does NOT include making a specific kind of eye contact (creepy), mimicking their body language (who does that?), saying “uh huh” throughout the discussion to show you’re interested (disruptive), or standing a particular distance from the other person (do we need advice on this?). 

So, instead of worrying about where your eyes are going to be focused, JUST think about learning something new about this other human.

Another fallacy: as you approach this person and your heart is pounding because you feel like you’re walking up to ask someone to dance at the 8th grade prom, you NEED TO REMEMBER THIS…the other person is feeling the same way watching you approach them (they’re thinking ‘oh no, what will this person say, are they weird, what if I don’t have anything to say, why don’t they look nervous like me, don’t say something stupid…’).

The big question we ALL ask and want someone to spoon-feed us is this: what’s the first thing I say? Great question. Another SECRET: NOBODY has a killer list of conversation starters. One size doesn’t fit all.

The key for the first words out of your mouth is this: be honest. If you’re disingenuous AT ALL, you may as well not talk to a soul and be content to be the person standing by yourself in the corner all night. You’re better off saying something honest and potentially offensive than something fake but complimentary. People will smell your insincerity as you speak…GUARANTEED. You can probably recall a recent interaction where someone talked to you with a clear agenda to sell you something or get you to do something.

We’re blasting off…now what?

Starting the conversation.

Starting the conversation.

So, what do you say to start things off? That’s up to you.

Do you like their jacket or watch or shoes? Say so? Does the weather really suck? Then bring it up (another SECRET: the weather is NOT the death nail of a conversation). Maybe use the weather to share where you’re from originally (‘The rain stinks but when you’re from Minneapolis like me you’ll take rain over snow any day!’) or share places you like to travel (‘I’d rather be sunburned in Baja on vacation…’).

Can’t think of anything at all to say, how about the ultimate truth? ‘I’m not great at this whole networking thing (or I know we haven’t really had a chance to chat in a while), but I wanted to introduce (or reintroduce) myself. I’m Ryan…’ Chances are the other person will agree with you and admit they’re not good at this either; they’ll be so thankful someone else had the nerve to say it first.  Why not follow it up with something like, ‘I’m glad you said that….if you don’t mind my asking, what brought you here tonight?’

By the way, regardless of which openning line you go for, you’ve learned something new about the other person like where they’re from, how they handle these situations, their name, etc. So, take the pressure off yourself and just focus on listening to your new acquaintance.

Something else to remember that you’ll learn at an expensive networking course but that’s common sense yet something we often forget: People generally like talking about themselves. Let them. People have fond memories and experiences they’d like to share WITH THE RIGHT PERSON. That’s the key, you want that other person to feel comfortable and even excited to share some of these experiences with you. If you’re REALLY listening, making this person feel comfortable won’t be a problem. It will ONLY be a problem if you’re not listening…or if you’re looking around the room for something better…or you’re trying so hard to look interested that you don’t hear what’s being said (it’ll come off like you don’t care even if you do).

If you can get someone else to share their one-in-a-lifetime experience with you, you’ve earned the ultimate prize: you’re guaranteed to have a new friend, a cool story, and someone you can share more with in return. You’ve won. Game over.

Leaving Earth’s atmosphere is bumpy…but you can’t turn around

So as the conversation continues, let’s remember the ONLY thing we’re trying to do: learn something new about this person. There will be bumps in the conversation; natural ebbs and flows. This does not mean we abort. We accept lulls and abrupt changes of topics and keep going.

We are still NOT trying to make some weird kind of eye contact or hold our drink in the correct hand so we don’t give a cold handshake. Just learn something new (JLSN) about your friend.

As things are moving along, don’t try to catalog everything the other person is saying like you’re Sherlock. There’s no test at the end. You also don’t need to stay on one specific topic for a certain amount of time or wait until you’ve exhausted that topic before raising something new. Feel free to jump around if that’s where the conversation is going.

For instance, if your new friend is talking about their job and offhandedly mentions a cool bike path near the office, jump on it…’oh, I didn’t realize you were a biker?’ (this is a GREAT question because it’s very open ended and offers the other person all kinds of responses). As the bike conversation winds down…THEN you can return to your new friend’s job. No harm, no foul.  And you know what? Even though you already talked about bikes, you can STILL return to the bike path later on (crazy right?)….’I have to say, just between us, I don’t understand bikers and spandex?’

Don’t press that button! Are you crazy?...Yes

Remember when people told us not to discuss politics or religion with other people? They’re wrong. If your new friend brings up either, feel free to engage. Keep one VERY important thought in mind: do not try to change the other person’s point of view. If you do this, your conversation is over and nobody wins. You NEED to feel free to raise whatever position you’d like but do not expect to change their mind. But what if the other person won’t stop?…’Um huh, I understand what you’re saying, I think we just see the problem differently. Fortunately our stellar politicians in [insert world capital] will solve this for us (chuckle because every human knows this is a good joke).’

"Is this the end of the mission? We haven’t even landed yet."

Ejecting early is discouraged.

Ejecting early is discouraged.

Just when you thought making the initial contact was hard….how about when you need to jettison from the conversation. You can’t just abruptly end and walk away. This can be a tough line to walk. Fortunately, we can fall back on our initial pointer: be honest. ‘Hey, this was really interesting. Thanks for telling me about good places to go biking in the area. I’m going to freshen up my drink [run to the restroom, make a quick call, do some power squats, whatever] and mingle some more. Here’s my contact info [optional]. Hopefully we’ll have time to chat again later [if you mean it].’

There’s no need to do an about-face and then run away. You can just turn, find the buffet, bar, bathroom, or whatever, and then casually make your way over.  If you find another person standing alone on your way to your intended destination, go ahead and start the process over. If not, go take a short break at the bar or wherever (this gives your new friend time to move a bit) and then come back and take another shot at it with a new person.

Quick note: when you are talking to person #2 (assuming you were truly paying attention to person #1), you’ll find commonalities between the two. This is an IDEAL opportunity to help both of these people by introducing them or just sharing that you know someone else they might like to meet. SIMPLE. You’ve now doubled your wolf pack. 

Pilot to Commander: “That was a rough landing. I’m such an idiot (right?).”                    Commander to Pilot: “You landed a spaceshuttle. It was great.”

If you’re like 90% of people out there, you wake up the day after one of these group social events and suffer from the Conversation Hangover (bet you didn’t know others did that too).

Ah...the old Conversation Hangover!

Ah...the old Conversation Hangover!

What’s a Conversation Hangover you ask? Simple, it’s when you scrutinize EVERY comment you made during your conversations the night before and completely break yourself down for anything you said that may have been taken the wrong way, come out awkwardly, insulting, in poor taste, embarrassing (this is a long list).  Also like 90% of people out there, you probably aren’t sitting there thinking of EVERY comment another person said to you. Instead, and for some reason, we’re willing to be overly critical of ourselves while not even being the slightest bit concerned about what others said.

Some psychologists describe this as a mild form of narcissism. I don’t see it that way. It’s a form of human nature where we want to be liked by others and seen as polite and memorable.  Instead, it breaks us down slowly over time.

For those who suffer from this, you NEED to be easier on yourself. I attended a @TimFerriss talk in Washington, DC recently and his advice was spot on when asked what he was working on: he said he was learning to be easier on himself (and this is coming from a very accomplished person). Let’s all learn from it.

Since very few of us will be able do this and forgive ourselves, however, I’m happy to share that if we can just follow the points outlined above, you won’t suffer from this any longer.

How is that possible? Well, if you approach each conversation as an opportunity to learn something new about someone else AND you’re honest, this won’t happen. No Conversation Hangover. How is that? You see, Conversation Hangover sets in because we’ve tried to act or behave like someone else and put on a show and talk about something we know nothing about while acting like we do or not actually paying attention and appearing fake. We can tell the other person sniffed it out and can tell we were an imposter.

NONE of these problems happen when you’re trying to learn something new and honest.

Now you can give this advice a shot on Convers8!

Good luck!

‘Psst…So what about times where I want to talk to a stranger?’ Good question. Check out our tips here.

Subscribe here for more original content like this.