Improvement Story – The conversation booster

In this post, I’ve collected my best, personally experienced, ice breaker questions for any kind of conversation. I use them for meetings while we wait for all to come in or for business dinners the most. As always, a short summary can be found at the end of this article. Have fun learning!

Let’s get into it:

Imagine you got your dream job and the first meeting is at a hotel for two days with all your new team members. You know you have to work with at least 10 of them each day for now. Now you have two options. Pass the days as “the new one” who don’t know any internal business topics so far, or as the guy who is charismatic and has interest in the teams live beside the job.

Seat picking

The first point on the agenda is lunch. You all had a long journey to come to this hotel from all over the globe. You choose the table with six seats instead of the one with two. Positioning is the first important step because the chances are higher to find conversation partners with whom it is easy to communicate.
You know that more seats mean more communication partners. If the conversation breaks up with one guy, another on the table is taking the word on. At a one on one conversation, it’s hard if the counterpart is not in the mood to talk. So you take the middle seat of the table side with the wall to your back. You know have all your new colleagues in sight and all of the persons who will join you will have the same distance to you. So you can understand any of them the same way, even it is loud at the restaurant.

The next colleagues arrive and two of them are taking place at your table. They sit opposite each other and begin talking. They know each other well and arrived together on the same plane. First, you are listening carefully and wait for a chance to jump into the conversation. The one is talking about business topics, but you can see the other gives quick answers like “Yep” or “Jea you are right” or “I don’t know”. He is not that interested. You wait until one of them is dedicated to his drink and jumps in with:

Did you see any good movie or Netflix series lately you can recommend?

This will steer communication in the private direction. At this moment another colleague sits down, has heard “Netflix” and starts to report from the series “House of money”. The persons who don’t know the series can listen to the story and the others can talk about their favorite characters.

Got any favorite quotes?” is a nice open-ended question, which leads to many opinions and talking. After a while, you expand the conversation further or switch the topic. Simply the best that serves the flow of speech. Actors are famous, so maybe a colleague has met one before?

Have you ever met a famous person?

This is a good one. One colleague met a famous IT CEO while he was walking a marathon. “They are just as normal as we are!”. This leads to films or other stories you can tell or listen to the ones of the others.
In the meantime, the table is fully seated and two conversations can take place. You see the others are more the kind of an introvert, they didn’t say anything the last 20 minutes. That’s your chance to ask them an open question, anyone has something to say about:

Seen anything lately that made you smile?

This has two effects. On the one hand he or she will recall the good feeling thing, and on the other hand, the lunch will turn better on their side. We all know a conversation we all sit quietly next to the others. It’s a bad feeling. So you turned this lunch into a good feeling thing for your counterpart. He won’t forget. Maybe someone was the first time skydiving and is excited to report on the experience he smiled a lot while falling. So he had been pleasantly surprised by anything lately. This question is also a good one.

The lunch ends, the team challenges begin. The goal of this two-day workshop is to know each other better and trust each other more for a better performance at the office. After that, we had dinner, another great way to meet other people. Everyone got time to freshen up and meet for dinner. Same seat picking as a few hours before and round #2 begins 😉

Got any phobias?

You could start talking about a spider in your room. Creepy little animals, kind of scary, but I don’t know why. “What is it that you fear?”, is a great transfer to pass the conversation on to the other person. There is no way to say just “Ok”.
Another way to make your counterpart feel good is a little question about their past:

What was your first job?

It is interesting to learn that a Manager once delivered newspapers when he was a child. Back then the life was easy and our biggest problem was to fill our free time with funny things. If we chose to work then with a reason. We needed something our parents didn’t want to pay for:

What was the first thing you bought with your own money?

In my case, it was a Gameboy Color with Pokémon Red. One of my greatest gaming experience, because I had to work a full year for it. The feeling after I got this was indescribable. Maybe some of your colleagues had similar experiences.
As a kid, our environment shapes us the most. So the next question can be a good boost:

As you grow up who had the most influence on you and why?

Maybe some action hero or a book author like Joanne K. Rowling, who wrote Harry Potter. Most of us have a person we like what he did. If books switch into the center of the conversation, this question maybe this question comes all on its own:

What book are you reading right now?

Books are great gates into other worlds. You now have the chance to find out which worlds your colleagues like and which recommendations you can exchange with each other. Maybe someone started reading a book because his life changed in certain areas. For instance got kids, want to manage their money or get lost in a story. Perhaps the opportunity for an exchange of books arises, so the second contact is guaranteed in any case.
After so much to eat, a little sport is not wrong. So you could ask all on your table if there is someone who wants to go for a walk with you.

Who wants to take an evening walk?

Ask for a walk. Maybe some of them took a run lastly, as I did the Tough Mudder. You do sport and talk. Last time I ran with a colleague who had a star wars t-shirt to run on. Star Wars is one of my favorite topics since I’m a kid.


He reported back that he liked the conversation because I had hit exactly his three favorite topics. It was a very interesting conversation. I learned a lot about him, his interests and how powerful specific questions could be…

Who do we prefer to have a conversation with? With a person who we feel to be great ourselves, or with someone who gives us the feeling. The last probably… Now you can be that person who gives that feeling to the people!