The Craft of Making Conversation

How You Can Break The Ice and Talk To Anyone

Isaac Mashman
4 min readOct 25, 2023

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Isaac Mashman pointing at a canvas of Little Rock, Arkansas.

To many, starting up a conversation with a complete stranger is a daunting and unpredictable task. Public speaking is one of the biggest fears of all and speaking to somebody for the first time falls right in line with that category in my opinion. It doesn’t have to be scary though. In this article, I’m going to share three strategies that I have personally used to spark discourse with people I’ve never spoken to before. Each strategy will have its pros and cons and particular use cases, but by putting them in your arsenal, you will be on your way to becoming a networking aficionado.

Why Is It Scary?

When I say scary, I’m not directly meaning that it’s going to raise your blood pressure or give you a panic attack, but it’s common for your gut to feel tense, and for you to slur over your words every now and again. This is okay and you’re not the only person. Chances are the person who is on the other end of the conversation is also going to feel a little tense. A complete stranger who they have no clue about is coming up to them to talk to them. They’re thinking to themselves “Who is this person? Are they a serial killer? What do they want from me? Why are they talking to me?”

It is your goal by initiating a conversation to ultimately put their mind and thoughts at ease, establish rapport, and by the end of the conversation, leave them feeling better than when you first started talking to them. It doesn’t matter if you’re looking to connect with somebody for your business opportunity, a potential sale, to grow your personal brand, for a casual friendship, or just because!

Strategy 1: The Compliment

This is the easiest of the three to implement and can be done as soon as today. What do people enjoy? I don’t know about you, but when somebody gives me a compliment, it makes me feel good! It lowers my guard. Try complementing a stranger on their watch or jewelry. I absolutely love nice watches. I remember last year when I was at a networking event in Washington, D.C. this gentleman who was sharply dressed, was wearing a beautiful watch. I complimented his timepiece and ended up getting into a 30-minute conversation. Turns out he was the owner of a fairly large trucking company. Boom. Compliment into a relationship. You can complement the other person on their clothes, their shoes, or whatever you think might genuinely think is nice. Notice how I said genuine. Being genuine about the interactions is vital. People are able to sniff out fake compliments and fake attitudes nine times out of ten.

Complementing somebody on something that you have a shared interest in is ideal because you can get a flow going, but any appropriate subject works.

Strategy 2: The Question

This strategy changes the dynamic of the relationship. Rather than starting off as equals, you are starting off as somebody who does not know something. This means that the other person in their mind subconsciously has leverage over you as the stranger. By asking a person at the store or networking event a specific question they likely know the answer to, you’re able to lower their guard and give them an opportunity to deliver something to you.

Once they answer your question or engage back, you’re able to keep the conversation going by asking more questions and adding to the discussion. You can ask questions about the person’s watch as a continuation to strategy one, The Compliment, what is their best brand of coffee while you’re at the store, or about their livelihoods and career.

Strategy 3: The Joke

This strategy is the most difficult of the three and is also the easiest to mess up and come across as disingenuous. Coming up with a carefully crafted joke off of the whim about the other person, or their particular behavior gives you an opportunity to come across as friendly and cordial. As long as it is not about something they could be self-conscious about, when the joke lands, they will laugh too. Sometimes people will be less receptive than others. You might get cold shoulder or they might not open up, and that’s okay.

Imagine you were out at a business conference and the convention center is gigantic. You see a group of people wandering about and they look confused. This is a perfect opportunity for you to crack a joke about being lost. You’re able to establish mutual rapport because you both are in the same situation of not knowing where you’re going and then you are given a reason to tag along with that group and find the proper destination. Now, obviously, this is an ideal situation, and it will not always work out like this, but making a simple remark or joke enables you to break the ice.

Breaking The Ice

All of the strategies when applied and practiced can help you make networking much easier and less scary for not only you but the other person. The last thing you need is to make a fool of yourself and creep the other person out because you can’t speak. If you struggle at first that’s okay but remind yourself that you are looking for an inlet to conversation.

It is up to you to decide in a matter of seconds whether or not the person that you’re speaking to is somebody that you would like to stay in contact with or remain a stranger you merely met once.

Share this across social media and with someone you know who is looking to step up their networking skills!

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Isaac Mashman

Addicted to coffee and standards. I help create, maintain, & scale unrivaled personal brands through my PR firm Mashman Ventures. Author, Investor, Speaker