The 3-Step Conversational Tool That Makes Shy People Far More Likable

Every new person is a gold mine when you treat them right.

Written on Apr 11, 2025

Young brunette trying a conversational tool for shy people Dean Drobot via Shutterstock
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Last night I went to a dinner party and one of the guests was so shy, his face alternated between deer-in-the-headlights to disgust as he observed the rest of us chatting and having fun. As a divorced man in his 60s who owns his own business, he should have been irresistible to the single women at the party, but his shyness — accompanied by a mild sneer — was social poison.

Harvard researchers found that when approaching someone for the first time, asking a question and two follow-up questions increases your likability. While the 2017 study recommended that asking three questions “dramatically increases your likability,” there’s a far more powerful conversational tool that I recommend. It works with the basic format from the Harvard study, but goes a little deeper

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The 3-step conversation trick that can make anyone more likable — including shy people

Consider the difference between asking questions and being empathetic, and notice the effect each of these sentences has. After your empathy statement and question, follow up with two more to make sure you've connected. 

1. Ask an empathy-based question first, using an Empathy Statement

What is an empathy statement?

Have empathy for the listener in which you guess what they are feeling and needing. The basic format is: "I’m guessing you feel ____ because you need ____"

1. Instead of: “Hi Bob, how’s your business doing?”

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Try an Empathy Statement: “Hi Bob, I know you’re in advertising, and I’m guessing with AI it’s a rocky road right now. I would love to hear what you’re experiencing.”

After asking this question, ask two more follow-up questions, as the Harvard research suggests!

2. Instead of: “Hi Jane, how are you feeling?” 

Try an Empathy Statement: “Jane, I’m so happy to see you tonight. I know you have been recuperating; please let me know how it’s going.”

3. Instead of: “Hi Linda, what are you shopping for?” 

Try an Empathy Statement: “HI Linda, I heard that you have a new granddaughter, you must be having a blast shopping for her!”

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4. Instead of: “Hi John, Wow! How did you get so fit?” versus

Empathy Statement: “John, I can only imagine all the strategies you’re using to have gotten so fit! You are the poster boy for living your healthiest life!

However, expressing a few empathy statements is only the beginning. My 3-Paragraph System is a system for highly effective written communication, and this is very easy to learn and use in conversation, too.

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Shy man is more likable in conversation by using empathy fizkes via Shutterstock

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2. Express your own take or opinion 

Starting with the empathy statement, imagine this:

You ask: “George, are you feeling bored now that you’re retired or do you love it?”

George replies, “I love being able to plan my days around reading and rowing and relaxing, it’s great!”

Now, you can add your self-expression statement to further connect.

You say: “I get that, but for me, the more free time I have the more I can study and learn new topics that interest me.”

George replies, “Yes, I’m studying an exotic form of whale behavior that has always been interesting to me.”

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3. Create a call to action 

Now that you've asked your questions, shared an opinion or expressed yourself, move on to inviting the person to move forward, if it feels appropriate. 

Depending on your preferences, you might reply in any of 100 ways, such as:

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  • “That's so great, could we speak about this next week? I’ve always loved whales.”
  • “How fascinating, what is one fact you’ve learned that you could share with me?” or if you feel flirty,
  • “Why don’t you sit down and tell me all about it, George?”

No matter what you envision as the outcome, learning three-part conversation tool will allow you to move the action forward once you reach the call to action, and wouldn’t you rather inspire someone rather than just focus on whether you’ve become slightly more likable?

Every time you meet a new person, you have an opportunity to create a new successful "stream" in your life, either for dating, business, family, health, or wealth, depending on that person's skills and connections. That makes every new person a gold mine, but only if you know how to connect and be much more than likable.

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Susan Allan is a certified mediator and coach and the founder of the Marriage Forum Inc. and creator of The 6 Part Conversation© and The 7 Stages of Marriage and Divorce training to help people understand their own needs and their partners.

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