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How to Start Great Conversations and Make Them Engaging

Updated: Jul 6, 2021

We continue today in our series about creating great first impressions. So we spoke about charisma, we spoke about first impressions, we spoke about likeability, and today episode is about how to always engage in amazing and fun conversations. Your goal in any conversation is to be memorable, engaging, impactful, and create a positive lasting impression. Today I will teach you how to do it.

So the 3 biggest secrets of engaging conversations are: be interested to be interesting, be a highlighter, look for similarities and opportunities to say me too.

Be interested to be interesting.

Be interested and fascinated with the people around you, instead of trying to be interesting to them be fascinated with and by them.

Why does this work? This is the reciprocity effect in action. What the reciprocity effect simply means is that we like people who like us. And we’re more inclined to enjoy being with people who visibly enjoy being with us.

The more you show interest in someone the more interested they will be in you. When you are with someone you enjoy, consciously engage the reciprocity effect.

Here are some ways to do it:

  • Start and end phone calls with “I’m so happy you called!”

  • Start and end emails with “I’m so glad you emailed me!”

  • Start and end interactions with “I so enjoyed spending time with you!”

  • Invite people to sit with you during lunch, and at parties and conferences.

  • When people join your group, table, or meeting, make them feel welcome.

  • As people leave your group, table, or meeting, thank them and tell them you appreciate their time.

Now let me tell you one thing that might blow your mind. You can be interested and even fascinated with someone even if you don’t like the way they behave. You always can approach them from a place of genuine interest. You can think – I wonder why do they act the way they do? And as you become more interested in them, they will like you and it can totally change your relationship.

What are the best ways to open a conversation and become memorable?

Here is my favorite framework for opening engaging conversations, using the power of being interested in others:

  • First – read the environment. Look for commonalities.

  • Then make a relevant comment that is context-specific, ideally related to the environment.

  • Finally engage with an open-ended question, again context-specific.

  • Then introduce yourself.

So here’s an example of how these strategies might look like:

Let’s say you’re at your company’s happy hour and you see a company executive. They make eye contact with you and you read that as a cue to start a conversation:

"The venue is great. Do you do this event every year?"

They respond – "Yes, this is a great occasion to chat informally."

Now you will introduce yourself: "I'm James and I'm thrilled to be here."

You will offer a handshake.

I also want you to use conversation sparkers whenever you can.

Conversation sparkers are the opposite of boring social scripts and small talk. Your goal with conversation sparkers is to find topics that light people up. When you find these topics, you will have a great conversation and produce more dopamine, which makes you more memorable. Ending small talk starts big connections.

A way to do this is to replace the common small talk phrases with more interesting conversation sparkers:

  • What was the highlight of your day?

  • Working on any personal passion projects?

  • Have any vacations coming up?

  • What are you up to this weekend?

You can also look for areas of interest in their environment. For example, you can say: I was just looking at your bookshelf – you have a great reading taste.

I saw you posted some great pictures of your new dog. What made you decide to get a dog?

Spark your conversations and you will become more memorable and likable.

So we spoke about being interested in other people, we spoke about conversation sparkers, now let’s talk about being a highlighter.

The best communicators serve as conversational highlighters. They listen to learn more about a person, to remember what was said, and then find the important points to act upon. Being a highlighter is about bringing out the best in people by highlighting their strengths.

Have you ever heard about the Pygmalion effect? What this effectively means is that great expectations are met with greatness. There has been extensive research that confirmed that this is a real thing. When a computer gives automated compliments to students, those students perform better. Even if they know that those compliments are automatic.

How can you use the Pygmalion effect to your advantage? Through positive labels. Humans love to be given positive labels. They improve our self-image and push us to be better versions of ourselves. Allow yourself to be impressed by the person across from you. Find ways to emphasize their strengths. Celebrate their excitement.

Some examples could be:

  • You know everyone here. – You must be a great networker!

  • I’m impressed by your efficiency – this team is so lucky to have you.

  • You are an expert in this subject. Thanks goodness you’re here.

Another way to show as a highlighter is through exponential excitement. Exponential excitement is about celebrating the successes of others as if they were your own. Good feelings multiply around other good feelings. When you see someone who is proud, excited, or passionate – mirror and match it. This associates you with their feelings of pleasure. You can say something like:

  • “I’m so thrilled for you!”

  • “How wonderful that must be!”

  • “That is the best news, congratulations!”

When you see something – anything that is awesome, always take the opportunity to highlight it.

Introductions are a fantastic opportunity to show up as a highlighter.

Use introductions as an opportunity to highlight other people and become memorable right from the beginning. When you use a variation of Jeff, this is Peter, Peter, this is Jeff, you are missing on an amazing opportunity to highlight. Even if you just know them for a few minutes there’s always something you can highlight about them.

“Jeff, meet Peter. He is killing it in the marketing research and just signed an important new contract.”

“Jeremy, meet Rita. Rita is an incredible singer.”

“Dimitri, let me introduce you to Veronica. She’s just telling me the most fascinating story of her trip to Australia.”

You can even do this when you’re introducing yourself:

“It’s a pleasure! Your name tag says you are a speaker here. That’s fascinating. What’s your area of research?”

“Great to know you! A friend of Richard is a friend of mine. He knows the most fascinating people!”

This way, you’re giving people positive labels right at the start and you get people talking about themselves – what they do and who they are. This produces dopamine! This is a total win-win.

Make people feel good and they will remember you. Make them want to be the best version of themselves. So highlight and expect the best in those around you. Being the highlighter helps you be the highlight.

Another strategy to being a highlight of any conversation is using people’s names.

A person’s name is to that person the sweetest, most important sound in any language. So remember and use your conversation partner’s name.

And in the last episode, we spoke about the importance of highlighting similarities. That’s one of the keys to increasing likeability. And it’s also a great way to have engaging conversations.

You should constantly be on the lookout for similarities and highlighting them. Find mutual likes. Once you find one similarity highlight it.

In a good meeting or date you will hear phrases like:

  • Oh, I love Bali. Maybe we were there at the same time?

  • Are you kidding? I’m a huge Real Madrid fan.

  • You’re into tennis? Me too!

A secret to a successful and engaging conversation is to always look for an opportunity to say – me too.

Here are some of the questions that can uncover those commonalities:

How do you know the host?

Are you a friend of the bride or groom?

How long have you been part of this group?

Do you usually come to this type of event?

Have you ever been to this conference/restaurant/event before?

Great venue, right?

How long have you been living here?

Love your pen, shirt, hat. I’m also a fan of…

How long have you been a fan?

I’m a fellow member of… How long have you been a part?

I saw you also went to / studied/are a part of…

Wasn’t that speaker/presentation interesting?

Every time you discover a common thread, it links you together.

If you ask one of these questions and don’t find a similarity, it’s totally OK. For example, if someone says – nope, never been here before, use that as an opener. You can say Me neither! What are your other favorite places around? Every answer you hear is one more step in getting to know them and being further along in the conversation.

Every interaction should be about finding these commonalities. They bring you closer to the person. The more commonalities you have the more socially attractive you become.

All right, let me repeat the three pillars of engaging conversations:

be interested to be interesting,

be a highlighter,

look for similarities and opportunities to say me too.

All right, that’s all for today.

Remember, for more great communication resources Join me over at And get your copy of 12 proven communication tactics to make a positive impact immediately.

Now if you realized that you need one on one help from me then reach out. Head on over to my website

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