The Best Conversation Starters

There are many conversation starters that work. In fact, I believe you can start a conversation with almost anything.

I recently started a conversation by asking a person if they know how to stop hiccups, because for some reason I had begun to hiccup. It all went naturally from there simply because I was curious, talkative and genuine.

However, the best conversation starters don’t just work, but they work incredibly well and no matter who the person you wanna talk with is, they will rarely fail you.

The best conversation starters are the ones you can rely one to start the conversation, engage the other person and make an impression, and they also making it easy to keep the chat going from there.

Based on my experience as a social confidence coach and a passionate about social dynamics, I concluded there are 4 qualities that the best conversation starters all have, and these 4 qualities are what makes them so great.

  1. They are personal. Forget about commenting about the weather and stuff like that. Go with conversation starters that relate to the other person. That way you get to learn something about that person, they’ll engage in the conversation more, and you’ll have more paths to take the conversation on from there.
  2. They’re not too personal. At the same time, it’s not the best idea to start a conversation with a person you don’t know by asking them something very personal, like “Do you have any insecurities?” That’s too forward and it has more chances to inhibit the other person rather than make them to open up.
  3. They reflect a genuine interest. Never ask or comment about anything you don’t really care about. Because if you don’t care about it, chances are you’re not gonna know how to keep the conversation going from there, or you’ll take it on a path that doesn’t really interest you.
  4. They are delivered with confidence. If you are self-assured when you start a conversation, you will make a good impression and suck the other person into the conversation. Confidence is like a magnet and it’s one of the best qualities you can convey to others from the get go.

That’s it. Not all conversation starters fit these criteria, but you can find many of them that do.

My advice is to go from here and come up with your own conversation starters based on these 4 criteria. It would be ineffective and condescending of me to actually tell you what conversation starters to use.

The best conversation starters vary based on your real interests. I will give you some examples though of conversation starters that I use and work really well, just for inspiration.

“How was your day/evening/weekend?” I love to ask people about this and learn about the things they’ve done recently. I try to relate what they say and also talk about the things I did, and the conversation moves on from there.

“What do you do?” I’m always interested in what a person does for a living and I often ask about this. In my experience, it’s an awesome conversation thread to go on with most people.

“That’s a nice shirt/suit/pair of glasses. Where did you get them?” Since I’m interested in style, I like to notice cool things in other people’s appearance and comment on them. It’s pretty easy for me from there to make the conversation take off.

As you can see, every conversation starter is a good match with my interests, and it’s also personal, but not too personal. This is the recipe I encourage you to follow.

Also, always keep in mind that when it comes to making conversation, the way you talk is often much more important that what you actually say. If you are confident and at ease, people will love talking with you and what you say becomes secondary.

If you lack conversation confidence, check out this presentation right now. It’s a presentation I created that shows you precisely where conversation confidence comes from and what are the steps to developing it. I’m sure you’ll find it very useful.

Equipped with the best conversation starters, you will stand out from the pack. You will find it easier to make conversation and astonish others. You will have that extra leverage that can make your social life infinitely better.

Small Talk Conversation Starters

Small talk is a common presence in social settings. Even the very best friendships, partnerships or relationships often start out with simple small talk, which then evolves into deeper conversation and connects individuals emotionally.

Small talk conversation starters play an important role here, because they get the dialogue going. Equipped with a good understanding of the art of making small talk and a few good small talk conversation starters, you can converse with anybody.

The 3 Traits of Small Talk Conversation Starters

Small talk conversation starters that work well, all share three key traits. Grasp these traits and you’ll find it easy to come up with your own small talk conversation starters and to adapt them to the context.

  1. They are not too intrusive. Small talk overall is not very intrusive. It’s light, social conversation. So it makes sense for the conversation starters you use to not be very intrusive either.
  2. They are authentic. Contrary to conventional wisdom, it’s not a good idea to use convo starters that take a conversation in a direction you’re not really interested in; even if it is just small talk.
  3. They are adapted. Don’t go running around with one conversation starter and use it to initiate small talk everywhere. Adapt your approach so it makes sense in the social context you’re in.

10 Conversation Starters for Small Talk

Myself and many of my coaching clients have tested numerous small talk conversation starters, and I’m going to share with you 10 of the best ones. Correlate these starters with your interests and the social context, and you can confidently rely on them.

1. “What do you think of this event/ party/ gathering?” – Simple and straightforward.

2. “Who do you know here?” – Also a good way to meet more people and make new friends.

3. “What field are you in?” – Works great at networking and business events.

4. “Have you ever been to this place before?” – Terrific starter if you like the location you’re at.

5. “That’s a nice watch. Where did you get it?” – Also works well for other accessories or clothing items.

6. “Tell me about yourself.” – A nice, broad request. It can really get the other person talking.

7. “Have you heard about (major and recent event)?” – A bit of talk about the latest news never hurts.

8. “Where are you from?” – An excellent conversation starter for events with people from multiple cities or countries.

9. “How is your day going?” – Kickoff the chat by getting the other person to share their day.

10. “What are you drinking?” – A particularly good one if you have an interest in drinks or drinking.

Use these simple and effective conversation starters when you’re making small talk, and you’ll get the conversational ball rolling.

I know that small talk may seem pointless, but it is a valuable part of social interactions, especially with new people. It’s a way to test the waters and to engage another person. Know how to make small talk and how to move beyond it, and you’ll actually enjoy it.

How to Improve Your Conversation Skills

Small but significant improvements such as getting good conversation starters can noticeably enhance your social life. However, it’s important to realize that they’re not in and of themselves a complete solution.

Working as a communication coach, one thing that became obvious to me is that most people who could benefit from learning how to start a conversation effectively also have other sticking points in the area of conversation skills they need to address.

Once they learn how to start a conversation, they need to learn how to keep it going, how to make small talk, how to express themselves authentically or how to create a connection with others. They often need to work on their conversation skills as a whole.

If this is the case for you, it’s time to consider going beyond conversation starters and figuring out the best ways to improve your conversation skills. Here are the methods I believe to be the most helpful:

1. Go Out, Get Social

It’s tempting to search for ways to improve your conversation skills that don’t demand engaging in conversations with people, so that when you do engage, you impress them with your masterful conversation skills from the get go.

Unfortunately, life doesn’t work like that. In order to improve your conversation skills, the single most important thing you can do is to go out more and socialize more.

Your ability to make masterful conversation develops through persistent practice more than anything else. As you meet people, initiate conversations and always seek to make better conversation, you slowly but surely improve in this area.

2. Model Good Conversationalists

Another thing that will help you immensely is to study the conversational style of successful conversationalists. The key idea here is not to clone them, but to pick bits and pieces from their conversational mannerisms and implement them in your own conversational style.

You can start by analyzing charismatic characters in movies or books from the comfort of your own home, but eventually you need to study real-life individuals with good conversational skills from a close proximity. Modeling these persons will provide a huge benefit for you.

3. Learn Principles and Techniques

An entire industry exists that’s focused on helping people become better conversationalists and enrich their social life. Some of the ideas popularized in this industry are hooey, but some of them have a lot of value and work wonders in practice.

There is no point in reinventing the wheel when others have done a lot of the work for you. The least you can do is to pick up a few good books on the topics of conversation skills, learn specific principles and techniques and put them into practice. If you want more, consider courses and training on this topic.

4. Have a System for Practice

There are two reasons why many people fail at improving their conversation skills: they either apply corny and ineffective ideas, or they don’t have a system to practice and make progress.

This second point means that people will pick a few tips, practice them a few times and then give up. You need a better approach to see visible improvements in the way you converse with others. You need to pick specific improvements goals for yourself, to set daily practice activities and to do these activities.

More than anything else, you want to act more than you read, and you want to do it methodically. Your skills develop by taking massive action in small, logical steps. If you want to move from using good conversation starters to charming people conversationally, this is the mindset you want to be in.

Using Context to Find Conversation Starters

When you want to find good conversation starters to use, one of the best places to start looking is the very context you’re in. Open your eyes and your mind, and you’ll discover all sorts of ways to start conversations provided by this context, whether it’s a party, a conference or a date.

The Power of Contextual Conversation Starters

I like to use conversation starters based on the context because I find them smooth and effective. They’re not personal and intrusive as “What do you do for a living?” but they’re also not impersonal and shallow as “What time is it?”

I also like contextual conversation starters because they’re adapted to the environment and thus, they make a lot of sense. When you’re using a contextual conversation starter, you’re not employing a memorized line robotically; you are using your head to come up with a good approach based on the context.

Where, Who and What

Using context to initiate conversations starts with noticing the context and asking yourself some questions about it. As you answer your own questions, you’ll also discover good conversation starters to employ.

Socializing and providing communication coaching, I discovered there are three key questions to ask yourself:

  1. Where? (The Location). Thus, you can come up with conversation starters such as: “What do you think of this club?”, “What is it like to work here?
  2. Who? (The People). Thus, you can come up with conversation starters such as: “What did you think of the speaker?”, “Who are you here with?”
  3. What? (The Event). Thus, you can come up with conversation starters such as: “What do you think of the party?”, “Have you been to similar conferences before?

Clutching On To the Details

Besides the general characteristics of the context (location, people and event) there are also specific details that can provide great conversation starters.

This is why I encourage you to be aware of what’s going on in your environment and notice the little details. As you do so, you’ll find opportunities to initiate conversations.

I often start conversations at events where there is a Swedish buffet while picking up some food at the buffet table, by making a honest comment about the food to the person next to me in line. If that person is eager to respond with a comment of their own, the conversation is on.

I recently kicked off a conversation on a train with the girl who sat next to me by commenting about the train conductor who seemed drunk to me and asking her opinion about this issue. We joked about it a bit, and the rest of our chat happened naturally from there.

Using context to find conversation starters is, in my view, a much finer art than simply choosing randomly a convo starter from your bag of tricks. It reflects much finer social calibration and it keeps you on your toes. For this reason, it is something I highly recommend you to master.

Business Conversation Starters

From my perspective, success in the business world depends as much on your ability to build trust-based relationships with other people as it does on delivering quality results.

The Business Conversation Challenge

Conversation is a natural tool to connect with people in the business world and build trust.

However, it can be tricky to kickoff a conversation with a client, a colleague or any other person in a professional context. The norms that regulate interactions in the business world seem to be somewhat slippery and this makes it harder to find the proper business conversation starters.

For example, I notice many people have a hard time figuring out if it’s appropriate or not to start a conversation with a client on a personal level, talking about family or hobbies.

Business Conversations Starters Ideas

For this reason, I’m presenting you with some of my top ideas for business conversation starters:

1. Comment clothing. Many people in the business world put a lot of time and effort in dressing well, especially when they’re going to a business meeting.

One of the best things you can do when starting an interaction is to notice what the other person is wearing and make a positive, honest comment on their clothes as a whole or one particular item. You can easily kickoff the conversation this way.

2. Use the context. The place you’re in, the event you’re at, these will often provide you with good conversation starters.

If you’re at a conference, you can initiate a conversation with someone by asking them something related to the conference, such as: “What do you think of the speakers so far?” If you’re in your client’s office, look around and if something makes an impression on you, you can make a comment about it.

3. Explore the job. When I’m meeting a person for the first time in a professional context, I will often ask them questions about their job.

I’ll usually start with “What do you do for a living?” if I don’t know that yet, and I may continue with questions such as “How did you get into this field?” or “What do you do precisely in this job?” These are surefire business conversation starters.

4. Explore the organization. A good alternative to asking about the other person’s job at the beginning of a conversation is asking about the company or organization they work for.

Consider questions such as “How did you start working in this company?” or “What’s the work environment here like, from your perspective?”

5. Explore the passing time. If this is not the first time you’ve met a person, it can be a good idea to initiate the conversations by finding out what happened in this person’s professional life in the time that has passed from your last meeting.

Questions such as “What have you been involved in lately?” or “What have you been doing since we’ve last met?” can work wonders.

6. Go personal. If you’re talking with a person you’ve met before and you know some things about their personal life as well, you can initiate a conversation talking about their personal life.

You may ask them “How’s the family”, “How are your tennis lessons going?” anything you’ve talked about before and you’re authentically interested in.

Last but not least, keep in mind that although business conversation can have some important stakes involved, you don’t want to blow its meaning out of proportion. A conversation is a conversation. Avoid over-strategizing it and have some fun with it.