How to be a great conversationalist

I've written a lot lately about prioritizing relationships, so now is an excellent time to explore the secret to creating new relationships - good conversation skills.

Conversation skills include having something to say, keeping a conversation going, and listening well.  Let's go over the stages of a good conversation.

Stage zero: preparation

Almost everything worth doing requires some preparation.  A good conversationalist is always ready to hold a conversation.  To prepare, let's look at two of the most common questions.

Prepare to answer the question, "How are you?"

Ninety-nine percent of the time, people don't expect you to give them an honest answer.  However, you can still use this as a chance to start a meaningful conversation by thinking of something that will arouse the curiosity of the other person.  If something wonderful is happening in your life, it is a good topic for conversation.  Get people's attention by saying, "I've never felt better!" or, "This is the best I have felt in years."

A person who sees the value in talking to you will likely ask what's going so well.

I love this creative response: "My kids are healthy and happy, and my husband is still trying to impress me."

At least you'll get a laugh from a response like this, and at best, the conversation will proceed effortlessly.

What if things aren't going so well? You can still create a bridge to a valuable conversation. Consider these possibilities:

  • I could write a book on that topic.
  • I'm ready to run a marathon, but my body is not cooperating.
  • Supposedly, "what doesn't kill you makes you stronger" - I should be the Hulk by now.
  • Right now I'm facing many challenges, but I have a lot of support and couldn't ask for any more.

These are lighthearted attempts to engage the other person in further conversation. Have a topic in mind to discuss that isn't too negative. Focus on the positive. Despite these challenges, what keeps you going?

Here are a couple of responses that really invite engagement:

What if someone asks, "What do you do?"

Unless you're a firefighter or an astronaut, this question can often lead to awkward conversations, but it doesn't have to.It's possible the person asking this question is feeling you out to determine your social status, either to know how much respect to give you or even to determine if you are worth their attention. In any case, try to ignore the person's possible motives and just use the question as a valuable springboard. You can answer this question in countless ways.  Preparing two or three in advance will ensure you won't regret missed opportunities for great conversations.

The underlying question they are asking is, "Can you give me something we can connect over?"This quote and some of the ideas below come from a great article on the subject at

So think about what you do in these terms:

  • Who do you help?
  • In what way does your work make a difference?
  • What are the results? Can your efforts save time or money, generate revenue, or reduce workload?
  • Why did you get into that line of work?
  • What is fun or inspiring to you about your work?
  • What would people benefit from knowing about your job or industry?
  • What's the most interesting thing you've learned recently?
  • How did you get to where you are now?
  • How do you envision your career going forward?
  • Tell a story about a day at work you found particularly exciting.
  • Tell about the challenges you faced during your journey and some of the sacrifices you made.
  • Talk about any of the answers to the above questions that don't apply to paid work.

Make a list of answers to some of the above questions and pick out the ones you think others would find most interesting.  Then, come up with an appealing way to answer the question, "What do you do?"

You can craft a one-liner using this formula: "I help <insert group of people here> to <insert their desired outcome here> by <insert what you actually do here>."

Some examples:

Now you're ready to get out and talk to people.

Stage one: engaging the other person

Wherever you go, there you are.  Your surroundings matter, especially when it comes to starting conversations.  The best topics for conversation are:

  1. The immediate environment
  2. Something positive or neutral about someone present

While you look around, think about:

  • What brought you here?
  • Who else is here that you already know or would like to meet?
  • What kinds of activities take place here?
  • What makes this place unique or interesting?
  • What can you learn about this place from someone else?
  • What previous experiences have you had here?
  • How do you feel about this place?
  • What do a person's clothes, age, build, speech pattern, jewelry, hairdo, or reading material tell you about them? Maybe there's a tattoo or t-shirt slogan you can ask about.

As you progress in the conversation, you can include nearby areas or related topics.

For instance, you could start a conversation with the person sitting next to you by saying, "Our host just got back from California." This gives them an opportunity to comment on the host, or California, or traveling. Pause, and if the other person doesn't pick up the conversational ball, you can ask them a question.  "Have you ever been to California?"

Stage two: keeping the conversation going

Once your conversation has moved beyond the immediate physical environment, you can start looking for other ways to connect.  During the conversation, anything can serve as a springboard to something closer to your interests, or better yet, closer to the other person's interests.

At an appropriate point in the conversation, consider discussing:

  • Your interest in a topic they mentioned earlier
  • Getting their opinion on something
  • Their free time activities
  • Briefly share something about yourself that's relevant

Other effective questions include:

  • Have you experienced any highlights this year?
  • Do you have a favorite mistake you've ever made?
  • What's one thing someone can do to stand out to you?
  • What would you do if you had more time to deal with X?

The answers to these questions will help the other person present themselves in a positive light, resulting in a deposit into your relationship bank account.

Your goal should be to identify the "hot button" topics of the other person, topics they enjoy talking about.  Having a positive conversation about these topics will almost always move the relationship forward.

As you build rapport with the person, you can ask questions to discover their 'hot buttons' or share your own:

  • When you're not working, what do you like to do?
  • What kind of activities do you enjoy?
  • Are you involved in any projects?
  • Do you have any hobbies that you enjoy?
  • Do you belong to any particular organizations?
  • I'm very excited about...
  • Guess what, I'm finally going to..
  • This weekend, I am looking forward to...
  • I just finished working on...

Stage three: responding to the other person

Speaking is just half of an effective conversation.  Listening is the other half, and it may be the most important. Concentrate on what the other person is saying and avoid thinking about what you will say next.

Keep your attention focused on what you're learning about the other person.  Don't ask nonstop questions.  Instead, share some of your own viewpoints and experiences.  But try to keep the conversation focused on the other person as much as they are comfortable with.  

Encourage the other person to continue talking once you have gotten them started.  There are many ways to do this:

  • That was an interesting thing you said. Is it because...?
  • From what you told me, I gather that you... Why do you say that?
  • Since you brought up the fact that..., can I ask you...?
  • I would have never guessed that you ... Thanks for letting me know that.
  • Restate the things they're telling you in your own words. "Let me just summarize what you’ve said."
  • In other words, what you're saying is...
  • Please tell me more.
  • Use the news reporter's open-ended questions: who, what, where, when, how, and why. 
  • A seemingly off-hand mention of something unrelated should be explored.
  • Pay attention to the things they say beyond what you asked for.
  • Try to discover what the other person knows that you don't.

Ask for clarification:

  • After that, what happened?
  • If I understand you correctly you want to ...
  • Let me see if I've got this straight. You're going to ... Is that right?
  • When do you expect it to happen?
  • How did that happen?
  • What did you do next?
  • How did it turn out?

Ask for and think of examples:

  • Like what, for instance?
  • What would that include?
  • How will I know?
  • Can you describe your idea of a good ...for me?
  • Would it include...

Watch for "iceberg statements," messages that indicate they wish to discuss the topic further.  Some examples:

  • My grandkids will be visiting this weekend.
  • I'm going to see a foreign film tonight with some people from my language class.
  • I hope the weather is good this weekend.
  • I'm considering some career training in...

Ask follow-up questions to get them to tell you more.

You may not know what to ask sometimes.  The person may not be giving you much to draw on.  But as long as they are talking, you'll have ways to encourage them to continue.  If someone tells you that the weather is hard on pets, simply ask "Hard on pets?" This will be interpreted as a request for more information, and the other person will be glad to provide it.

Stage four: moving the relationship forward

Congratulations on making it this far; you are an effective conversationalist. You have shown that you can start a conversation, keep it moving, and respond effectively to the other person. Hopefully, you share some interests with them. If nothing else, you've learned something useful, and you've provided value to the other person by engaging in an interesting conversation.

If you decide that it would benefit you to continue the relationship, don't miss the opportunity.

Find a way to keep in touch. If you don't think the other person would be comfortable giving you their contact information, offer them yours. Provide a phone number, email address, or social media handle. Where there is the potential for mutual benefit, set up some expectations. Call them or email them by a specified date. And be sure to follow through.

The benefits don't have to be immediate.  Then it would be like you had opened a new bank account that may soon pay rich dividends.  

If you have already built some relationship capital with the person, you may want to ask for a favor.  Don't be afraid to ask them directly.  The worst thing that could happen is that they will say no.  Accept it graciously.

If you get along well, take the initiative to arrange a specific meeting or plan an activity around something you both enjoy. When saying goodbye, use the person's name.

At an appropriate time and place, record the facts and details related to the person. Make sure you remember as much as you can.  If someone asks you how you remember something they said, how would you respond?  It's okay to tell them you took notes. People are just as impressed that you cared enough about their conversation to keep track of what they've said.

To close this article, I will share these beautifully written words that swept across Twitter while I wrote this: