John Addison: 8 Tips to Master the Beginning, Middle and End of a Conversation

UPDATED: June 8, 2023
PUBLISHED: October 26, 2015

Have you ever stood shoulder to shoulder with your boss’s boss in an elevator, just knowing it was your prime opportunity, your chance, to say something—anything!—but nothing comes to you? Nothing except, “How ‘bout those [insert sports team here]?”

Some people are just good at talking. You know who they are, the smooth talkers. They have a knack for creating conversations and a natural ability to keep them going. It doesn’t matter where they are—waiting in line at a coffee bar, sitting in an airport terminal, standing in an elevator—or who they’re talking to—a client, a stranger, their CEO—they effortlessly engage the person next to them. Pretty soon they’re smiling and laughing and exchanging business cards. How do they do it?

Successful people are good at conversations, and for many of them, it is a learned skill. Which means you can learn it, too. So even if you’re not naturally outgoing, you can learn the art of conversation—and how to skillfully talk your way through the beginning, the middle and the end of your next elevator encounter:

BEGINNING: Create Connection

1. Be friendly.

Smile. Be open. This might be easier for you after you’ve stood in the coffee bar line, but go ahead and make the effort. You really don’t need anything more to smile about than the chance of a pleasant moment.

2. Be observant.

Take cues from the other person’s body language. People who are avidly engaged in their phones aren’t looking to engage with you. Those who are glancing around are more open to casual conversation. Choose to talk to the people who aren’t focused on something else.

MIDDLE: Create Engagement

3. Be mindful.

Share common ground. The key here is twofold. First, ask an open-ended question. If they can respond “yes” or “no,” then you’ll feel like you’re playing 20 questions. Second, make your remark pleasant. Observations about slow service, inclement weather or late flights sound like complaints—which can lead them to chime in with their own, and then you’ll be stuck listening to everything that is wrong with their day.

4. Be relevant.

Talk about what is relatable. Random remarks that can’t be linked to what is easily observable are confusing. Mysterious strangers are great plot elements but are just irritating outside of a novel or movie. If something playing on a nearby TV sparks your remark, gesture slightly toward the screen as you speak.

5. Be relaxed.

Every conversation has the potential to be enjoyable. Even if you’re in an elevator with the CEO, remember that your goal is simply to connect and engage—not to have an intense connection that could make or break your career.

6. Be attentive.

Don’t do all the talking. If you notice the conversation has turned into a monologue and you’re the only one talking, then ask an open-ended question about them. Focus on finding out what the other person thinks rather than on sharing your opinion.

END: Create Opportunity for Reconnection

7. Be conscientious.

Recognize the connection—or lack of one. If the conversation lasts a few minutes, then it’s clear there’s mutual interest; you’ve made a connection. When the two of you don’t find common ground, or it’s apparent that one of you isn’t interested, it’s perfectly acceptable to recognize that by politely smiling and looking away.

8. Be graceful.  

Exit gracefully. Offer your business card and say you’d love to connect on LinkedIn or via email. For conversations that don’t establish a reason for further connection, simply finish with, “It’s been nice talking with you.”

Conversation, for most people, is a learned skill. So if you’re not a natural at it, then at least make a point to become proficient at it. That’s what successful people do.

Do you want people to listen to you and take you seriously? Well, it’s not just what you say; it’s how you say it. Check out 9 tips to optimize the impact of your voice.

John Addison is the Leadership Editor for SUCCESS and the author of Real Leadership: 9 Simple Practices for Leading and Living with Purpose, a Wall Street Journal and USA Today best-seller. Renowned for his insight and wisdom on leadership, personal development and success, John is a sought-after speaker and motivator. Read more on his blog, and follow John on Facebook and Twitter.