How to Know What to Say at the Right Time

Admit that you don't know what to say.

When someone delivers uncomfortable or shocking news, be honest. People don't expect you to be prepared for anything they might possibly say and sometimes they say something that catches you off guard. Being honest about the fact that you don't know what to say is genuine and appropriate. For example, if a friend tells you that their dog died yesterday, you might say, "Oh, wow. I'm so sorry. I don't know what to say." You might also say, "Oh, I have no words." With bad news, saying you don't know what to say can be better than using a stock phrase or cliché that has lost its meaning with repetition.

Empathize with the other person's emotions.

Watch the person's body language for clues to their emotional state. Pay attention to not only what the other person is saying but how they're saying it. This can help you understand how they're feeling about what they're telling you. Then, you can comment on those emotions to show that you empathize with them. It gives you a ready response, regardless of the topic of conversation. For example, suppose someone is telling you about how they were late to work because their dog was sick and they had to take it to the vet. As they're telling this story, they tense up and their eyes get wide, showing they were scared at that moment. You might say, "Oh wow, that must have been scary for you." You can also figure out what someone really wants through empathy. For example, suppose someone recounts a busy day and ends by saying, with a sigh, that they ended up having to get drive-through fast food again. You might say, "Hmm, it sounds like you really want to eat more healthy."

Memorize some common responses for everyday situations.

Most small talk and casual conversation cover similar territory. In most conversations, there are common responses that people practically expect to hear. You're unlikely to say the wrong thing when you use these phrases because they're familiar and people are comfortable with them. Here are some to get you started: Upon meeting: "It's good to meet you" or "It's good to see you again" (if you've met once before). To encourage someone: "I'm sure you'll do great," or "good luck." To reassure someone: "I'm sure it'll be fine," "It's no problem," or "Try not to worry." Responses to good news: "Wow, that's great," "I'm so happy for you," or "That's so good to hear." Responses to bad news: "Oh, that's too bad," "I'm sorry to hear that," or "I'm sorry you have to deal with that."

Ask questions to encourage the other person to open up.

Open-ended questions are best because they require a longer response. After the other person finishes what they're saying, ask something about what they've just said. Use questions that start with "how" or "why" when possible—these questions give the other person an opportunity to expand on what they just said. Questions that can be answered with a yes or no tend to lead to awkward silences. For example, suppose someone is talking about their upcoming vacation to Hawaii. You might ask "Why did you decide to go to Hawaii?" This gives them an opportunity to tell you the motivation behind their decision and what they're looking forward to about the trip. If you don't know what question to ask, you might try responding by simply saying something like, "Oh yeah?" You could also say, "Really?" Typically, the other person will continue talking after that. They might go on to explain what happened next, or how something made them feel.

Use one-word responses to show that you're interested.

Say things such as "wow" and "interesting" while the person is talking. As you're listening, pepper in common responses so the person recognizes that you're listening and paying attention to what they're saying. Use their name while talking. Just be careful not to go on auto-pilot with this! Make sure you're actively listening and using an appropriate response. Mix up your responses rather than repeating the same thing over and over. For example, you might start with "right," then say "oh, okay," then say, "that's cool."

Repeat the last thing said as a question.

This technique is sure to keep the conversation going. When you repeat the last thing the person said as a question, it sends them a signal to keep talking. It also shows them that you were actively listening to what they were saying. For example, suppose someone is telling you about teaching their cat to play fetch. They end by saying, "And then he finally brought the toy back to me." You might say, "So he brought it back to you?" The person might respond, "Yeah, it was really amazing! And then he did it again!" You don't want to use this technique all the time—it can get really tedious on someone if you use it more than a couple of times in a row. Keep it in your conversational arsenal and use it when you're totally at a loss or need more to go on before you can come up with a response. You can also repeat the last thing they said and ask directly what happened next. For example, if your friend is telling you about an argument with their roommate, you might say, "So he refused to take out the trash. What did you say to that?"

Share a related experience.

Tell your own story when the person says something you're familiar with. As someone talks, they're likely to touch on something that you have some experience with. Mentioning your own experience builds rapport between the person and enhances your conversation. For example, suppose the person is talking about their upcoming vacation to New York City. If you have a friend who lives there, you might say, "Oh, I love New York—my friend Kelly lives there. Do you want me to ask them for restaurant recommendations?" You can also use common ground to share a personal experience of your own. For example, if the person mentions that they're just starting to learn how to sew, you might say, "I just started to learn myself last year. I have the hardest time threading needles, though! What's been your biggest challenge so far?"

Follow up on an earlier detail to expand the conversation.

When there's a lull in conversation, go back to something mentioned earlier. If you've been listening actively, you'll remember key details from your conversation. Draw on those details to reduce a lagging conversation and avoid that dreaded awkward silence. For example, suppose someone had previously been talking about their last vacation in Hawaii. You might say, "You previously mentioned you traveled to Hawaii. What's next on your travel list?" You can also use the follow-up to share a story or experience of your own. For example, you might say, "You know, when you were talking about Hawaii, it reminded me of when I took surfing lessons. If I lived in Hawaii, I'd probably surf every day. Did you do any surfing while you were there?"

Probe someone's reasoning when you disagree.

Use this strategy to steer the conversation away from a contentious issue. You're not going to agree with anyone all the time. It can be super awkward when someone says something you don't agree with and you don't know how to respond. Instead of pretending to agree with them, try asking them why they feel that way. You'll increase your understanding as well as help move the conversation into more neutral territory. For example, suppose you're chatting with someone about a recent election and find out they voted for a different candidate than you did. You might say, "What was it about their campaign that spoke to you?" Even if you disagree with their choice, this will help you understand what motivated them. If the person mentions something that you also care about, you can talk about this as a way to gently change the topic. To continue with the previous example, suppose the person voted for a different candidate because they want to protect their children. You might say, "It's true that our children should be protected from danger." Just focus on what you agree on to avoid conflict.

Apologize and acknowledge when you make a mistake.

Say "I'm sorry, I misunderstood," and move on. If you don't make a big deal out of your mistake, the other person won't either. Everyone makes mistakes in conversation—nobody's perfect! While you might be embarrassed, acknowledging the mistake and apologizing can help keep it from eating at you. Likewise, if you're caught in a moment of inattention, acknowledge that fact rather than trying to guess at the appropriate thing to say. For example, you might say, "I'm sorry, I was distracted. Can you repeat that?" If you're having a hard time paying attention due to surrounding circumstances, let the other person know. For example, you might say, "I'm sorry, it's hard for me to focus with so much going on around us. Can we move this conversation somewhere quieter?"

Listen actively when someone else is talking.

Give the other person your full attention during a conversation. Talking is only half of a conversation—the other half is listening. When you listen, you'll naturally pick up on opportunities to say something in response. For example, suppose someone is telling you about a recent trip they took to California. You might ask where in California they traveled or what they liked the best. If you've been to California, you might share your story. This can be tough if you're anxious about not knowing what to say. You might have the tendency to constantly think about what you're going to say next rather than listening to the other person. Practice with a trusted friend and you'll get better at it! After they say something, say "I hear you saying," then repeat what they said.

Follow nonverbal cues to end a conversation.

Wrap it up if the person is looking around or glancing at their watch. These are nonverbal cues that a person wants to end a conversation. If you notice these, you can say something like, "Well, it was nice talking to you, but I need to get going." People use verbal cues as well, such as starting sentences with "well" or "so." For example, suppose you're chatting with someone when you see them glancing around the room. You might say, "Hey, it was great chatting, but I've gotta run. Catch you later!" This gives them an easy out and ends the conversation without awkwardness. You can use these same cues to end a conversation as well. If you use a verbal cue, be prepared to immediately follow up on it to minimize the awkwardness. For example, if you say, "Well, it was nice to meet you, but I need to go find my partner," start moving away from the person at the same time. If you're sitting, you might stand up as you're saying it.

Observe people who are good conversationalists.

You can learn a lot by watching people who converse well. Think about people you enjoy talking to and why you enjoy talking to them. What makes them good at conversations? Next time you're talking to them, pay attention to their body language and how they respond to you when you're talking. Add these habits to your own repertoire to up your own conversation game. Don't be afraid to ask a good conversationalist for pointers! Most people are flattered if you compliment them on a skill and will be happy to share tips with you. You don't have to know someone to learn from them. Next time you're out in a public place, like a café, pay attention to the conversation around you. If there's a particularly good conversation, listen and take note of what makes it a good conversation.