How to Keep Any Conversation Going: 15 Tips for Endless Discussion

Thanks to the rise of digital communication, the way that humans approach social interactions has undergone a major shift over the last decade.

And the secludedness, quarantining, and isolation that came as a result of the pandemic only shifted the social landscape more drastically.

With all of that in mind, it’s no surprise that nearly 60% of adults report finding it harder now to build relationships than ever before.

Person-to-person conversation — both small talk and deeper, more meaningful dialogue — is the key to building productive, trusting professional relationships. Conversation skills are important for networking and client relationships alike.

And, with more than half of sales leaders reporting sales conversations as one of the most important metrics to track for success, developing conversation skills is especially important for salespeople.

In this article, we’ll go over everything you need to know about how to keep a conversation going with data-backed tips and techniques.

Making small talk is one thing, but keeping conversations flowing smoothly for longer interactions can feel much more daunting.

Whether you’re mingling at a party, meeting someone new, or just want to have an engaging discussion with friends, it takes skill to keep conversation lively and energetic.

The good news is that with the right mindset and communication techniques, you can steer conversations confidently no matter the scenario or who you’re speaking with.

In this comprehensive guide, I’ll share my top strategies for sustaining great conversations that never hit a lull Here are 15 tips and tricks to try

1. Come Prepared with Good Topics in Mind

The easiest way to keep conversation going is arriving armed with some topics in your back pocket. Here are some foolproof categories to have in mind before any interaction:

  • Recent pop culture – Did you see the latest hit show or viral video?

  • Local happenings – Ask about any events or news in your shared city or town.

  • Current affairs – What are their thoughts on a trending news story?

  • Hobbies – Everyone has something they geek out on in their free time.

  • Travel – Where has your conversation partner been lately? Dream destinations?

  • Entertainment – Seen any great movies, shows, or bands recently?

  • Family & friends – People usually enjoy talking about loved ones.

When conversation hits a lull, transitioning to a new pre-planned topic prevents awkward pauses.

2. Find Common Interests to Connect Over

An easy way to fuel the conversation is tapping into common interests you share with the other person.

Listen for hints of things you both enjoy and dive deeper into those themes. A few shared interests to look out for:

  • Pop culture obsessions – Same favorite TV show or band? Discuss!

  • Sports teams – Local or national ones you both cheer for.

  • Hobbies – Cooking, reading, gaming, anything leisurely.

  • Career fields – Mutual industries, companies, or roles.

  • Backgrounds – Did you go to the same school or are from the same hometown?

Discovering mutual interests gives you an endless stream of things to discuss back and forth.

3. Inquire with Open-Ended Questions

Closed-ended questions that can be answered in just a few words hit dead ends fast. Keep conversation flowing by asking open-ended questions that provide room for detailed responses.

Some examples:

  • What do you enjoy most about your work?

  • Where is the most interesting place you’ve ever visited?

  • How did you get into your hobby?

  • What’s on your travel bucket list?

  • What are you reading right now?

Prompting others to elaborate keeps the ball rolling by encouraging more than brief replies.

4. Listen Actively and Build On Responses

Don’t just wait for your turn to speak again. Listen closely to what the other person says and use it to spur new tangents for the conversation to unfold on.

Ways to listen actively and build on responses:

  • Ask follow-up questions – “How did you get into that field?”

  • Paraphrase back key points – “So you find cooking relaxing after a stressful day?”

  • Make connections to your experiences – “I also love hiking! What are your favorite local trails?”

  • Share relevant opinions or stories – “Sushi is my favorite food too! This sushi place just opened downtown we have to try…”

Let the dialogue grow organically based on what you both have to say, rather than just changing topics randomly.

5. Get Personal and Share Your Stories

Be open to occasionally sharing personal anecdotes and glimpses into your life. This fosters a meaningful back-and-forth.

Types of personal stories that help connect:

  • Funny incidents from childhood or school days

  • Adventures from your travels around the world

  • How you got into your interests or career

  • Lessons learned from life experiences

  • Embarrassing mistakes that you can look back on with humor

By exchanging stories and experiences, you form bonds that bring conversations to a more substantial level.

6. Don’t Fear Moments of Silence

A lull in conversation isn’t necessarily awkward, it’s normal! You don’t need to scramble desperately to fill every moment with constant chatter.

Let natural pauses happen, collect your thoughts, then continue flowing. Silence allows conversations to breathe. Don’t stress about gaps.

7. Circle Back to Earlier Topics

If you feel the conversation veering off aimlessly, neatly guide it back on track by returning to an earlier topic.

Say something like:

“Speaking of [topic] that we were talking about earlier…”

Then bridge into expanding on the initial theme or a related new angle.

Looping back prevents losing momentum as you wander between too many disjointed subjects.

8. Weave In Humor When Authentically Possible

Humor goes a long way in keeping spirits high during long interactions. Look for safe opportunities to interject playful jokes or witty banter.

Ways to naturally work in humor:

  • Funny anecdotes from your own life

  • Reacting with a punchline when the moment feels right

  • Self-deprecating jokes if they fit your style

  • Silly observations about surroundings

  • Light teasing in a friendly way

Laughter and amusement are the ultimate energizers for conversations.

9. Compliment Outside of Just Appearance

An easy way to boost the vibes is complimenting the other person. But skip cliché lines about pretty eyes – get creative!

Consider praising:

  • Their wit – “You always know the perfect thing to say!”

  • Thoughtfulness – “I really appreciate you reaching out to check on me.”

  • Work ethic – “It’s so impressive seeing how hard you work at everything.”

  • Style – “I love your sense of fashion.”

  • Talents – “You’re incredibly skilled at photography/coding/etc!”

Sincere compliments make people feel seen. But focus more on character than appearances.

10. Relate to the Other Person’s Statements

To show you’re actively engaged, relate their statements back to your own experiences when possible.

If they say:

“My family loves going camping in the summer.”


“Camping is the best! I have such fond memories camping with my family growing up too.”

Finding parallels in your perspectives strengthens bonding.

11. Don’t Dominate the Conversation

While sharing about yourself is important, don’t hog the conversation.

Aim for a balanced give-and-take where you speak about 40% of the time and listen the other 60%.

Also avoid interrupting. Let the other fully finish their thoughts before interjecting.

Conversations should flow back and forth, with neither party dominating. Provide space for both to contribute.

12. Watch for Non-Verbal Cues of Interest

Observe the other person’s body language for signs they are engaged and enjoying the interaction.

Positive non-verbal cues include:

  • Eye contact – They’re staying focused on you

  • Smiling & laughing – They’re connecting with your humor

  • Open posture – Not crossed arms or hunched over

  • Nodding along – They’re actively listening to your stories

  • Leaning in – They’re captivated by the dialogue

If you notice distracted body language, switch gears to get their interest back.

13. Don’t Let Phones Distract

Few things derail conversations as abruptly as phones buzzing with notifications and divides attention.

Commit to being fully present by:

  • Silencing devices so they don’t interrupt

  • Keeping phones in bags or pockets, not the tabletop

  • Refraining from checking notifications during chats

  • Ignoring impulse to glance at screens during lulls

Staying off our devices ensures conversations get the undivided attention they deserve.

14. Have a Back Pocket Question Ready

When conversation starts stalling, have a go-to question ready to refresh momentum.

A few get-to-know-you options:

  • “What’s your favorite childhood memory?”

  • “Where is the most beautiful place you’ve been?”

  • “What’s your perfect idea of a relaxing weekend?”

  • “What motivates you most in life?”

Having a backup question eliminates pressure in moments of desperation.

15. End at the Right Time

Finally, know when to bring engaging conversations to a close on the right note.

Signs it’s time to start wrapping up:

  • Energy is winding down

  • Pauses are getting longer between responses

  • Attention starting to stray

  • Conversation is going in repetitive circles

Leave people wanting more by ending chatter while it’s still lively and enjoyable for both parties.

The hallmark of great conversations is that they seem to flow effortlessly. But

how to keep a conversation going

Use Active Listening

Active listening is one of the most important components of a productive sales conversation. It involves listening not only to hear a speaker’s words but to truly understand their message in its entirety. How to keep a conversation going: active listeningSkilled active listening is a sign of high emotional intelligence, and is reported as the number one most desirable trait in salespeople by buyers. It helps buyers feel understood and valued by the seller, and it helps the seller create a personalized solution for them.

Active listening also helps salespeople retain more details about their sales conversations.

Ask Open-Ended Questions

One of the easiest yet most effective ways to open up conversation is to ask open-ended questions instead of closed-ended ones. how to keep a conversation going: ask open-ended questionsOpen-ended questions are ones that can’t be answered with a simple “yes” or “no.”

Open-ended questions encourage the prospect to elaborate on their thoughts and help sales reps uncover their deepest pain points and challenges.

One invisible way to keep the conversation going is to consciously reframe your mindset to one of curiosity.

Instead of making judgments on how your conversation counterparty is responding, or mentally preparing your next response, listen to your co-converser with curiosity. This will help you stay engaged in the conversation and can help subconsciously elicit more thorough candid responses.

Just remember to be sincere with this strategy. Curious can turn into creepy pretty quickly if you aren’t mindful about how and when you ask follow-up questions.

Simple Ways to Keep a Conversation Going

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