How to Keep a Conversation Going: 6 Proven Strategies to Engage and Connect

In the world of business, conversations are the currency of success. The difference between a lost opportunity and your next big deal often comes down to how well you can keep a productive discussion going.

Consider this: a staggering 93% of our communication is non-verbal, conveyed through subtle cues like tone, body language, and facial expressions (Source: UCLATMC). To truly connect with someone, you need to master the nuances of conversation on multiple levels.

As a sales expert and online marketing strategist, I‘ve seen firsthand how the ability to hold engaging, value-driven conversations can open doors and transform relationships. It‘s not about idle chit chat or pushy sales tactics. It‘s about building genuine rapport, unearthing needs and concerns, and collaborating on solutions.

Whether you‘re meeting a prospect for the first time, networking at a conference, or sitting down with an important client – the way you manage the dialog matters. To help you navigate even the most challenging conversation with ease, I‘ve compiled my top 6 strategies, backed by research and real-world results.

1. Find Common Ground to Create an Instant Connection

One of the easiest ways to spark engagement and build trust in a conversation is to establish common ground. A study by social psychologist Robert Cialdini found that we tend to like and comply with requests from people we perceive as similar to us (Source: Influence).

Take the first few minutes of a conversation to discover shared interests, experiences or perspectives that you can both relate to. Some go-to conversation starters:

• "I noticed your company recently [business event]. How has that impacted your department?"
• "What‘s the most interesting thing happening in your industry right now?"
• "I saw on LinkedIn that you [accomplishment]. How did you make that happen?"

The key is to do your homework beforehand. Check out their website, social media profiles, or recent press. Come prepared with a few tailored ice-breakers.

Once you‘ve found some common ground, ask follow up questions and share your own relatable stories or opinions. Just remember to steer clear of controversial topics that could derail the conversation. Stick to positive, productive angles you can both get behind.

2. Encourage Elaboration with Strategic Open-Ended Questions

To move beyond surface level small talk, you need to invite the other person to open up and share more. The best way to do that? Ask open-ended questions that require more than a simple yes/no answer.

According to Harvard research, when doctors asked patients open-ended questions like "What concerns you most about your symptoms?" and showed empathy, visits lasted just 1 minute longer on average. Yet patients felt less anxious and more informed about their condition (Source: JABFM).

The same principle applies in sales conversations. By prompting the other person to share more about their situation, challenges, and objectives, you gain valuable context. You demonstrate genuine interest. And you identify ways to tailor your pitch and deliver relevant value.

Some open-ended sales questions to try:

• "What‘s your biggest priority/challenge these days?"
• "How does this initiative fit into your overall strategy?"
• "If you could wave a magic wand, what would ideal look like?"

The phrasing of these questions matters. They‘re expansive, not restrictive. They invite reflection and elaboration vs. shutting the discussion down.

One caveat: make sure you actually listen to their answers. There‘s nothing more annoying than feeling like you‘re being prodded through a checklist vs. having an authentic dialog. Pick up on interesting threads you can explore together – and don‘t be afraid of tactical pauses to give them space to gather their thoughts.

3. Demonstrate Presence and Understanding with Active Listening Techniques

Active listening is more than just hearing words. It‘s the ability to be fully tuned in, present and focused on the other person. By some estimates, we spend 70-80% of our waking hours communicating. But research suggests most of us only remember 25-50% of what we hear (Source: MIT).

The costs of not listening in sales interactions can be steep. You might miss crucial points about the prospect‘s needs or constraints. You could come off as self-centered or tone-deaf. Worst of all, you fail to build the trust and understanding needed to advance the relationship.

To practice more active, engaged listening in your conversations:

• Maintain comfortable eye contact and open body language
• Avoid interruptions or fidgeting with distractions like your phone
• Paraphrase key points to confirm you understood correctly
• Ask clarifying questions to fill in gaps: "What did you mean by…?"
• Notice what‘s not being said – tone, energy, facial expressions

When you demonstrate that you‘re fully present and attuned, the other person will naturally feel more at ease. They‘ll share more openly. And you‘ll pick up on crucial nuances you might otherwise miss. Conversations shift from feeling transactional to feeling like a true collaboration.

4. Elevate the Discussion with Compelling Stories and Insights

While questions are essential to guide a conversation, at some point you also need to add your own substance and perspective. This is your chance to differentiate yourself – by sharing memorable stories, thought-provoking facts, and fresh viewpoints that educate and engage.

There‘s a reason storytelling is such a powerful communication tool. Research shows that character-driven stories stimulate the release of oxytocin in the brain, a feel-good hormone that promotes connection and empathy (Source: HBR).

Say you‘re talking to a prospect about how to improve their customer onboarding process. You could share a vivid before-and-after story about how you helped a similar company reduce churn by 30% in 90 days. Highlight the emotions and challenges involved to make it relatable.

Or maybe you‘re discussing emerging trends in your industry. Reference a surprising statistic from a reputable source. Share a unique insight based on your experience working with other clients. Offer a fresh angle that gets them thinking.

The idea is to be intentional about the value you contribute to the conversation. Don‘t just fill the air with more words. Make your message persuasive and sticky. Give them something to ponder and respond to.

One tip: just like the best stories have a clear beginning, middle and end – so should your conversational vignettes. Keep your points crisp and relevant. Leave room for their reactions and build. A little bit of planning goes a long way.

5. Balance Leading and Following Based on Situational Cues

Conversations are a dynamic dance. Like a tango, sometimes you need to take the lead and direct the discussion. Other times, you need to follow your partner‘s cues and let them drive. The key is to strike the right balance.

In one analysis of 25,537 sales calls, top performing reps had a talk-to-listen ratio of about 43:57. Meaning they let the prospect do most of the talking (Source: Gong).

There are moments when you‘ll need to steer the conversation to keep it on a productive track. Maybe it‘s getting sidetracked by tangents. Maybe it‘s veering into inappropriate territory. Or maybe it‘s simply losing steam. When you sense the discussion needs a reboot, try:

• "That‘s an interesting point. It actually reminds me of [related topic]…"
• "I‘d love to revisit [topic] in a bit. While we‘re on the subject of Y, what are your thoughts on…"

On the flip side, sometimes the most powerful thing you can do is get out of the way. If they‘re sharing a fascinating story, or having an aha moment – don‘t interrupt the flow. Encourage them to elaborate:

• "Wow, that‘s a great insight. Can you tell me more about…"
• "I can see you‘re passionate about this. What motivated you to…"

By calibrating your approach based on the real-time dynamics, you keep the conversation feeling natural vs. forced. You create space for them to process and share. You build a sense of reciprocity and rapport.

6. Leave Every Interaction on an Actionable, Positive Note

We‘ve focused a lot on how to propel conversations forward. But equally important is setting the right tone as you wrap up. The final moments of an interaction have a big impact on what the other person remembers and feels (Source: PS).

Make the ending count. Recap key points. Agree on next steps and timelines. And whenever possible – close with positivity and gratitude.

• "I can‘t wait to dig into this further. As a next step, I‘ll send over…"
• "You‘ve given me a lot to think about. I really appreciate you taking the time to…"
• "Sounds like we‘re aligned on the game plan. I‘m excited to work together to…"

An effective follow up email can also go a long way. Briant University found that simple, friendly emails focused on next steps and mutual interests increased response rates by over 300% vs.generic templates (Source: Forbes).

So invest a few extra minutes to send a personalized thank you and action items. Reference details from your conversation to jog their memory. Keep the momentum and goodwill going.

The goal is to make every conversation feel like the start of something bigger. Even if you covered a lot of ground in this one discussion – position it as an on-ramp to a valuable longer-term relationship.

The Bottom Line

Keeping a conversation going is both an art and a science. By applying these 6 strategies consistently, you‘ll be able to navigate even the most challenging scenarios with poise and purpose:

Strategy	Why it Works
1. Finding common ground	Creates instant affinity and connection
2. Asking open-ended questions	Encourages sharing and unearths needs
3. Practicing active listening	Demonstrates empathy and understanding
4. Sharing compelling stories	Makes messaging memorable and impactful
5. Striking a lead-follow balance	Keeps conversations dynamic and two-way
6. Ending on an upbeat, actionable note	Lays groundwork for productive next steps

But just like any other skill – it takes practice. I often tell my sales coaching clients to treat every interaction as a learning lab. Pay attention to what works and what doesn‘t. Solicit feedback from others on how you show up.

With a little intention and effort, you can transform your conversations from hum-drum exchanges into catalysts for deeper trust, collaboration and results. You‘ll be able to uncover hidden opportunities. Defuse objections and concerns. Co-create solutions. And ultimately – win more hearts, minds and revenue.

So the next time you find yourself in the conversational hot seat – take a deep breath. Summon your inner talk show host. And remember: there‘s no better feeling than turning a tenuous chat into the start of a loyal, lucrative relationship. You‘ve got this!