Why Even Great Conversations Go Off the Rails—and How to Course-Correct Fast

Last week, I met with someone who was struggling to connect with their client. They explained how, throughout the meeting, they kept talking about one thing while their client was responding as if they were discussing something entirely different. The disconnect remained no matter how they tried to steer the conversation back on track.

By the end of the meeting, they hadn’t made much progress, and it wasn’t until afterward—through a follow-up email and additional discussions—that they were able to align. Unfortunately, by then, valuable meeting time had been wasted, and worse, trust had been eroded. This experience raised an important question: What could have been done differently?

The Struggle of Being on Different Wavelengths

This situation isn’t unique. We’ve all been in conversations where we couldn’t get on the same page. It happens in all kinds of professional interactions:

• A boss explaining a new initiative to an employee, only to realize their message isn’t landing as intended.
• A salesperson outlining the benefits of a product while the potential customer seems focused on an entirely different concern.
• Two colleagues brainstorming solutions but talking past each other, leading to confusion rather than progress.
• Executives deliver company-wide messaging that gets misinterpreted, leading to unnecessary resistance or misunderstanding.

When these disconnects happen, a lot is lost:

• Good outcomes may never be realized.
• Time and energy are wasted.
• Deals are lost because of misunderstandings.
• Creative solutions are overlooked due to a lack of alignment.
• Trust is broken when people feel unheard or misrepresented.

So, what can you do when you find yourself in a conversation that just isn’t connecting? Here are three key strategies to improve communication and alignment.

Prime the Conversation

One of the best ways to keep a conversation on track is by priming it at the beginning. In behavioral economics, priming refers to exposure to something may influence how people think and respond later. Noteworthy behavioral economists like Daniel Kahneman and Dan Ariely have studied how priming shapes decision-making and perception.

A simple example: you walk into a movie theater and smell popcorn—suddenly, you want popcorn. The scent acts as a subconscious cue that influences your behavior.

Conversations work the same way. The way a discussion starts influences how the rest of it unfolds. If you want someone to focus on a specific topic, you must set the stage early.

For example, if you’re a manager introducing a change in process, don’t just dive into logistics. Instead, set the context by explaining why the change is necessary and how it aligns with the team’s goals. If you’re a salesperson, take a moment to understand what’s on the customer’s mind before pitching your product. When you prime a conversation effectively, you guide the other person’s thought process, making alignment easier.

Ask More Questions and Listen More Than You Speak

When you realize that a conversation isn’t connecting, stop talking and start listening. Often, the disconnect isn’t because the other person is ignoring you—it’s because they’re coming from a different perspective. The best way to bridge that gap is by asking clarifying questions.

• Instead of assuming you understand their stance, ask: “Can you walk me through how you’re thinking about this?”
• Look for common ground by asking: “What’s most important in this situation?”
• If something doesn’t make sense, clarify: “Just so I’m on the same page, are you saying that your biggest concern is X?”

A key element of good questioning is ensuring you don’t put the other person on the defensive. If someone feels embarrassed or attacked, they’ll shut down, making alignment even harder. Approach questions with curiosity, not confrontation. When you listen more than you speak, you allow yourself to understand their perspective first—then, you can tailor your response in a way that resonates.

Reflect and Follow Up

Sometimes, despite your best efforts, you won’t fully align during the conversation. That’s okay. What matters is what you do afterward.

• Reflect on your role in the misalignment. Ask yourself: Did I really listen? Did I communicate my thoughts clearly?
• Follow up with a summary. Send a quick message or email outlining your key takeaways and ask if they align with the other person’s perspective. For example: “Hey, after our conversation, here’s what I understood: [Key points]. Does that sound right to you?”
• Suggest a follow-up conversation. If there’s still misalignment, propose another discussion. Sometimes, a little extra time and a fresh mindset can make all the difference.

Final Thoughts

Misalignment in conversations happen, but it doesn’t have to lead to wasted time and broken trust. By priming your discussions, asking more questions, and following up effectively, you can dramatically improve how you connect with others.

The next time you find yourself in a conversation where you and the other person aren’t seeing eye-to-eye, take a step back and try one of these approaches. You might be surprised at how quickly things start to click when you shift from simply talking to truly communicating.

What’s your go-to strategy for getting a conversation back on track? Share your thoughts in the comments or reach out—I’d love to hear your perspective! If you have specific questions, I’d be happy to connect with you individually.