Is This Conversation Going Anywhere? Using Critical Thinking to Steer Discussions Productively

Targan Wehye-Jones • March 20, 2025

Ever been in a conversation that feels like a car stuck in neutral? Wheels spinning. Nowhere to go. It’s awkward, frustrating, and—if we’re honest—a little boring. It doesn’t matter if it’s a casual chat at a networking event or a formal business meeting, these dead-end discussions waste time and energy.

But here’s the good news: it doesn’t have to be that way.

You have the power to guide conversations so they actually go somewhere. It’s all about using critical thinking to stay focused and intentional with your words.

Why Conversations Derail

Conversations fall apart when there’s no purpose driving them forward. No clear goal. No meaningful questions. Just vague back-and-forths that fade into nothing.

And you know what happens when this becomes a habit? Missed connections. Lost opportunities.

If you’re serious about growing your business, building relationships, or even just being memorable in a room full of people, you need to keep your conversations sharp.

Critical thinking is your secret weapon to make it happen.

How to Keep Conversations On Track

1. Start With a Goal

What’s the point of this conversation?

It sounds simple, but most people jump into discussions without thinking about their end goal. Are you networking? Solving a problem? Pitching an idea? Before you say a word, get clear on what you want to achieve.

For example:

  • At a networking event your goal might be to connect with three new people and learn about their businesses.
  • In a meeting, your goal might be to finalize next steps for a project.

A goal gives you focus. Without it, the conversation will wander—and so will your impact.

2. Ask Better Questions

Want to avoid small talk that goes nowhere? Ask questions that make people think.

Open-ended questions are your best friend. They encourage deeper, more meaningful dialogue. Plus they show you’re genuinely interested.

Here’s an upgrade:

  • Instead of: “Did you like the event?”
  • Try: “What’s been the most valuable part of the event for you so far?”

Notice the difference? The first question gets a one-word answer. The second sparks a real conversation.

3. Listen. Really Listen.

Let’s be honest—most people don’t actually listen. They’re too busy planning what to say next.

But you’re not “most people.”

When you listen actively, you pick up on details that others miss. These details are golden opportunities to steer the conversation toward something meaningful.

Pro tip: Repeat back what you hear. Not like a robot—just enough to show you’re paying attention.

  • “So you’re looking to expand into new markets. Tell me more about that.”

This small step builds trust (and keeps the conversation flowing naturally.)

4. Steer It Back When It Drifts

Sometimes conversations wander off course. It happens.

Maybe the other person starts venting about their neighbor’s barking dog. Or the meeting derails into a side topic about last week’s lunch.

Here’s how to gently pull it back:

  • “That’s an interesting point! Just to circle back to what we talked about before, how do you think we should move forward?”
  • “I love where this is going, but I want to make sure we cover our main goal before we wrap up.”

You’re not shutting anyone down. You’re just keeping things on track.

5. Wrap It Up With Purpose

Ever leave a conversation wondering, “What just happened?”

Don’t let that be you. Before you wrap up summarize the key points and confirm any next steps. This makes sure everyone is on the same page—and leaves a good impression.

For example:

  • “It sounds like we’re both on the same page about collaborating on this project. I’ll send over some ideas next week, and we can go from there.”
  • “I really enjoyed learning more about what you do. Let’s exchange contact info and keep in touch.”

It’s simple, but it makes all the difference.

Why This Matters

Steering productive conversations isn’t just a “nice-to-have” skill. It’s a need-to-have.

From boardrooms to coffee shops, the way you interact shapes how people see you. Your tone. Your body language. Even the questions you ask. They all work together in sync.

And let’s face it: you don’t just want to participate in conversations. You want to own them.

Ready to Take Your Professionalism to the Next Level?

At Connected Momentum , we’re here to help. Our professional business etiquette training services are designed to teach professionals like you the art of effective communication and business etiquette. From mastering your handshake to learning the right words to use in any situation, we’ve got you covered.

If you’re in the Tampa Bay area, check out our professional development training in Tampa Bay. Or visit our homepage to explore how we can help you sharpen your skills in no time.

The next time you find yourself in a conversation, ask yourself: “Is this going anywhere?”

And if it’s not, take the reins. You’ve got the tools to take it where it needs to go.

By Targan Wehye-Jones May 22, 2025
It’s part of any given work day: Your phone’s buzzing. Emails are piling up. That Slack notification? Feels like it needs an immediate response. But here’s the thing—when you’re in a meeting, none of that matters as much as what’s happening in the room. Think about it. Someone’s sharing an idea, and you’re busy checking […] The post Mind Your Manners: A Guide to Proper Device Use in Meetings first appeared on .
By Targan Wehye-Jones December 30, 2024
I want to shed light on a topic I have witnessed more than a few times and don’t know if many have really known what they are witnessing if they come across it. Childcare has been a long running issue in the United States but our working, strong willed, independent moms or dads are encountering […] The post No one is talking about struggles in childcare leading to kids on shift too.. first appeared on .
By Targan Wehye-Jones December 20, 2024
Yet, space after space and place after place just can’t figure it out. If we evaluate this from the most simplest of levels. When someone looks disheveled we in that moment make judgement. We go thru a mental rolodex of possibilities. First impression or Presentation in this case, is the first line before we go […] The post The Power of Presentation can Make or Break Business first appeared on .
By Targan Wehye-Jones December 11, 2024
I have been a parent in all facets of schooling, literally my kids have done public, private, e-school, charter school, homeschool with co-ops and with out. That’s a lotta schooling but my kids are moving and grooving and doing their thang. Now you may wonder as the parent orchestrating all of these methods which was […] The post Is Homeschool the new Machine? first appeared on .
By Targan Wehye-Jones May 29, 2024
The Power of Perception in Business What do you think in business can ruin our chances at success or enhance them? Perception which ties to your presentation abilities. I want you to think of how many times you as a customer has walked into an establishment or received service and thought. How can this be […] The post Perception is reality first appeared on .
By Targan Wehye-Jones March 13, 2024
Unlocking Potential in Future Careers   I recently participated in a business development day for over 400 high school seniors to learn and explore what their community had to offer in terms of high paying jobs. These careers are often dismissed by young people.  Many with such ease of entry. As the M.C. of my […] The post Future Careers first appeared on .