Introducing Better Conversations


By Grace Judson


What does it mean to have “better” conversations?

This new monthly column will address that question in many ways.

Let’s start with a general overview.

When you gain the skills and tools to have better conversations, you’ll enjoy better relationships. It’s that simple.

Whether with your boss, coworkers, friends, family, or even your dry cleaner or auto mechanic, when you know how to communicate cleanly, clearly, concisely, and, yes, compassionately, you’ll achieve better results with less hassle. Even in situations where you may disagree with someone, or flat-out not like them very much—or even be in conflict with them—you’ll discover that the tools we’ll talk about here will help you feel less anxiety and more ease in your interactions.

And for those relationships where you already feel at ease and might be good friends—or at least good colleagues—you’ll be glad to know you can develop even greater connection and opportunity for collaboration.

Where shall we start?

standing-out-in-your-officeLet’s begin with a fun, easy exercise in simple observation.

When I assign this practice to clients, they’re always surprised and pleased by how it changes the conversations they have with even the most casual acquaintances. How does it change them? They tell me they feel more depth and more connection, and the conversations are noticeably more interesting—in short, better.

Here’s the practice.

For everyone you meet—your boss, coworkers, the barista at your coffee shop, the checkout clerk at the grocery store, your family—everyone—observe them carefully and see if you can tell what they’re feeling in that moment.

What’s their emotional experience? What’s going on for them, under the surface?

How does that change what you do or say in your interaction with them?

And if you want to try a more advanced version, here’s Part Two.

Choose someone you’re comfortable with—a good friend, your spouse or partner, or a close family member. (I would not recommend starting with a coworker, and definitely not with a supervisor. We’ll discuss how to use this practice in high-stakes situations in a later article.)

Choose a time when you’re not in a rush, and when things are comfortable between the two of you.

Explain what you’re doing: that you’re practicing observing people to see if you can reach a conclusion (or at least make a good guess) about what they’re feeling. Ask them if they’d be willing to validate (or correct!) your estimation of what they are feeling right now.

It’s very important that you accept their choice. If they say, “No,” drop the subject and move on. Even with someone you’re close to, they may not want to be that vulnerable in that moment, and that needs to be okay.

If they say, “Yes,” then describe what you’re observing, using this type of structure: “It seems to me that you might be feeling…

Again: very important to use this conditional language. You never want to tell someone how they’re feeling, or, worse yet, tell them how they should be feeling! (I’m sure you’ve experienced times when someone has done that to you, so you know how bad it feels.)

My guess is that you’ll find yourself adapting your approach to people based on what you start learning about them. In doing so, you’ll probably discover—as my clients do—that you have more open, real, better conversations, and that your relationships improve.

Good luck!

And if you have questions, follow the link below to my Facebook group, where we talk about this and many other communication, conversation, and connection-related topics.

Grace JudsonGrace Judson is an expert on communication, conflict transformation, and negotiation. She works with individuals, teams, and leaders to help them have the clean, clear, honest conversations that improve relationships and build careers. She can be reached on her website,, and in her private Facebook group, the Connection Incubator, where she’s happy to answer questions and help solve communication challenges.

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