How to have better conversations

Illustration of two professionals having a conversation with text bubbles surrounding them

There was a chapter in my life where I was obsessed with figuring out how to have better conversations.

I was a few years out of college. I’d landed a decent office job that called for near-constant social contact with colleagues and customers. Yet, for all that A-game adulting, I had a painful little secret:

I dreaded conversations.

I just felt so awkward! Whether I was stuck awkwardly riding an elevator with a colleague or talking on the phone with a customer, it felt as though a small but vocal parrot of self-judgment would perch on my shoulder to listen. As I waded grimly through my daily conversations, that little parrot would shake its feathered head, screech, and remind me yet again of just how bad I was at the art of conversation.

The art of conversation… that phrase would flutter around inside my brain. I remember listening to the smooth conversational jazz of people around me and grieving that this was a magic I could never obtain—just as I’d never paint sunflowers like Van Gogh or deliver a perfectly executed eyebrow waggle like Dwayne “The Rock” Johnson.

If you too have heard that parrot’s voice (or some other imaginary equivalent), I have good news for you. I got better at conversations, and you can too! With practice and the careful application of a few techniques, you can find your way to better conversations.

That path starts with a simple realization: Conversation may be an art form, but it’s also a skill you can practice and build on. We here at Ruby are all about forging meaningful connections, so we’ve assembled seven tips to start you on your journey to conversational mastery. Get a few of these techniques under your belt, try them out with an open mind, and you’ll start to notice you’re having better conversations—and sooner than you might think.

So real talk: Are you ready to have a conversation about conversations?

Because we’d love to talk this out.

Table of contents

Why do conversations matter?

OK, so let’s begin at the beginning. Why do conversations matter? Do they actually matter? I mean, we live in an information-drenched age. We’re surrounded by technologies that summarize, quantify and simplify the daily data of life. Why garble all that digital precision up with this human thing they call conversation?

Well, to state the obvious, humans are social creatures. In his oft-touted hierarchy of needs, seminal psychologist and philosopher Abraham Maslow plonked social belonging just one tier above our basic need for physical safety. We need connections! We thrive when we work together, and conversations form the vital social adhesive that catalyzes all that connectivity.

Whether you’re in a phone conversation, an online chat session, or speaking face to face, good conversational skills equip you to:

  • Establish rapport and a sense of being “in this together.”
  • Foster a sense of empathy for one another, along with a greater awareness of each other’s emotional state.
  • Build a common understanding of context — who we are, why we’re speaking, and what we hope to achieve together.
  • Set up a solid foundation of trust, paving the way for openness and honesty.

Combine these social assets together, and conversation is a vital starting point for good business outcomes. When everything is smooth sailing, conversations are on the ground floor of your company’s idea factory. It fosters that vital swirl of inventiveness. When there are rougher seas ahead, conversations foster the group’s overall resilience by making sure people know—and feel—that they’re all part of this together.

Now, the fun part! How do we make those good things happen? While you have a lifetime ahead of you to refine your conversational game, here are some clear, practical steps you can take right now to have better conversations.

Tips for better conversations

1. Embrace all that emotional stuff.

We live in a transactional world where information is a commodity. But conversations don’t work like that; they happen between people, and people’s brains are a psychological jam-filled donut of complexity. Our heads are filled with squishy emotions, memories, and ideas one can’t readily quantify but that impact every moment of our waking lives.

So, your first point of departure on the road to better conversations is to get comfy with the idea that all conversations, to some degree, are personal. Yep, even when you’re talking to Gordon from accounting about pivot charts, or helping a customer on the phone with a support inquiry, or in an online chat session with colleagues whom you’ve never met. Whoever you’re gabbing with, your conversational dance partner is not just a demographic, a potential customer, or a business colleague. They’re a person with complicated motivations.

OK, that’s great. But what do you do with that information? How can you make that broad awareness a practical reality?

One useful paradigm to help bridge the gap from theory to practice is the notion of “intersectionality,” a concept coined by lawyer and civil rights advocate Kimberlé Crenshaw. In essence, intersectionality crystallizes the idea that no person is the product of just one influence; we’re the product of many things.

You can read more about intersectionality here, but let’s take that idea and bolt it onto the nitty-gritty of how to have better conversations. Intersectionality reminds us to think beyond the main topic. Let’s say you’re on the phone with a customer. While on a surface level, the person you’re speaking to may want information or a resolution to a problem, they’ll also want other things. They might feel anxious about their purchase. They may feel a need to vent.

Your conversational mission, should you choose to accept it, is to listen in for all those other influences and respond accordingly.

Taking all of that stuff in may feel like juggling greased irascible ferrets, but consider that your human brain is equipped with eons of human evolution to fast-track this kind of advanced social trigonometry. Oh, and you can always check out our tips for how to identify and understand emotions during a phone conversation. You’re welcome.

2. Practice active listening.

With those theoretical foundations laid, let’s talk about active listening—because if this skill isn’t a conversational superpower, it’s as close as makes no difference.

It’s easy to think of conversations as talking. We’ve all had that horribly stilted conversation where an inner voice in our head screams, “Oh god, what should I say next? I can’t think of anything to say!” All too easily, panic can set in, and before you know it, all you can hear is that frantic parrot voice (remember him?) telling you you’ve got nothing.

Active listening flips the idea of good conversation on its head. Instead of focusing on what you should say next, active listening is about doubling down on your attentiveness to gain a more complete understanding of what your conversation partner is really trying to tell you.

This active listening lark might sound abstract at first glance, so let’s take some cues from this Harvard Business Review article to break it down into some practical steps. Active listening happens when you:

  • Regularly ask questions: Of course, questions help you check that you fully understand. But you can also use questioning to nudge the conversation toward finding deeper insights. Good listening isn’t just passive silence; it’s an active attentiveness spiced with dialog to further understanding.
  • Encourage the other person: People often feel vulnerable in conversations—even when that person is a potential paying customer and calling the shots. A good listener has a knack for making their conversation feel encouraged and confident with positive feedback. Face to face, you can convey that positivity with good eye contact, nodding, and engagement. Over the phone, you’ll need to fall back on good verbal cues.
  • Become an active participant: Help navigate! If you see a productive path for the conversation, find a moment to offer it as a suggestion. The goal here is not to take over but to send a strong message that you’re a cooperative conversational partner, as vested in finding a good outcome as they are.

A key point of leveling up your listening in a customer service conversation is to give your customer a voice. Take your eyes away from the clock and give the person the time and space they need to have their say. Another big advantage of active listening is that it primes you for empathy, a state of emotional understanding through which you can gain a deeper insight into the other person’s perspective — how they feel and what they really hope to gain through communicating with you.

3. Think like an interviewer.

Have you ever seen an interviewer on television and just marveled at their poise? Nothing appears to phase them. Whatever direction their conversational partner takes, the interviewer is right there with them, adding new layers with an observant remark or a new insight that somehow elevates the conversation.

What is this strange manner of word wizardry, you may ask? And how do I get me some of it?

I had the same questions. Then one day, I was given the opportunity to see an interviewer whom I admired in action behind the scenes. Over the course of a few weeks, I watched as this interviewer digested every facet of their interview subject’s life, from their biography to their work history to the thoughts they’d opined through social media. It turns out that the interviewer’s magic act wasn’t magic at all. In fact, all that conversational game was the binary opposite of smoke and mirrors.

The interviewer’s effortless conversational poise just boiled down to a lot of effort behind the scenes.

So here’s the take-home message. If you want good conversations, never be afraid of a little elbow grease.

Now, of course, you can’t commit to twenty hours of studying a customer’s life history before fielding their questions about your product or service. But you can make every effort to have the info you’re likely to need at your fingertips.

In a business phone conversation or an online chat session, you can have notes on standby, along with pertinent facts about their customer journey to date. You can also make sure you’re aware of the customer’s whole conversation with your company to date. As Zendesk points out in its 2020 report on customer experience trends, customers expect you to be up-to-date with their history across your company. So if they’ve already covered a lot of ground via other channels, make sure you know what that is so that they needn’t repeat themselves.

Oh, and a great side benefit here is that solid preparation is one of the best things you can do to deal with the foul specter of phone anxiety.

4. Leap from “no, but” to “yes, and.”

We’ve already talked a bit about how the ideal conversation is one in which the two speakers are working together as a team to find a good outcome. The best conversations aren’t adversarial. But let’s face it; sometimes you’ll find yourself dealing with a tricky customer. Inevitably, at some point, we all end up in a conversation where there’s a disagreement of some kind.

It may be more fact-based, where you’re just disagreeing about information. Or the conversation can be more emotionally fraught, where tensions begin to run high. And because we humans are complex, some conversations can start at the fact-based end and rapidly transmogrify into the more blood pressure-building variety. Those are the worst.

More often than not, in these kinds of conversations, one little word reigns supreme: “but.”

“Yes, I understand what you’re saying,” the conversation will go, “but here’s the situation I’m dealing with.” Even if your situation is entirely reasonable, even if you genuinely do understand your conversation partner and want to work with them to find a good outcome, that one little rebuttal can send a conversation spiraling down the proverbial plug hole.

Here’s what the beautiful “yes, and” does differently, with thanks to Finch Communication Solutions for such a neat summation: “Yes, and” is an acknowledgment of the offer your partner just made, with a contribution of your own to then move the action forward.”

Note the one-two punch of agreeableness here. You aren’t just acknowledging that you heard your conversational partner. You’ve built on that understanding with an active commitment to move the whole shebang forward. With one little phrase, you’ve made clear that you’re their copilot in this conversational adventure.

Sounds hard to action in practice? It can be! But so are chopsticks at first, or learning how to make your coffee just how you like it. As with so many of life’s most important things, practice makes perfect.

5. Know when to slow it down.

Here’s a weird little question for you. When you think of an awkward person, are they moving slow or fast? Are they leaning back, arms outstretched and gazing languidly at the world around them? Or are they leaning forward, fidgeting and twitching while they speak?

Most of the time, nervous awkwardness makes people speed up, probably because they’re subconsciously eager to be somewhere—anywhere—else.

While there are all kinds of practical tips you can use to combat conversational awkwardness, one simple first step is just to slow down the speed with which you speak. This takes practice to realize, but slowing down can also give you space to gather not just more information from your conversation partner, but to glean different kinds of information.

If you’re face to face, you may find that slowing down gives you a greater appreciation of social cues like facial expressions and body language. If you’re in a phone call or chatting online with a customer, slowing down the speed with which you communicate gives the person you’re talking to space to organize their thoughts.

Slow down how quickly you get to the point too! Small talk might seem onerous when you’re in a rush, but remember a touch of small talk helps you establish rapport and “warm your way” into the topic—almost like a practice run.

If in doubt, keep it frosty.

6. Know when to wind it up.

And here’s the yin to the previous section’s yang (or the zig to its zag, if you prefer). Sometimes you just have to know when to wrap it up.

Right off the bat, it’s worth making a special mention of phone conversations because phone calls are infamous for being hard to shut down sometimes. So if you’re looking for advice on how to make phone calls manageable, check out how to find the perfect moment to end a phone call.

More generally, however, the trick to finding the wrap-up is to be mindful. There’s no perfect solution or magical elixir for finding the right moment to end a conversation. The best advice is just to keep one eye open. When that moment arrives, announce it confidently and part ways on a polite, upbeat note.

Oh, and if the person you’re conversing with yawns theatrically and looks at their watch, that moment was about five minutes ago.

7. Be excellent to each other.

In the day-to-day flurry of running a business, it’s so easy to forget that your intent plays a huge role in the quality of connections you can create. Sure, you can get better at conversations by refining your communication technique, but the quality that elevates conversation to an art form is the authentic desire to be real with someone—to understand and to be understood.

What does that look like?

Much of the art of keeping a conversation flowing in a good direction is just about being … well … nice. Give the person your full attention, make an active effort not to interrupt them (even when you’re really excited!), and give the person room to guide you to the kinds of solutions and outcomes they need. Ultimately (and hopefully, this isn’t too schmaltzy a thing to say), good conversational outcomes are most likely to happen when you’re coming from a good place. Or, as Bill and Ted so righteously put it, when we’re trying to be excellent to each other.

Visit Ruby’s small business hub for more ways to build great conversations with the people you serve.