The Guide to Great Conversations

Read time: 4 minutes

Welcome to The Ascend Archives Saturday Edition where I share insights from the brightest minds in business and life and how I'm applying them to my life.

When was the last time you had a great conversation?

One where you were constantly engaged, deeply curious about the other person, and energized when you walked away.

I’ve been fortunate to have many of these conversations recently. They are oftentimes the best part of my week.

Why Care About Communication?

Whether we realize it or not, much of our success and happiness hinges on how well we communicate.

It’s tough for an entire day let alone a few hours to go by without communicating with someone. Talking to a checkout guy at the grocery store, a text message from a friend, or an email from your boss. Sure we are taught the basics of how to read, write, and speak as kids. But are we taught how to be great communicators?

There are specific skills beyond the basics that are needed to be great communicators like conveying concise opinions and understanding how to learn from the person you are communicating with. We have plenty of opportunities to practice these skills every day, but are we intentional about it? Or are we just conversing with people just to converse?

The majority of communication these days happens through texts, emails, Slack messages, WhatsApp, and even Snapchat. But reading and writing is very different from speaking and listening.

My uncle has a saying, “If you can’t make your point in 2 sentences, then pick up the phone”.

Speaking with someone directly can help resolve issues much quicker, help us make better decisions, and allow us to connect with the other person more than written messages back and forth.

Yet, it can be intimidating.

Conversations unfold fluidly. They require active listening and reacting to the other person in real time. It opens the door to vulnerability and showing emotion. There is no room for revision or hiding behind a screen.

So how do we have great conversations?

I’m a member of Shane Parrish’s Farnum Street Community. They created an FS Guide Series to capture advice, wisdom, and tactics from those who have already figured out (or failed and learned from it!). They cover a wide range of topics on certain aspects of living that universally challenge all of us.

Here are their 4 principles for great conversations.

1. Active Listening

There is a difference between hearing someone and listening to someone.

People often mistake just being present vs. being present and attentive. We have all experienced the parent telling us no before we finish our sentence or the customer service agent reading a cookie cutter answer from their manual that doesn’t address the question we asked. It’s pretty rare to have people who actually listen to us (outside of our therapist who gets paid to do it).

Active listening means that we are retaining more of what the other person says than the minimum necessary for a reply. This allows us to respond thoughtfully. If we are not learning from the other person, then we’re not listening.

Exercise to practice: Try having a conversation where you aim to listen most of the time and talk less. How does the other person respond?

2. Find Ways to Connect

Having conversations is a major way we achieve and maintain relationships with people.

As Celeste points out, we have a natural tendency to look for ways to bond with people over a common interest, ability, or experience. On the flip side, when there isn’t a lot in common it becomes easy to exclude people by using jargon they are unfamiliar with, speaking a different language, or talking about topics they can’t contribute to.

One of the biggest obstacles comes when one person sees themselves as superior to the other person. Even when there is a power imbalance like a boss and employee, it’s important to still speak with one another on equal ground. It’s important to remember that we can learn from anyone and we don’t have all the answers.

Exercise to practice: When you find yourself talking to someone you consider yourself superior to, try mentally placing yourself on the same footing. What changes?

3. Ask Good Questions

To Krista’s point, it’s hard to meet a simplistic question with anything but a simplistic answer. It’s hard to overcome a combative question. It’s hard to resist a generous question.

The questions we ask are important. They shouldn’t be yes/no but they should invite elaboration. Active listening positions us to ask better questions.

Great questions come from a place of genuine curiosity to learn about the other person and bring out the best in them. At the same time, it’s important to note that questions are not the only way to continue a conversation. Silence is one of the great arts of conversation.

A welcoming silence and a nod can be the best way to invite further elaboration because it allows the speaker to ask themselves the question they’d like to hear.

Exercise to practice: Try using silence instead of questions in a conversation. How does the other person respond?

4. Disagree the Right Way

Great conversations are about learning from alternative perspectives, not changing people’s minds.

Part of having these conversations is knowing how to approach a difference of opinion. We are accustomed to defending our beliefs and convincing other people. But what if we just look for the humanity behind the words of the other person like Krista says?

It’s important to remember that we tend to mirror people. If we get attacked, we attack back. So instead of trying to convince someone with an alternate opinion, we can try listening to them. When we actively listen, they will be more inclined to listen back when we talk.

The goal is not to change their mind but to understand where they are coming from and show humility.

Exercise to practice: During a time you find yourself in a minor disagreement with someone, try learning from them instead of seeking to change their mind. What happens?

Final Thoughts

In reflecting on my best conversations from the past few weeks, many of the components from this guide stand out: focused listening to learn from the other person, great questions that invite the person to elaborate, and finding common ground between each other.

The biggest aha for me was the advice on silence. Silence feels awkward to me. I fill it with questions or “ums”. I’m going to practice letting the silence happen in upcoming conversations and see what happens.

Thank you for reading! As always please reply and let me know what resonated, what didn’t, or what you question. I love chatting about this stuff!

Cheers,

Andrew

P.S. Reply to this email if you want to read the full FS Guide to Great Conversations and I’ll send you the PDF!