Diary of a CEO & The Art of Good Conversation

Borrowed

“Communication is the most important skill in life. We spend most of our waking hours communicating. But consider this: You’ve spent years learning how to read and write, years learning how to speak. But what about listening? What training or education have you had that enables you to listen so that you really, deeply understand another human being from that individual’s own frame of reference?”

From The 7 Habits of Highly Effective People by Stephen R. Covey [Book]

Learned

I’ve been listening to The Diary of a CEO with Steven Bartlett lately, and it’s quickly become a regular in my podcast rotation. No matter the topic, the way Steven runs his interviews makes it a pleasure to listen and learn—even when they go over 1.5 hours long.

It got me thinking: What makes these conversations so engaging?

Here are some themes that stand out to me. I think there’s a lot from each that we can carry into our everyday conversations—whether we’re talking to clients, colleagues, or even friends and family.

Prepared, but Flexible

Steven always does his homework. In preparation for his interview with endurance athlete Russ "Hardest Geezer" Cook, Steven sat down with people close to Cook—his girlfriend, dad, and others—to get a broader perspective. With breathwork expert and "Ice Man" Wim Hof, Steven read every study in detail ahead of the interview, giving him firsthand context and understanding on the impact of Hof's work.

But what makes the conversation work is that he’s not rigid. He knows what he wants to cover, but he lets the conversation go where it needs to, following the guest’s lead while keeping things on track.

I’m not suggesting we conduct research for every conversation, but coming in with context and empathy, rather than focusing solely on our agenda, can lead to deeper and more meaningful engagement.

Active Listening  

Even though I haven’t watched The Diary of a CEO episodes on YouTube yet, I don't need to see Steven's body language to know he is actively engaged in every conversation.

By being fully present, Steven often picks up on subtle remarks, sometimes a single word, and dives deeper, bringing out insights that would have otherwise gone unnoticed. He also doesn't rush to fill the silence when guests take long pauses to respond. It's happened in almost every episode I've listened to so far.

In a world full of Zoom calls, there's often so much vying for our attention. It’s a reminder of the power of active listening—you miss a lot if you’re only half there!

Honesty and Vulnerability

Steven’s not afraid to go deep and be direct. Take his interview with George Heaton, Co-Founder of Represent Clothing, where Steven told him that he seemed to be living in a prison of his own making after Heaton touched on how he prioritizes his life and work. As a listener, it’s one of those “wow, he actually said it” moments, and yet, it pushes the guest to open up.

He even asked former Mafia boss Michael Franzese if he’d ever killed anyone.

At the same time, Steven doesn’t shy away from sharing his faults. In that same interview with Franzese, he asks his staff if he's a micromanager and admits to where he can hold on to projects too closely.

It’s a good reminder to cut through the noise and get to the heart of the matter, especially when faced with a tough conversation. But what really makes a difference is pairing that honesty with vulnerability—sharing your own challenges or story.

Curiosity Drives Engagement

No matter the topic—whether it’s trends like Ozempic or someone's journey—Steven brings the same curiosity and energy to the conversation. It’s clear he’s genuinely interested, and that interest pulls more out of his guests.

I think about past new business calls with clients whose businesses seem dull at face value. But when I show up with curiosity, the conversation almost always ends somewhere fascinating.

Knowing When to Step Back

A host can make or break a podcast, even with the perfect guest. One thing I appreciate about Steven is that he knows when not to speak. He doesn’t comment on everything or make the conversation about himself. When he shares something personal, it’s to add context, not to hijack the conversation.

Over the years, I’ve become more conscious of this, resisting the urge to add unnecessary comments to a dialogue. It's incredible how powerful this restraint can be, especially in tough conversations with clients or team members.

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Here are some episodes to start (these titles make me laugh, though):

• Former Mafia Boss: ‘I Was Running The Biggest Scam In The World! $1.4 Million A Day!’
• Former Netflix CEO: ‘They’re Lying To You About Hard Work! Building a $300B Business & Wealth Secrets’
• The Ozempic Expert: Ozempic Transforms Your Gut Microbiome! People Are Being Overdosed On Ozempic!
• Wim Hof: They’re Lying To You About Disease & Inflammation!

Thought

Am I listening to understand or just waiting for my turn to speak?