This week in the world’s #1 newsletter on leadership communication:
- How to Small Talk
- FREE Workshop: AI for Leaders
- How to Speak Like a Top 1% Leader
- Is the Medium Really The Message?
How to Small Talk
Most people loathe small talk.
“How are you?”
“What do you do?”
“Nice weather, isn’t it?”
But the dislike isn’t evenly distributed.
The younger and more introverted you are, the more likely you are to cringe at small talk about traffic, the weather, or last night’s game.
I spare you the research because it's kind of obvious.
What's more interesting is, how can you connect smarter?
Here are 10 ways to make an impression by asking deeper questions.
10 Ways To Start a Meaningful Conversation
❌ Don’t say: “How are you?”
✅ Say instead: “Who are you?” (h/t Peter Sorgenfrei)
❌ Don’t say: “What do you do?”
✅ Say instead: “What excites you right now?”
❌ Don’t say: “Where are you from?”
✅ Say instead: “What’s something unique about where you grew up?”
❌ Don’t say: “Are you busy these days?”
✅ Say instead: “What’s something that recently made your day?”
❌ Don’t say: “Been on holiday?”
✅ Say instead: “Where do you feel most at home?”
❌ Don’t say: “Do you have any hobbies?”
✅ Say instead: “What’s something you can talk about for hours?”
❌ Don’t say: “How was your weekend?”
✅ Say instead: “What was the highlight of your week?”
❌ Don’t say: “How’s work?”
✅ Say instead: “What’s a recent win you’re proud of?”
❌ Don’t say: “Is this your first time here?”
✅ Say instead: “What brought you here today?”
❌ Don’t say: “Are you married?”
✅ Say instead: “Who’s someone in your life who really inspires you?”
These questions invite stories, not one-word answers. They unlock what people care about, not just what they do.
What next? Pick one and try it out with the next person you meet.
FREE WORKSHOP
AI for Leaders
AI is reshaping how we think, decide, communicate, and lead. But many leaders feel:
- Behind the curve – while peers seem to be moving ahead
- Unsure where to start – tools and jargon feel overwhelming
- Concerned about credibility – how do you speak about AI with confidence?
- Pressed for time – no room to “experiment” in a high-stakes role.
Yet one thing is clear: The leaders who build an AI edge now will create lasting impact in their organizations – and their careers.
My friend JD Meier and I want to help you get that edge in two free workshops.
In these live workshops you will:
- Learn how to think better with AI → faster decisions, sharper clarity
- Learn how to communicate better with AI → more effective leadership messages
- Learn how to learn better with AI → stay ahead as the technology evolves
- Build confidence in your ability to lead AI conversations in any room
JD is the Former Head Innovation Coach for Microsoft CEO Satya Nadella (the world’s most valuable company and an AI leader).
He is also the bestselling author of Getting Results the Agile Way. JD helps top leaders master high performance, innovation and leadership with AI.
The workshops are on
- June 18th, 10 AM PST / 7pm CEST
- June 20th, 10 AM PST / 7pm CEST
This is not the usual hacky stuff about the latest tools and tricks that are outdated tomorrow, but the foundational knowledge for any leader who wants to be relevant tomorrow.
PODCAST
How to Speak Like a Top 1% Leader
I do a podcast to help you become a top 1% communicator. I’d appreciate it if you subscribed.
This week, I am a guest on the Amplified Leadership podcast hosted by Oliver Degnan.
Oliver and I explore what it truly means to "Speak like a CEO."
We explore how effective communication isn't just about conveying information, but about inspiring action and driving results.
We discuss how to make your story sticky, how to create a compelling vision, how to communicate better as a team, how to build trust, and much more.
This is a value-packed half an hour with lots of actionable advice!
Listen to the full episode here:
BOOK RECOMMENDATION
Is the Medium Really The Message?
In the 1960s, Marshall McLuhan famously coined the phrase “the medium is the message”.
“The medium of our time – electric technology – is reshaping every aspect of our personal life. Societies have always been shaped more by the nature of the media by which men communicate than by the content of the communication.”
He is right. Just think how the printing press, mass media and now social media have changed societies. And who knows how AI will impact us.
But – as usual – reality is a bit more complicated.
First, the messenger matters. Trust in institutions is down while trust in individuals is up. Think certain politicians, podcasters and personal brands.
Second, the message matters. "Kamala is for they/them, President Trump is for you." According to one analysis, the ad shifted the race by 2.7 percentage points in Trump's favor.
How to succeed in this environment? Get the right message across via the right messenger on the right media.
BTW, the book title is not a misprint. It really is “The Medium is the Massage”. In a word play on his famous statement, McLuhan argues that the media “leave no part of us untouched”.
On that note, have an inspired weekend!
Oliver
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